dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c29fad66fc74395b988834494b86fcf | CC(C)(C)c1cc2c(cc1CCl)Cc1cc(CCl)c(C(C)(C)C)cc1-2>>Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)c(C)cc1C2 | ClCC1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)CCl.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)C | Cl[CH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([CH3:9])([CH3:10])[CH3:11])-[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([CH2:20]Cl)[cH:21][c:22]1[CH2:23]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([CH3:9])([CH3:10])[CH3:11])-[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([C... | CC(C)(C)c1cc2c(cc1CCl)Cc1cc(CCl)c(C(C)(C)C)cc1-2 | Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)c(C)cc1C2 | null | null | C1CCOC1 | Reduction | OtherReaction | 08b86defb3b5580aed331da5dc7754668e37b1b39f9663cb706534752b6127fc | 3f30f36a4e8e967eaf7e0f33d6513b631552ae2da40a7eec53d1244abf3c514c | c1ccc2c(c1)Cc1ccccc1-2 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].Cl-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8] | 85 | [{"value": 85.0, "product": "CC1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,7-dichloromethyl-3,6-di-t-butylfluorene (0.75 g, 2.0 mmol) in THF (15 ml) was added a small portion of LiAlH4 (220 mg, 5.8 mmol) under stirring and the mixture was refluxed for 4 hours. The reaction was quenched with water and NaOH and extracted with ether. The ether solution was evaporated under vac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | null | c1ccc2c(c1)Cc1ccccc12 | Other | C1CCOC1 | null | null | CC(C)(C)c1cc2c(cc1CCl)Cc1cc(CCl)c(C(C)(C)C)cc1-2>C1CCOC1>Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)c(C)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f77d0a20d8f2418da5743c778ff494b1 | C=CC#N.OCC(CO)(CO)CO>>N#CCCOCC(COCCC#N)(COCCC#N)COCCC#N | C(C=C)#N.O.[OH-].[K+].OCC(CO)(CO)CO>>C(#N)CCOCC(COCCC#N)(COCCC#N)COCCC#N | [N:1]#[C:2][CH:3]=[CH2:12].[CH2:4]([OH:5])[C:7]([CH2:6][OH:15])([CH2:18][OH:9])[CH2:22][OH:21]>>[N:1]#[C:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH2:8][O:9][CH2:10][CH2:11][C:12]#[N:13])([CH2:14][O:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:20][O:21][CH2:22][CH2:23][C:24]#[N:25] | C=CC#N.OCC(CO)(CO)CO | N#CCCOCC(COCCC#N)(COCCC#N)COCCC#N | null | null | O1CCOCC1 | Functional Group Addition | OtherReaction | 7e9131de8f60c3c7a75bed3da9f107804e0e94cf19fd304d70ed895b2179225a | b2cbfafbaa0356f4cf2f72a20ddc6ea4aeb3d20fbc967c0758309408e43f9e72 | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[OH;D1;+0:5]-[CH2;D2;+0:6]-[C;H0;D4;+0:7](-[CH2;D2;+0:8]-[OH;D1;+0:9])(-[CH2;D2;+0:10]-[OH;D1;+0:11])-[CH2;D2;+0:12]-[OH;D1;+0:13]>>[C:14]-[C:15]-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-[C:16]-[C;H0;D4;+0:7](-[C:17]-[O;H0;D2;+0:5]-[C:18]-[C:19]-[C;H0;D2;+0:8]#[N;D1;H0:20])(-[C:21]-[O... | null | [] | 0 | CELSIUS | 48 | HOUR | Pentaerythritol (6.84 g, 50 mmol) was dissolved in 20 ml dioxane and 2 ml water and mixed up with 40% aqueous potassium hydroxide solution (w/v, 1 ml). After cooling to 0° C. in an ice bath, acrylonitrile (16.2 g, 300 mmol) was added and the mixture stirred for 48 h at room temperature. Solvents were evaporated, the re... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Vinyl | Ether.Ether.Ether.Ether.Nitrile.Nitrile.Nitrile | null | null | null | Other | O1CCOCC1 | 0 | 48 | C=CC#N.OCC(CO)(CO)CO>O1CCOCC1>N#CCCOCC(COCCC#N)(COCCC#N)COCCC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-796ff312c8e04ffba5526c15fe31e9ab | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(N)c2)c1)c1ccccc1.Nc1ccccc1N.S=C(Cl)Cl>>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1 | C1(=C(C=CC=C1)N)N.NC=1C=C(C=CC1)C1=CC(=CC=C1)S(=O)(=O)NC(CC(=O)OCC)C1=CC=CC=C1.C(=S)(Cl)Cl>>NC1=C(NC(=S)NC=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)NC(CC(=O)OCC)C2=CC=CC=C2)C=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]([NH2:22])[cH:33]2)[cH:34]1)[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1.[NH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[NH2:32].Cl[C:23](Cl)=[S:24]>>[CH3:1][CH2:2][O:3][C:4... | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(N)c2)c1)c1ccccc1.Nc1ccccc1N.S=C(Cl)Cl | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1 | null | null | O1CCCC1.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 4e8b170f580e3da17796594c623bc3cf2eb189ff71ccd3ce0129c7dc171f35d0 | dd8726f6c994b794df619cd6dc3bdbbbd17ddf103f540d4703301ac4d1f03cca | O=S(=O)(NCc1ccccc1)c1cccc(-c2cccc(NC(=S)Nc3ccccc3)c2)c1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[S;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 12 | HOUR | 31.84 g (75 mmol) ethyl 3-{[(3′-amino[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate 10.1.2 were dissolved in 600 ml toluene and 8.62 g thiophosgene were added. The mixture was refluxed for 2 h, evaporated and the residue dissolved in 200 ml toluene. This solution was added dropwise to a solution of o-phenylen... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine.Primary amine | Thiourea | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C | null | 12 | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(N)c2)c1)c1ccccc1.Nc1ccccc1N.S=C(Cl)Cl>O1CCCC1.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-660d63e58a12491cb152bc9a8923af2b | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1>>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nc4ccccc4[nH]3)c2)c1)c1ccccc1 | NC1=C(NC(=S)NC=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)NC(CC(=O)OCC)C2=CC=CC=C2)C=CC=C1>>N1C(=NC2=C1C=CC=C2)NC=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)NC(CC(=O)OCC)C2=CC=CC=C2 | S=[C:23]([NH:22][c:21]1[cH:20][cH:19][cH:18][c:17](-[c:16]2[cH:15][cH:14][cH:13][c:12]([S:9]([NH:8][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)(=[O:10])=[O:11])[cH:33]2)[cH:32]1)[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]1[NH2:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2... | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1 | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nc4ccccc4[nH]3)c2)c1)c1ccccc1 | null | [Hg]=O | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 10065cf2a92e484e7ecc68c3657aad051d9537dce223e40606b5112b0d924ccc | f61b063bf4994f6edccc1b1060d88412a3778b312c2ed8ff2a2362ea8f39e99f | O=S(=O)(NCc1ccccc1)c1cccc(-c2cccc(Nc3nc4ccccc4[nH]3)c2)c1 | S=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[c:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[nH;D2;+0:8]:1 | null | [] | null | null | null | null | 43 g (75 mmol) of Ethyl 3-{[(3′-{[(2-aminoanilino)carbothioyl]amino}[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate 11.1.1 and 16.24 g (75 mmol) of yellow mercury oxide were mixed with 1.51 CHCl3 and refluxed for 6 h. The resulting material was purified via flash chromatography (dichloromethane/acetic acid eth... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1 | Other | [Hg]=O.C(Cl)(Cl)Cl | null | null | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=S)Nc3ccccc3N)c2)c1)c1ccccc1>[Hg]=O.C(Cl)(Cl)Cl>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nc4ccccc4[nH]3)c2)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eeba8983ef704b9db8cf16948c3268c1 | CCOc1c(OCC)c(=O)c1=O.COC(=O)[C@H](Cc1ccc(-c2cccc(N)c2)cc1)NS(=O)(=O)c1c(C)cc(C)cc1C>>CCOc1c(Nc2cccc(-c3ccc(C[C@H](NS(=O)(=O)c4c(C)cc(C)cc4C)C(=O)OC)cc3)c2)c(=O)c1=O | NC=1C=C(C=CC1)C1=CC=C(C=C1)C[C@@H](C(=O)OC)NS(=O)(=O)C1=C(C=C(C=C1C)C)C.C(C)OC=1C(C(C1OCC)=O)=O>>C(C)OC1=C(C(C1=O)=O)NC=1C=C(C=CC1)C1=CC=C(C=C1)C[C@@H](C(=O)OC)NS(=O)(=O)C1=C(C=C(C=C1C)C)C | CCO[c:5]1[c:4]([O:3][CH2:2][CH3:1])[c:40](=[O:41])[c:38]1=[O:39].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([CH2:16][C@H:17]([NH:18][S:19](=[O:20])(=[O:21])[c:22]3[c:23]([CH3:24])[cH:25][c:26]([CH3:27])[cH:28][c:29]3[CH3:30])[C:31](=[O:32])[O:33][CH3:34])[cH:35][cH:36]2)[cH:37]1>>[CH3:1][CH2:2]... | CCOc1c(OCC)c(=O)c1=O.COC(=O)[C@H](Cc1ccc(-c2cccc(N)c2)cc1)NS(=O)(=O)c1c(C)cc(C)cc1C | CCOc1c(Nc2cccc(-c3ccc(C[C@H](NS(=O)(=O)c4c(C)cc(C)cc4C)C(=O)OC)cc3)c2)c(=O)c1=O | null | null | C(CC)O | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by primary amine | 9dedfc19e0ba9cb5f6b2ec38e6b237aa6f389bf8eeaadf9f4914985fa479dd7c | 953ca34981f329c845365ec5b25a3d27fa72aebd3e467f4e6ef8becba38a9d76 | O=c1cc(Nc2cccc(-c3ccc(CCNS(=O)(=O)c4ccccc4)cc3)c2)c1=O | C-C-O-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:1-[#8:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:6]-[c:5]1:[c:4]:[c:2](=[O;D1;H0:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 59 | [{"value": 59.0, "product": "C(C)OC1=C(C(C1=O)=O)NC=1C=C(C=CC1)C1=CC=C(C=C1)C[C@@H](C(=O)OC)NS(=O)(=O)C1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2 g of Methyl (2S)-3-(3′-amino[1,1′-biphenyl]-4-yl)-2-mesitylsulfonylamino-propanoate 12.1.2 were mixed with 0.75 g 3,4-diethoxy-3-cyclobuten-1,2-dion in 40 ml 1 propanol and refluxed for 20 h. Purification by flash chromatography (dichloromethane/acetic acid ethyl ester 10+1) yielded 1,5 g of the title compound.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | C1=CC=C1 | C1=CC=C1 | C1=CC=C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(CC)O | null | null | CCOc1c(OCC)c(=O)c1=O.COC(=O)[C@H](Cc1ccc(-c2cccc(N)c2)cc1)NS(=O)(=O)c1c(C)cc(C)cc1C>C(CC)O>CCOc1c(Nc2cccc(-c3ccc(C[C@H](NS(=O)(=O)c4c(C)cc(C)cc4C)C(=O)OC)cc3)c2)c(=O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed743768047447f58cadda2ee9a69749 | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(N)=S)c2)c1)c1ccccc1.CI>>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=N)SC)c2)c1)c1ccccc1 | NC(=S)NC=1C=C(C=CC1)C1=CC(=CC=C1)S(=O)(=O)NC(CC(=O)OCC)C1=CC=CC=C1.IC>>N=C(SC)NC=1C=C(C=CC1)C1=CC(=CC=C1)S(=O)(=O)NC(CC(=O)OCC)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]([NH:22][C:23]([NH2:24])=[S:25])[cH:27]2)[cH:28]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.I[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH:8][S:9](=[O:10])(=[O... | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(N)=S)c2)c1)c1ccccc1.CI | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=N)SC)c2)c1)c1ccccc1 | null | null | CO | Protection | OtherReaction | 59949cbb86b9d01262ab89656f20694d7e1773b168cf63a037992f685d94e94c | a0ca802577e0e3884829fc44ed71b0071415680a11de14d1c207997d2fc58a99 | O=S(=O)(NCc1ccccc1)c1cccc(-c2ccccc2)c1 | I-[CH3;D1;+0:1].[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[S;H0;D1;+0:4])-[#7:5]-[c:6]>>[CH3;D1;+0:1]-[S;H0;D2;+0:4]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[#7:5]-[c:6] | null | [] | null | null | null | null | 2.42 g of Ethyl 3-[({3′-[(aminocarbothioyl)amino][1,1′-biphenyl]-3-yl}sulfonyl)-amino]-3-phenylpropanoate 14.1.1 were dissolved in 80 ml methanol and 0.89 g Iodomethan were added. After reflux for 2 h, the reaction mixture was concentrated and crystalized from ether to obtain 3.1 g.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HI | CO | null | null | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(N)=S)c2)c1)c1ccccc1.CI>CO>CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(NC(=N)SC)c2)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d92c58b0faca44eeb43c64c494c5501b | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1>>O=C(O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1 | C1(=CC=CC=C1)C(CC(=O)OCC)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)NC=1SC=CN1.ClCCl.C(C)OC(C)=O>>C1(=CC=CC=C1)C(CC(=O)O)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)NC=1SC=CN1 | CC[O:3][C:2](=[O:1])[CH2:4][CH:5]([NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][c:21]3[n:22][cH:23][cH:24][s:25]3)[cH:26]2)[cH:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c... | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1 | O=C(O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1 | null | null | [Li+].[OH-].C(OC)COC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(NCc1ccccc1)c1cccc(-c2cccc(Nc3nccs3)c2)c1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | 0.2 g of Ethyl 3-phenyl-3-{[3′-(1,3-thiazol-2-ylamino)[1,1′-biphenyl]-3-yl]sulfonylamino}-propanoate 15.1.1 were saponified in 15 ml dimethoxyethane 12 ml water and 0.2 g LiOH. After aqueos work-up and flash chromatography (dichloromethane/methanol 10+1) 65 mg were obtained.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1cscn1.c1ccccc1 | Other | [Li+].[OH-].C(OC)COC | null | null | CCOC(=O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1>[Li+].[OH-].C(OC)COC>O=C(O)CC(NS(=O)(=O)c1cccc(-c2cccc(Nc3nccs3)c2)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbbe01d0477a4d4698a0113451e5fa1f | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1>>CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 | C(=O)(O)[O-].[Na+].Cl(=O)(=O)(=O)O.N1[C@@H](CCC1=O)C(=O)O.C(C)(=O)OC(C)(C)C.C(=O)(O)[O-].[Na+]>>O=C1CC[C@H](N1)C(=O)OC(C)(C)C | CC(=O)[O:5][C:2]([CH3:1])([CH3:3])[CH3:4].O[C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[NH:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[NH:13]1 | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 | null | null | null | Acylation | OtherReaction | 5eda8161d36467b4dc537f76ab93cf348d82102ac40d865b5fccff23d019462d | 03baa9d39762bbc48d7dd927c5c80fc17976a560c4f5aa44c95e8b810d3c70c8 | O=C1CCCN1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[C:9])-[#7:10]-[C:11]=[O;D1;H0:12]>>[C:9]-[C:8](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5])-[#7:10]-[C:11]=[O;D1;H0:12] | 72 | [{"value": 72.0, "product": "O=C1CC[C@H](N1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a suspension of L-pyroglutamic acid (13.2 g, 102 mmol) in t-butyl acetate (200 mL), was added perchloric acid (70%, 9.7 mL, 113 mmol). The mixture was stirred at rt for 20 h, then poured into sat. NaHCO3. NaHCO3 (s) was added until neutral. The aqueous phase was extracted with EtOAc (6×). The combined organic extrac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester | null | null | C1CCNC1 | HO- | null | null | 20 | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1>>CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-585925510a744f649fc62878129472d8 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1 | O=C1CC[C@H](N1)C(=O)OC(C)(C)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>S=C1CC[C@H](N1)C(=O)OC(C)(C)C | O=[C:11]1[CH2:10][CH2:9][C@@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[NH:13]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:12])S2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[S:12])[NH:13]1 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | a810566bfc0bf517e461b6aa91fbdc7be56d76c30289d00ae28eb077255dfe7b | 558580c5823c2cfab2cae548a45ef991ba9b53d2e5812b481e23ff3540a5940e | S=C1CCCN1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2]1-[#7:3]-[C:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]-1>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]1-[#7:3]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[C:9]-[C:8]-1 | 191.1 | [{"value": 95.0, "product": "S=C1CC[C@H](N1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 191.1, "product": "S=C1CC[C@H](N1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of t-butyl pyroglutamate (1a) (10.12 g, 54.6 mmol) in benzene (250 mL), was added Lawesson's reagent (11.05 g, 27.3 mmol). The mixture was stirred at reflux for 15.5 h, then concentrated. The resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3) to afford 10.50 g (95%) of t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide.Monosulfide.Monosulfide | Thioamide | C1CCNC1.c1ccccc1.P1SPS1.c1ccccc1 | C1CCNC1 | C1CCNC1 | Other | C1=CC=CC=C1 | null | null | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1=CC=CC=C1>CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b0a2c977b72425c90a00e57ab227d60 | CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1>>CSC1=N[C@H](C(=O)OC(C)(C)C)CC1 | S=C1CC[C@H](N1)C(=O)OC(C)(C)C.C1CCOC1>>CSC=1CC[C@H](N1)C(=O)OC(C)(C)C | [S:2]=[C:3]1[NH:4][C@H:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14]1>>[CH3:1][S:2][C:3]1=[N:4][C@H:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1 | CSC1=N[C@H](C(=O)OC(C)(C)C)CC1 | null | null | null | Miscellaneous | OtherReaction | 3e55d7bc84acdab2b03bbcfcc6a2c183a5e9b5fce7845f21baab4bcdd49429b6 | 4731524fa4fd3802aeb6747286881f7975701b251211a07e749148b50a6e3a98 | C1=NCCC1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C:10]-[C;H0;D3;+0:11](=[S;H0;D1;+0:12])-[NH;D2;+0:13]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C:10]-[C;H0;D3;+0:11](-[S;H0;D2;+0:12]-[C;D1;H3:14])=[N;H0;D2;+0:13]-1 | 91 | [{"value": 91.0, "product": "CSC=1CC[C@H](N1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a solution of thiolactam 1b (10.50 g, 52.2 mmol) in 200 mL THF at rt, was added Mel (13.0 mL, 208.7 mmol). The mixture was stirred for 3.5 h, then concentrated. The residue was partitioned between CH2Cl2 and sat. NaHCO3 and the aqueous phase was extracted with CH2Cl2 (3×). The combined organic extract was dried (Na2... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | C1CCNC1 | C1=NCCC1 | C1=NCCC1 | Other | null | null | 3.5 | CC(C)(C)OC(=O)[C@@H]1CCC(=S)N1>>CSC1=N[C@H](C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85fb21590b4046809f1a625100fcca34 | COC(=O)c1cnc2n(c1=O)[C@H](C(=O)OC(C)(C)C)CC2>>CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21 | O=C1C(=CN=C2N1[C@@H](CC2)C(=O)OC(C)(C)C)C(=O)OC.[Li+].[OH-]>>C(C)(C)(C)OC(=O)[C@@H]1CCC=2N1C(C(=CN2)C(=O)O)=O | C[O:17][C:15]([c:14]1[cH:13][n:12][c:11]2[n:20]([c:18]1=[O:19])[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][c:11]2[n:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[c:18](=[O:19])[n:20]21 | COC(=O)c1cnc2n(c1=O)[C@H](C(=O)OC(C)(C)C)CC2 | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccnc2n1CCC2 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:7]:[#7;a:8] | 85 | [{"value": 85.0, "product": "C(C)(C)(C)OC(=O)[C@@H]1CCC=2N1C(C(=CN2)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "C(C)(C)(C)OC(=O)[C@@H]1CCC=2N1C(C(=CN2)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1e (14.15 g, 48.1 mmol) in 250 mL MeOH at 0° C. was slowly added aqueous LiOH (1M, 48 mL, 48 mmol) over 15 min. The reaction was allowed to warm to rt overnight with stirring. The organic solvent was removed in vacuo. The residual aqueous solution was partitioned with Et2O, then the organic phase was e... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cn2c(nc1)CCC2 | Other | CO | null | null | COC(=O)c1cnc2n(c1=O)[C@H](C(=O)OC(C)(C)C)CC2>CO>CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-834073e0ca044b46a874997ac8390157 | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)O.C(C)(C)(C)OC(=O)[C@@H]1CCC=2N1C(C(=CN2)C(=O)O)=O.C(C)N(CC)CC.C=1C=CC(=CC1)P(=O)(C=2C=CC=CC2)N=[N+]=[N-]>>C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C | O[C:16]([c:14]1[cH:13][n:12][c:11]2[n:28]([c:26]1=[O:27])[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)=[O:17].[OH:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[N-]=[N+]=[N:15]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][c:11]2[n... | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | O1CCOCC1 | Protection | OtherReaction | 85984b8c9534c0789a0aed978ddad7a9f98cf11752d8b4e0e08d8e239f9dd816 | aa6034c174fc48fa7e86a3e3e456bc7f49699778f1361299699fbbc966318b2e | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7](:[c:8]:1=[O;D1;H0:9])-[C:10]-[C:11](-[#8:12])=[O;D1;H0:13].O=P(-[N;H0;D2;+0:14]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[OH;D1;+0:15]-[C:16]-[c:17]>>[#8:12]-[C:11](=[O;D1;H0:13])-[C:10]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]:[c;H0;D3;+0:3](-[NH;D2;... | 73 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of carboxylic acid 1f (11.4 g, 40.7 mmol), triethylamine (5.67 mL, 40.7 mmol), and DPPA (8.86 mL, 40.7 mmol) in 180 mL 1,4-dioxane was heated at reflux for 2 h. Benzyl alcohol (4.67 mL, 45 mmol) was added and the mixture was heated at reflux for an additional 3 h. The mixture was concentrated in vacuo and th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Primary alcohol | Carbamic ester.Ether | c1cn2c(nc1)CCC2.c1ccccc1.c1ccccc1 | c1cn2c(nc1)CCC2 | c1cn2c(nc1)CCC2.c1ccccc1 | HO- | O1CCOCC1 | null | null | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(C(=O)O)c(=O)n21.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O1CCOCC1>CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c8fff419c2447b49520742bc9dd3e53 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1 | C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O | O=C(OCc1ccccc1)[NH:26][c:25]1[cH:24][n:23][c:22]2[n:29]([c:27]1=[O:28])[CH:19]([C:17]([NH:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[NH:10])[cH:31][cH:30]1)=[O:18])[CH2:20][CH2:21]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[c... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]:1=[O;D1;H0:8])-[C:9]-[C:10](-[#7:11])=[O;D1;H0:12]>>[#7:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:7]:1=[O;D1;H0:8] | 84 | [{"value": 84.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of intermediate 1i (74.8 mg, 0.134 mmol) in 3 mL MeOH, was added 80 mg 10% Pd/C. The mixture was evacuated and flushed with H2 (3×), then it was stirred under an atmosphere of H2 for 24 h. The mixture was filtered and concentrated to afford 48 mg (84%) of intermediate 1j. MS (ESI) 427.08 (M+H+).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | [Pd].CO | null | 24 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1>[Pd].CO>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dd495067f7e4572983b6e970c23d3a3 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCCc4ccccc4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCCC2=CC=CC=C2)=O)=N)=O | CC(C)(C)OC(=O)N[C:27](=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][c:22]3[n:23][cH:24][c:25]([NH:26][CH2:28][c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[c:35](=[O:36... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCCc4ccccc4)c(=O)n32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 02f7e8ced052935d942f0abf21b90584ba1646631fb0258cce66719d8a299eae | 8e4b2bf6cf42ba3563388d9ce03f29850fefe100bad3840edf3395d49540f26d | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NCCc3ccccc3)c(=O)n21 | C-C(-C)(-C)-O-C(=O)-N-[C;H0;D3;+0:1](=N)-c1:c:c:c(-C-N-C(=O)-[C@H]2-C-C-c3:n:c:c(-N):c(=O):n:3-2):c:c:1.[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[CH2;D2;+0:12]-[c:13](:[c:14]):[c:15]):[c:16]:1=[O;D1;H0:17]>>[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]:[c:1... | 54 | [{"value": 54.0, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCCC2=CC=CC=C2)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 1k, intermediate 1j (60 mg, 0.14 mmol), phenylacetyladehyde (67.3 mg, 0.56 mmol) and NaBH(OAc)3 (326.4 mg, 1.54 mmol) yielded 40 mg (54%) of intermediate 2a. MS (ESI) 531.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amide.Primary amine.Secondary amine.Boc | Secondary amine | c1ccccc1.c1cnc2n(c1)CCC2 | null | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCCc4ccccc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-316141eaf6f54c0c9fa9c844294e9890 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O>>CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C(C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O | c1cc[c:5]([CH2:4][NH:3][c:6]2[cH:7][n:8][c:9]3[n:10]([c:11]2=[O:12])[C@H:13]([C:14](=[O:15])[NH:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([C:22](=[NH:23])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:32][cH:33]2)[CH2:34][CH2:35]3)cc1.O=[CH:2][CH3:1]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][n:8... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O | CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ef8839dd6d05639d3961ef8e1885a4f26d175ff33c3c3e7e3acd4675a8c79ec3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](-[NH;D2;+0:12]-[C:13]-[c;H0;D3;+0:14]2:c:c:c:c:c:2):[c:15]:1=[O;D1;H0:16]>>[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](-[N;H0;D3;+0:12](-[C:13]-[CH3;D1;+0:14])-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:15]... | 100 | [{"value": 100.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 1k, intermediate 1j (48 mg, 0.113 mmol), acetaldehyde (39.6 mg, 0.90 mmol) and NaBH(OAc)3 (216.2 mg, 1.02 mmol) yielded 56 mg (100%) of intermediate 3a. MS (ESI) 483.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O>>CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cd4dd8bceef24f458c22091fe1e77ead | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)=O>>CC(C)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.CC(=O)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC(C)C)=O)=O | c1ccc(C[NH:4][c:5]2[cH:6][n:7][c:8]3[n:9]([c:10]2=[O:11])[C@H:12]([C:13](=[O:14])[NH:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([C:21](=[NH:22])[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31][cH:32]2)[CH2:33][CH2:34]3)cc1.O=[C:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][n:7][c:8]2[n:... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)=O | CC(C)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a57cbe533233c5b188479323b051f16273a0edbaba40995c7b9fa8edd82cce0 | 48eadfee81a370c6c73884fb90eefb76a7abc86e6799be9f2584b34297252e5a | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[c:12](-[NH;D2;+0:13]-C-c2:c:c:c:c:c:2):[c:14]:1=[O;D1;H0:15]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[c:12](-[NH;D2;+0:13]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:14]:1=[O;D1;H0:15... | 65 | [{"value": 65.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (60 mg, 0.14 mmol), acetone (97.6 mg, 1.68 mmol) and NaBH(OAc)3 (385.7 mg, 1.82 mmol) yielded 43 mg (65%) of intermediate 4a. MS (ESI) 469.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)=O>>CC(C)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dec900fe3a18477f9448870755acb47b | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O>>CCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C(C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC)=O)=O | c1ccc(C[NH:3][c:4]2[cH:5][n:6][c:7]3[n:8]([c:9]2=[O:10])[C@H:11]([C:12](=[O:13])[NH:14][CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20](=[NH:21])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][cH:31]2)[CH2:32][CH2:33]3)cc1.O=[CH:2][CH3:1]>>[CH3:1][CH2:2][NH:3][c:4]1[cH:5][n:6][c:7]2[n:8]([c:9]1=[O:10])... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O | CCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cdd5965b0521c8c5bc527a0ecb02af68aaed318130abe72a9a2e2839e74a963a | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](-[NH;D2;+0:12]-C-c2:c:c:c:c:c:2):[c:13]:1=[O;D1;H0:14]>>[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11](-[NH;D2;+0:12]-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:13]:1=[O;D1;H0:14] | 60.5 | [{"value": 60.5, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (101 mg, 0.24 mmol), acetaldehyde (21.1 mg, 0.48 mmol) and NaBH(OAc)3 (141.99 mg, 0.67 mmol) yielded 66 mg (60.5%) of intermediate 5a. MS (ESI) 455.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC=O>>CCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77ff826270494a869c96dd5332baae40 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.O=C1CCCC1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC4CCCC4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C1(CCCC1)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC2CCCC2)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][c:22]3[n:23][cH:24][c:25]([NH2:26])[c:32](=[O:33])[n:34]32)[cH:35][cH:36]1.O=[C:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7]... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.O=C1CCCC1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC4CCCC4)c(=O)n32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b85679fed5f5625b57908374666b40667904d1ae7fb913f5564f84f7e4e3c6f0 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NC3CCCC3)c(=O)n21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14](-[NH2;D1;+0:15]):[c:16]:1=[O;D1;H0:17]>>[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14](-[NH;D2;+0:15]-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]-2):[c:16]:1=[O;D1;H0:17] | 57.3 | [{"value": 57.3, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC2CCCC2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (115.2 mg, 0.27 mmol), cyclopentanone (68.1 mg, 0.81 mmol) and NaBH(OAc)3 (217.5 mg, 1.03 mmol) yielded 76.5 mg (57.3%) of intermediate 6a. MS (ESI) 496.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCC1 | C1CCCC1 | c1ccccc1.c1cn2c(nc1)CCC2.C1CCCC1 | Other | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.O=C1CCCC1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC4CCCC4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-763cb5f9978a42268dca685b5a7d9574 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O>>CC(C)CNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C(C(C)C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC(C)C)=O)=O | c1ccc(C[NH:5][c:6]2[cH:7][n:8][c:9]3[n:10]([c:11]2=[O:12])[C@H:13]([C:14](=[O:15])[NH:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([C:22](=[NH:23])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:32][cH:33]2)[CH2:34][CH2:35]3)cc1.O=[CH:4][CH:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[cH:7... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O | CC(C)CNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cdd5965b0521c8c5bc527a0ecb02af68aaed318130abe72a9a2e2839e74a963a | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13](-[NH;D2;+0:14]-C-c2:c:c:c:c:c:2):[c:15]:1=[O;D1;H0:16]>>[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13](-[NH;D2;+0:14]-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:15]:... | 79 | [{"value": 79.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (97.1 mg, 0.228 mmol), isobutyraldehyde (32.8 mg, 0.455 mmol) and NaBH(OAc)3 (135.1 mg, 0.638 mmol) yielded 87.4 mg (79%) of intermediate 7a. MS (ESI) 483.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O>>CC(C)CNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b5f62a93bc94fccbdf6fca3d3a407e6 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CCC=O>>CCCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C(CC)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCCC)=O)=O | c1ccc(C[NH:4][c:5]2[cH:6][n:7][c:8]3[n:9]([c:10]2=[O:11])[C@H:12]([C:13](=[O:14])[NH:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([C:21](=[NH:22])[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31][cH:32]2)[CH2:33][CH2:34]3)cc1.O=[CH:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][n:7][c:8]2[n:9]... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CCC=O | CCCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cdd5965b0521c8c5bc527a0ecb02af68aaed318130abe72a9a2e2839e74a963a | 7adcd96acc7986e995a59780d11a29072ec6cdad41c8d7f65df5f25f2d933fc4 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[c:12](-[NH;D2;+0:13]-C-c2:c:c:c:c:c:2):[c:14]:1=[O;D1;H0:15]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[c:12](-[NH;D2;+0:13]-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:14]:1=[O;D1;H0:15] | 46 | [{"value": 46.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (100 mg, 0.234 mmol), propionaldehyde (15 mg, 0.258 mmol) and NaBH(OAc)3 (74.5 mg, 0.352 mmol) yielded 50.9 mg (46%) of intermediate 8a. MS (ESI) 469.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CCC=O>>CCCNc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ae7b2d9548841909fb347af3a2a420c | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O>>CC(C)CN(CC(C)C)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C(C(C)C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC(C)C)CC(C)C)=O)=O | CC(C)(OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1)[CH3:9].c1cc[cH:8][c:7]([CH2:6][NH:5][c:10]2[cH:11][n:12][c:13]3[n:14]([c:15]2=[O:16])[C@H:17]([C:18](=[O:19])[NH:20][CH2:21][c:22]2[cH:23][cH:24][c:25]([C:26](=[NH:27])[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:36][cH:37]2)[CH2:38][CH... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O | CC(C)CN(CC(C)C)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 54ed5bf956ef8cb3ba5e296b24f3e7aa4a5f8e8ca81079602b518863c4956456 | 55de830b382c7b17795ad9a7960af2d819516a4b35a29ec13e45606a2ccd5294 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | C-C(-C)(-[CH3;D1;+0:1])-O-C(=O)-N-C(=N)-c1:c:c:c(-C-N-C(=O)-[C@H]2-C-C-c3:n:c:c(-N):c(=O):n:3-2):c:c:1.O=[CH;D2;+0:2]-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14](-[NH;D2;+0:15]-[C:16]-[c;H0;D3;+0:17]2:[cH;D2;+0:18]:c:c:c:c:2):[c:19]:1=[O;D1;H0:20]>>[#7:6]-[... | 79.5 | [{"value": 79.5, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC(C)C)CC(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (97.1 mg, 0.228 mmol), isobutyraldehyde (32.8 mg, 0.455 mmol) and NaBH(OAc)3 (135.1 mg, 0.638 mmol) yielded 87.4 mg (79.5%) of intermediate 9a. MS (ESI) 539.2 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Secondary amide.Primary amine.Secondary amine.Boc | Tertiary amine | c1ccccc1.c1cnc2n(c1)CCC2.c1ccccc1 | null | c1ccccc1.c1cn2c(nc1)CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1.CC(C)C=O>>CC(C)CN(CC(C)C)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-426cc82d056b47df9fa707ca8f83e735 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CCC(=O)CC>>CCC(CC)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.CCC(CC)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC(CC)CC)=O)=O | [NH2:6][c:7]1[cH:8][n:9][c:10]2[n:11]([c:12]1=[O:13])[C@H:14]([C:15](=[O:16])[NH:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([C:23](=[NH:24])[NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]1)[CH2:35][CH2:36]2.O=[C:3]([CH2:2][CH3:1])[CH2:4][CH3:5]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[NH:6][c:7]1... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CCC(=O)CC | CCC(CC)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4]-[C;D1;H3:5].[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14](-[NH2;D1;+0:15]):[c:16]:1=[O;D1;H0:17]>>[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14](-[NH;D2;+0:15]-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4]-[C;D1;H3:5]):[c:16]:1... | 24 | [{"value": 24.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NC(CC)CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (100 mg, 0.234 mmol), 3-pentanone (33.8 mg, 0.469 mmol) and NaBH(OAc)3 (139.1 mg, 0.657 mmol) yielded 27.8 mg (24%) of intermediate 11a. MS (ESI) 497.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1cn2c(nc1)CCC2 | Other | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CCC(=O)CC>>CCC(CC)Nc1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57e4e8218a3f420ba2104755af395843 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.CS(=O)(=O)Cl>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][c:22]3[n:23][cH:24][c:25]([NH2:26])[c:31](=[O:32])[n:33]32)[cH:34][cH:35]1.Cl[S:27]([CH3:28])(=[O:29])=[O:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1 | null | null | CCOC(=O)C.N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCc1ccccc1)[C@@H]1CCc2nccc(=O)n21 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]:1=[O;D1;H0:16]>>[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13](-[NH;D2;+0:14]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:... | 22 | [{"value": 22.0, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.0, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 16 | HOUR | To a solution of 1j (50 mg, 0.117 mmol) in 0.5 mL pyridine at 0° C. was added methanesulfonyl chloride (14.8 mg, 0.129 mmol). The solution was stirred at rt for 16 h. The mixture was diluted with 50 mL EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated to afford 13 mg (22%) of intermediate 16a. MS (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cn2c(nc1)CCC2 | HCl | CCOC(=O)C.N1=CC=CC=C1 | null | 16 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1.CS(=O)(=O)Cl>CCOC(=O)C.N1=CC=CC=C1>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d866ff3aac6341b991520d51ab1c5ea3 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccccc4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N)=O)=O.C1(=CC=CC=C1)S(=O)(=O)Cl>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=CC=C2)=O)=N)=O | CS(=O)(=O)[NH:26][c:25]1[cH:24][n:23][c:22]2[n:38]([c:36]1=[O:37])[C@H:19]([C:17]([NH:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[NH:10])[cH:40][cH:39]1)=[O:18])[CH2:20][CH2:21]2.Cl[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][C:2]... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccccc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccccc4)c(=O)n32)cc1 | null | null | null | Acylation | OtherReaction | 65f51c4be3dedecd8ee62e00fa8acb4d8e99a40aeb601b8f69c566e8b24b380a | 2401986f5e69efca48e6b1e53ecffc48dc571fb6ffe2395e61e07441c6c3692d | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)c3ccccc3)c(=O)n21 | C-S(=O)(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]:1=[O;D1;H0:8])-[C:9]-[C:10](-[#7:11])=[O;D1;H0:12].Cl-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16](:[c:17]):[c:18]>>[#7:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2](-[NH;D2;+0:1]-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0... | 80.1 | [{"value": 80.1, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=CC=C2)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 16a, intermediate 1j (50 mg, 0.117 mmol) and benzene sulfonyl chloride (22.8 mg, 0.129 mmol) yielded 53.6 mg (80.1%) of intermediate 17a. MS (ESI) 567.0 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccccc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3893d05062934c729de80100e116eee3 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2.Nc1ccccc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2 | C(C=C)N(C1=CN=C2N(C1=O)[C@@H](CC2)C(=O)O)C(=O)OCC2=CC=CC=C2.NC1=CC=CC=C1.C1=CC2=C(N=C1)N(N=N2)O.C(=O)(O)[O-].[Na+].CCN=C=NCCCN(C)C>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2)C(NC2=CC=CC=C2)=O)CC=C)=O | O[C:23]([C@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[CH2:33][CH2:32]1)=[O:24].[NH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12]... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2.Nc1ccccc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2 | null | null | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:4] | null | [] | null | null | null | null | To a solution of 18a (5.50 g, 14.89 mmol) and aniline (1.93 mL, 22.3 mmol) in 75 mL 5:1 CH2Cl2/DMF at 0° C., was added HOAT (2.23 g, 16.4 mmol), NaHCO3 (2.50 g, 29.8 mmol), and EDCI (4.00 g, 20.8 mmol). The mixture was stirred and allowed to warm to rt over 72 h. The reaction was diluted with EtOAc and the organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cn2c(nc1)CCC2 | HO- | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2.Nc1ccccc1>CCOC(=O)C.C(Cl)Cl.CN(C)C=O>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-832d2b39b7bf4896951ab0ab2b27acfd | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)C[C@@]2(C)N=[N+]=[N-] | CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C.CC(=O)O.C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2C)C(NC2=CC=CC=C2)=O)CC=C)=O.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NC2=CC=CC=C2)=O)CC=C)=O | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH2:32][CH:33]2[CH3:34].CC(C)c1cc(C(C)C)c(S(=O)(=O)[N:35]=[N+:36]=[N-:37])c(C(C)C)c1>>[CH2:1]=[CH:2]... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)C[C@@]2(C)N=[N+]=[N-] | null | null | C1CCOC1.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4878f79a2305d8177b5e1be6085826ac6c619cbde73851f1d6f76eea8861e6d8 | 416557d8db25ba7ecc0f0d06f72e3202f6d89c7ade39dc289b802f47f65faae3 | O=C(Nc1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2)OCc1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-[N;H0;D2;+0:1]=[#7;+:2]=[N;-;D1;H0:3]):c(-C(-C)-C):c:1.[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[c:11](:[#7;a:12]:[c:13]):[#7;a:14]-1:[c:15]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C@@;H0;D4;+0:9](-[C;D1;H3:10])(-[N;H0;D2;+0:1]=[#7;+:2]=[N;-;D1;H0:3])-[... | 65 | [{"value": 65.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NC2=CC=CC=C2)=O)CC=C)=O", "details": "CALCULATEDPERCENTYIE... | -78 | CELSIUS | 5 | MINUTE | To a solution of the methyl diastereomers (18c) (3.90 g, 8.51 mmol) in 40 mL THF at −78° C., was added LiHMDS (IM in THF, 17.9 mL, 17.9 mmol). The red solution was stirred at −78° C. for 5 min, then a solution of trisyl azide (2.90 g, 9.36 mmol) in 8 mL THF was added. The reaction was stirred at −78° C. for 1.5 h, then... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Azide | c1cn2c(nc1)[CH]CC2.c1ccccc1 | C1CCn2cccnc21 | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | C1CCOC1.CCOC(=O)C | -78 | 0.083333 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1>C1CCOC1.CCOC(=O)C>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)C[C@@]2(C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dd172fdc643473ca0eacc165e9de0d6 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-].OO>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-] | [O-]S(=O)[O-].[Na+].[Na+].[Li+].[OH-].C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)CC=C)=O.OO>>C(C=C)N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)O)C(=O)OCC2=CC=CC=C2 | CC(C)(C)OC(=O)N(c1ccccc1)[C:23]([C@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[C@:27]([CH3:28])([N:29]=[N+:30]=[N-:31])[CH2:26]1)=[O:24].O[OH:25]>>[CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10]... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-].OO | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-] | null | null | C1CCOC1.O | Acylation | OtherReaction | 3fbaabb4b18b7d0ff96cdbfc0f6d81e189be3d2c5f31dc35e2b72231b8963a65 | a11fc6035aaf7fc298c6c10684720bc4b39f126d4126b694d44ae3c654997440 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8])-c1:c:c:c:c:c:1.O-[OH;D1;+0:9]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:9])-[C:4] | 80.1 | [{"value": 80.0, "product": "C(C=C)N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)O)C(=O)OCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "C(C=C)N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)O)C(=O)OCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | 0 | CELSIUS | 45 | MINUTE | To a solution of 18e (480 mg, 0.800 mmol) in 10 mL THF/H2O (4:1) at 0° C., was added 30% H2O2 (1.28 mL, 11.3 mmol) and IN LiOH (1.28 mL, 1.28 mmol). The mixture was stirred at 0° C. of 45 min, then Na2SO3 (1.51 g, 12 mmol) was added. The mixture was stirred 30 min, then evaporated in vacuo. The residue was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Peroxide.Boc | Carboxylic acid | c1ccccc1 | null | c1ccccc1.C1CCn2cccnc21 | HO- | C1CCOC1.O | 0 | 0.75 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-].OO>C1CCOC1.O>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d03171be84a4409a5d812f09daa32c8 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-].N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N=[N+]=[N-] | C(C=C)N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)O)C(=O)OCC2=CC=CC=C2.C(C1=CC=CC=C1)OC(NC(=N)C1=CC=C(C=C1)CN)=O.C1=CC2=C(N=C1)N(N=N2)O.C(=O)(O)[O-].[Na+].CCN=C=NCCCN(C)C>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O | O[C:23]([C@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[C@:47]([CH3:48])([N:49]=[N+:50]=[N-:51])[CH2:46]1)=[O:24].[NH2:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-].N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N=[N+]=[N-] | null | null | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11])-[C:4] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=... | null | null | 15 | HOUR | To a solution of 18f (270 mg, 0.636 mmol) and [(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (272 mg, 0.763 mmol) in 6 mL CH2Cl2/DMF (5:1) at 0° C., were added HOAT (95 mg, 0.700 mmol), NaHCO3 (187 mg, 2.23 mmol), and EDCI (171 mg, 0.890 mmol). The mixture was allowed to warm to rt and stir for 15 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | null | 15 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-].N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>CCOC(=O)C.C(Cl)Cl.CN(C)C=O>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dbb075c2b7a4f469c22e0890a95e7e6 | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CI>>CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C.CI>>C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:10][CH2:11][c:12]2[n:13][cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][CH2:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27](=[O:28])[n:29]21.I[CH3:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C:8]1([CH3:9])[CH2:10][CH2:11][c:12]2[n:13][cH:14][c:15](... | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CI | CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_tertiary | 217fbe059441ca888a7cc3e1601042ab47f7079ec85f1b52fcc4ffeb7515cb61 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]-1:[c:16]>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9]1(-[CH3;D1;+0:1])-[C:10]-[C:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]-... | 160.9 | [{"value": 18.0, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 160.9, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 5 | MINUTE | To a solution of intermediate 1g (200 mg, 0.519 mmol) in 5 mL THF at −78° C., was added a 1M solution of LIHMDS in THF (1.09 mL, 1.09 mmol). The mixture was stirred for 5 min, then MeI (162 mL, 2.60 mmol) was added. The mixture was stirred with warming to −30° C. over 1 h, then was quenched with sat. NH4Cl. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1cn2c(nc1)CCC2 | C1CCc2ncccn21 | C1CCc2ncccn21.c1ccccc1 | HI | C1CCOC1 | -30 | 0.083333 | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CI>C1CCOC1>CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87b4f71a3c464d95bdbbcf9b03be006a | CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C.C(=O)(C(F)(F)F)O.C(Cl)Cl>>C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C | CC(C)(C)[O:5][C:3]([C:2]1([CH3:1])[CH2:6][CH2:7][c:8]2[n:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23](=[O:24])[n:25]21)=[O:4]>>[CH3:1][C:2]1([C:3](=[O:4])[OH:5])[CH2:6][CH2:7][c:8]2[n:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:2... | CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | CC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | O | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]>>[#7;a:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 105.5 | [{"value": 105.5, "product": "C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of intermediate 19a (55 mg, 0.138 mmol) in 4 mL 1:1 TFA/CH2Cl2 with 2 drops water was stirred at rt for 12 h. The mixture was concentrated in vacuo, then coevaporated with CCl4 to afford 50 mg of intermediate 19b (quantitative), which was used without further purification in the following step.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCc2ncccn21.c1ccccc1 | Other | O | null | null | CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>O>CC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7977f68c4da0489ebc38176d5555ba59 | C=CCI.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C.C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C.C(C=C)I>>C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC=C | I[CH2:3][CH:2]=[CH2:1].[C@@H:4]1([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][c:14]2[n:15][cH:16][c:17]([NH:18][C:19](=[O:20])[O:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:29](=[O:30])[n:31]21>>[CH2:1]=[CH:2][CH2:3][C:4]1([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][... | C=CCI.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | C-C Coupling | OtherReaction | e79c737227a5883b3ff7673a450525053343376e0504a0044208314aa5d73eaf | 004d9bbde855ea6a20935a7929fb4c869d25b8db6104e99b9ee1ab33b13dc784 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | I-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[C@@H;D3;+0:11]1-[C:12]-[C:13]-[c:14](:[#7;a:15]:[c:16]):[#7;a:17]-1:[c:18]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:11]1(-[C:9](=[O;D1;H0:10])-[#8:8]-[C:5](-[C;D1;H3:4])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:12]-[C:... | 55 | [{"value": 55.0, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with allyl iodide afforded 153 mg (55%) of intermediate 20a. MS (ESI) 426.4 (M+H+), 448.4 (M+Na+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Allyl | c1cn2c(nc1)CCC2 | C1CCc2ncccn21 | C1CCc2ncccn21.c1ccccc1 | HI | null | null | null | C=CCI.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d45c586cabb4917b9a6fcec37daf85e | C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C.C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC=C>>C(C=C)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O | CC(C)(C)[O:7][C:5]([C:4]1([CH2:3][CH:2]=[CH2:1])[CH2:8][CH2:9][c:10]2[n:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25](=[O:26])[n:27]21)=[O:6]>>[CH2:1]=[CH:2][CH2:3][C:4]1([C:5](=[O:6])[OH:7])[CH2:8][CH2:9][c:10]2[n:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][C... | C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]>>[#7;a:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 86.3 | [{"value": 86.0, "product": "C(C=C)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "C(C=C)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19b, intermediate 20a (127 mg, 0.298 mmol) was deprotected to afford 95 mg (86%) of intermediate 20b. MS (ESI) 368.2 (M−H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCc2ncccn21.c1ccccc1 | Other | null | null | null | C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f57f987a2284ab48972c433a6c34bef | C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1>>C=CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C=C)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CN)=O>>C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)CC=C)=O | O[C:5]([C:4]1([CH2:3][CH:2]=[CH2:1])[CH2:25][CH2:26][c:27]2[n:28][cH:29][c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]3[cH:37][cH:38][cH:39][cH:40][cH:41]3)[c:42](=[O:43])[n:44]21)=[O:6].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[NH:14])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH... | C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1 | C=CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc2n(c1=O)C(C(=O)NCc1ccccc1)CC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5]=[C;D1;H2:6])(-[C:7])-[#7;a:8](:[c:9]):[c:10]:[#7;a:11].[NH2;D1;+0:12]-[C:13]-[c:14]>>[#7;a:11]:[c:10]:[#7;a:8](:[c:9])-[C:3](-[C:4]-[C:5]=[C;D1;H2:6])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:13]-[c:14])-[C:7] | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19c, intermediate 20b (50 mg, 0.135 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester to afford 70 mg (86%) of intermediate 20c.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCc2ncccn21.c1ccccc1 | HO- | null | null | null | C=CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1>>C=CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b16c628544f4f00817a94976294639b | BrCc1ccccc1.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C.C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C.C(C1=CC=CC=C1)Br>>C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC2=CC=CC=C2 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:16][CH2:17][c:18]2[n:19][cH:20][c:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[c:33](=[O:34])[n:35]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C:8]1([CH2:9]... | BrCc1ccccc1.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | C-C Coupling | OtherReaction | 247e9571744cfb8a9baf8e624863133c2e1dd2666a09d36dbaa993edf5a90341 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)CC2)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[C@@H;D3;+0:12]1-[C:13]-[C:14]-[c:15](:[#7;a:16]:[c:17]):[#7;a:18]-1:[c:19]>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D4;+0:12]1(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:... | 55 | [{"value": 55.0, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with benzyl bromide afforded 170 mg (55%) of intermediate 21a. MS (ESI) 476.5 (M+H+), 498.5 (M+Na+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cn2c(nc1)CCC2 | C1CCc2ncccn21 | c1ccccc1.C1CCc2ncccn21.c1ccccc1 | HBr | null | null | null | BrCc1ccccc1.CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20c0265f8dc641c1a630eeba3226f3e7 | CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C.C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC2=CC=CC=C2>>C(C1=CC=CC=C1)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O | CC(C)(C)[O:21][C:19]([C:11]1([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:8]2[c:7]([n:6][cH:5][c:4]([NH:3][C:2](=[O:1])[O:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[c:9]2=[O:10])[CH2:23][CH2:22]1)=[O:20]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6][c:7]2[n:8]([c:9]1=[O:10])[C:11]([CH2:12][c:13]1[cH:14][c... | CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1 | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)CC2)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]>>[#7;a:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 95.2 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "C(C1=CC=CC=C1)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19b, intermediate 21a (149 mg, 0.313 mmol) was deproteted to afford 125 mg (95%) of intermediate 21b. MS (ESI) 420.4 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.C1CCc2ncccn21.c1ccccc1 | Other | null | null | null | CC(C)(C)OC(=O)C1(Cc2ccccc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-012f6202a1704b24b330c77a049c3fbc | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2(Cc3ccccc3)CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | C(C1=CC=CC=C1)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C(=O)O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CN)=O>>C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)CC2=CC=CC=C2)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH2:16])[cH:47][cH:48]1.O[C:17](=[O:18])[C:19]1([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28][c:29]2[n:30][cH:31][c:32]([NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3[cH:39][cH:40][cH:41][cH:42]... | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2(Cc3ccccc3)CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)NCc1ccccc1)CC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[#7;a:6](:[c:7]):[c:8]:[#7;a:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:9]:[c:8]:[#7;a:6](:[c:7])-[C:3](-[C:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12])-[C:5] | null | [] | null | null | null | null | According to the procedure for the preparation of intermediate 19c, intermediate 21b (50 mg, 0.119 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester to afford 77 mg (quantitative) of intermediate 21c.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCc2ncccn21.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(Nc1cnc2n(c1=O)C(Cc1ccccc1)(C(=O)O)CC2)OCc1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2(Cc3ccccc3)CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dc1cddd72cd4749963abab6ce95c3ee | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CCI>>CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C.C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C.C(C)I>>C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC | [C@@H:3]1([C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][c:13]2[n:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:28](=[O:29])[n:30]21.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][c:13]2[n... | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CCI | CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | C-C Coupling | OtherReaction | 247e9571744cfb8a9baf8e624863133c2e1dd2666a09d36dbaa993edf5a90341 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[#8:7]-[C:8](=[O;D1;H0:9])-[C@@H;D3;+0:10]1-[C:11]-[C:12]-[c:13](:[#7;a:14]:[c:15]):[#7;a:16]-1:[c:17]>>[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D4;+0:10]1(-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:11]-[C:12]-[c:13](:[#... | 18 | [{"value": 18.0, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with ethyl iodide afforded 47 mg (18%) of intermediate 22a. MS (ESI) 414.4 (M+H+), 436.4 (M+Na+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cn2c(nc1)CCC2 | C1CCc2ncccn21 | C1CCc2ncccn21.c1ccccc1 | HI | null | null | null | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.CCI>>CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59bf92b943f54d59b86c2b1a12e61f69 | CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C.C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)CC>>C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)CC | CC(C)(C)[O:6][C:4]([C:3]1([CH2:2][CH3:1])[CH2:7][CH2:8][c:9]2[n:10][cH:11][c:12]([NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24](=[O:25])[n:26]21)=[O:5]>>[CH3:1][CH2:2][C:3]1([C:4](=[O:5])[OH:6])[CH2:7][CH2:8][c:9]2[n:10][cH:11][c:12]([NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]3[cH... | CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]>>[#7;a:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19b, intermediate 22a (41 mg, 413.47 mmol) was deprotected to afford 35 mg (99%) of intermediate 22b. MS (ESI) 358.3 (M+H+), 356.2 (M−H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCc2ncccn21.c1ccccc1 | Other | null | null | null | CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb6ccc65119b4e95b56e88ab95c1b6e5 | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)CC.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CN)=O>>C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(CC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[NH:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1.O[C:4]([C:3]1([CH2:2][CH3:1])[CH2:24][CH2:25][c:26]2[n:27][cH:28][c:29]([NH:30][C:31](=[O:32])[O:33][CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[c:41](=[O:42])[n:43]21)=[O:5]>>[... | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc2n(c1=O)C(C(=O)NCc1ccccc1)CC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[#7;a:6](:[c:7]):[c:8]:[#7;a:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:9]:[c:8]:[#7;a:6](:[c:7])-[C:3](-[C:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12])-[C:5] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(CC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19c, intermediate 22b (34.5 mg, 0.0965 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester to afford 57 mg (100%) of intermediate 22c.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCc2ncccn21.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.CCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>CCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2fe581f8f38b40a180f0106c06d749ed | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.COCCl>>COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)C.C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)[C@@H](CC2)C(=O)OC(C)(C)C.COCCl>>C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)COC | [C@@H:4]1([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][c:14]2[n:15][cH:16][c:17]([NH:18][C:19](=[O:20])[O:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:29](=[O:30])[n:31]21.Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][C:4]1([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2... | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.COCCl | COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | C-C Coupling | OtherReaction | 2a520d62bfb8f1175a3bd088c6a66321219130a6262e9738c06bddbfd3201cd4 | 8ef4a7f3c2aa2c61ba42c1b7d8665a33daf968ae3eb9e2122661626a98ff3349 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[C@@H;D3;+0:11]1-[C:12]-[C:13]-[c:14](:[#7;a:15]:[c:16]):[#7;a:17]-1:[c:18]>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:11]1(-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3])-[C:12]-... | 36 | [{"value": 36.0, "product": "C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)COC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with methoxymethylchloride afforded 101 mg (36%) of intermediate 23a. MS (ESI) 430.4 (M+H+), 452.4 (M+Na+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ether | c1cn2c(nc1)CCC2 | C1CCc2ncccn21 | C1CCc2ncccn21.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21.COCCl>>COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96eaada888e34835aeae2998f8196457 | COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)C.C(C)(C)(C)OC(=O)C1(CCC=2N1C(C(=CN2)NC(=O)OCC2=CC=CC=C2)=O)COC>>C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)COC | CC(C)(C)[O:7][C:5]([C:4]1([CH2:3][O:2][CH3:1])[CH2:8][CH2:9][c:10]2[n:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25](=[O:26])[n:27]21)=[O:6]>>[CH3:1][O:2][CH2:3][C:4]1([C:5](=[O:6])[OH:7])[CH2:8][CH2:9][c:10]2[n:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:1... | COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7;a:5]>>[#7;a:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | According to the procedure for the preparation of intermediate 19b, intermediate 23a (87 mg, 0.203 mmol) was deprotected to afford 76 mg (quantitative) of intermediate 23b. MS (ESI) 418.3 (M 2Na++H+), 372.2 (M−H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCc2ncccn21.c1ccccc1 | Other | null | null | null | COCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e044293813a0477f8e6f434a4d06c847 | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>COCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | C(C1=CC=CC=C1)OC(=O)NC1=CN=C2N(C1=O)C(CC2)(C(=O)O)COC.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CN)=O>>C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(COC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O | [NH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[NH:14])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1.O[C:5]([C:4]1([CH2:3][O:2][CH3:1])[CH2:25][CH2:26][c:27]2[n:28][cH:29][c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]3[cH:37][cH:38][cH:39][cH:40][cH:41]3)[c:42](=[O:43])[n:44]21)=[O... | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | COCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cnc2n(c1=O)C(C(=O)NCc1ccccc1)CC2)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[#7;a:6](:[c:7]):[c:8]:[#7;a:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;a:9]:[c:8]:[#7;a:6](:[c:7])-[C:3](-[C:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12])-[C:5] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)(COC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of intermediate 19c, intermediate 23b (57.8 mg, 0.155 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester to afford 94 mg (100%) of intermediate 23c.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCc2ncccn21.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.COCC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21>>COCC1(C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0d4c49598e642f9a8b23b814d8fa918 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1.FC(F)(F)c1cccc(CBr)c1>>O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21 | FC(C=1C=C(CBr)C=CC1)(F)F.[H-].[Na+].C(C1=CC=CC=C1)OC(NC1=CN=C2N(C1=O)C(CC2)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OC(C)(C)C)=O)=O.C1CCOC1>>C(C1=CC=CC=C1)OC(=O)N(C1=CN=C2N(C1=O)[C@@H](CC2)C(=O)O)CC2=CC(=CC=C2)C(F)(F)F | CC(C)(C)[O:3]C(=O)NC(=N)c1ccc(CN[C:2](=[O:1])[CH:4]2[CH2:5][CH2:6][c:7]3[n:8][cH:9][c:10]([NH:11][C:23](=[O:24])[O:25][CH2:26][c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[c:33](=[O:34])[n:35]32)cc1.Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1.FC(F)(F)c1cccc(CBr)c1 | O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21 | null | CCCC[N+](CCCC)(CCCC)CCCC.[I-] | null | Protection | OtherReaction | b4fd3d8fec6e969bdf9b222a9b26e255ec41900ec5b2eb6a9282e34bc58c5329 | 58fc7732ac7527d96628681652edbb7fe610d9d02dd5085116e3e781fbfcbbc0 | O=C(OCc1ccccc1)N(Cc1ccccc1)c1cnc2n(c1=O)CCC2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-C(=O)-N-C(=N)-c1:c:c:c(-C-N-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH;D3;+0:8]2-[C:9]-[C:10]-[c:11]3:[#7;a:12]:[c:13]:[c:14](-[NH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19]):[c:20](=[O;D1;H0:21]):[#7;a:22]:3-2):c:c:1>>[C:19]-[#8:18]-[C:16](=[O;D1;H0:17])-[N;H0;... | 93 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)OC(=O)N(C1=CN=C2N(C1=O)[C@@H](CC2)C(=O)O)CC2=CC(=CC=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a mixture of acid 1i (4.50 g, 13.7 mmol) in 70 mL THF at 0° C., was added 3-(trifluoromethyl)benzyl bromide (8.35 mL, 54.7 mmol), NaH (60% dispersion in oil, 1.64 g, 41.4 mmol), and TBAI (100 mg, catalytic). The reaction was stirred at rt for 15 h, then quenched with the addition of 50 mL H2O. The volatile solvents ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Carbamic ester.Ether.Secondary amide.Boc | Carbamic ester.Carboxylic acid | c1ccccc1 | null | c1cn2c(nc1)CCC2.c1ccccc1.c1ccccc1 | HBr | CCCC[N+](CCCC)(CCCC)CCCC.[I-] | null | 15 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)C2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1.FC(F)(F)c1cccc(CBr)c1>CCCC[N+](CCCC)(CCCC)CCCC.[I-]>O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f36da15899fd4af9811f6c580396af9c | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N(Cc4cccc(C(F)(F)F)c4)C(=O)OCc4ccccc4)c(=O)n32)cc1 | C(C1=CC=CC=C1)OC(=O)N(C1=CN=C2N(C1=O)[C@@H](CC2)C(=O)O)CC2=CC(=CC=C2)C(F)(F)F.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CN)=O.C(=O)(O)[O-].[Na+].C1=CC2=C(N=C1)N(N=N2)O.CCN=C=NCCCN(C)C>>C(C)(C)(C)OC(=O)NC(C1=CC=C(CNC(=O)[C@@H]2CCC=3N2C(C(=CN3)N(C(OCC3=CC=CC=C3)=O)CC3=CC(=CC=C3)C(F)(F)F)=O)C=C1)=N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[NH:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH2:16])[cH:51][cH:52]1.O[C:17](=[O:18])[C@@H:19]1[CH2:20][CH2:21][c:22]2[n:23][cH:24][c:25]([N:26]([CH2:27][c:28]3[cH:29][cH:30][cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]3)[C:38](=[O:39])[O:40][CH2:41][c:4... | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N(Cc4cccc(C(F)(F)F)c4)C(=O)OCc4ccccc4)c(=O)n32)cc1 | null | null | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(N(Cc3ccccc3)C(=O)OCc3ccccc3)c(=O)n21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11])-[C:4] | 79.2 | [{"value": 79.0, "product": "C(C)(C)(C)OC(=O)NC(C1=CC=C(CNC(=O)[C@@H]2CCC=3N2C(C(=CN3)N(C(OCC3=CC=CC=C3)=O)CC3=CC(=CC=C3)C(F)(F)F)=O)C=C1)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "C(C)(C)(C)OC(=O)NC(C1=CC=C(CNC(=O)[C@@H]2CCC=3N2C(C(=CN3)N(C(OCC3=CC=CC=C3)=O)CC3=CC(=CC=C3)C(F)(F)F... | null | null | 20 | HOUR | To a solution of intermediate 25a (0.281 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (84 mg, 0.337 mmol) in 3 mL 5:1 CH2Cl2/DMF at 0° C., were added NaHCO3 (59 mg, 0.703 mmol), HOAT (42.1 mg, 0.309 mmol), and EDCI (75.5 mg, 0.393 mmol). The mixture was allowed to warm to rt and stir 2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1.c1ccccc1 | HO- | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | null | 20 | CC(C)(C)OC(=O)NC(=N)c1ccc(CN)cc1.O=C(O)[C@@H]1CCc2ncc(N(Cc3cccc(C(F)(F)F)c3)C(=O)OCc3ccccc3)c(=O)n21>CCOC(=O)C.C(Cl)Cl.CN(C)C=O>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N(Cc4cccc(C(F)(F)F)c4)C(=O)OCc4ccccc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79a9dac262764605b237450889acef21 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC=O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NCC | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O.C(C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)NCC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2... | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3[cH:39][cH:40][cH:41][cH:42][cH:43]3)[cH:44][cH:45... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC=O | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NCC | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4](:[#7;a:5])-[C:6](-[C;D1;H3:7])(-[NH2;D1;+0:8])-[C:9]>>[#7;a:3]:[c:4](:[#7;a:5])-[C:6](-[C;D1;H3:7])(-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:9] | 54 | [{"value": 54.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)NCC)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, 26a (30.0 mg, 0.045 mmol), acetaldehyde (2.2 mg, 0.050 mmol) and NaBH(OAc)3 (14.4 mg, 0.068 mmol) yielded 16.9 mg (54%) of 26b. MS (ESI) 692.5 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | Other | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC=O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ece1c29cc1b4b1eab7b6792a465b241 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NC(C)C | C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NCC2=CC=CC=C2)=O)=O.C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O.CC(=O)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)NC(C)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)... | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3[cH:39][cH:40][cH:41][cH:42][cH:43]3)[cH:44][cH:45... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NC(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8f29ebfd8b55e61e8a5799e9d8c3faba934a92c9f3c7c0f5e26dcad2af6bbc28 | 8e4b2bf6cf42ba3563388d9ce03f29850fefe100bad3840edf3395d49540f26d | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C(=O)-N-C(=N)-c1:c:c:c(-C-N-C(=O)-[C@H]2-C-C-c3:n:c:c(-N-C-c4:c:c:c:c:c:4):c(=O):n:3-2):c:c:1.[#7;a:4]:[c:5](:[#7;a:6])-[C:7](-[C;D1;H3:8])(-[NH2;D1;+0:9])-[C:10]>>[#7;a:4]:[c:5](:[#7;a:6])-[C:7](-[C;D1;H3:8])(-[NH;D2;+0:9]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:10] | 28.1 | [{"value": 28.1, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)NC(C)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 1k, 26a (30 mg, 0.045 mmol), acetone (5.3 mg, 0.090 mmol) and NaBH(OAc)3 (26.8 mg, 0.127 mmol) yielded 8.9 mg (28.1%) of 27a. MS (ESI) 706.2 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amide.Primary amine.Secondary amine.Boc | Secondary amine | c1ccccc1.c1cnc2n(c1)CCC2.c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f51d0ab866974f10b8c0efcd2b1d03dd | C=CC[C@@H]1C[C@@H](C(=O)N(C(=O)OC(C)(C)C)c2ccccc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.OO>>C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O | [O-]S(=O)[O-].[Na+].[Na+].C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@H]2CC=C)C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)CC=C)=O.OO.[Li+].[OH-]>>C(C=C)[C@@H]1C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O | CC(C)(C)OC(=O)N(c1ccccc1)[C:7]([C@@H:6]1[CH2:5][C@@H:4]([CH2:3][CH:2]=[CH2:1])[c:11]2[n:10]1[c:29](=[O:30])[c:14]([N:15]([CH2:16][CH:17]=[CH2:18])[C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[cH:13][n:12]2)=[O:8].O[OH:9]>>[CH2:1]=[CH:2][CH2:3][C@@H:4]1[CH2:5][C@@H:6]([C:7](=[O:8])[OH:9])[n:1... | C=CC[C@@H]1C[C@@H](C(=O)N(C(=O)OC(C)(C)C)c2ccccc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.OO | C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O | null | null | C1CCOC1.O.O | Acylation | OtherReaction | 3fbaabb4b18b7d0ff96cdbfc0f6d81e189be3d2c5f31dc35e2b72231b8963a65 | a11fc6035aaf7fc298c6c10684720bc4b39f126d4126b694d44ae3c654997440 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8])-c1:c:c:c:c:c:1.O-[OH;D1;+0:9]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:9])-[C:4] | 96 | [{"value": 96.0, "product": "C(C=C)[C@@H]1C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of 28c (311 mg, 0.532 mmol) in 5 mL THF/H2O (4:1) at 0° C., were added 30% H2O2 (0.241 mL, 2.13 mmol) and IM LiOH (0.851 mL, 0.851 mmol). The mixture was stirred at 0° C. for 2 h, then Na2SO3 and 10 mL H2O were added. The organic solvent was evaporated under a stream of nitrogen. The precipitate was filte... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Peroxide.Boc | Carboxylic acid | c1ccccc1 | null | c1cn2c(nc1)CCC2.c1ccccc1 | HO- | C1CCOC1.O.O | 0 | 2 | C=CC[C@@H]1C[C@@H](C(=O)N(C(=O)OC(C)(C)C)c2ccccc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.OO>C1CCOC1.O.O>C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-384eab5d229c455fb8dd63aeadcf8621 | C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CC[C@@H]1C[C@@H](C(=O)NCc2ccc(C(=N)NC(=O)OCc3ccccc3)cc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O | C(C=C)[C@@H]1C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O.Cl.C(C1=CC=CC=C1)OC(NC(=N)C1=CC=C(C=C1)CN)=O.C1=CC2=C(N=C1)N(N=N2)O.C(=O)(O)[O-].[Na+].CCN=C=NCCCN(C)C>>C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](C[C@H]2CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O | O[C:7]([C@@H:6]1[CH2:5][C@@H:4]([CH2:3][CH:2]=[CH2:1])[c:31]2[n:30]1[c:49](=[O:50])[c:34]([N:35]([CH2:36][CH:37]=[CH2:38])[C:39](=[O:40])[O:41][CH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1)[cH:33][n:32]2)=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[NH:16])[NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]2[... | C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | C=CC[C@@H]1C[C@@H](C(=O)NCc2ccc(C(=N)NC(=O)OCc3ccccc3)cc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O | null | null | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11])-[C:4] | 20.8 | [{"value": 20.8, "product": "C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](C[C@H]2CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | To a solution of 28d (172 mg, 0.420 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride (180 mg, 0.504 mmol) in 3.6 mL CH2Cl2/DMF (5:1) at 0° C., was added HOAT (113 mg, 0.588 mmol), NaHCO3 (141 mg, 1.68 mmol), and EDCI (113 mg, 0.588 mmol). The mixture was allowed to warm to rt and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HO- | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | null | 64 | C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>CCOC(=O)C.C(Cl)Cl.CN(C)C=O>C=CC[C@@H]1C[C@@H](C(=O)NCc2ccc(C(=N)NC(=O)OCc3ccccc3)cc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dfdbf4c619de41a5b993938d44077dc6 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)CC2(CC=C)CC=C.C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C | C(C=C)[C@@H]1C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O.C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](CC2(CC=C)CC=C)C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C>>C(C=C)C1(C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O)CC=C | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)CC2(CC=C)[CH2:31][CH:32]=[CH2:33].[CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[OH:25])[CH2:26][C@H:27]2[CH2:28][CH:29]=[CH2:... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)CC2(CC=C)CC=C.C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C | null | null | null | C-C Coupling | OtherReaction | f7041a58d9fb0cd6cba5c05b8619edd6835b013560d175f97e994ce7c427b819 | ef4acd71365b8283bf96ee3e53b7c139d4ea1f888d5308edd28082313253ca66 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N(-C(=O)-[C@H]1-C-C(-C-C=C)(-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-c2:n:c:c(-N(-C-C=C)-C(=O)-O-C-c3:c:c:c:c:c:3):c(=O):n:2-1)-c1:c:c:c:c:c:1.[C;D1;H2:4]=[C:5]-[C:6]-[C@@H;D3;+0:7]1-[C:8]-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[#7;a:13](:[c:14]):[c:15]-1:[#7;a:16]:[c:17]>>[C;D1;H2:4]=[C:5]-[C:6]-[C;H0... | 76 | [{"value": 76.0, "product": "C(C=C)C1(C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O)CC=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of 28d, 29c (372 mg, 0.595 mmol) afforded 202 mg (76%) of 29d. MS (ESI) 450.4 (M+H+), 448.2 (M−H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Substituted dicarboximide.Allyl.Allyl.Allyl.Boc | Allyl | c1ccccc1.c1ccccc1.c1cnc2n(c1)CCC2.c1cn2c(nc1)CCC2 | C1CCn2cccnc21 | c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)CC2(CC=C)CC=C.C=CC[C@@H]1C[C@@H](C(=O)O)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f9a90965b4c40a7adc1535c3ce407ad | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)CC2(CC=C)CC=C | Cl.C(C1=CC=CC=C1)OC(NC(=N)C1=CC=C(C=C1)CN)=O.C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](C[C@H]2CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O.C(C=C)C1(C[C@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)O)CC=C>>C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](CC2(CC=C)CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=... | O[C:23]([C@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[C:47]([CH2:48][CH:49]=[CH2:50])([CH2:51][CH:52]=[CH2:53])[CH2:46]1)=[O:24].[NH2:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)CC2(CC=C)CC=C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11])-[C:4] | 66 | [{"value": 66.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.0, "product": "C(C=C)N(C(OCC1=CC=CC=C1)=O)C1=CN=C2N(C1=O)[C@@H](CC2(CC=C)CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of 28e, 29d (162 mg, 0.360 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride to afford after flash chromatography (66% EtOAc/hexanes) 105 mg (41%) of 29e. MS (ESI) 715.5 (M+H+), 737.5 (M+Na+).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)CC2(CC=C)CC=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52e7df54d8284410b978de744febdd8b | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4cccc5ccccc45)c(=O)n32)cc1>>NS(=O)(=O)c1cccc2ccccc12 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=CC1=CC=CC=C21)=O)=N)=O>>C1(=CC=CC2=CC=CC=C12)S(=O)(=O)N | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc([NH:1][S:2](=[O:3])(=[O:4])[c:5]4[cH:6][cH:7][cH:8][c:9]5[cH:10][cH:11][cH:12][cH:13][c:14]45)c(=O)n32)cc1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4cccc5ccccc45)c(=O)n32)cc1 | NS(=O)(=O)c1cccc2ccccc12 | null | null | null | Reduction | OtherReaction | 7cd8ad00ea42a2e22a91d8c67b4bb89bab2a4f88acabee7a731f9832dd1d1f83 | b95409a98ef23eb7bb74d68beb93619c9cdd3d020df96160225ee29ad446a6ce | c1ccc2ccccc2c1 | C-C(-C)(-C)-O-C(=O)-N-C(=N)-c1:c:c:c(-C-N-C(=O)-[C@H]2-C-C-c3:n:c:c(-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]):c(=O):n:3-2):c:c:1>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 30 | [{"value": 30.0, "product": "C1(=CC=CC2=CC=CC=C12)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 1-napthylene sulfonyl chloride (39.8 mg, 0.176 mmol) yielded 21.7 mg (30.0%) of 1-napthalene sulfonamide intermediate 30a. MS (ESI) 617.0 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Ether.Secondary amide.Boc | Sulfonamide | c1ccccc1.c1cnc2n(c1)CCC2 | null | c1ccc2ccccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4cccc5ccccc45)c(=O)n32)cc1>>NS(=O)(=O)c1cccc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab7d74dafc3f48528fad4da7326d5315 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.COc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.COC1=CC=C(C=C1)S(=O)(=O)Cl>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)OC)=O)=N)=O | C[S:7](=[O:8])(=[O:9])[NH:10][c:11]1[cH:12][n:13][c:14]2[n:15]([c:16]1=[O:17])[C@H:18]([C:19](=[O:20])[NH:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([C:27](=[NH:28])[NH:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37][cH:38]1)[CH2:39][CH2:40]2.O=S(=O)(Cl)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42][cH:41]... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.COc1ccc(S(=O)(=O)Cl)cc1 | COc1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f7d7035681eec9424ed537aa12cef9f996ca1cdde46575be56b05b9c454d74ff | 16512f50a8b90b3ee487b72c3ddce73600f1cb782814fcf533a2c0c2a32b6c09 | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)c3ccccc3)c(=O)n21 | C-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]:[#7;a:7]):[c:8]:[#7;a:9].Cl-S(=O)(=O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:7]:[c:6]:[c:5](-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:8]:[#7;a:9] | 46.2 | [{"value": 46.2, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)OC)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 4-methoxybenzene sulfonyl chloride (31.4 mg, 0.152 mmol) yielded 32.2 mg (46.2%) of 31a. MS (ESI) 597.0 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cn2c(nc1)CCC2 | HCl | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.COc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de70dcd92b8a454b981be1181eb29201 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(F)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(F)cc4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.FC1=CC=C(C=C1)S(=O)(=O)Cl>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)F)=O)=O | C[S:27]([NH:26][c:25]1[cH:24][n:23][c:22]2[n:39]([c:37]1=[O:38])[C@H:19]([C:17]([NH:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[NH:10])[cH:41][cH:40]1)=[O:18])[CH2:20][CH2:21]2)(=[O:28])=[O:29].O=S(=O)(Cl)[c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1>>[CH3:... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(F)cc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(F)cc4)c(=O)n32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f7d7035681eec9424ed537aa12cef9f996ca1cdde46575be56b05b9c454d74ff | 16512f50a8b90b3ee487b72c3ddce73600f1cb782814fcf533a2c0c2a32b6c09 | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)c3ccccc3)c(=O)n21 | C-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]:[#7;a:7]):[c:8]:[#7;a:9].Cl-S(=O)(=O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:7]:[c:6]:[c:5](-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:8]:[#7;a:9] | 41 | [{"value": 41.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 4-fluorobenzene sulfonyl chloride (29.6 mg, 0.158 mmol) yielded 28.2 mg (41.0%) of 32a. MS (ESI) 585.0 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(F)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(F)cc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c34701dba374642a831397d727793bd | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(OC(F)(F)F)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(OC(F)(F)F)cc4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.FC(OC1=CC=C(C=C1)S(=O)(=O)Cl)(F)F>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)OC(F)(F)F)=O)=N)=O | CS(=O)(=O)[NH:26][c:25]1[cH:24][n:23][c:22]2[n:43]([c:41]1=[O:42])[C@H:19]([C:17]([NH:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[NH:10])[cH:45][cH:44]1)=[O:18])[CH2:20][CH2:21]2.Cl[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([O:34][C:35]([F:36])([F:37])[... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(OC(F)(F)F)cc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(OC(F)(F)F)cc4)c(=O)n32)cc1 | null | null | null | Acylation | OtherReaction | 65f51c4be3dedecd8ee62e00fa8acb4d8e99a40aeb601b8f69c566e8b24b380a | 2401986f5e69efca48e6b1e53ecffc48dc571fb6ffe2395e61e07441c6c3692d | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)c3ccccc3)c(=O)n21 | C-S(=O)(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]:1=[O;D1;H0:8])-[C:9]-[C:10](-[#7:11])=[O;D1;H0:12].Cl-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16](:[c:17]):[c:18]>>[#7:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2](-[NH;D2;+0:1]-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0... | 41.6 | [{"value": 41.6, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)OC(F)(F)F)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 4-(trifluoromethoxy)benzene sulfonyl chloride (39.6 mg, 0.152 mmol) yielded 31.7 mg (41.6%) of 33a. MS (ESI) 651.0 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)c1ccc(OC(F)(F)F)cc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)c4ccc(OC(F)(F)F)cc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02cb432b381b4fc7ae5a7f95794986bb | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1>>CC(=O)c1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)Cl>>C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)C(C)=O)=O)=O | Cl[S:8]([c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:43][cH:42]1)(=[O:9])=[O:10].CS(=O)(=O)[NH:11][c:12]1[cH:13][n:14][c:15]2[n:16]([c:17]1=[O:18])[C@H:19]([C:20](=[O:21])[NH:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([C:28](=[NH:29])[NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:38][cH:39]1)[CH2:40... | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1 | CC(=O)c1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 | null | null | null | Acylation | OtherReaction | 65f51c4be3dedecd8ee62e00fa8acb4d8e99a40aeb601b8f69c566e8b24b380a | 2401986f5e69efca48e6b1e53ecffc48dc571fb6ffe2395e61e07441c6c3692d | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)c3ccccc3)c(=O)n21 | C-S(=O)(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]:1=[O;D1;H0:8])-[C:9]-[C:10](-[#7:11])=[O;D1;H0:12].Cl-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16](:[c:17]):[c:18]>>[#7:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2](-[NH;D2;+0:1]-[S;H0;D4;+0:13](=[O;D1;H0:14])(=[O;D1;H0... | 42 | [{"value": 42.0, "product": "C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C2=CC=C(C=C2)C(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 4-acetylbenzene sulfonyl chloride (30.6 mg, 0.14 mmol) yielded 30.0 mg (42.0%) of 35a. MS (ESI) 609.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1cn2c(nc1)CCC2 | HCl | null | null | null | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1>>CC(=O)c1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a6fd4c349944d84a199b793e2056916 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)Cc1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)Cc4ccccc4)c(=O)n32)cc1 | C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)C)=O)=N)=O.C(C)(C)(C)OC(NC(=N)C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)N(CC)CC)=O)=O.C1(=CC=CC=C1)CS(=O)(=O)Cl>>C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)CC2=CC=CC=C2)=O)=N)=O | C[S:27]([NH:26][c:25]1[cH:24][n:23][c:22]2[n:39]([c:37]1=[O:38])[C@H:19]([C:17]([NH:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[NH:10])[cH:41][cH:40]1)=[O:18])[CH2:20][CH2:21]2)(=[O:28])=[O:29].O=S(=O)(Cl)[CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3... | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)Cc1ccccc1 | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)Cc4ccccc4)c(=O)n32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dd710b0524c1f9a318c5ef2d9cb572eb116640a90105e79d7b398062d7aa17d1 | 16512f50a8b90b3ee487b72c3ddce73600f1cb782814fcf533a2c0c2a32b6c09 | O=C(NCc1ccccc1)[C@@H]1CCc2ncc(NS(=O)(=O)Cc3ccccc3)c(=O)n21 | C-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]:[#7;a:7]):[c:8]:[#7;a:9].Cl-S(=O)(=O)-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:7]:[c:6]:[c:5](-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:[#7;a:9] | 44 | [{"value": 44.0, "product": "C(C)(C)(C)OC(NC(C1=CC=C(C=C1)CNC(=O)[C@@H]1CCC=2N1C(C(=CN2)NS(=O)(=O)CC2=CC=CC=C2)=O)=N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and alpha-toluene sulfonyl chloride (26.7 mg, 0.14 mmol) yielded 35.6 mg (44%) of 36a. MS (ESI) 581.1 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cn2c(nc1)CCC2.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1.O=S(=O)(Cl)Cc1ccccc1>>CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(=O)(=O)Cc4ccccc4)c(=O)n32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-099639eee6ab4646a8db056db0679e3a | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2.CCI.CCI>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2(CC)CC | C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2)C(NC2=CC=CC=C2)=O)CC=C)=O.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.C1CCOC1.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.C(C)I.C(C)I>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2(CC)CC)C(NC2=CC=CC=C2)=O)CC=C)=O | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH2:32][CH2:33]2.I[CH2:34][CH3:35].I[CH2:36][CH3:37]>>[CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2.CCI.CCI | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2(CC)CC | null | null | null | C-C Coupling | OtherReaction | 86795c43c99c56bb124fc3642182ed415a11a04f30fb9d3b968b59b898f88a29 | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | O=C(Nc1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2)OCc1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].I-[CH2;D2;+0:3]-[C;D1;H3:4].[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[CH2;D2;+0:10]-[c:11](:[#7;a:12]:[c:13]):[#7;a:14]-1:[c:15]>>[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C;H0;D4;+0:10](-[CH2;D2;+0:1]-[C;D1;H3:2])(-[CH2;D2;+0:3]-[C;D1;H3:4])-[c:11](:[#7;a:12]:[c:13]):[#7;a:14]-1:[c:15] | 72 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2(CC)CC)C(NC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a solution of phenyl amide 18b (100 mg, 0.225 mmol) in 1 mL THF at −78° C., was added LiHMDS (IM in THF, 0.720 mL, 0.720 mmol). The orange solution was stirred at −78° C. for 5 min, then EtI (0.045 mL, 0.563 mmol) was added. The reaction was stirred and allowed to slowly warm to −30° C. over 45 min. Additional LiHMD... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1cn2c(nc1)CCC2 | C1CCn2cccnc21 | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HI | null | -78 | 0.083333 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2.CCI.CCI>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2(CC)CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d64943344df842839afee007706c4b16 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)(C)OC(=O)CBr>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C | BrCC(=O)OC(C)(C)C.C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](CC2C)C(NC2=CC=CC=C2)=O)CC=C)=O.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NC2=CC=CC=C2)=O)C)=O | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH2:32][CH:33]2[CH3:34].Br[CH2:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42]>>[CH2:1]=[... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)(C)OC(=O)CBr | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 43417f10239d23abfa53160b2e66105b988a238966f9b74ed76bd584a4669849 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C(Nc1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)CC2)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]1-[C:13]-[CH;D3;+0:14](-[C;D1;H3:15])-[c:16](:[#7;a:17]:[c:18]):[#7;a:19]-1:[c:20]>>[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]1-[C:13]-[C@@;H0;D4;+0:14](-[C;D1;H3:15])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])... | 59 | [{"value": 59.0, "product": "C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NC2=CC=CC=C2)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To Intermediate 18c (495.7 mg, 1.08 mmol) in THF at −78° C. was added LiHMDS (2.268 mL, 2.268 mmol) dropwise. After 10 min, tert-butyl bromoacetate was added and the mixture was stirred at −78° C. for 20 min. It was allowed to warm to −40° C. over 20 min, then quenched with NH4Cl. The reaction mixture was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cn2c(nc1)[CH]CC2 | C1CCn2cccnc21 | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HBr | C1CCOC1 | -78 | 0.166667 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)Nc1ccccc1)CC2C.CC(C)(C)OC(=O)CBr>C1CCOC1>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a42c8550554944cb81be6dab778dd8cf | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-]>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C | C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)CC=C)=O.C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NC2=CC=CC=C2)=O)C)=O>>C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)C)=O | c1ccc(N[C:23]([C@@H:22]2[n:19]3[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]4[cH:10][cH:11][cH:12][cH:13][cH:14]4)[c:20]3=[O:21])[C@:40]([CH3:41])([CH2:42][C:43](=[O:44])[O:45][C:46]([CH3:47])([CH3:48])[CH3:49])[CH2:39]2)=[O:24])cc1.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)[... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-] | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C | null | null | null | Protection | OtherReaction | 959b149e33eb0ff05b6dd2218a87813e4d85e7c9d36d25205e1733032c43db41 | 5b93f56f770f7f7b6a4c1020ba0a9a34e6b5b2a9c8e23d00d61b276d5e0fe7b7 | O=C(Nc1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)CC2)OCc1ccccc1 | C-[C@@]1(-N=[N+]=[N-])-C-[C@H](-C(=O)-[N;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[c:9](:[c:10]):[c:11])-n2:c-1:n:c:c(-N(-C-C=C)-C(=O)-O-C-c1:c:c:c:c:c:1):c:2=O.[#7;a:12]:[c:13]:[#7;a:14](:[c:15])-[C:16](-[C;H0;D3;+0:17](=[O;D1;H0:18])-N-c1:c:c:c:c:c:1)-[C:19]>>[#7;a:12]:[c... | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 18e, intermediate 38a (435.9 mg, 0.76 mmol), was protected to give 418.9 mg (82%) of intermediate 38b. MS (ESI) 673.4 (M+H+), 695.3 (M+Na+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Azide.Substituted dicarboximide.Secondary amide.Allyl | Carbamic ester.Substituted dicarboximide | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | null | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)Nc1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)N=[N+]=[N-]>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f48e92db5f75411fa21ca293595467aa | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-]>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C | C(C=C)N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N=[N+]=[N-])C(=O)O)C(=O)OCC2=CC=CC=C2.C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(=O)N(C2=CC=CC=C2)C(=O)OC(C)(C)C)C)=O>>C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)OC(C)(C)C)C(=O)O)C(=O)OCC2=CC=CC=C2 | CC(C)(C)OC(=O)N(c1ccccc1)[C:23]([C@@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[C@:27]([CH3:28])([CH2:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:26]1)=[O:24].C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-] | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C | null | null | null | Acylation | OtherReaction | ddfac7029433a4e3ed3165e3530dc42e3e31473cf2d23f3a87143317e2b2a8a2 | de52a63a721d4029b5d4f8e438d14c5e0e76ba9920932b2a4aedee7c24ae6aa2 | O=C(Nc1cnc2n(c1=O)CCC2)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8])-c1:c:c:c:c:c:1.C-[C@@]1(-N=[N+]=[N-])-C-[C@H](-C(=O)-[OH;D1;+0:9])-n2:c-1:n:c:c(-N(-C-C=C)-C(=O)-O-C-c1:c:c:c:c:c:1):c:2=O>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:9])-[C:4] | 89 | [{"value": 89.0, "product": "C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)OC(C)(C)C)C(=O)O)C(=O)OCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure for the preparation of 18f, intermediate 38b (413.9 mg, 0.62 mmol) was deprotected to afford 273.9 mg (89%) of intermediate 38c. MS (ESI) 498.4 (M+H+), 496.2 (M−H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Carboxylic acid.Ether.Ether.Azide.Substituted dicarboximide.Allyl.Boc | Carboxylic acid | c1ccccc1.c1ccccc1.C1CCn2cccnc21 | null | c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)N(C(=O)OC(C)(C)C)c1ccccc1)C[C@@]2(C)CC(=O)OC(C)(C)C.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)C[C@@]2(C)N=[N+]=[N-]>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c502c53106154f779abd910b4f76f1a5 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C | C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)OC(C)(C)C)C(=O)O)C(=O)OCC2=CC=CC=C2.C(C1=CC=CC=C1)OC(NC(=N)C1=CC=C(C=C1)CN)=O>>C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C)=O | O[C:23]([C@@H:22]1[n:19]2[c:18]([n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20]2=[O:21])[C@:47]([CH3:48])([CH2:49][C:50](=[O:51])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[CH2:46]1)=[O:24].[NH2:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:3... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7;a:5](:[c:6]):[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:5](:[c:6])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11])-[C:4] | 64 | [{"value": 64.0, "product": "C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NCC2=CC=C(C=C2)C(=N)... | null | null | null | null | Following a procedure similar to that for the preparation of 18 g, intermediate 38c (268.9 mg, 0.54 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (223.9 mg, 0.70 mmol) to provide 262.3 mg (64%) of intermediate 38d. MS (ESI) 763.5 (M+H+).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C.N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-060cc32606934662a50b466e7bc01a34 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O | C(C)(C)(C)OC(C[C@@]1(C[C@@H](N2C1=NC=C(C2=O)N(C(=O)OCC2=CC=CC=C2)CC=C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C)=O>>C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C(=O)OCC2=CC=CC=C2 | CC(C)(C)[O:52][C:50]([CH2:49][C@@:47]1([CH3:48])[c:18]2[n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20](=[O:21])[n:19]2[C@@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O | null | null | O1CCOCC1.Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 102 | [{"value": 100.0, "product": "C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C(=O)OCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.0, "product": "C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C(=O)OC... | null | null | null | null | A solution of intermediate 38d (262.3 mg, 0.34 mmol) in 5 mL 4M HCl dioxane was stirred at rt for 2 h. The solvent was removed in vacuo, then the compound was triturated with ether to afford 245 mg (100%) of intermediate 39a. MS (ESI) 707.4 (M+H+), 705.3 (M−H+).
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | Other | O1CCOCC1.Cl | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C>O1CCOCC1.Cl>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-002a8eb87a59427d8655a91589e79e04 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O.Nc1ccccc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)Nc1ccccc1 | C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C(=O)OCC2=CC=CC=C2.NC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(NC2=CC=CC=C2)=O)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O | O[C:50]([CH2:49][C@@:47]1([CH3:48])[c:18]2[n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20](=[O:21])[n:19]2[C@@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3[cH:39][cH:40... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O.Nc1ccccc1 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)Nc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@H]2CC(CC(=O)Nc3ccccc3)c3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 57 | [{"value": 57.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(NC2=CC=CC=C2)=O)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.6, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(NC2=CC=CC=C2)=O)C)C(NCC2=CC=C(C=C2)C(=N)N... | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 18 g, intermediate 39a (20 mg, 0.028 mmol) was coupled with aniline (3.39 mg, 0.036 mmol) to provide 12.4 mg (57%) of intermediate 40a. MS (ESI) 782.3 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21.c1ccccc1 | HO- | null | null | null | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O.Nc1ccccc1>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)Nc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dab4932fb5d1424e8f1c73ce5b065778 | C1CCNCC1.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)N1CCCCC1 | C(C=C)N(C1=CN=C2N(C1=O)[C@H](C[C@@]2(C)CC(=O)O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)C(=O)OCC2=CC=CC=C2.N1CCCCC1>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(N2CCCCC2)=O)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O | [NH:52]1[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]1.O[C:50]([CH2:49][C@@:47]1([CH3:48])[c:18]2[n:17][cH:16][c:15]([N:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:20](=[O:21])[n:19]2[C@@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]2[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33... | C1CCNCC1.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)N1CCCCC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@H]2CC(CC(=O)N3CCCCC3)c3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 72.5 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(N2CCCCC2)=O)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(CC(N2CCCCC2)=O)C)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC... | null | null | null | null | Following a procedure similar to that for the preparation of intermediate 18 g, intermediate 39a (20 mg, 0.028 mmol) was coupled with piperidine (8.1 mg, 0.14 mmol) to provide 15.7 mg (71%) of intermediate 41a. MS (ESI) 774.5 (M+H+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21.C1CC[NH]CC1 | HO- | null | null | null | C1CCNCC1.C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8aca7148692f4ee8a269e8efde4e1fcd | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.O=CO>>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@]2(C)NC=O | C1CCC(CC1)N=C=NC2CCCCC2.C(=O)O.C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@@H](C[C@@]2(C)N)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O.N1=CC=CC=C1>>C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(C)NC=O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O | [CH2:1]=[CH:2][CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][n:17][c:18]2[n:19]([c:20]1=[O:21])[C@H:22]([C:23](=[O:24])[NH:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([C:31](=[NH:32])[NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]3[cH:39][cH:40][cH:41][cH:42][cH:43]3)[cH:44][cH:45... | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.O=CO | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@]2(C)NC=O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(NC(=O)OCc1ccccc1)c1ccc(CNC(=O)[C@H]2CCc3ncc(NC(=O)OCc4ccccc4)c(=O)n32)cc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[#7;a:3]:[c:4](:[#7;a:5])-[C:6](-[C;D1;H3:7])(-[NH2;D1;+0:8])-[C:9]>>[#7;a:3]:[c:4](:[#7;a:5])-[C:6](-[C;D1;H3:7])(-[NH;D2;+0:8]-[CH;D2;+0:1]=[O;D1;H0:2])-[C:9] | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(C)NC=O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "C(C1=CC=CC=C1)OC(N(C1=CN=C2N(C1=O)[C@H](C[C@]2(C)NC=O)C(NCC2=CC=C(C=C2)C(=N)NC(=O)OCC2=CC=CC=C2)=O)CC=C)=... | null | null | 2 | HOUR | To a solution of DCC (18.6 mg, 0.090 mmol) and formic acid (8.28 mg, 0.180 mmol) in CH2Cl2 that had been stirred at 0° C. for 10 min, was added intermediate 26a (30 mg, 0.045) in a solution of pyridine. The reaction was stirred at 0° C. for 15m then at rt for 2 h. The reaction mixture was concentrated in vacuo, then ta... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCn2cccnc21 | HO- | C(Cl)Cl | null | 2 | C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N.O=CO>C(Cl)Cl>C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@]2(C)NC=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-befb3972b18f4d6196654710f6ab3286 | CC1(C)c2ccccc2-c2ccc(Br)cc21.Nc1ccc(Cl)cc1>>CC1(C)c2ccccc2-c2ccc(Nc3ccc(Cl)cc3)cc21 | BrC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C.ClC1=CC=C(N)C=C1.CC(C)([O-])C.[Na+].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>>ClC1=CC=C(C=C1)NC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C | Br[c:13]1[cH:12][cH:11][c:10]2[c:23]([cH:22]1)[C:2]([CH3:1])([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-2.[NH2:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1>>[CH3:1][C:2]1([CH3:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[cH:2... | CC1(C)c2ccccc2-c2ccc(Br)cc21.Nc1ccc(Cl)cc1 | CC1(C)c2ccccc2-c2ccc(Nc3ccc(Cl)cc3)cc21 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1.CCCCCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | dbfd11e3d1928970d008145285b70ce4fea3bf715e3cf0e2f97ca73334128360 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3c(c2)Cc2ccccc2-3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 66 | HOUR | A 500 ml, 5-neck reaction flask was charged with 2-bromo-9,9-dimethyl-9H-fluorene (25.0 g) (as prepared above), 4-chloroaniline (12.9 g), sodium tert-butoxide (12.3 g), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (rac-BINAP) (0.4 g), tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3) (0.2 g) and 1,4-dioxane (180... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.CCCCCC | 80 | 66 | CC1(C)c2ccccc2-c2ccc(Br)cc21.Nc1ccc(Cl)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.CCCCCC>CC1(C)c2ccccc2-c2ccc(Nc3ccc(Cl)cc3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-526f417124d842ee909b2a74f393688d | COc1ccc2[nH]c(C=O)cc2c1.O=C(C=P(c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1>>COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=CC(=O)OCC1=CC=CC=C1.COC=1C=C2C=C(NC2=CC1)C=O>>COC=1C=C2C=C(NC2=CC1)/C=C/C(=O)OCC1=CC=CC=C1 | O=[CH:9][c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][c:22]2[cH:21]1.c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19... | COc1ccc2[nH]c(C=O)cc2c1.O=C(C=P(c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1 | COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1 | null | null | C(Cl)Cl | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | O=C(/C=C/c1cc2ccccc2[nH]1)OCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])/[CH;D2;+0:10]=[CH;D2;+0:1]/[c:2](:[c:3]):[#7;a:4]:[c:5] | 87 | [{"value": 87.0, "product": "COC=1C=C2C=C(NC2=CC1)/C=C/C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Benzyl (triphenylphosphoranylidene)acetate (49.2 g, 0.120 mol) was added to a stirred solution of 5-methoxy-1H-indole-2-carbaldehyde (1) (20.0 g, 0.114 mol) in CH2Cl2 (500 mL) and the solution was stirred at room temperature for 4 h. The solvent was removed in vacuo and the residue slurried with methanol (200 mL), wher... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | C(Cl)Cl | null | 4 | COc1ccc2[nH]c(C=O)cc2c1.O=C(C=P(c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1>C(Cl)Cl>COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36741b298f1b463fa159685ada03fbe1 | COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3 | C1(C=CC(N1)=O)=O.COC=1C=C2C=C(NC2=CC1)/C=C/C(=O)OCC1=CC=CC=C1>>COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:30]=[CH:19]/[C:20](=[O:21])[O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:9][c:10]2[cH:11]1.[CH:12]1=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[CH:12]1[C:13](=[O:14])[NH:15][C:16]... | COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1.O=C1C=CC(=O)N1 | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | bb75970bb19d6d0978b63cf87a59d45a1a95a28b57882211c61d917048b3222d | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | O=C(OCc1ccccc1)C1Cc2[nH]c3ccccc3c2C2C(=O)NC(=O)C12 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7]1:[#7;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[cH;D2;+0:13]:1.[O;D1;H0:14]=[C:15]1-[#7:16]-[C:17](=[O;D1;H0:18])-[CH;D2;+0:19]=[CH;D2;+0:20]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3... | 83 | [{"value": 83.0, "product": "COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Maleimide (4.82 g, 0.050 mol) was added to a solution of benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate, (12.71 g, 0.041 mol) prepared as in example 1 in THF (150 mL) in a 250 mL flat-bottomed flask and the mixture was stirred until homogeneous. The THF was removed in vacuo and the residue dried under high vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccccc1.c1ccc2c3c([nH]c2c1)CCC1CNCC31 | null | C1CCOC1 | null | null | COc1ccc2[nH]c(/C=C/C(=O)OCc3ccccc3)cc2c1.O=C1C=CC(=O)N1>C1CCOC1>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c48ec1b004294a5695b6e0e507c3ff9a | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3>>COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O | COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:23]([c:24]2[cH:25]1)[CH:22]1[CH:21]([CH:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9]3)[C:29](=[O:30])[NH:28][C:26]1=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10]([C:11](=[O:12])[O:13][CH2:14][c:15]4[cH:16][... | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3 | COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O | null | [O-2].[O-2].[Mn+4] | O1CCOCC1 | Oxidation | OtherReaction | dc62b408f92aa76c073d67474c0985b2ab1bb9ee5f4da1ee310245ffef49e4ee | 3f9f2bd91cd4db95a5db1518cc116b1382c2a9c42faef93a6281ccb72c6178f0 | O=C(OCc1ccccc1)c1cc2[nH]c3ccccc3c2c2c1C(=O)NC2=O | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2-[CH;D3;+0:12]2-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:18]-1-2>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:[c;H0;D3;+0:12]2:[c;H0;D3;+0:18]:1-... | 91.6 | [{"value": 91.5, "product": "COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Activated manganese dioxide (69 g) was added to a solution of benzyl 9-methoxy-1,3-dioxo-1,2,3,3a,4,5,6,10c-octahydropyrrolo[3,4-c]carbazole-4-carboxylate (13.76 g, 0.034 mol), prepared as in example 2, in p-dioxane (300 mL) and the mixture was refluxed with vigorous stirring for 0.5–2 h. The mixture was filtered while... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | [O-2].[O-2].[Mn+4].O1CCOCC1 | null | null | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(C(=O)OCc1ccccc1)C3>[O-2].[O-2].[Mn+4].O1CCOCC1>COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1b111ca8e4c4298b8f3ecc762956f0d | COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O>>COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O | COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)O)C(NC4=O)=O | c1ccc(C[O:13][C:11]([c:10]2[cH:9][c:8]3[nH:7][c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][c:17]4[c:16]3[c:15]3[c:14]2[C:22](=[O:23])[NH:21][C:19]3=[O:20])=[O:12])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10]([C:11](=[O:12])[OH:13])[c:14]4[c:15]([c:16]3[c:17]2[cH:18]1)[C:19](=[O:20])[NH:21][C:22]4=[O... | COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O | COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O | null | [Pd] | CN(C)C=O.CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NC(=O)c2c1ccc1[nH]c3ccccc3c21 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | null | [] | null | null | 2 | HOUR | A solution of benzyl 9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazole-4-carboxylate (2.00 g), prepared as in example 3, in DMF/MeOH (4:1) (50 mL) containing 5% Pd-C (0.50 g) was hydrogenated at 60 psi for 2 h (Parr apparatus). The solution was filtered through a plug of Celite, which was washed 6 times wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | Other | [Pd].CN(C)C=O.CO | null | 2 | COc1ccc2[nH]c3cc(C(=O)OCc4ccccc4)c4c(c3c2c1)C(=O)NC4=O>[Pd].CN(C)C=O.CO>COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a73b7af270cf42e6b11cc84eb5367f8f | COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>COc1ccc2[nH]c3cc(N)c4c(c3c2c1)C(=O)NC4=O | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)O)C(NC4=O)=O.CCN(CC)CC>>NC1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC | O=C(O)[c:10]1[cH:9][c:8]2[nH:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][c:15]3[c:14]2[c:13]2[c:12]1[C:20](=[O:21])[NH:19][C:17]2=[O:18].[N-]=[N+]=[N:11]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10]([NH2:11])[c:12]4[c:13]([c:14]3[c:15]2[cH:16]1)[C:17](=[O:18])[NH:19][C:20]4=[O... | COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COc1ccc2[nH]c3cc(N)c4c(c3c2c1)C(=O)NC4=O | null | null | C(Cl)Cl.FC(C(=O)O)(F)F.C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 39924ff2d9c9ee7280786b27206caefa37770f6a7ebe89e49621aadba8e2d062 | c4869b2e15981984090372c3f8725c0a3f1a2d8cd3a4eec59edd04a0d3b2a386 | O=C1NC(=O)c2c1ccc1[nH]c3ccccc3c21 | O-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O=P(-[N;H0;D2;+0:14]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[NH2;D1;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13... | 93.4 | [{"value": 93.0, "product": "NC1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "NC1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Diphenylphosphoryl azide (1.81 mL, 8.38 mmol) was added to a mixture of the 9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazole-4-carboxylic acid (2.55 g, 8.22 mmol), prepared as in example 4, and Et3N (1.17 mL, 8.38 mmol) in anhydrous t-butanol (300 mL) and the mixture was refluxed under an atmosphere of nit... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide | Primary amine | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HO- | C(Cl)Cl.FC(C(=O)O)(F)F.C(C)(C)(C)O | null | 1 | COc1ccc2[nH]c3cc(C(=O)O)c4c(c3c2c1)C(=O)NC4=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C(Cl)Cl.FC(C(=O)O)(F)F.C(C)(C)(C)O>COc1ccc2[nH]c3cc(N)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-821c8a69027f4a4db5de142cdbbeb36c | COc1ccc2[nH]c3cc(I)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | IC1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O | C[O:17][c:16]1[cH:15][cH:14][c:13]2[nH:12][c:11]3[cH:10][c:8]([I:9])[c:7]4[c:6]([c:20]3[c:19]2[cH:18]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8]([I:9])[cH:10][c:11]1[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[c:20]21 | COc1ccc2[nH]c3cc(I)c4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1ccc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89.5 | [{"value": 89.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Powdered 4-Iodo-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (0.50 g, 1.27 mmol) prepared as in example 6 was added in one portion to dry, freshly-prepared pyridine hydrochloride melt at 200° C. under a CaCl2 drying tube and the mixture was stirred at this temperature for 15 min. Water was added and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | O | null | 0.25 | COc1ccc2[nH]c3cc(I)c4c(c3c2c1)C(=O)NC4=O>O>O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6f215557f6b417b8f4a6b2176b51e11 | COc1ccc(B(O)O)cc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.OC=1C=C(C=CC1OC)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=C(C=C1)OC)O)C(NC4=O)=O | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([OH:28])[cH:26]1.I[c:7]1[cH:8][c:9]2[nH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[c:18]2[c:19]2[c:20]1[C:21](=[O:22])[NH:23][C:24]2=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[nH:10][c:11]4[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]4[c:18]3... | COc1ccc(B(O)O)cc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]... | 51 | [{"value": 51.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=C(C=C1)OC)O)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-hydroxy-4-methoxybenzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(3-hydroxy-4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (10) (1, Ar=3-hydroxy-4-methoxyphenyl) (5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | COc1ccc(B(O)O)cc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e8055b9779548408caffc318cb31728 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccsc1>>O=C1NC(=O)c2c1c(-c1ccsc1)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.S1C=C(C=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CSC=C1)C(NC4=O)=O | I[c:8]1[c:7]2[c:6]([c:24]3[c:15]([cH:14]1)[nH:16][c:17]1[cH:18][cH:19][c:20]([OH:21])[cH:22][c:23]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB(O)[c:9]1[cH:10][cH:11][s:12][cH:13]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][s:12][cH:13]1)[cH:14][c:15]1[nH:16][c:17]3[cH:18][cH:19][c:20]([OH:21])[cH:... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccsc1 | O=C1NC(=O)c2c1c(-c1ccsc1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a1a7a8847b0c461023b62c24cf856a544fb996be85692f300fc8c53d05effc7f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccsc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[#16;a:17]:[c:18]:1>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14]3:[c:15]:[c:16]:[#... | 74 | [{"value": 74.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CSC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-thienylboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (12) (I, Ar=3-thienyl) in a 74% yield; mp 247° C. (dec). 1H NMR δ [(CD3)2S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccsc1 | c1ccsc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccsc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccsc1>>O=C1NC(=O)c2c1c(-c1ccsc1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9a2e3ba2de040a58a6377e05c1dc1ef | Nc1cccc(B(O)O)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Nc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.NC=1C=C(C=CC1)B(O)O>>NC=1C=C(C=CC1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([NH2:1])[cH:26]1.I[c:7]1[cH:8][c:9]2[nH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[c:18]2[c:19]2[c:20]1[C:21](=[O:22])[NH:23][C:24]2=[O:25]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[nH:10][c:11]4[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]4[c:18]3[c:19]3[c:20]... | Nc1cccc(B(O)O)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | Nc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]... | 62 | [{"value": 62.0, "product": "NC=1C=C(C=CC1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-aminobenzeneboronic acid according to the procedure described in example 8 gave 4-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (15) (I, Ar=3-aminophenyl) in a 62% yield; mp 279–284° C. 1H NMR ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | Nc1cccc(B(O)O)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Nc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03f61ac48ef24891b73944c38c052aba | CC1(C)OB(c2ccc(N)cc2)OC1(C)C.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Nc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.CC1(OB(OC1(C)C)C1=CC=C(C=C1)N)C>>NC1=CC=C(C=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | CC1(C)OB([c:5]2[cH:4][cH:3][c:2]([NH2:1])[cH:26][cH:25]2)OC1(C)C.I[c:6]1[cH:7][c:8]2[nH:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[c:17]2[c:18]2[c:19]1[C:20](=[O:21])[NH:22][C:23]2=[O:24]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]3[nH:9][c:10]4[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]4[c:17]3[c:18]3[... | CC1(C)OB(c2ccc(N)cc2)OC1(C)C.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | Nc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 8bda9424ac37bc14d021ea22ccb1f0405d87de0d8b7436d440519f7edbbcb3d9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[#7;a:9]:[c:10]):[c:11]:[c:12]2:[c:13]:1-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17]-2=[O;D1;H0:18]>>[O;D1;H0:15]=[C:14]1-[#7:16]-[C:17](=[O;D1;H0:18])-[c:12]2:[c:11]:[c:8](:[#7;a:9]:[c:10]):[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](... | 57 | [{"value": 57.0, "product": "NC1=CC=C(C=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as in example 7 with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine according to the procedure described in example 8 gave 4-(4-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (16) (I, Ar=4-aminophenyl) in a 57%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | CC1(C)OB(c2ccc(N)cc2)OC1(C)C.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Nc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3cbe4f73481439a9addb114abecb359 | Cc1cccc(C)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Cc1cccc(C)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.CC1=C(C(=CC=C1)C)B(O)O>>CC1=C(C(=CC=C1)C)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | OB(O)[c:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH3:7].I[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[c:20]2[c:21]2[c:22]1[C:23](=[O:24])[NH:25][C:26]2=[O:27]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1-[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:1... | Cc1cccc(C)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | Cc1cccc(C)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15](-[C;D1;H3:16]):[c:17]):[c:18](-[C;D1;H3:19]):[c:20]>>[C;D1;H3:16]-[c:15](:[c:17]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9... | 62 | [{"value": 62.0, "product": "CC1=C(C(=CC=C1)C)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2,6-dimethylbenzeneboronic acid according to the procedure described in example 8 gave 4-(2,6-dimethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (17) (I, Ar=2,6-dimethylphenyl) in a 62% yield; mp 230–... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | Cc1cccc(C)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>Cc1cccc(C)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23f300f9fcb1453a9803c071809cca00 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccc(Cl)c1Cl>>O=C1NC(=O)c2c1c(-c1cccc(Cl)c1Cl)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.ClC1=C(C=CC=C1Cl)B(O)O>>ClC1=C(C=CC=C1Cl)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | I[c:8]1[c:7]2[c:6]([c:27]3[c:18]([cH:17]1)[nH:19][c:20]1[cH:21][cH:22][c:23]([OH:24])[cH:25][c:26]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB(O)[c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]1[Cl:16]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]1[Cl:16])[cH:17][c:18]1[nH... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccc(Cl)c1Cl | O=C1NC(=O)c2c1c(-c1cccc(Cl)c1Cl)cc1[nH]c3ccc(O)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5077d941385ca337094dfabfe694a06b4918785ac792f47943aa8f1333de6a69 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[Cl;D1;H0:18]):[c:19]>>[Cl;D1;H0:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:1... | 27 | [{"value": 27.0, "product": "ClC1=C(C=CC=C1Cl)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2,3-dichlorobenzeneboronic acid according to the procedure described in example 8 gave 4-(2,3-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (18) (I, Ar=2,3-dichlorophenyl) in a yield 27%; mp 233–... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccc(Cl)c1Cl>>O=C1NC(=O)c2c1c(-c1cccc(Cl)c1Cl)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85df1732c626402a8b775bd55215bcb2 | COc1cccc(OC)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cccc(OC)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.COC1=C(C(=CC=C1)OC)B(O)O>>COC1=C(C(=CC=C1)OC)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | OB(O)[c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[O:8][CH3:9].I[c:11]1[cH:12][c:13]2[nH:14][c:15]3[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]3[c:22]2[c:23]2[c:24]1[C:25](=[O:26])[NH:27][C:28]2=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH3:9])[c:10]1-[c:11]1[cH:12][c:13]2[nH:14][c:15]3[cH:16][cH:17][c... | COc1cccc(OC)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1cccc(OC)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15](-[#8:16]):[c:17]):[c:18](-[#8:19]):[c:20]>>[#8:16]-[c:15](:[c:17]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10]... | 43 | [{"value": 43.0, "product": "COC1=C(C(=CC=C1)OC)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2,6-dimethoxybenzeneboronic acid according to the procedure described in example 8 gave 4-(2,6-dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (19) (I, Ar=2,6-dimethoxyphenyl) in a 43% yield; mp 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | COc1cccc(OC)c1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cccc(OC)c1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8595786c5434a588cfc7acc7176f917 | COc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.COC1=C(C=CC=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)OC)C(NC4=O)=O | OB(O)[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.I[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[c:20]2[c:21]2[c:22]1[C:23](=[O:24])[NH:25][C:26]2=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[... | COc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[#8:18]):[c:19]>>[#8:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-... | 75 | [{"value": 75.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)OC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-methoxybenzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (20) (I, Ar=2-methoxyphenyl) in a 75% yield, mp 216° C. 1H NM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | COc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5a515491f4e47feb6dde98846db0141 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OCc1ccc(B(O)O)cc1>>O=C1NC(=O)c2c1c(-c1ccc(CO)cc1)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.OCC1=CC=C(C=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=C1)CO)C(NC4=O)=O | I[c:8]1[c:7]2[c:6]([c:27]3[c:18]([cH:17]1)[nH:19][c:20]1[cH:21][cH:22][c:23]([OH:24])[cH:25][c:26]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB(O)[c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16]1)[cH:17][c:18]... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OCc1ccc(B(O)O)cc1 | O=C1NC(=O)c2c1c(-c1ccc(CO)cc1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5077d941385ca337094dfabfe694a06b4918785ac792f47943aa8f1333de6a69 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]... | 34 | [{"value": 34.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=C1)CO)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 4-hydroxymethylbenzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(4-hydroxymethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (21) (I, Ar=4-hydroxymethylphenyl) in a 34% yield... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OCc1ccc(B(O)O)cc1>>O=C1NC(=O)c2c1c(-c1ccc(CO)cc1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28d9d76d2d9f4954aa1e97b069f520f3 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccccc1C(F)(F)F>>O=C1NC(=O)c2c1c(-c1ccccc1C(F)(F)F)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.FC(C1=C(C=CC=C1)B(O)O)(F)F>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)C(F)(F)F)C(NC4=O)=O | I[c:8]1[c:7]2[c:6]([c:29]3[c:20]([cH:19]1)[nH:21][c:22]1[cH:23][cH:24][c:25]([OH:26])[cH:27][c:28]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccccc1C(F)(F)F | O=C1NC(=O)c2c1c(-c1ccccc1C(F)(F)F)cc1[nH]c3ccc(O)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5077d941385ca337094dfabfe694a06b4918785ac792f47943aa8f1333de6a69 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[C:18](-[F;D1;H0:19])(-[F;D1;H0:20])-[F;D1;H0:21]):[c:22]>>[F;D1;H0:19]-[C:18](-[F;D1;H0:20])(-[F;D1;H0:21])-[c:17](:[c:22]):[c;H0;D3;+0:14](-[c;H0;D3;+0... | 47 | [{"value": 47.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)C(F)(F)F)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-trifluoromethylbenzeneboronic acid according to the procedure described in example 8 gave 9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (22) (I, Ar=2-trifluoromethylphenyl) in a 47%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1ccccc1C(F)(F)F>>O=C1NC(=O)c2c1c(-c1ccccc1C(F)(F)F)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d65fb38e6e741e9922297145075bdcd | COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)ccc1O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.COC1=C(C=CC(=C1)B1OC(C(O1)(C)C)(C)C)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=C(C=C1)O)OC)C(NC4=O)=O | CC1(C)OB([c:5]2[cH:4][c:3]([O:2][CH3:1])[c:27]([OH:28])[cH:26][cH:25]2)OC1(C)C.I[c:6]1[cH:7][c:8]2[nH:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[c:17]2[c:18]2[c:19]1[C:20](=[O:21])[NH:22][C:23]2=[O:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]3[nH:9][c:10]4[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]4[c... | COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1cc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)ccc1O | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 8bda9424ac37bc14d021ea22ccb1f0405d87de0d8b7436d440519f7edbbcb3d9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[#7;a:9]:[c:10]):[c:11]:[c:12]2:[c:13]:1-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17]-2=[O;D1;H0:18]>>[O;D1;H0:15]=[C:14]1-[#7:16]-[C:17](=[O;D1;H0:18])-[c:12]2:[c:11]:[c:8](:[#7;a:9]:[c:10]):[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](... | 58 | [{"value": 58.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=C(C=C1)O)OC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol according to the procedure described in example 8 gave 9-hydroxy-4-(4-hydroxy-3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (23) (I, Ar=4-hy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d557bcc8372498786e80538b61d2742 | CCc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>CCc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.C(C)C1=C(C=CC=C1)B(O)O>>C(C)C1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | OB(O)[c:8]1[c:3]([CH2:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.I[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[c:20]2[c:21]2[c:22]1[C:23](=[O:24])[NH:25][C:26]2=[O:27]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:1... | CCc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | CCc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[C:18]):[c:19]>>[C:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C... | 69 | [{"value": 69.0, "product": "C(C)C1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-ethylbenzeneboronic acid according to the procedure described in example 8 gave 4-(2-Ethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (501) (I; Ar=2-ethylphenyl) in a 69% yield; mp (MeOH/CH2Cl2/hexan... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | CCc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>CCc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-393318a5d3624563b2558d3147430d5f | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB1OCc2ccccc21>>O=C1NC(=O)c2c1c(-c1ccccc1CO)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.B1(C2=CC=CC=C2CO1)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)CO)C(NC4=O)=O | I[c:8]1[c:7]2[c:6]([c:27]3[c:18]([cH:17]1)[nH:19][c:20]1[cH:21][cH:22][c:23]([OH:24])[cH:25][c:26]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15][O:16]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[CH2:15][OH:16])[cH:17][c:18]1[nH:1... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB1OCc2ccccc21 | O=C1NC(=O)c2c1c(-c1ccccc1CO)cc1[nH]c3ccc(O)cc3c21 | null | null | C1CCOC1.C(Cl)Cl.CCCCCC | C-C Coupling | OtherReaction | 7933f45302c2f4289af5b5db3d516047a834dc4b519d4b8a8c0e2ab1e8bab367 | a12ca276bb8a0b38a6f1d74ded83195a142850462b233d3fad29abdedede9300 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B1-[O;H0;D2;+0:14]-[C:15]-[c:16](:[c:17]):[c;H0;D3;+0:18]-1:[c:19]:[c:20]>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:18](... | 57 | [{"value": 57.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)CO)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-(hydroxymethyl)benzeneboronic acid cyclic monoester according to the procedure described in example 8 gave 9-Hydroxy-4-[2-(hydroxymethyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (503) (I; Ar=2-(hydroxymethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary alcohol | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.B1OCc2ccccc21 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | I-.B | C1CCOC1.C(Cl)Cl.CCCCCC | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB1OCc2ccccc21>C1CCOC1.C(Cl)Cl.CCCCCC>O=C1NC(=O)c2c1c(-c1ccccc1CO)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20d287d6f64d4e9ea73641b7925232f5 | CCOc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>CCOc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.C(C)OC1=C(C=CC=C1)B(O)O>>C(C)OC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | OB(O)[c:9]1[c:4]([O:3][CH2:2][CH3:1])[cH:5][cH:6][cH:7][cH:8]1.I[c:10]1[cH:11][c:12]2[nH:13][c:14]3[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]3[c:21]2[c:22]2[c:23]1[C:24](=[O:25])[NH:26][C:27]2=[O:28]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][c:12]2[nH:13][c:14]3[cH:15][cH:16][c:17]([OH:18]... | CCOc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | CCOc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[#8:18]):[c:19]>>[#8:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-... | 74 | [{"value": 74.0, "product": "C(C)OC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-ethoxybenzeneboronic acid according to the procedure described in example 8 gave 4-(2-ethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (504) (I; Ar=2-ethoxyphenyl) in a 74% yield; mp (THF/CH2Cl2/hex... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | CCOc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>CCOc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-afa00cd55c8c4518af21430b59e7bcd7 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccs1>>O=C1NC(=O)c2c1c(-c1cccs1)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.S1C(=CC=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C=1SC=CC1)C(NC4=O)=O | I[c:8]1[c:7]2[c:6]([c:24]3[c:15]([cH:14]1)[nH:16][c:17]1[cH:18][cH:19][c:20]([OH:21])[cH:22][c:23]13)[C:4](=[O:5])[NH:3][C:2]2=[O:1].OB(O)[c:9]1[cH:10][cH:11][cH:12][s:13]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][s:13]1)[cH:14][c:15]1[nH:16][c:17]3[cH:18][cH:19][c:20]([OH:21])[cH:... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccs1 | O=C1NC(=O)c2c1c(-c1cccs1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | a1a7a8847b0c461023b62c24cf856a544fb996be85692f300fc8c53d05effc7f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1cccs1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14]3:[#16;a:15]:[c:16... | 69 | [{"value": 69.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C=1SC=CC1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as in example 7 with 2-thiopheneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(2-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (505) (1; Ar=2-thienyl) in a 69% yield; mp (THF/CH2Cl2/hexane) 179–184° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccsc1 | c1ccsc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccsc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.OB(O)c1cccs1>>O=C1NC(=O)c2c1c(-c1cccs1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6364c659f35d44cfb4db8b5ef35cce51 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1cccc(B(O)O)c1>>O=Cc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.C(=O)C=1C=C(C=CC1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C=1C=C(C=O)C=CC1)C(NC4=O)=O | I[c:8]1[cH:9][c:10]2[nH:11][c:12]3[cH:13][cH:14][c:15]([OH:16])[cH:17][c:18]3[c:19]2[c:20]2[c:21]1[C:22](=[O:23])[NH:24][C:25]2=[O:26].OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:27]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[nH:11][c:12]4[cH:13][cH:14][c:15]([OH:16])[cH:17][c:18]4[c:19]3[... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1cccc(B(O)O)c1 | O=Cc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]-[C:17]=[O;D1;H0:18]):[c:19]:[c:20]>>[O;D1;H0:18]=[C:17]-[c:16]:[c:15]:[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O... | 69 | [{"value": 69.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C=1C=C(C=O)C=CC1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-formylbenzeneboronic acid according to the procedure described in example 8 gave 3-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde (507) (I; Ar=3-formylphenyl) in a 69% yield; mp (T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1cccc(B(O)O)c1>>O=Cc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98f64418f5764e489d7aefe7baf82a82 | CSc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | CO.C(Cl)Cl.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.CSC1=C(C=CC=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)SC)C(NC4=O)=O | OB(O)[c:8]1[c:3]([S:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.I[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[c:20]2[c:21]2[c:22]1[C:23](=[O:24])[NH:25][C:26]2=[O:27]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]3[... | CSc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | CCCCCC | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[#16:18]):[c:19]>>[#16:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11... | 72 | [{"value": 72.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)SC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-(methylthio)benzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (508) (I; Ar=2-(methylsulfanyl)phenyl) in a 72%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | CCCCCC | null | null | CSc1ccccc1B(O)O.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>CCCCCC>CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34dbcb15aab6471fb2c36dc4fe0fdbfe | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1ccc(B(O)O)cc1>>O=Cc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.C(=O)C1=CC=C(C=C1)B(O)O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=O)C=C1)C(NC4=O)=O | I[c:7]1[cH:8][c:9]2[nH:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[c:18]2[c:19]2[c:20]1[C:21](=[O:22])[NH:23][C:24]2=[O:25].OB(O)[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:27][cH:26]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[nH:10][c:11]4[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]4[c:18]3[c:19]3[... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1ccc(B(O)O)cc1 | O=Cc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 70d5a3e2a14b7a8a6f408abdf096adc826ce7afd950d871011a899decb4f2716 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[#7:11]-[C:12]-2=[O;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[O;D1;H0:10]=[C:9]1-[#7:11]-[C:12](=[O;D1;H0:13])-[c:7]2:[c:6]:[c:3](:[#7;a:4]:[c:5]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]... | 52 | [{"value": 52.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=O)C=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 4-formylbenzeneboronic acid according to the procedure described in example 8 gave 4-(9-hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde (509) (I; Ar=4-formylphenyl) in a 52% yield; mp (T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI.B | null | null | null | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=Cc1ccc(B(O)O)cc1>>O=Cc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ca742a96a8a47d7846b28718434176e | CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=S(=O)(c1ccccc1)N1OC1c1ccccc1>>CS(=O)c1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)SC)C(NC4=O)=O.C1(=CC=CC=C1)S(=O)(=O)N1OC1C1=CC=CC=C1>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)S(=O)C)C(NC4=O)=O | [CH3:1][S:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][c:12]2[nH:13][c:14]3[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]3[c:21]2[c:22]2[c:23]1[C:24](=[O:25])[NH:26][C:27]2=[O:28].O=S(=O)(c1ccccc1)N1C(c2ccccc2)[O:3]1>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][c:12]2[nH:13][c:14]3[cH:1... | CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=S(=O)(c1ccccc1)N1OC1c1ccccc1 | CS(=O)c1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | null | C1CCOC1 | Oxidation | Sulfanyl to sulfinyl_sulfonyl | 7bfca6b2d91e829a54b6d67114560b32481fd75fada7e7003fe3ba4671c4f594 | 1135622d483cd7dfdd7dfec13000528bd6a6736fbb03e0ce07273fb1059c002d | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O=S(=O)(-N1-[O;H0;D2;+0:1]-C-1-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | 86 | [{"value": 86.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)S(=O)C)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2.5 | HOUR | A mixture of the 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (508) (34.5 mg, 0.092 mmol), prepared according to example 25, and 2-phenylsulfonyl-3-phenyloxaziridine (Davis reagent) (26.5 mg, 0.102 mmol) in THF (10 mL) was stirred at 20° C. for 2.5 h, then adsorbed directly onto silica... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Monosulfide | Sulfoxide | c1ccccc1.c1ccccc1.C1NO1 | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HO- | C1CCOC1 | 20 | 2.5 | CSc1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=S(=O)(c1ccccc1)N1OC1c1ccccc1>C1CCOC1>CS(=O)c1ccccc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d320a739e89434084f2648f376f549b | COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1>>O=C1NC(=O)c2c1c(-c1ccc(O)cc1)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=C1)OC)C(NC4=O)=O.B(Br)(Br)Br.COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=C1)O)C(NC4=O)=O | C[O:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[c:7]3[c:6]([c:26]4[c:17]([cH:16]2)[nH:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:24][c:25]24)[C:4](=[O:5])[NH:3][C:2]3=[O:1])[cH:15][cH:14]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1)[cH:16][c:17]1[nH:18][c:19]3[cH:20]... | COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1 | O=C1NC(=O)c2c1c(-c1ccc(O)cc1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=C(C=C1)O)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9-hydroxy-4-(4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as decribed in example 34 with BBr3 using the procedure described in example 80 of Scheme 2 gave 9-Hydroxy-4-(4-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (24) (I, Ar=4-hydroxyphenyl) in a 92% yield; mp 230° C. (d... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | null | null | null | COc1ccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)cc1>>O=C1NC(=O)c2c1c(-c1ccc(O)cc1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b68b64895da645b296feebd4e1aed28a | COc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1>>O=C1NC(=O)c2c1c(-c1cccc(O)c1)cc1[nH]c3ccc(O)cc3c21 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=CC=C1)OC)C(NC4=O)=O.B(Br)(Br)Br.COC1=CC=2C=3C4C(C(CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=CC=C1)O)C(NC4=O)=O | C[O:14][c:13]1[cH:12][cH:11][cH:10][c:9](-[c:8]2[c:7]3[c:6]([c:26]4[c:17]([cH:16]2)[nH:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:24][c:25]24)[C:4](=[O:5])[NH:3][C:2]3=[O:1])[cH:15]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:15]1)[cH:16][c:17]1[nH:18][c:19]3[cH:20]... | COc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1 | O=C1NC(=O)c2c1c(-c1cccc(O)c1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 88 | [{"value": 88.0, "product": "OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC(=CC=C1)O)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 9-Hydroxy-4-(3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (prepared as decribed in example 35) was reacted with BBr3 using the procedure described in the proceedure described in example 80 of Scheme 2 to give 9-hydroxy-4-(3-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (25) (I, Ar=3-hydroxyphenyl) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | null | null | null | COc1cccc(-c2cc3[nH]c4ccc(O)cc4c3c3c2C(=O)NC3=O)c1>>O=C1NC(=O)c2c1c(-c1cccc(O)c1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c6ae40223f9402a82a15bbacc3512f7 | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>>COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCCO[Si](C)(C)C(C)(C)C | [Si](C)(C)(C(C)(C)C)OCCCBr.[H-].[Na+].ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)OC>>[Si](C)(C)(C(C)(C)C)OCCCN1C(=CC2=CC(=CC=C12)OC)C=CC1=C(C=CC=C1)Cl | Br[CH2:21][CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[nH:20]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[cH... | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCCO[Si](C)(C)C(C)(C)C | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]-[C:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:7](-[C:6]=[C:5]-[c:4]):[c:8]:[c:9]:[c:10]:1:[c:11] | null | [] | null | null | 5 | MINUTE | Sodium hydride (1.05 g of a 50% dispersion in mineral oil, 0.022 mol) was added to a solution of the 2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole prepared according to example 37 (4.13 g, 0.014 mol) in DMF (30 mL) and the solution was stirred at room temperature for 5 min. 3-Bromopropyl tert-butyl(dimethyl)silyl e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | O.CN(C)C=O | null | 0.083333 | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>O.CN(C)C=O>COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCCO[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a94facf86c9243e5a21ad99eb2b723d6 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO[Si](C)(C)C(C)(C)C)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O | Cl.[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)OC>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO | CC(C)(C)[Si](C)(C)[O:26][CH2:25][CH2:24][CH2:23][n:22]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]21)[C:27](=[O:28])[NH:29][C:30]3=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO[Si](C)(C)C(C)(C)C)C(=O)NC3=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O | null | null | C1CCOC1.CO | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 88 | [{"value": 88.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3N HCl (50 mL) was added to a solution of 6-(3-{[tert-Butyl(dimethyl) silyl]oxy}propyl)-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (4.87 g, 8.85 mmol) prepared according to example 39 in 1:1 THF/methanol (200 mL). After stirring at room temperature for 2 h most of the solvents were removed in ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | C1CCOC1.CO | null | 2 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO[Si](C)(C)C(C)(C)C)C(=O)NC3=O>C1CCOC1.CO>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edee55bf520b4f37adbc078a7c1a78ec | BrCCOC1CCCCO1.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>>COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO | Cl.ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)OC.O1C(CCCC1)OCCBr>>ClC1=C(C=CC=C1)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO | Br[CH2:21][CH2:22][O:23]C1CCCCO1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[nH:20]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[n:20]2[CH2:21][CH2:2... | BrCCOC1CCCCO1.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5bdb109ced449a92be1a7b3e8be3085307f898894988c9c549ac181330363d9e | 99bb6d9234ad4c68b21abd97484a68f1ed0a9dfeb0ccd83bf5a372d494646f20 | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[c:4]-[C:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:7](-[C:6]=[C:5]-[c:4]):[c:8]:[c:9]:[c:10]:1:[c:11] | 86 | [{"value": 86.0, "product": "ClC1=C(C=CC=C1)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Alkylation of 2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole (27) prepared according to example 37 with 2-bromoethyl tetrahydro-2H-pyran-2-yl ether using the procedure described in example 38 followed by reaction of the crude product with 2N HCl in methanol gave 2-{2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether | Primary alcohol | C1CCOCC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | CO | null | null | BrCCOC1CCCCO1.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>CO>COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c0e1b6db3f34a84be1395fb66bcc132 | COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO.O=C1C=CC(=O)N1>>O=C1NC(=O)C2CCC3Nc4ccccc4C3=C12 | ClC1=C(C=CC=C1)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO.ClC1=C(C=CC=C1)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO.C1(C=CC(N1)=O)=O>>C1(NC(C2CCC3NC=4C=CC=CC4C3=C21)=O)=O | COc1cc[c:11]2[n:10](CCO)[c:9]([CH:8]=[CH:7]c3c(Cl)[cH:15][cH:14][cH:13][cH:12]3)[cH:17][c:16]2c1.[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]=[CH:18]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]2[CH2:7][CH2:8][CH:9]3[NH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[C:17]3=[C:18]12 | COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO.O=C1C=CC(=O)N1 | O=C1NC(=O)C2CCC3Nc4ccccc4C3=C12 | null | null | null | C-C Coupling | OtherReaction | 6ea8693a035721c621b8ffd6927e2a72e294d40066a73c923c4d43c3edc5c127 | 3717a5f9f255935216c0b4fe9e974e287b2cbdd9c238e66256a035f6209d3f6f | O=C1NC(=O)C2CCC3Nc4ccccc4C3=C12 | C-O-c1:c:c:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2](:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[CH;D2;+0:5]=[CH;D2;+0:6]-c3:[cH;D2;+0:7]:[c:8]:[c:9]:[cH;D2;+0:10]:c:3-Cl):[n;H0;D3;+0:11]:2-C-C-O):c:1.[O;D1;H0:12]=[C:13]1-[#7:14]-[C:15](=[O;D1;H0:16])-[CH;D2;+0:17]=[CH;D2;+0:18]-1>>[O;D1;H0:12]=[C:13]1-[#7:14]-[C:15](=[O;D1;H0:16])-[CH;D3;+0:... | 79 | [{"value": 79.0, "product": "C1(NC(C2CCC3NC=4C=CC=CC4C3=C21)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 2-{2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}ethanol (III; Ar=2-chlorophenyl, R10═CH2CH2OH) (44) prepared according to example 41 with maleimide according to the procedure described in example 68 gave 4-(2-Chlorophenyl)-6-(2-hydroxyethyl)-9-methoxy-4,5,6,1 Oc-tetrahydropyrrolo[3,4-c]carbazole-1,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary alcohol | Secondary amine | c1cc2ccccc2[nH]1.c1ccccc1.C1=CCNC1 | c1ccc2c(c1)NC1CCC3CNCC3=C21 | c1ccc2c(c1)NC1CCC3CNCC3=C21 | HCl | null | null | null | COc1ccc2c(c1)cc(C=Cc1ccccc1Cl)n2CCO.O=C1C=CC(=O)N1>>O=C1NC(=O)C2CCC3Nc4ccccc4C3=C12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f1b9ba14d3e54230a51534c4c554d328 | COc1ccc2c(c1)c1c(n2CCO)CC(c2ccccc2Cl)C2C(=O)NC(=O)C12>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O | ClC1=C(C=CC=C1)C1CC=2N(C=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC)CCO>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:21]([n:22]2[CH2:23][CH2:24][OH:25])[CH2:20][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[CH:11]2[CH:10]1[C:29](=[O:30])[NH:28][C:26]2=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16]... | COc1ccc2c(c1)c1c(n2CCO)CC(c2ccccc2Cl)C2C(=O)NC(=O)C12 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O | null | O=[Mn]=O | null | Oxidation | OtherReaction | 4257b1652504b28bd39a91b6e2753238ea04159028d308128fe1ebd11b4268d4 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[c:6]:1-[CH2;D2;+0:7]-[CH;D3;+0:8](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[Cl;D1;H0:13]):[c:14])-[CH;D3;+0:15]1-[C:16](=[O;D1;H0:17])-[#7:18]-[C:19](=[O;D1;H0:20])-[CH;D3;+0:21]-1-2>>[C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[c:6]:1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:9](:[c:10]:[c:11]... | 72 | [{"value": 72.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4-(2-Chlorophenyl)-6-(2-hydroxyethyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H, 3aH)-dione (IV; Ar=2-chlorophenyl, R10═CH2CH2OH) (45) prepared according to example 42 was reacted with MnO2 using the procedure described in example 79 except that the reaction time was 18 h gave 4-(2-Chlorophenyl)-6-(2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | O=[Mn]=O | null | 18 | COc1ccc2c(c1)c1c(n2CCO)CC(c2ccccc2Cl)C2C(=O)NC(=O)C12>O=[Mn]=O>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a666bfb512464351b53fc074eea6a230 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCO | B(Br)(Br)Br.ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO.ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCO | C[O:22][c:21]1[cH:20][c:19]2[c:18]3[c:6]4[c:7]([c:8](-[c:9]5[cH:10][cH:11][cH:12][cH:13][c:14]5[Cl:15])[cH:16][c:17]3[n:26]([CH2:27][CH2:28][OH:29])[c:25]2[cH:24][cH:23]1)[C:2](=[O:1])[NH:3][C:4]4=[O:5]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15])[cH:16][c:17]1[c:... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCO | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 4-(2-Chlorophenyl)-6-(2-hydroxyethyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chlorophenyl, R10═CH2CH2OH) (46) prepared according to example 43 with BBr3 using the procedure described in example 80 gave the 4-(2-Chlorophenyl)-6-(2-hydroxyethyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCO)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3b23bced8d541d3b1f3575920f404ea | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3 | COC=1C=C2C=C(NC2=CC1)C=CC1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-].C1(C=CC(N1)=O)=O>>[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([CH:32]=[CH:19][c:20]3[cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]3)[cH:9][c:10]2[cH:11]1.[CH:12]1=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[CH:12]1[C:13](=[O:... | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.O=C1C=CC(=O)N1 | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3 | null | null | null | C-C Coupling | OtherReaction | f4dfd9249675065a438272ee31ebbe56b42434dbbe67b7314944f01b1550fb32 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11](-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16]):[#7;a:17]:[c:18]:1:[c:19]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[c;H0;D3;+0:10]1:[c:9](:[c:8]):[c:18](:[c:19]):[#7;a:17]:... | 89 | [{"value": 89.0, "product": "[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 5-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole (II; Ar=3,5-dinitrophenyl) (40) prepared as described in example 46 with maleimide using the procedure described in example 69 gave 4-(3,5-Dinitrophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=3,5-dinitrophenyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccccc1.c1ccc2c3c([nH]c2c1)CCC1CNCC31 | null | null | null | null | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3 |
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