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-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e290b33ebd64195870254e393a6bf70 | CC(C)Oc1ccc(C(=O)O)cc1C#N.N[C@H](CCO)Cc1ccc(Br)cc1>>CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(Br)cc2)cc1C#N | C(C)(C)N(C(C)C)CC.Cl.N[C@H](CCO)CC1=CC=C(C=C1)Br.C(#N)C=1C=C(C(=O)O)C=CC1OC(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F>>BrC1=CC=C(C=C1)C[C@@H](CCO)NC(C1=CC(=C(C=C1)OC(C)C)C#N)=O | O[C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:25]([C:26]#[N:27])[cH:24]1)=[O:10].[NH2:11][C@H:12]([CH2:13][CH2:14][OH:15])[CH2:16][c:17]1[cH:18][cH:19][c:20]([Br:21])[cH:22][cH:23]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][C@H:12]([CH2:13][CH2:14][OH:15])[CH2:16][c:17]2[... | CC(C)Oc1ccc(C(=O)O)cc1C#N.N[C@H](CCO)Cc1ccc(Br)cc1 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(Br)cc2)cc1C#N | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78.7 | [{"value": 78.0, "product": "BrC1=CC=C(C=C1)C[C@@H](CCO)NC(C1=CC(=C(C=C1)OC(C)C)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "BrC1=CC=C(C=C1)C[C@@H](CCO)NC(C1=CC(=C(C=C1)OC(C)C)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a suspension of (3S)-3-Amino-4-(4-bromophenyl)-1-butanol hydrochloride (1.80 g, 6.42 mmol) in dry DMF (32 mL) was added N,N-diisopropylethyl amine (2.49 g, 19.3 mmol) and the resultant clear solution was stirred for 3 min. 3-Cyano-4-[(1-methylethyl)oxy]benzoic acid (1.45 g, 7.06 mmol) and HBTU (2.68 g, 7.06 mmol) we... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 0.05 | CC(C)Oc1ccc(C(=O)O)cc1C#N.N[C@H](CCO)Cc1ccc(Br)cc1>CN(C)C=O>CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(Br)cc2)cc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b4a8f3b0f7347b4a1f638591e81ba41 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(C(=O)CBr)cc2)cc1C#N.Cc1cccnc1N>>Cc1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 | C(=O)(O)[O-].[Na+].BrCC(=O)C1=CC=C(C=C1)C[C@@H](CCO)NC(C1=CC(=C(C=C1)OC(C)C)C#N)=O.NC1=NC=CC=C1C>>C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C=CC1OC(C)C | O=[C:8]([CH2:7]Br)[c:9]1[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][CH2:16][OH:17])[NH:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][c:24]([O:25][CH:26]([CH3:27])[CH3:28])[c:29]([C:30]#[N:31])[cH:32]2)[cH:33][cH:34]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:36]1[NH2:35]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c... | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(C(=O)CBr)cc2)cc1C#N.Cc1cccnc1N | Cc1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 | null | null | CC(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 70.3 | [{"value": 70.0, "product": "C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | To a solution of N-((1S)-1-{[4-(bromoacetyl)phenyl]methyl}-3-hydroxypropyl)-3-cyano-4-[(1-methylethyl)oxy]benzamide (300 mg, 0.634 mmol) in i-PrOH (6 mL) was added 2-amino-3-picoline (Aldrich, 69 mg, 0.634 mmol) followed by solid NaHCO3 (64 mg, 0.761 mmol). The resultant suspension was heated to 80° C. After 7 h, a maj... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | HBr | CC(C)O | null | 7 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(C(=O)CBr)cc2)cc1C#N.Cc1cccnc1N>CC(C)O>Cc1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0988497415649d58633ccc387509d59 | Nc1ncccc1C=O>>CC(O)c1cccnc1N | NC1=NC=CC=C1C=O.C1CCOC1.[O-][Mn](=O)(=O)=O.[K+]>>NC1=NC=CC=C1C(C)O | [CH:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[NH2:10]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[NH2:10] | Nc1ncccc1C=O | CC(O)c1cccnc1N | null | null | null | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccncc1 | [N;D1;H2:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]>>[C;D1;H3:9]-[CH;D3;+0:6](-[OH;D1;+0:7])-[c:5](:[c:8]):[c:2](-[N;D1;H2:1]):[#7;a:3]:[c:4] | null | [] | null | null | null | null | To a dry flask (dried with a heat gun under argon purge) was added dry THF (400 mL) and MeLi-LiBr (137 mL of a 1.5 M solution in Et2O, 204.9 mmol) via cannula. This solution was cooled to −78° C. when a solution of 2-aminopyridine-3-carboxaldehyde (10.0 g, 82.0 mmol) in THF (150 mL) was added dropwise via a pressure eq... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccncc1 | Other | null | null | null | Nc1ncccc1C=O>>CC(O)c1cccnc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc631dfab8ca41659de32fe1acc8901c | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CCO)N(C(=O)[O-])C(C)(C)C)cc3)nc12>>CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | CC(C)(C)N(C([O-])=O)[C@H](CCO)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1.Cl.O1CCOCC1.C(C)(C)N(C(C)C)CC.ClC=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C>>ClC=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C | Fc1c(F)c(F)c(O[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:36]([Cl:37])[cH:35]2)=[O:10])c(F)c1F.CC(C)(C)[N:11](C(=O)[O-])[C@H:12]([CH2:13][CH2:14][OH:15])[CH2:16][c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][n:23]3[cH:24][cH:25][cH:26][c:27]([CH:28]([CH3:29])[OH:30])[c:31]3[n:32]2)[cH:33][cH:34]1>>[CH3:1]... | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CCO)N(C(=O)[O-])C(C)(C)C)cc3)nc12 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | null | null | O | Acylation | OtherReaction | 99c7e5ccb14cd05d201fc9d814902a93f26d22f6be437b04170d6760e6ca8897 | 42472522721b7f81fc665a4fc38a467af73eaadcae06dde15cdffe1a6c2c71eb | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | C-C(-C)(-C)-[N;H0;D3;+0:1](-C(=O)-[O-])-[C:2](-[C:3])-[C:4].F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]):c(-F):c:1-F>>[C:3]-[C:2](-[C:4])-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9] | 53 | [{"value": 53.0, "product": "ClC=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "ClC=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 1,1-dimethylethyl[(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate (1.08 g, 2.54 mmol) and 4M HCl in 1,4-dioxane (8.0 mL, 32 mmol) was stirred at room temperature for 30 minutes. The reaction was concentrated to dryness redissolved in DMF (25 mL), and to thi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carbamic acid.Ester | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HF | O | null | 0.5 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CCO)N(C(=O)[O-])C(C)(C)C)cc3)nc12>O>CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-478a448d2e5e45c7bb3668396804fe41 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CN4C(=O)c5ccccc5C4=O)N(C(=O)[O-])C(C)(C)C)cc3)nc12>>CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | CC(C)(C)N(C([O-])=O)[C@H](CN1C(C2=CC=CC=C2C1=O)=O)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1.Cl.O1CCOCC1.C(C)(C)N(C(C)C)CC.ClC=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C>>ClC=1C=C(C(=O)N[C@H](CN2C(C3=CC=CC=C3C2=O)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C | Fc1c(F)c(F)c(O[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:45]([Cl:46])[cH:44]2)=[O:10])c(F)c1F.CC(C)(C)[N:11](C(=O)[O-])[C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][n:20]3[cH:21][cH:22][cH:23][c:24]([CH:25]([CH3:26])[OH:27])[c:28]3[n:29]2)[cH:30][cH:31]1)[CH2:32][N:33]1[C:34](=[O:35])[... | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CN4C(=O)c5ccccc5C4=O)N(C(=O)[O-])C(C)(C)C)cc3)nc12 | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | null | null | O | Acylation | OtherReaction | 99c7e5ccb14cd05d201fc9d814902a93f26d22f6be437b04170d6760e6ca8897 | 42472522721b7f81fc665a4fc38a467af73eaadcae06dde15cdffe1a6c2c71eb | O=C(N[C@@H](Cc1ccc(-c2cn3ccccc3n2)cc1)CN1C(=O)c2ccccc2C1=O)c1ccccc1 | C-C(-C)(-C)-[N;H0;D3;+0:1](-C(=O)-[O-])-[C:2](-[C:3])-[C:4].F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]):c(-F):c:1-F>>[C:3]-[C:2](-[C:4])-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9] | 100 | [{"value": 100.0, "product": "ClC=1C=C(C(=O)N[C@H](CN2C(C3=CC=CC=C3C2=O)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "ClC=1C=C(C(=O)N[C@H](CN2C(C3=CC=CC=C3C2=O)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "CALCU... | null | null | 45 | MINUTE | A mixture of 1,1-dimethylethyl[(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]carbamate (1.79 g, 3.31 mmol) and 4 M HCl in 1,4-dioxane (20 mL, 80 mmol) was stirred at room temperature for 45 minutes. The reaction was concentrated to dryness and re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carbamic acid.Ester | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccc2c(c1)C[NH]C2 | HF | O | null | 0.75 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.CC(O)c1cccn2cc(-c3ccc(C[C@@H](CN4C(=O)c5ccccc5C4=O)N(C(=O)[O-])C(C)(C)C)cc3)nc12>O>CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13830506cd3842dfbbdbd14368e7f92f | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl>>CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | ClC=1C=C(C(=O)N[C@H](CN2C(C3=CC=CC=C3C2=O)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C.O.NN>>NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O | O=C1c2ccccc2C(=O)[N:14]1[CH2:13][C@@H:12]([NH:11][C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:35]([Cl:36])[cH:34]1)=[O:10])[CH2:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][n:22]3[cH:23][cH:24][cH:25][c:26]([CH:27]([CH3:28])[OH:29])[c:30]3[n:31]2)[cH:32][cH:33]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6... | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 100 | [{"value": 100.0, "product": "NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fals... | 57 | CELSIUS | null | null | A mixture of 3-chloro-N-[(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-4-[(1-methylethyl)oxy]benzamide (2.10 g, 3.30 mmol) and hydrazine monohydrate (0.83 g, 16.5 mmol) in ethanol (30 mL) was heated at 57° C. overnight. The reaction was cooled, ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | C(C)O | 57 | null | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl>C(C)O>CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b356287b5efa4f85b4f2763401f046a9 | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl.CN(C)CC(=O)O>>CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)CN(C)C)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C(C)O)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O.CCN=C=NCCCN(C)C.C(C)(C)N(C(C)C)CC.CN(CC(=O)O)C>>ClC=1C=C(C(=O)N[C@H](CNC(CN(C)C)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][C@H:12]([CH2:13][NH2:14])[CH2:21][c:22]2[cH:23][cH:24][c:25](-[c:26]3[cH:27][n:28]4[cH:29][cH:30][cH:31][c:32]([CH:33]([CH3:34])[OH:35])[c:36]4[n:37]3)[cH:38][cH:39]2)[cH:40][c:41]1[Cl:42].O[C:15](=[O:16])[CH2:17][N:18]([CH3:19])[CH3:20]>>[CH3:1][... | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl.CN(C)CC(=O)O | CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)CN(C)C)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl | null | null | O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 48.3 | [{"value": 48.0, "product": "ClC=1C=C(C(=O)N[C@H](CNC(CN(C)C)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "ClC=1C=C(C(=O)N[C@H](CNC(CN(C)C)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C(C)O)C2)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 8 | HOUR | A mixture of N-[(1S)-2-amino-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-3-chloro-4-[(1-methylethyl)oxy]benzamide (0.912 g, 1.80 mmol), EDCI (0.69 g, 3.6 mmol), N,N-diisopropylethylamine (0.466 g, 3.6 mmol), and N,N-dimethylglycine (0.372 g, 3.6 mmol) in methylene chloride (17 mL) was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | O.C(Cl)Cl | null | 8 | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl.CN(C)CC(=O)O>O.C(Cl)Cl>CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)CN(C)C)Cc2ccc(-c3cn4cccc(C(C)O)c4n3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e45590cc49e643b99b114b7b14e81c1d | CC(C)(C)N(C(=O)[O-])[C@@H](Cc1ccc(-c2cn3cccc(Br)c3n2)cc1)CN1C(=O)c2ccccc2C1=O.CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl>>CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | C(C)(C)N(CC)C(C)C.CC(C)(C)N(C([O-])=O)[C@@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2Br)C1)CN1C(C2=CC=CC=C2C1=O)=O.Cl.ClC=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C>>BrC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)C[C@@H](CN2C(C1=CC=CC=C1C2=O)=O)NC(C2=CC(=C(C=C2)OC(C)C)Cl)=O | CC(C)(C)[N:11](C(=O)[O-])[C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][n:20]3[cH:21][cH:22][cH:23][c:24]([Br:25])[c:26]3[n:27]2)[cH:28][cH:29]1)[CH2:30][N:31]1[C:32](=[O:33])[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]2[C:40]1=[O:41].Fc1c(F)c(F)c(O[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[... | CC(C)(C)N(C(=O)[O-])[C@@H](Cc1ccc(-c2cn3cccc(Br)c3n2)cc1)CN1C(=O)c2ccccc2C1=O.CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | null | null | O1CCOCC1.C(C)(=O)OCC | Acylation | OtherReaction | 99c7e5ccb14cd05d201fc9d814902a93f26d22f6be437b04170d6760e6ca8897 | 42472522721b7f81fc665a4fc38a467af73eaadcae06dde15cdffe1a6c2c71eb | O=C(N[C@@H](Cc1ccc(-c2cn3ccccc3n2)cc1)CN1C(=O)c2ccccc2C1=O)c1ccccc1 | C-C(-C)(-C)-[N;H0;D3;+0:1](-C(=O)-[O-])-[C:2](-[C:3])-[C:4].F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]):c(-F):c:1-F>>[C:3]-[C:2](-[C:4])-[NH;D2;+0:1]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1,1-dimethylethyl{(1S)-2-[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2yl)methyl]ethyl)carbamate (3.5 mmol) and hydrogen chloride in 1,4-dioxane (20 mL, 4.0 M) was stirred for 1 h at RT. The reaction was concentrated to dryness and redissolved in N,N-dimethylformamid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carbamic acid.Ester | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1.c1ccc2c(c1)C[NH]C2 | HF | O1CCOCC1.C(C)(=O)OCC | null | null | CC(C)(C)N(C(=O)[O-])[C@@H](Cc1ccc(-c2cn3cccc(Br)c3n2)cc1)CN1C(=O)c2ccccc2C1=O.CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl>O1CCOCC1.C(C)(=O)OCC>CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae0b6e6c8e8a4274b8119ea5763f3b0d | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl>>CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl | BrC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)C[C@@H](CN2C(C1=CC=CC=C1C2=O)=O)NC(C2=CC(=C(C=C2)OC(C)C)Cl)=O.O.NN>>NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2Br)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O | O=C1c2ccccc2C(=O)[N:14]1[CH2:13][C@@H:12]([NH:11][C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:33]([Cl:34])[cH:32]1)=[O:10])[CH2:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][n:22]3[cH:23][cH:24][cH:25][c:26]([Br:27])[c:28]3[n:29]2)[cH:30][cH:31]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9... | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | 50 | CELSIUS | 18 | HOUR | To a solution of N-{(1S)-2-[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide (1.5 mmol) in ethanol (10 mL) was added hydrazine monohydrate (7.6 mmol). The reaction stirred for 18 h at 50° C. upon which a white precipitate form... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | C(C)O | 50 | 18 | CC(C)Oc1ccc(C(=O)N[C@@H](Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)CN2C(=O)c3ccccc3C2=O)cc1Cl>C(C)O>CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a7192fcea0e4e09a803dec294fa9dfd | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)[C@@H](C)N)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl | NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2Br)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O.CC(C)(C)OC(=O)N[C@H](C)C(=O)O.CCN=C=NCCCN(C)C.Cl>>N[C@H](C)C(=O)NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2Br)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][C@H:12]([CH2:13][NH2:14])[CH2:20][c:21]2[cH:22][cH:23][c:24](-[c:25]3[cH:26][n:27]4[cH:28][cH:29][cH:30][c:31]([Br:32])[c:33]4[n:34]3)[cH:35][cH:36]2)[cH:37][c:38]1[Cl:39].CC(C)(C)OC(=O)[NH:19][C@@H:17]([C:15](O)=[O:16])[CH3:18]>>[CH3:1][CH:2]([CH... | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)[C@@H](C)N)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl | null | null | O1CCOCC1.C(Cl)Cl | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;H0;D3;+0:4](-O)=[O;D1;H0:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:1] | 25 | [{"value": 25.0, "product": "N[C@H](C)C(=O)NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2Br)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of N-((1S)-2-amino-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide (0.28 mmol), N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (0.56 mmol), EDCI (0.56 mmol), and TEA (1.12 mmol) stirred in methylene chloride (2 mL) at RT for 18 h. The reaction was then t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | O1CCOCC1.C(Cl)Cl | null | 1 | CC(C)Oc1ccc(C(=O)N[C@H](CN)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl.C[C@@H](NC(=O)OC(C)(C)C)C(=O)O>O1CCOCC1.C(Cl)Cl>CC(C)Oc1ccc(C(=O)N[C@H](CNC(=O)[C@@H](C)N)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b38ea44be01460e8865c06d3f979b70 | CC(C)(N)C(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)C(C)(C)N)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O.CC(N)(C)C(=O)O>>ClC=1C=C(C(=O)N[C@H](CNC(C(N)(C)C)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C=CC1OC(C)C | O[C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[NH2:22].[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH2:16])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12>>[CH3:1][c:2]1[cH:3]... | CC(C)(N)C(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)C(C)(C)N)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[N;D1;H2:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[N;D1;H2:6] | null | [] | null | null | null | null | Following the procedure described above with N-((1S)-2-amino-1-{[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide and N-[(1,1-dimethylethyl)oxy]carbonyl)-2-methylalanine provided the title product as a white solid. ESMS [M+H]+: 563.2.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)(N)C(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)C(C)(C)N)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be0cd13a66f44130ae9280cb4c5a7999 | CN(C)CC(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)CN(C)C)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | NC[C@H](CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O.CN(CC(=O)O)C>>ClC=1C=C(C(=O)N[C@H](CNC(CN(C)C)=O)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C=CC1OC(C)C | O[C:17](=[O:18])[CH2:19][N:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH2:16])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12>>[CH3:1][c:2]1[cH:3][c... | CN(C)CC(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)CN(C)C)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | Following the procedure described above with N-((1S)-2-amino-1-{[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide and N,N-dimethylglycine provided the title product as a white solid. ESMS [M+H]+: 563.2.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CN(C)CC(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)CN(C)C)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46065ad871d84bb58407ba5a331b2437 | BrBr.CC(=O)c1ccc(I)cc1>>O=C(CBr)c1ccc(I)cc1 | IC1=CC=C(C=C1)C(C)=O.BrBr>>BrCC(=O)C1=CC=C(C=C1)I | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1 | BrBr.CC(=O)c1ccc(I)cc1 | O=C(CBr)c1ccc(I)cc1 | null | null | O1CCOCC1 | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 10 | MINUTE | A solution of 1-(4-iodophenyl)ethanone (55.9 mmol) in dioxane (160 mL) was cooled to 10° C. Bromine (1.1 equiv, 61.6 mmol) was added dropwise to the reaction mixture. After 10 min, the cooling bath was removed and the reaction mixture was stirred at room temperature. After 1.5 h, the reaction mixture was concentrated i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 0.166667 | BrBr.CC(=O)c1ccc(I)cc1>O1CCOCC1>O=C(CBr)c1ccc(I)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e80663ca80cd48d2beea8a417da76a1e | Cc1cccnc1N.O=C(CBr)c1ccc(I)cc1>>Cc1cccn2cc(-c3ccc(I)cc3)nc12 | BrCC(=O)C1=CC=C(C=C1)I.NC1=NC=CC=C1C.C([O-])(O)=O.[Na+]>>IC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:17]1[NH2:16].O=[C:8]([CH2:7]Br)[c:9]1[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]3)[n:16][c:17]12 | Cc1cccnc1N.O=C(CBr)c1ccc(I)cc1 | Cc1cccn2cc(-c3ccc(I)cc3)nc12 | null | null | C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 71 | [{"value": 71.0, "product": "IC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "IC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of crude 2-bromo-1-(4-iodophenyl)ethanone (18.2 g), 2-amino-3-picoline (1.1 equiv, 61.6 mmol), and sodium bicarbonate (1.3 equiv, 72.8 mmol) in isopropanol (160 mL) was heated at 80° C. for 16 h. After concentrating the reaction mixture in vacuo, water (100 mL) was added and the resultant tan slurry was filte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | C(C)(C)O | 80 | null | Cc1cccnc1N.O=C(CBr)c1ccc(I)cc1>C(C)(C)O>Cc1cccn2cc(-c3ccc(I)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-057d255f7ce842748c57ff1c6fb2c454 | CNOC.Cn1cc(-c2ccc(Br)cc2)nc1C(=O)O>>CON(C)C(=O)c1nc(-c2ccc(Br)cc2)cn1C | [Na].BrC1=CC=C(C=C1)C=1N=C(N(C1)C)C(=O)O.CN1CCOCC1.Cl.CNOC.ClC(=O)OCC(C)C>>BrC1=CC=C(C=C1)C=1N=C(N(C1)C)C(=O)N(OC)C | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[n:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][n:18]1[CH3:19]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[n:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][n:18]1[CH3:19] | CNOC.Cn1cc(-c2ccc(Br)cc2)nc1C(=O)O | CON(C)C(=O)c1nc(-c2ccc(Br)cc2)cn1C | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(-c2c[nH]cn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[#8:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:8]-[#7;a:7]1:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11](-[C;D1;H3:12])-[#8:10]-[C;D1;H3:9] | 32 | [{"value": 32.0, "product": "BrC1=CC=C(C=C1)C=1N=C(N(C1)C)C(=O)N(OC)C", "details": "PERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 15 | MINUTE | To a solution of ethyl 4-(4-bromophenyl)-1-methyl-1H-imidazole-2-carboxylate (1.66 g, 5.37 mmol) in MeOH (38 mL) was added 1N NaOH solution (19 mL). The reaction turned cloudy white and was stirred at room temperature for 30 minutes. The reaction mixture was concentrated in vacuo and pumped under high vacuum overnight ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1cnc[nH]1.c1ccccc1 | HO- | C(Cl)Cl | -15 | 0.25 | CNOC.Cn1cc(-c2ccc(Br)cc2)nc1C(=O)O>C(Cl)Cl>CON(C)C(=O)c1nc(-c2ccc(Br)cc2)cn1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71375fbc69e444e4a55da1804283eee2 | CC(C)(C)OC(=O)CC[C@H](CI)NC(=O)OC(C)(C)C.Cc1cccn2cc(-c3ccc(I)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12 | BrCCBr.Cl[Si](C)(C)C.CC(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)CI.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.IC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1>>CC(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | I[CH2:13][C@@H:14]([CH2:15][CH2:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].I[c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][n:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:35]3[n:34]2)[cH:33][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]... | CC(C)(C)OC(=O)CC[C@H](CI)NC(=O)OC(C)(C)C.Cc1cccn2cc(-c3ccc(I)cc3)nc12 | Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12 | null | [Zn].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] | CN(C)C=O.CCOC(=O)C | C-C Coupling | Negishi | 530a9bd1eaaebd54d09786b6168a1d1d89df12b3fda60e0c00afadb98df85946 | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | c1ccc(-c2cn3ccccc3n2)cc1 | I-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].I-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:3]-[C:2](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH2;D2;+0:1]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16] | 90 | [{"value": 90.0, "product": "CC(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | A flask containing zinc dust (6.0 equiv, 325 mesh, Strem) was heated with a heat gun while evacuating and filling with nitrogen (3 times). Under nitrogen, degassed DMF (14 mL) was added via syringe followed by 1,2-dibromoethane (0.35 equiv). The grey reaction mixture was stirred in an oil bath at 100° C. for 15 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccn2ccnc2c1.c1ccccc1 | I- | [Zn].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].CN(C)C=O.CCOC(=O)C | 100 | 0.25 | CC(C)(C)OC(=O)CC[C@H](CI)NC(=O)OC(C)(C)C.Cc1cccn2cc(-c3ccc(I)cc3)nc12>[Zn].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].CN(C)C=O.CCOC(=O)C>Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d72ee98388eb46d4be26dc716f355c6d | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)O)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | C(C)(C)NC(C)C.CC(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1.FC(C(=O)O)(F)F.ClC=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C.C(C)[SiH](CC)CC>>ClC=1C=C(C=CC1OC(C)C)C(=O)N[C@H](CCC(=O)O)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | Fc1c(F)c(F)c(O[C:21](=[O:22])[c:23]2[cH:24][cH:25][c:26]([O:27][CH:28]([CH3:29])[CH3:30])[c:31]([Cl:32])[cH:33]2)c(F)c1F.CC(C)(C)OC(=O)[NH:20][C@@H:14]([CH2:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][n:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:37]3[n:36]2)[cH:35][cH:34]1)[CH2:15][CH2:16][C:17](=[O:18])[O:19]C(C)(C)C>>[CH3... | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12 | Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)O)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | null | null | C(Cl)Cl | Protection | OtherReaction | 9b3d2ad13665a37c756c1725995b29ed925d85c55a22d6291c1d088613f27582 | 545d38d838a170ec25ef129ae973a0f72fde2e06b47ea8db25c0a3c0098b77bf | O=C(NCCc1ccc(-c2cn3ccccc3n2)cc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C(-C)(-C)-C.F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]):c(-F):c:1-F>>[C:3]-[C:2](-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8])-[NH;D2;+0:1]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13] | 61 | [{"value": 61.0, "product": "ClC=1C=C(C=CC1OC(C)C)C(=O)N[C@H](CCC(=O)O)CC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 1,1-dimethylethyl (4R)-4-(([(1,1-dimethylethyl)oxy]carbonyl}amino)-5-[4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl]pentanoate (1.35 g, 2.82 mmol) in CH2Cl2 (14 mL) was added trifluoroacetic acid (10 mL) followed by triethylsilane (2.5 equiv, 7.04 mmol). The reaction was stirred for 45 minutes at room t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Ester.Ester.Ether.Boc.Boc | Carboxylic acid.Secondary amide | c1ccccc1 | null | c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | HF | C(Cl)Cl | null | 0.75 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc3)nc12>C(Cl)Cl>Cc1cccn2cc(-c3ccc(C[C@@H](CCC(=O)O)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b006af1c25e4eab9109a00f18f384e4 | CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C>>CC(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C | ClC=1C=C(C=CC1OC(C)C)C(=O)N[C@H](CCC(=O)O)CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(=O)N(OC)C.C[Mg]Br>>C(C)(=O)C=1N(C=C(N1)C1=CC=C(C=C1)C[C@@H](CCC(=O)O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)C | CON(C)[C:2](=[O:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH2:11][C@@H:12]([CH2:13][CH2:14][C:15](=[O:16])[OH:17])[NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([O:25][CH:26]([CH3:27])[CH3:28])[c:29]([Cl:30])[cH:31]3)[cH:32][cH:33]2)[cH:34][n:35]1[CH3:36]>>[CH3:1][C:2](=[O:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9... | CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C | CC(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | O=C(NCCc1ccc(-c2c[nH]cn2)cc1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8]>>[C;D1;H3:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of crude (4R)-4-[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]-5-[4-(1-methyl-2-{[methyl(methyloxy)amino]carbonyl}-1H-imidazol-4-yl)phenyl]pentanoic acid (3.18 mmol) in anhydrous THF (16 mL) under nitrogen at 0° C. was added methylmagnesium bromide (10.6 mL, 10 equiv, 3.0 M in ether) dropwise by... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1cnc[nH]1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | 0 | 0.5 | CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C>C1CCOC1>CC(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c7ddc9d030f47529d456ea9745fa805 | CC(=O)c1nc(-c2ccc(C[C@@H](CCO)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C.COP(=O)(Cl)OC>>COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1 | CCOC(=O)C.CO.P(=O)(OC)(OC)Cl.C(C)(=O)C=1N(C=C(N1)C1=CC=C(C=C1)C[C@@H](CCO)NC(C1=CC(=C(C=C1)OC(C)C)Cl)=O)C.P(=O)(OC)(OC)Cl>>P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(OC)OC | [OH:7][CH2:8][CH2:9][C@H:10]([CH2:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][n:18]([CH3:19])[c:20]([C:21]([CH3:22])=[O:23])[n:24]2)[cH:25][cH:26]1)[NH:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][c:33]([O:34][CH:35]([CH3:36])[CH3:37])[c:38]([Cl:39])[cH:40]1.Cl[P:3]([O:2][CH3:1])(=[O:4])[O:5][CH3:6]>>[CH3:1][O:2][P:3](=[... | CC(=O)c1nc(-c2ccc(C[C@@H](CCO)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C.COP(=O)(Cl)OC | COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1 | null | CN(C)C=1C=CN=CC1.CN(C)C=1C=CN=CC1 | C(Cl)Cl | Miscellaneous | OtherReaction | f468963cd150795c559ea97eef415e4c6e817d5e41b8e41bf56e6fc6478dce9b | 0450d2d3d6169ebd913d75de6102597ba0029b73d4e4cd2ca50ccc23bda73392 | O=C(NCCc1ccc(-c2c[nH]cn2)cc1)c1ccccc1 | Cl-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6] | 77.1 | [{"value": 77.0, "product": "P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(OC)OC", "details": "CALCULATEDPERCENTYIELD",... | null | null | 30 | MINUTE | To a solution of N-((1S)-1-{[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]methyl}-3-hydroxypropyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide (500 mg, 1.04 mmol) in dry CH2Cl2 (10 mL) under N2, was added dimethyl chlorophosphate (748 mg, 5.18 mmol) followed by DMAP (660 mg, 5.41 mmol) at rt. After 30 min, TLC (95:5 EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1c[nH]cn1.c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 0.5 | CC(=O)c1nc(-c2ccc(C[C@@H](CCO)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C.COP(=O)(Cl)OC>CN(C)C=1C=CN=CC1.CN(C)C=1C=CN=CC1.C(Cl)Cl>COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a364b73772ed4c06a987b41907701bd9 | COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1>>CC(=O)c1nc(-c2ccc(C[C@@H](CCOP(=O)(O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C | P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(OC)OC>>P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(O)O | C[O:18][P:16]([O:15][CH2:14][CH2:13][C@H:12]([CH2:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[n:5][c:4]([C:2]([CH3:1])=[O:3])[n:37]([CH3:38])[cH:36]2)[cH:35][cH:34]1)[NH:20][C:21](=[O:22])[c:23]1[cH:24][cH:25][c:26]([O:27][CH:28]([CH3:29])[CH3:30])[c:31]([Cl:32])[cH:33]1)(=[O:17])[O:19]C>>[CH3:1][C:2](=[O:3])[c:4]1[n:5][c:6](-... | COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1 | CC(=O)c1nc(-c2ccc(C[C@@H](CCOP(=O)(O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C | null | null | CC(=O)O.Br | Deprotection | OtherReaction | b49938033a0fd56e13d2f970a169ac47cce77c866363ab153142c53fe34d7d82 | ecac314cca8b931f5bfebb391dc97e333d1eca60b386dbe5c9a60f4d76cdb838 | O=C(NCCc1ccc(-c2c[nH]cn2)cc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C>>[#8:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | 19 | [{"value": 19.0, "product": "P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.5, "product": "P(=O)(OCC[C@H](CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(C)=O)NC(=O)C1=CC(=C(C=C1)OC(C)C)Cl)(O)O", "details": "CALCULATEDPERCENTYIELD", "is... | 60 | CELSIUS | 8 | HOUR | A yellow solution of (3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dimethyl phosphate (475 mg, 0.804 mmol) in 30% HBr in AcOH was placed in a pre-heated (60° C.) bath for 10 min, then immediately allowed to cool to rt. The reaction mixture was conc... | 10.6084/m9.figshare.5104873.v1 | null | null | Phosphate ester | null | null | c1cnc[nH]1.c1ccccc1.c1ccccc1 | Other | CC(=O)O.Br | 60 | 8 | COP(=O)(OC)OCC[C@H](Cc1ccc(-c2cn(C)c(C(C)=O)n2)cc1)NC(=O)c1ccc(OC(C)C)c(Cl)c1>CC(=O)O.Br>CC(=O)c1nc(-c2ccc(C[C@@H](CCOP(=O)(O)O)NC(=O)c3ccc(OC(C)C)c(Cl)c3)cc2)cn1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5699166f64e5406d837e82fe89aebc36 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1C#N.Cc1noc(C)c1B(O)O>>Cc1noc(C)c1-c1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 | BrC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)C[C@@H](CCO)NC(C2=CC(=C(C=C2)OC(C)C)C#N)=O.CC1=NOC(=C1B(O)O)C.C(=O)([O-])[O-].[K+].[K+]>>C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C=3C(=NOC3C)C)C2)C=CC1OC(C)C | Br[c:8]1[cH:9][cH:10][cH:11][n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([CH2:19][C@@H:20]([CH2:21][CH2:22][OH:23])[NH:24][C:25](=[O:26])[c:27]4[cH:28][cH:29][c:30]([O:31][CH:32]([CH3:33])[CH3:34])[c:35]([C:36]#[N:37])[cH:38]4)[cH:39][cH:40]3)[n:41][c:42]12.OB(O)[c:7]1[c:2]([CH3:1])[n:3][o:4][c:5]1[CH3:6]>>[CH3:1]... | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1C#N.Cc1noc(C)c1B(O)O | Cc1noc(C)c1-c1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 | null | null | CN(C)C=O | C-C Coupling | Suzuki coupling with boronic acids | a733f0cb9ddc6219931356bfd9d2fb02959abad7e10e6cfb4c00073a10f09758 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(NCCc1ccc(-c2cn3cccc(-c4cnoc4)c3n2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11](-[C;D1;H3:12]):[#7;a:13]:[#8;a:14]:[c:15]:1-[C;D1;H3:16]>>[C;D1;H3:12]-[c:11]1:[#7;a:13]:[#8;a:14]:[c:15](-[C;D1;H3:16]):[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:... | 22 | [{"value": 22.0, "product": "C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C=3C(=NOC3C)C)C2)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.8, "product": "C(#N)C=1C=C(C(=O)N[C@H](CCO)CC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C=3C(=NOC3C)C)C2)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD",... | 100 | CELSIUS | 22 | HOUR | To a solution of N-((1S)-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl)-3-hydroxypropyl)-3-cyano-4-[(1-methylethyl)oxy]benzamide (200 mg, 0.366 mmol) in dry DMF (2 mL) were added 3,5-dimethyl-isoxazole-4-boronic acid (63 mg, 0.439 mmol), tetrakistriphenylphosphine palladium(0) (21 mg, 0.018 mmol) and 2.0 M aqu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1cnoc1 | c1cnoc1.c1ccn2ccnc2c1 | c1cnoc1.c1ccn2ccnc2c1.c1ccccc1.c1ccccc1 | HBr.B | CN(C)C=O | 100 | 22 | CC(C)Oc1ccc(C(=O)N[C@H](CCO)Cc2ccc(-c3cn4cccc(Br)c4n3)cc2)cc1C#N.Cc1noc(C)c1B(O)O>CN(C)C=O>Cc1noc(C)c1-c1cccn2cc(-c3ccc(C[C@@H](CCO)NC(=O)c4ccc(OC(C)C)c(C#N)c4)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c822f19a093c49beb1311b4299041411 | NC(=O)[C@@H](N)Cc1ccc(O)cc1>>c1ccc2[nH]cnc2c1 | N[C@@H](CC1=CC=C(C=C1)O)C(=O)N.Cl.C(C)N(CC)CC.FC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)(F)F>>N1=CNC2=C1C=CC=C2 | O=[C:6]([C@H](C[c:4]1[cH:3][cH:2][c:1](O)[cH:9][cH:8]1)[NH2:5])[NH2:7]>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | NC(=O)[C@@H](N)Cc1ccc(O)cc1 | c1ccc2[nH]cnc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8122077837d574c1833e90acf44c3fd8221ff4c194f4f1f3e2c3974049e231a7 | 073fb5aa4cd15969a74799a193e5a035fb3eef58e311c8a52c655b67e20989e7 | c1ccc2[nH]cnc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-C-[C@H](-[NH2;D1;+0:5])-[C;H0;D3;+0:6](=O)-[NH2;D1;+0:7]):[cH;D2;+0:8]:[c:9]:1>>[c:2]1:[c:3]:[c;H0;D3;+0:4]2:[nH;D2;+0:5]:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[c;H0;D3;+0:8]:2:[c:9]:[cH;D2;+0:1]:1 | 193.1 | [{"value": 50.0, "product": "N1=CNC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 193.1, "product": "N1=CNC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a 0° C. crude solution of compound 2 (4.1 g, 15.34 mmol) and triethylamine (6.4 mL, 46.02 mmol) in dicholoromethane (200 mL) was added pentafluorophenyl trifluoroacetate (6.35 mL, 36.82 mmol) via syringe over 3 min. After another 5 min, the ice bath was removed and the reaction mixture stirred while warming to room ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | null | null | 0.083333 | NC(=O)[C@@H](N)Cc1ccc(O)cc1>>c1ccc2[nH]cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3c146894f7c4d3bbbe43f82e2c786cc | COC(=O)c1ccc(O)cc1.ClI>>COC(=O)c1ccc(O)c(I)c1 | OC1=CC=C(C(=O)OC)C=C1.ICl>>OC1=C(C=C(C(=O)OC)C=C1)I | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.Cl[I:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([I:11])[cH:12]1 | COC(=O)c1ccc(O)cc1.ClI | COC(=O)c1ccc(O)c(I)c1 | null | null | CC(=O)O.C(C)(=O)O | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-[I;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8](-[O;D1;H1:9]):[c:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[I;H0;D1;+0:1]):[c:8](-[O;D1;H1:9]):[c:10] | 90.3 | [{"value": 90.3, "product": "OC1=C(C=C(C(=O)OC)C=C1)I", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 5 | HOUR | Methyl 4-hydroxybenzoate (35.5 g, 0.233 mol) was dissolved in 200 mL of acetic acid, and the stirred mixture was warmed to 65° C. A solution of ICl (37.8 g, 0.233 mol) in 50 mL of AcOH was added dropwise over 40 min. The mixture was stirred at 65° C. for 5 h and then stirred an additional 16 h at room temperature. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CC(=O)O.C(C)(=O)O | 65 | 5 | COC(=O)c1ccc(O)cc1.ClI>CC(=O)O.C(C)(=O)O>COC(=O)c1ccc(O)c(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1663a1f970f469990f7e8f069bbcfb4 | COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | OC1=C(C=C(C(=O)OC)C=C1)I.C(#N)[Cu].[C-]#N.[Na+]>>C(#N)C=1C=C(C(=O)OC)C=CC1O | I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[O;D1;H1:8]):[c:9]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:10]#[N;D1;H0:11]):[c:7](-[O;D1;H1:8]):[c:9] | 101.6 | [{"value": 100.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.6, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 18 | HOUR | 28 g (0.1 mol) of methyl 4-hydroxy-3-iodobenzoate 2 dissolved in 100 mL of DMF was treated with 9.92 g (0.11 mol) of CuCN and 0.49 g (0.11 mol) of NaCN. The system was flushed with nitrogen after which the mixture warmed to 105° C. and stirred to 18 h. The mixture was allowed to cool to room temperature, and any precip... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | I- | CN(C)C=O | 105 | 18 | COC(=O)c1ccc(O)c(I)c1>CN(C)C=O>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fca985d0f37c4db894293c1c47a3ff43 | CC(C)Br.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.BrC(C)C.C([O-])([O-])=O.[K+].[K+]>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | Br[CH:10]([CH3:11])[CH3:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CC(C)Br.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.5, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | Methyl 3-cyano-4-hydroxybenzoate 3 (18 g, 0.1 mol) was dissolved in 100 mL of DMF and treated with 14.2 mL (0.15 mol) of 2-bromopropane and 41.9 g (0.3 mol) of anhydrous potassium carbonate. The system was flushed with nitrogen, and the mixture was heated to 90° C. with stirring overnight. After cooling to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | 90 | 8 | CC(C)Br.COC(=O)c1ccc(O)c(C#N)c1>CN(C)C=O>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de925e9d139e4a2dbba1bff9dc6f6f3c | COC(=O)c1ccc(OC(C)C)c(C#N)c1.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F>>CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1C#N | C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C.[OH-].[Na+].FC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)(F)F.C(C)N(CC)CC>>C(#N)C=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C | CO[C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:24]([C:25]#[N:26])[cH:23]1)=[O:10].O=C(C(F)(F)F)[O:11][c:12]1[c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19]([F:20])[c:21]1[F:22]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][c:12]2[c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19... | COC(=O)c1ccc(OC(C)C)c(C#N)c1.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1C#N | null | null | O.CO | Acylation | OtherReaction | 580054fc0b51b792707ad4b668033c84495f9aead4f098ebc488ee73871837ea | 4458c2810029240f45ce48457089b9a8e19de9f2b2e0fc29ef56ddad657ed962 | O=C(Oc1ccccc1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].F-C(-F)(-F)-C(=O)-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 84 | [{"value": 83.5, "product": "C(#N)C=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "C(#N)C=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 20.5 g (0.093 mol) of methyl 3-cyano-4-isopropoxybenzoate 4 was dissolved in 200 mL of a 6:4 mixture of methanol and water. To this was added 5.61 g (0.14 mol) of NaOH and the mixture stirred for 2 hours at room temperature. The solution was then filtered through a silica gel plug and the solvents removed under vacuum.... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ester.Ester | Ester | null | null | c1ccccc1.c1ccccc1 | HF | O.CO | null | 2 | COC(=O)c1ccc(OC(C)C)c(C#N)c1.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F>O.CO>CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c1da52e41474b6697b13198665d08cb | CC(C)I.CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc2)cn1C>>COC(=O)c1ccc(O)c(I)c1 | CC(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)CC1=CC=C(C=C1)C=1N=C(N(C1)C)C(=O)N(OC)C.IC(C)C.CCN(C(C)C)C(C)C.CN(C)C=O>>OC1=C(C=C(C(=O)OC)C=C1)I | C[CH:10]([I:11])[CH3:12].CN([O:2][CH3:1])[C:3](=[O:4])[c:5]1nc(-[c:8]2ccc(C[C@@H](CCC(OC(C)(C)C)=[O:9])NC(=O)OC(C)(C)C)[cH:6][cH:7]2)cn1C>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([I:11])[cH:12]1 | CC(C)I.CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc2)cn1C | COC(=O)c1ccc(O)c(I)c1 | null | null | null | Acylation | OtherReaction | bdc1f46afe698d9edd26392dbcd953815f1ab48bc01fe39842adc4a9d53bec2e | 2908d920a73258e3597d947094497249f48b631e1ac541ab8d68b33e393d3f9b | c1ccccc1 | C-N(-[O;H0;D2;+0:1]-[C;D1;H3:2])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:n:c(-[c;H0;D3;+0:6]2:[c:7]:[cH;D2;+0:8]:c(-C-[C@@H](-C-C-C(=[O;H0;D1;+0:9])-O-C(-C)(-C)-C)-N-C(=O)-O-C(-C)(-C)-C):c:c:2):c:n:1-C.C-[CH;D3;+0:10](-[CH3;D1;+0:11])-[I;D1;H0:12]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c;H0;D3;+... | 20 | [{"value": 20.0, "product": "OC1=C(C=C(C(=O)OC)C=C1)I", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | To a solution of compound 1 (200 mg, 1.077 mmol) and 2-iodopropane (322 uL, 3.23 mmol) in DMF (10 mL) was added DIEA (750 uL, 4.31 mmol). The reaction mixture was heated to 80° C. and stirred overnight. When complete by LC/MS, the reaction was cooled to room temperature, quenched with HCl (0.5 N, 30 mL) and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbamic ester.Ester.Ether.Tertiary amide.Boc.Boc | Aromatic halide.Ester.Aromatic alcohol | c1ncc[nH]1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 80 | 8 | CC(C)I.CON(C)C(=O)c1nc(-c2ccc(C[C@@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc2)cn1C>>COC(=O)c1ccc(O)c(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-920b5700f55d4c98978c714fdc49dafd | COC(=O)c1ccc(O)c(C#N)c1.O=C1CCC(=O)N1Cl>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.ClN1C(CCC1=O)=O>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1.O=[C:10]1N(Cl)[C:11](=O)C[CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | COC(=O)c1ccc(O)c(C#N)c1.O=C1CCC(=O)N1Cl | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 583eebb8475c3e0259acdbe4597e93f53d9f697a23b264ed51b6dda3df53c69f | 05bc6928a21991bad9931d6f39f8fcb40a9f20a9e409334ab947e3e3fa1c19df | c1ccccc1 | Cl-N1-[C;H0;D3;+0:1](=O)-[CH2;D2;+0:2]-C-[C;H0;D3;+0:3]-1=O.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:3]-[CH;D3;+0:1](-[CH3;D1;+0:2])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 80.2 | [{"value": 29.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | A portion of residue 3 (4.19 g, ˜7.45 mmol) was dissolved in acetonitrile (50 mL) and treated with N-chlorosuccinimide (1.19 g, 8.94 mmol) at room temperature. The temperature was raised to 65° C. and the mixture stirred overnight. When LC/MS showed complete conversion of starting material, the mixture was cooled to ro... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Aromatic alcohol | Ether | C1CCNC1 | null | c1ccccc1 | Other | C(C)#N | 65 | 8 | COC(=O)c1ccc(O)c(C#N)c1.O=C1CCC(=O)N1Cl>C(C)#N>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e0a544a12ff4aa98f2559e51de7b16d | COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | OC1=C(C=C(C(=O)OC)C=C1)I.[H-].[Na+].CN(C)C=O>>C(#N)C=1C=C(C(=O)OC)C=CC1O | I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[O;D1;H1:8]):[c:9]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:10]#[N;D1;H0:11]):[c:7](-[O;D1;H1:8]):[c:9] | null | [] | null | null | 16 | HOUR | A solution of compound 2 (6.46 g, 24.1 mmol) in DMF (30 mL) was treated with sodium hydride (1.94 g of 60% dispersion in mineral oil, 48.6 mmol) portionwise at room temperature. The resulting mixture was stirred at room temperature for 16 hours and then partitioned between water (100 mL) and EtOAc (350 mL). The layers ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | I- | null | null | 16 | COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e8a3d54af1542a99d90dff7cc6f10d0 | COC(=O)c1ccc(O)c(C#N)c1.C[CH2][Zn][CH2]C>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | [NH4+].[Cl-].C(#N)C=1C=C(C(=O)OC)C=CC1O.ClCI.[NH4+].[OH-].C(C)[Zn]CC>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1.[CH2]([Zn][CH2][CH3:12])[CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | COC(=O)c1ccc(O)c(C#N)c1.C[CH2][Zn][CH2]C | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | ClCCCl.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | [CH3;D1;+0:1]-[CH2]-[Zn]-[CH2]-[CH3;D1;+0:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[CH3;D1;+0:1]-[C:7](-[CH3;D1;+0:2])-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 30 | [{"value": 30.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Compound 3 (5.56 g, 24.0 mmol) was added to a solution of chloroiodomethane (5.59 mL, 76.8 mmol) in 1,2-dichloroethane (35 mL) under an atmosphere of nitrogen. The solution was cooled to 0° C. with an ice bath and diethyl zinc (38.4 mL, 1.0 M in hexanes, 38.4 mmol) was added over 10 minutes. The resulting mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | Zn | ClCCCl.CCOC(=O)C | 0 | 0.5 | COC(=O)c1ccc(O)c(C#N)c1.C[CH2][Zn][CH2]C>ClCCCl.CCOC(=O)C>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1d0828f83814ed690ab3dadd32f6a9f | C[C@@H](NC(=O)CCCCl)c1nc(-c2ccc(I)cc2)cn1C>>C[C@H](c1nc(-c2ccc(I)cc2)cn1C)N1CCCC1=O | CCOC(=O)C.ClCCCC(=O)N[C@H](C)C=1N(C=C(N1)C1=CC=C(C=C1)I)C.C1CCOC1.CC(C)([O-])C.[K+]>>IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)N1C(CCC1)=O | Cl[CH2:17][CH2:18][CH2:19][C:20]([NH:16][C@H:2]([CH3:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]2)[cH:13][n:14]1[CH3:15])=[O:21]>>[CH3:1][C@H:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]2)[cH:13][n:14]1[CH3:15])[N:16]1[CH2:17][CH2:18][CH2:19][C:20]1=[O:21] | C[C@@H](NC(=O)CCCCl)c1nc(-c2ccc(I)cc2)cn1C | C[C@H](c1nc(-c2ccc(I)cc2)cn1C)N1CCCC1=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 62f43057f012567ee0d9bea97538013537b046013f70e56d5406a05691c3dc0d | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCN1Cc1nc(-c2ccccc2)c[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[c:9](:[#7;a:10]):[#7;a:11]>>[#7;a:10]:[c:9](-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-1=[O;D1;H0:5]):[#7;a:11] | 86 | [{"value": 86.0, "product": "IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)N1C(CCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | To a 20-dram vial was added (R)-4-chloro-N-(1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)ethyl)butanamide and THF (10 mL). The vial was cooled to 0° C. under a nitrogen atmosphere and potassium t-butoxide (214 mg, 1.91 mmol) was added. The reaction was stirred for 1.5 h. To the reaction mixture was added EtOAc (50 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | C1CC[NH]C1 | c1cnc[nH]1.c1ccccc1.C1CC[NH]C1 | HCl | O | 0 | 1.5 | C[C@@H](NC(=O)CCCCl)c1nc(-c2ccc(I)cc2)cn1C>O>C[C@H](c1nc(-c2ccc(I)cc2)cn1C)N1CCCC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a2a4d712e6a4a46ab05384dc8900b8d | CN[C@H](C)c1nc(-c2ccc(I)cc2)cn1C.COC(=O)Cl>>COC(=O)N(C)[C@H](C)c1nc(-c2ccc(I)cc2)cn1C | IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)NC.ClC(=O)OC.C(=O)([O-])[O-].[Na+].[Na+].C1CCOC1>>IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)N(C(OC)=O)C | [NH:5]([CH3:6])[C@H:7]([CH3:8])[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([I:16])[cH:17][cH:18]2)[cH:19][n:20]1[CH3:21].Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[N:5]([CH3:6])[C@H:7]([CH3:8])[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([I:16])[cH:17][cH:18]2)[cH:19][n:20]1[CH3:21] | CN[C@H](C)c1nc(-c2ccc(I)cc2)cn1C.COC(=O)Cl | COC(=O)N(C)[C@H](C)c1nc(-c2ccc(I)cc2)cn1C | null | null | O.CCOC(=O)C | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1ccc(-c2c[nH]cn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7;a:5]:[c:6](-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C;D1;H3:10]):[#7;a:11]>>[#7;a:5]:[c:6](-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4]):[#7;a:11] | 41.3 | [{"value": 41.0, "product": "IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)N(C(OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.3, "product": "IC1=CC=C(C=C1)C=1N=C(N(C1)C)[C@@H](C)N(C(OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a 250 mL round bottom flask was added (R)-1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)-N-methylethanamine (3.1 g, 9.1 mmol), methyl chloroformate (0.84 mL, 10.9 mmol), Na2CO3 (1.15 g, 10.9 mmol), and THF (100 mL). The reaction was stirred for 2 hours, followed by the addition of EtOAc (50 mL) and water (10 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1cnc[nH]1.c1ccccc1 | HCl | O.CCOC(=O)C | null | 2 | CN[C@H](C)c1nc(-c2ccc(I)cc2)cn1C.COC(=O)Cl>O.CCOC(=O)C>COC(=O)N(C)[C@H](C)c1nc(-c2ccc(I)cc2)cn1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e030e56358fc49f284fb01b326239fb1 | CCOC(=O)CBr.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)OCC>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | O=[C:10](OC[CH3:12])[CH2:11]Br.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CCOC(=O)CBr.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 0acf459bf686003717df84cdcc64b7e9112cbac95ec05a938cd5030dbca78e71 | f70d7bf1e28f3adbba70880b540f7d6c0ef11f9028ba0dd0b253425838a0a3ab | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-O-C-[CH3;D1;+0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 189.5 | [{"value": 91.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 189.5, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a solution of compound 3 (2.66 g, 7.27 mmol) in DMF (15 mL) was added K2CO3 (2.00 g, 15 mmol) and ethyl bromoacetate (1.61 mL, 14.5 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over N... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 60 | 3 | CCOC(=O)CBr.COC(=O)c1ccc(O)c(C#N)c1>O.CN(C)C=O>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b50a8b6695f44fe6b0f3f331f83d2e58 | CC(C)(C)OC(=O)C(N)CBr.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.C(=O)([O-])[O-].[K+].[K+].C(=O)(OC(C)(C)C)C(CBr)N>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | C[C:10](OC(=O)C(N)CBr)([CH3:11])[CH3:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CC(C)(C)OC(=O)C(N)CBr.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | d647953592dc0ff19485d3d76908e40e976b37d36428179cea834c18dbe35c6c | 3e561a7fd54c45848554c88ca1b48fe4ef24292d518b5a7f61512c34f16d817e | c1ccccc1 | Br-C-C(-N)-C(=O)-O-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 109.5 | [{"value": 55.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.5, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a solution of compound 3 (5.000 g, 17 mmol) in DMF (15 mL) was added K2CO3 (3.51 g, 26 mmol) and Boc-2-amino ethyl bromide (4.56 g, 20.35 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol.Primary amine.Boc | Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 60 | 3 | CC(C)(C)OC(=O)C(N)CBr.COC(=O)c1ccc(O)c(C#N)c1>O.CN(C)C=O>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b618945e8ee4a949f3775139fc56571 | CN(C)C.COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.OC1=C(C=C(C(=O)OC)C=C1)I.CN(C)C.O1CCOCC1>>C(#N)C=1C=C(C(=O)OC)C=CC1O | C[N:12](C)[CH3:11].I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | CN(C)C.COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | O | C-C Coupling | OtherReaction | 1a14070cbe6fe5f59309149001ffa2dfc322a156a861405855acfdd6362705a6 | 951efce9f7401e9a96fe9b4f90874368f054ec53732a86c28b3b95242d371d1a | c1ccccc1 | C-[N;H0;D3;+0:1](-C)-[CH3;D1;+0:2].I-[c;H0;D3;+0:3](:[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9](-[O;D1;H1:10]):[c:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:3](-[C;H0;D2;+0:2]#[N;H0;D1;+0:1]):[c:9](-[O;D1;H1:10]):[c:11] | 154.5 | [{"value": 97.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 154.5, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | (Boc)2O (44.7 g, 0.21 mol) was added portion-wise over 10 min to a 0° C. solution of compound 2 (42 g, 0.19 mol), trimethyl amine (51.9 mL, 0.37 mol), dioxane (140 mL) and water (56 mL). After another 10 min, the ice bath was removed and the reaction mixture was stirred while warming to room temperature for another 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | O | null | 0.166667 | CN(C)C.COC(=O)c1ccc(O)c(I)c1>O>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfc606fe8ccd4addb3c5045bc889d98b | CCN(C(C)C)C(C)C.COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | OC1=C(C=C(C(=O)OC)C=C1)I.CCN(C(C)C)C(C)C.ClC(=O)OCC1=CC=CC=C1>>C(#N)C=1C=C(C(=O)OC)C=CC1O | CC(C)[N:12](C(C)C)[CH2:11]C.I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | CCN(C(C)C)C(C)C.COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 1a14070cbe6fe5f59309149001ffa2dfc322a156a861405855acfdd6362705a6 | 951efce9f7401e9a96fe9b4f90874368f054ec53732a86c28b3b95242d371d1a | c1ccccc1 | C-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-C(-C)-C)-C(-C)-C.I-[c;H0;D3;+0:3](:[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9](-[O;D1;H1:10]):[c:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2]):[c:9](-[O;D1;H1:10]):[c:11] | 100 | [{"value": 100.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of 2 (0.376 mol), DIEA (196 mL, 1.13 mol) and THF (200 mL) was added benzyl chloroformate (59.0 mL, 0.414 mol) dropwise. After the reaction solution was stirred at room temperature for 1 hr, the solution was concentrated on a rotovap. The residue was partitioned between sat. NaHCO3 (300 mL) and di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | C1CCOC1 | null | 1 | CCN(C(C)C)C(C)C.COC(=O)c1ccc(O)c(I)c1>C1CCOC1>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f29e0524d2bb4f16898678943a66f3e1 | C1CCOC1.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.[OH-].[Li+].C1CCOC1>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | C1O[CH2:10][CH2:11][CH2:12]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | C1CCOC1.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | af6431764d7b6a0c53b29e6ba52c7e7b20102fffae4ff7bf8df31e9993d83889 | c914f6fa2d9eafe4b7954ab7b93ff3a695a6ab65e94131aace66d55280701a93 | c1ccccc1 | C1-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:2]-[CH;D3;+0:1](-[CH3;D1;+0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | To a solution of 3 (0.376 mol) in THF (200 mL) and water (100 mL) was added lithium hydroxide (31.6 g, 0.752 mol) and the mixture stirred for 2 hours. The reaction mixture was filtered through a silica gel plug (the pH of the filtrate was about 7) and concentrated. The residue was dried under vacuum to give 4 (0.376 mo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether | C1CCOC1 | null | c1ccccc1 | HO- | O | null | 2 | C1CCOC1.COC(=O)c1ccc(O)c(C#N)c1>O>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f16339f8d9b1499c868c368060cf71af | CNOC.COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | OC1=C(C=C(C(=O)OC)C=C1)I.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C=1C=CC2=C(C1)N=NN2O.Cl.CNOC.CCN(C(C)C)C(C)C>>C(#N)C=1C=C(C(=O)OC)C=CC1O | CO[NH:12][CH3:11].I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | CNOC.COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 0ddd49a1ca8b111466f27ea4250bfb9e859aa35592534618400427517f0d77d6 | 0f2f52485e0ef8d6cbb70f9be8e5a149bfe9ccf0be105523f3e66890b5410df9 | c1ccccc1 | C-O-[NH;D2;+0:1]-[CH3;D1;+0:2].I-[c;H0;D3;+0:3](:[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9](-[O;D1;H1:10]):[c:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:3](-[C;H0;D2;+0:2]#[N;H0;D1;+0:1]):[c:9](-[O;D1;H1:10]):[c:11] | 295.8 | [{"value": 78.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 295.8, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2 (1.49 g, 2.29 mmol), HBTU (1.3 g, 3.44 mmol), HOBt (530 mg, 3.44 mmol), and N,O-dimethylhydroxylamine HCl salt (340 mg, 3.44 mmol) in DMF (20 mL) was added DIEA (785 uL, 4.58 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The resulting... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | CN(C)C=O | null | 2 | CNOC.COC(=O)c1ccc(O)c(I)c1>CN(C)C=O>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc0cd75241084bb68e017a12ce2302cb | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | [H-].[Na+].C(#N)C=1C=C(C(=O)OC)C=CC1O.BrCCO[Si](C)(C)C(C)(C)C>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | C[Si](C)(OCCBr)[C:10](C)([CH3:11])[CH3:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | CN(C)C=O.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 7f22a03d1c7e423e260723257a54d81f1d7cd177ee2db6ae056344e211816325 | e5e494b410b54158ffcc29f62b8b911f348201ee0ca0a61b5b612710c1345ff8 | c1ccccc1 | Br-C-C-O-[Si](-C)(-C)-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 84.2 | [{"value": 41.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a suspension of NaH (0.39 g, 9.3 mmol) in DMF (15 mL) was added a solution of 3 (1.9 g, 6.5 mmol) in DMF (10 mL) at 0° C. under nitrogen. The reaction was stirred for 1.5 h, and then (2-bromoethoxy)-tert-butyldimethylsilane (2.09 mL, 9.7 mmol) was added. The reaction mixture was stirred overnight, diluted with EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol.TMS ether protective group | Ether | null | null | c1ccccc1 | HBr | CN(C)C=O.CCOC(=O)C | null | 1.5 | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)c1ccc(O)c(C#N)c1>CN(C)C=O.CCOC(=O)C>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac7799ce05b84b0c934960ba95b9a2f2 | CO.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 | C(#N)C=1C=C(C(=O)OC)C=CC1O.[BH4-].[Na+].C1CCOC1.CO>>C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C | O[CH3:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:13]([C:14]#[N:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([C:14]#[N:15])[cH:16]1 | CO.COC(=O)c1ccc(O)c(C#N)c1 | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4622e7934dd5328af1014056d8882932e5f303d08f873e671539ebf0ad57f848 | 51e77d0fe280879eec2f84298441067b61501ac5af19ab94008f56517f7456b2 | c1ccccc1 | O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C:7](-[CH3;D1;+0:1])-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 99 | [{"value": 99.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3 (3.0 g, 10.8 mmol) in THF/MeOH (10 mL/10 mL) was slowly added NaBH4 (407 mg, 10.8 mmol). The mixture was stirred for 10 min, quenched by saturated NH4Cl and partitioned between EtOAc and H2O. The organic layer was washed with sat NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to give ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether | null | null | c1ccccc1 | null | null | null | 0.166667 | CO.COC(=O)c1ccc(O)c(C#N)c1>>COC(=O)c1ccc(OC(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ca2049a89034a2283d41632e74ea623 | CN.COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 | CN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CN(C)C=O.OC1=C(C=C(C(=O)OC)C=C1)I.CCN(C(C)C)C(C)C>>C(#N)C=1C=C(C(=O)OC)C=CC1O | [CH3:11][NH2:12].I[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | CN.COC(=O)c1ccc(O)c(I)c1 | COC(=O)c1ccc(O)c(C#N)c1 | null | null | null | C-C Coupling | OtherReaction | 72645260c477d5d59b8c28a3f4573e1873a19c2dd5bbf1a5cee92a7bb55ad2bd | 331eba5143cc034fe99c4177c9125849def30dd58d39bbddf9a53d024fc826ff | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[O;D1;H1:8]):[c:9].[CH3;D1;+0:10]-[NH2;D1;+0:11]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]):[c:7](-[O;D1;H1:8]):[c:9] | 144.6 | [{"value": 63.0, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 144.6, "product": "C(#N)C=1C=C(C(=O)OC)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 11n DMF (158 mg, 0.41 mmol) were added amino acid 2 (100 mg, 0.52 mmol) and DIEA (272 μL, 0.16 mmol). The reaction was stirred for 14 h. Methylamine (2 M in THF, 0.4 mL) and HBTU (295 mg, 0.78 mmol) were then added. The reaction mixture was stirred for 5 h. The product was purified by RP-HPLC using a m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | null | null | 14 | CN.COC(=O)c1ccc(O)c(I)c1>>COC(=O)c1ccc(O)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a30d3f277fd4fedbbdb5f96906d6dfe | CC(C)Oc1ccc(C(=O)O)cc1Cl.CO>>COC(=O)c1ccc(OC(C)C)c(Cl)c1 | ClC=1C=C(C(=O)O)C=CC1OC(C)C.O=S(Cl)Cl.CO>>ClC=1C=C(C(=O)OC)C=CC1OC(C)C | O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([Cl:14])[cH:15]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[c:13]([Cl:14])[cH:15]1 | CC(C)Oc1ccc(C(=O)O)cc1Cl.CO | COC(=O)c1ccc(OC(C)C)c(Cl)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | A solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (1.00 g, 4.66 mmol) in methanol (10.0 mL) was treated with SOCl2 (0.68 mL, 9.32 mmol). After stirring overnight at ambient temperature, the solution was concentrated in vacuo and taken on without purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.04 (d, J=2.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | 8 | CC(C)Oc1ccc(C(=O)O)cc1Cl.CO>>COC(=O)c1ccc(OC(C)C)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae51bcc327cb458ea8bb426605580193 | COc1cc(CO)ccc1OCc1ccccc1.CS(=O)(=O)Cl>>COc1cc(COS(C)(=O)=O)ccc1OCc1ccccc1 | COC=1C=C(CO)C=CC1OCC1=CC=CC=C1.CS(=O)(=O)Cl.CCN(CC)CC>>CS(=O)(=O)OCC1=CC(=C(C=C1)OCC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.Cl[S:8]([CH3:9])(=[O:10])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][O:7][S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COc1cc(CO)ccc1OCc1ccccc1.CS(=O)(=O)Cl | COc1cc(COS(C)(=O)=O)ccc1OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(COc2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | 1 | HOUR | A solution of 3-(methoxy)-4-(benzyloxy)benzyl alcohol (0.244 g, 1.00 mmol) in CH2Cl2 (2.0 mL) was treated with methanesulfonylchloride (0.085 mL, 1.10 mmol) and Et3N (0.160 mL, 1.15 mmol). After stirring 1 h at ambient temperature, the reaction mixture was filtered through a short plug of silica gel using CH2Cl2 as the... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | COc1cc(CO)ccc1OCc1ccccc1.CS(=O)(=O)Cl>C(Cl)Cl>COc1cc(COS(C)(=O)=O)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-552fe5579ef244128c921a2d04d6d12b | COC(=O)c1ccc(N)c(N)c1.O=Cc1ccccc1>>COC(=O)c1ccc2[nH]c(-c3ccccc3)nc2c1 | O.NC=1C=C(C(=O)OC)C=CC1N.OS(=O)[O-].[Na+].C(C1=CC=CC=C1)=O>>C1(=CC=CC=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:18]([NH2:17])[cH:19]1.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]2[cH:19]1 | COC(=O)c1ccc(N)c(N)c1.O=Cc1ccccc1 | COC(=O)c1ccc2[nH]c(-c3ccccc3)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c:8](:[c:9]):[c:10](:[c:12]):[nH;D2;+0:11]:1):[c:5]:[c:6] | 97.1 | [{"value": 97.0, "product": "C1(=CC=CC=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "C1(=CC=CC=C1)C1=NC2=C(N1)C=CC(=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | An aqueous solution of NaHSO3 (21.0 mL, 40% in water) was treated benzaldehyde (2.00 mL, 20.0 mmol) and stirred at ambient temperature for 1 h. A solution of methyl 3,4-diaminobenzoate (3.32 g, 20.0 mmol) in ethanol (15.0 mL) was added and the solution was heated to reflux for 6 h. Upon cooling, the solution was poured... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | C(C)O | null | 1 | COC(=O)c1ccc(N)c(N)c1.O=Cc1ccccc1>C(C)O>COC(=O)c1ccc2[nH]c(-c3ccccc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e31a158b2454566ac7ae5cdb4d06eaf | COC(=O)c1ccc(C=O)cc1.Nc1ccccc1N>>COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 | OS(=O)[O-].[Na+].C(=O)C1=CC=C(C(=O)OC)C=C1.C=1(C(=CC=CC1)N)N>>N1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2 | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19][cH:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[NH2:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(C=O)cc1.Nc1ccccc1N | COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[nH;D2;+0:11]:[c:10]:1:[c:12] | 100.6 | [{"value": 100.0, "product": "N1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.6, "product": "N1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | An aqueous solution of NaHSO3 (20.0 mL, 40% in water) was treated with a solution of methyl 4-formylbenzoate (2.20 g, 13.4 mmol) in ethanol (15.0 mL) and stirred at ambient temperature for 1 h. 1,2-benzenediamine (1.45 g, 13.4 mmol) was added and the solution was heated to reflux overnight. Upon cooling, the solution w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)O | null | 1 | COC(=O)c1ccc(C=O)cc1.Nc1ccccc1N>C(C)O>COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab9c3cf2391943e49c30e3416d793f1f | CC(C)(C)C(=N)N.O=C(CBr)c1ccc(Br)cc1>>CC(C)(C)c1nc(-c2ccc(Br)cc2)c[nH]1 | BrCC(=O)C1=CC=C(C=C1)Br.CC(C)(C)C(=N)N.Cl.C(=O)([O-])[O-].[K+].[K+]>>BrC1=CC=C(C=C1)C=1N=C(NC1)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[NH:6])[NH2:16].O=[C:7]([c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1)[CH2:15]Br>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][nH:16]1 | CC(C)(C)C(=N)N.O=C(CBr)c1ccc(Br)cc1 | CC(C)(C)c1nc(-c2ccc(Br)cc2)c[nH]1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | d2a4eb5efb5d3f8ece8990722bf83ca46747550c01c6b5b8655072b32188db66 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2c[nH]cn2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[NH;D1;+0:14]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+... | 81 | [{"value": 81.0, "product": "BrC1=CC=C(C=C1)C=1N=C(NC1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "BrC1=CC=C(C=C1)C=1N=C(NC1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A solution of 2,4′-dibromoacetophenone (4.17 g, 15.0 mmol) in N,N-dimethylformamide (60.0 mL) was treated with t-butylcarbamidine hydrochloride (2.05 g, 15.0 mmol) and K2CO3 (4.15 g, 30.0 mmol) and heated to 50° C. for 4 h. Following cooling, the reaction was quenched with water, diluted with brine, and extracted thric... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HBr | CN(C=O)C | 50 | null | CC(C)(C)C(=N)N.O=C(CBr)c1ccc(Br)cc1>CN(C=O)C>CC(C)(C)c1nc(-c2ccc(Br)cc2)c[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-645cad6ba0e440379f971cb754f59817 | CC(C)Oc1ccc(C(=O)O)cc1C#N.NN>>CC(C)Oc1ccc(C(=O)NN)cc1C#N | O.NN.C(#N)C=1C=C(C(=O)O)C=CC1OC(C)C.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(#N)C=1C=C(C(=O)NN)C=CC1OC(C)C | O[C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:14]([C:15]#[N:16])[cH:13]1)=[O:10].[NH2:11][NH2:12]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][NH2:12])[cH:13][c:14]1[C:15]#[N:16] | CC(C)Oc1ccc(C(=O)O)cc1C#N.NN | CC(C)Oc1ccc(C(=O)NN)cc1C#N | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 95 | [{"value": 95.0, "product": "C(#N)C=1C=C(C(=O)NN)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "C(#N)C=1C=C(C(=O)NN)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (0.300 g, 1.46 mmol) in tetrahydrofuran (10.0 mL) was treated with 1,1′-carbonyldiimidazole (0.261 g, 1.61 mmol). After stirring 2 h at ambient temperature, hydrazine monohydrate (0.213 mL, 4.39 mmol) was added. After stirring an additional 2 h at ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 2 | CC(C)Oc1ccc(C(=O)O)cc1C#N.NN>O1CCCC1>CC(C)Oc1ccc(C(=O)NN)cc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-674d5f4a03694de6ac3e816dbc7769c0 | BrCC1CCCCC1.O=Cc1ccc(O)cc1>>O=Cc1ccc(OCC2CCCCC2)cc1 | BrCC1CCCCC1.C(=O)([O-])[O-].[K+].[K+].OC1=CC=C(C=O)C=C1.BrCC1CCCCC1.C(=O)([O-])[O-].[K+].[K+].BrCC1CCCCC1.C(=O)([O-])[O-].[K+].[K+]>>C1(CCCCC1)COC1=CC=C(C=O)C=C1 | Br[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][cH:16]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | BrCC1CCCCC1.O=Cc1ccc(O)cc1 | O=Cc1ccc(OCC2CCCCC2)cc1 | null | null | CC#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:4] | 82.5 | [{"value": 82.0, "product": "C1(CCCCC1)COC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "C1(CCCCC1)COC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 4-hydroxybenzaldehyde (0.244 g, 2.00 mmol) in CH3CN (4.0 mL) was treated with bromomethylcyclohexane (0.279 g, 2.00 mmol) and K2CO3 (0.332 g, 2.40 mmol). The reaction mixture was heated to 100° C. for 1 h in a Biotage Initiator microwave synthesizer. Additional bromomethylcyclohexane (0.279 g, 2.00 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CCCCC1 | HBr | CC#N | 100 | null | BrCC1CCCCC1.O=Cc1ccc(O)cc1>CC#N>O=Cc1ccc(OCC2CCCCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-969c5a80582646b09154468ddd0b1d70 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.N#CCCNN.O=Cc1ccc(OCc2ccccc2)cc1>>CC(C)Oc1ccc(C(=O)NN(CCC#N)Cc2ccc(OCc3ccccc3)cc2)cc1Cl | C(C1=CC=CC=C1)OC1=CC=C(C=O)C=C1.C(#N)[BH3-].[Na+].O.C1(=CC=C(C=C1)S(=O)(=O)O)C.ClC=1C=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC1OC(C)C.N(N)CCC#N.C(C1=CC=CC=C1)OC1=CC=C(C=O)C=C1.C(#N)[BH3-].[Na+].O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C(C(=O)NN(CC2=CC=C(C=C2)OCC2=CC=CC=C2)CCC#N)C=CC1OC(C)C | Fc1c(F)c(F)c(O[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:33]([Cl:34])[cH:32]2)=[O:10])c(F)c1F.[NH2:11][NH:12][CH2:13][CH2:14][C:15]#[N:16].O=[CH:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][cH:31]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8](... | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.N#CCCNN.O=Cc1ccc(OCc2ccccc2)cc1 | CC(C)Oc1ccc(C(=O)NN(CCC#N)Cc2ccc(OCc3ccccc3)cc2)cc1Cl | null | null | CO | Acylation | OtherReaction | 4f44b51689e1f4833a0397da7a50cc8df7324d129854859806740bbba48c649d | 43d3d2eb9378ed442d985c6d5bfd8e2bbd03cb1a22ded2b68a4ab3785a383157 | O=C(NNCc1ccc(OCc2ccccc2)cc1)c1ccccc1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):c(-F):c:1-F.O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[NH2;D1;+0:13]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 61.3 | [{"value": 61.0, "product": "ClC=1C=C(C(=O)NN(CC2=CC=C(C=C2)OCC2=CC=CC=C2)CCC#N)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.3, "product": "ClC=1C=C(C(=O)NN(CC2=CC=C(C=C2)OCC2=CC=CC=C2)CCC#N)C=CC1OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (0.100 g, 0.263 mmol) in methanol (5.0 mL) was treated with 3-hydrazinopropanenitrile (0.023 mL, 0.289 mmol) and heated to reflux for 1 h. Following cooling, 4-(benzyloxy)benzaldehyde (0.067 g, 0.315 mmol), sodium cyanoborohydride (0.020 g, 0.315 m... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aldehyde.Ester | Acylhydrazine | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HF | CO | null | 0.5 | CC(C)Oc1ccc(C(=O)Oc2c(F)c(F)c(F)c(F)c2F)cc1Cl.N#CCCNN.O=Cc1ccc(OCc2ccccc2)cc1>CO>CC(C)Oc1ccc(C(=O)NN(CCC#N)Cc2ccc(OCc3ccccc3)cc2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1214585e18644ff0b15cadc6b737a489 | C#CCOC.COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>>COCC#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | C(C)(C)NC(C)C.IC1=CC=C(C2=C1OCO2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2.C(C#C)OC>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)NC1=CC=C(C=2OCOC21)C#CCOC | [CH3:1][O:2][CH2:3][C:4]#[CH:5].I[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][n:14][c:15]3[cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[c:28]([O:29][CH3:30])[cH:31][c:32]23)[c:33]2[c:34]1[O:35][CH2:36][O:37]2>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([NH... | C#CCOC.COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | COCC#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 30.6 | [{"value": 30.6, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)NC1=CC=C(C=2OCOC21)C#CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Bis(Triphenyl-phosphine)palladium(II) chloride (94 mg), copper iodide (19 mg) and diisopropylamine (68 mg) were added to a stirred solution of N-(7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (200 mg) and methyl propargyl ether (47 mg) in ethyl acetate (5 mls) at −20° C. The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)(=O)OCC | null | 16 | C#CCOC.COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)(=O)OCC>COCC#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc31d262ef28486bb411c7e7a1c90a3a | CO.O=C(O)c1cccc(O)c1O>>COC(=O)c1cccc(O)c1O | OC1=C(C(=O)O)C=CC=C1O.CO>>OC1=C(C(=O)OC)C=CC=C1O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]1[OH:12] | CO.O=C(O)c1cccc(O)c1O | COC(=O)c1cccc(O)c1O | null | S(O)(O)(=O)=O | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | null | null | A mixture of 2,3-dihydroxybenzoic acid (5 g), methanol (50 ml) and concentrated sulphuric acid (10 drops) was stirred and heated to 60° C. for 24 hours. The mixture was evaporated and the residue was taken up in ethyl acetate. The organic solution was washed with a saturated solution of sodium bicarbonate, dried over m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | S(O)(O)(=O)=O | 60 | null | CO.O=C(O)c1cccc(O)c1O>S(O)(O)(=O)=O>COC(=O)c1cccc(O)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-689ca49645354ed7b4eb7185c06147f4 | Nc1cccc2c1OCO2>>Nc1ccc(I)c2c1OCO2 | I(=O)(=O)Cl.I(=O)(=O)Cl.C(C1=CC=CC=C1)[N+](C)(C)C.O1COC2=C1C=CC=C2N.C([O-])([O-])=O.[Ca+2]>>IC1=CC=C(C2=C1OCO2)N | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:7]2[c:8]1[O:9][CH2:10][O:11]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([I:6])[c:7]2[c:8]1[O:9][CH2:10][O:11]2 | Nc1cccc2c1OCO2 | Nc1ccc(I)c2c1OCO2 | null | null | ClCCl.O.CO | Functional Group Addition | Aromatic iodination | 6ba82dee4826ea9605d6e45f3fbe0149be15f482d7d85b7cfe266d92504d953d | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc2c(c1)OCO2 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1>>[I;D1;H0:9]-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | null | null | 1.5 | HOUR | Benzyltrimethylammonium dichloroiodate (2.8 g) was added portionwise over 10 minutes to a stirred mixture of 1,3-benzodioxol-4-amine (1 g), calcium carbonate (0.95 g) in methanol (5 ml) and dichloromethane (10 ml). The reaction mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was diluted w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | Other | ClCCl.O.CO | null | 1.5 | Nc1cccc2c1OCO2>ClCCl.O.CO>Nc1ccc(I)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fdd00c07e954c4ea497c729e85dc65b | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | NC1=C(C(=O)N)C=C(C(=C1)OCC1=CC=CC=C1)OC.[Cl-].CN(C=NC=[N+](C)C)C.O1CCOCC1.C(C)(=O)[O-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0798449d56bc7e7756a703d33bd60780d26c4986e39e1809e15228456c95135b | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 83.9 | [{"value": 83.9, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem., 1977, 20, 146-149; 10 g), (3-dimethylamino-2-azaprop-2-en-1-ylidene)dimethylammonium chloride (Gold's reagent, 7.4 g) and dioxane (100 ml) was stirred and heated to reflux for 24 hours. Sodium acetate (3.02 g) and acetic acid (1.65 ml) were added and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | C(C)(=O)O | null | null | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>C(C)(=O)O>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8eb7f267ef34b4f88c5382363ff5b97 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | After repetition of the reaction so described, a mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (35 g), thionyl chloride (440 ml) and DMF (1.75 ml) was heated to reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue was azeotroped with toluene three times. The residue was di... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3228802d071348aba37b9700ebabcbe4 | C1COCCN1.ClCCCBr>>ClCCCN1CCOCC1 | N1CCOCC1.BrCCCCl>>O1CCN(CC1)CCCCl | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[CH2:4][CH2:3][CH2:2][Cl:1]>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | C1COCCN1.ClCCCBr | ClCCCN1CCOCC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1COCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#8:4]-[C:5]-[C:6]-1 | null | [] | 70 | CELSIUS | null | null | A mixture of morpholine (52.2 ml), 1-bromo-3-chloropropane (30 ml) and toluene (180 ml) was heated to 70° C. for 3 hours. The solid was removed by filtration and the filtrate was evaporated under vacuum. The resultant oil was decanted from the additional solid which was deposited and the oil was purified by vacuum dist... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HBr | C1(=CC=CC=C1)C | 70 | null | C1COCCN1.ClCCCBr>C1(=CC=CC=C1)C>ClCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a504a42da584de49401a76c01ed7ad0 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc(I)c2c1OCO2>>COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.IC1=CC=C(C2=C1OCO2)N>>IC1=CC=C(C2=C1OCO2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]([I:12])[c:13]2[c:14]1[O:15][CH2:16][O:17]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]([I:12])[c:13]4[c:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc(I)c2c1OCO2 | COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | O1CCOCC1.CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 70.6 | [{"value": 70.6, "product": "IC1=CC=C(C2=C1OCO2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 4.0M HCl in Dioxane (0.37 ml) was added to a stirred suspension of 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (500 mg) and 7-iodo-1,3-benzodioxol-4-amine (0.39 g) in DMA (1 ml). The resultant mixture was stirred and heated to 80° C. for 10 mins. A grey precipitate was formed which was filtered and washed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | O1CCOCC1.CC(=O)N(C)C | 80 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc(I)c2c1OCO2>O1CCOCC1.CC(=O)N(C)C>COc1cc2c(Nc3ccc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-977e051cf17b49c0acda6249e6ba60e5 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | C[Si](N[Si](C)(C)C)(C)C.[Na].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:34]2[c:35]1[O:36][CH2:37][O:38]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[c:29]([O:30][CH3:31])[cH:32][c:33]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8](... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 72.2 | [{"value": 72.2, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Sodium hexamethyldisilazane (1M solution in THF; 1.0 ml) was added to a mixture of 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.16 g) and 5-chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amine (0.12 g) in DMA (5 ml) that was cooled to 0° C. The resultant mixture was stirred and allowed to warm to amb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CC(=O)N(C)C | 0 | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CC(=O)N(C)C>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91b21b00d834420dbe555ee53af2550b | C#CCOC.Nc1c(Cl)cc(I)c2c1OCO2>>COCC#Cc1cc(Cl)c(N)c2c1OCO2 | C(C)(C)NC(C)C.ClC1=C(C2=C(OCO2)C(=C1)I)N.C(C#C)OC>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N | [CH3:1][O:2][CH2:3][C:4]#[CH:5].I[c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:12]2[c:13]1[O:14][CH2:15][O:16]2>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:12]2[c:13]1[O:14][CH2:15][O:16]2 | C#CCOC.Nc1c(Cl)cc(I)c2c1OCO2 | COCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | null | null | null | null | Bis(Triphenyl-phosphine)palladium(II) chloride (472 mg), copper iodide (192 mg) and diisopropylamine (680 mg) were added to a stirred solution of 5-chloro-7-iodo-1,3-benzodioxol-4-amine (1000 mg) and methyl propargyl ether (471 mg) in ethyl acetate (10 mls) at −20° C. The reaction was allowed to warm to ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)(=O)OCC | null | null | C#CCOC.Nc1c(Cl)cc(I)c2c1OCO2>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)(=O)OCC>COCC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4708001b55df41498dd9dd946d2cabec | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:35]2[c:36]1[O:37][CH2:38][O:39]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]3)[c:30]([O:31][CH3:32])[cH:33][c:34]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[c... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 65.7 | [{"value": 65.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | A solution of sodium bis(trimethylsilyl)amide (1.33 ml) in tetrahydrofuran (1.0 Mol/L, 1.33 mmol) was added to a solution of 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (0.212 g) and 5-chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amine (0.16 g) in DMF (3 ml) cooled to 0° C. under a nitrogen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | 1.5 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1>[Cl-].[NH4+].CN(C)C=O>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b46ce9e6979b4ab6819c04f86aa029d8 | CN1CCNCC1.OCCCBr>>CN1CCN(CCCO)CC1 | BrCCCO.CN1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>OCCCN1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:10][CH2:11]1.Br[CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][OH:9])[CH2:10][CH2:11]1 | CN1CCNCC1.OCCCBr | CN1CCN(CCCO)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | A mixture of 3-bromopropanol (20 ml), N-methylpiperazine (29 ml), potassium carbonate (83 g) and ethanol (200 ml)was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The resultant mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HBr | C(C)O | null | null | CN1CCNCC1.OCCCBr>C(C)O>CN1CCN(CCCO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aedeedf1385e407d97a14ec9f40f6b3f | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.OCCCN1CCN(CC1)C.C(C)N(CC)CC>>C1(=CC=C(C=C1)S(=O)(=O)OCCCN1CCN(CC1)C)C | [OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]2)[cH:20][cH:21]1 | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCCN1CCNCC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 4-Toluenesulphonyl chloride (3.2 g) was added to a stirred mixture of 1-(3-hydroxypropyl)-4-methylpiperazine (2.4 g), triethylamine (4.6 ml) and methylene chloride (60 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The solution was washed in turn with a saturated aqueous sodium bicarbonat... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1C[NH]CC[NH]1 | HCl | C(Cl)Cl | null | null | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>C(Cl)Cl>Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ac602cf09f74dc2b42b2152ae962975 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | NC1=C(C(=O)N)C=C(C(=C1)OCC1=CC=CC=C1)OC.[Cl-].CN(C=NC=[N+](C)C)C.O1CCOCC1.C(C)(=O)[O-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0798449d56bc7e7756a703d33bd60780d26c4986e39e1809e15228456c95135b | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 83.9 | [{"value": 83.9, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem., 1977, 20, 146-149; 10 g), (3-dimethylamino-2-azaprop-2-en-1-ylidene)dimethylammonium chloride (Gold's reagent, 7.4 g) and dioxane (100 ml) was stirred and heated to reflux for 24 hours. Sodium acetate (3.02 g) and acetic acid (1.65 ml) were added and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | C(C)(=O)O | null | null | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>C(C)(=O)O>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9975e79f132408fb3402d78e1cb5a69 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | After repetition of the reaction so described, a mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (20.3 g), thionyl chloride (440 ml) and DMF (1.75 ml) was heated to reflux for4 hours. The thionyl chloride was evaporated under vacuum and the residue was azeotroped with toluene three times to give 7-benzylox... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a06e974057146cbb001ce968350b1b5 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | COC=1C=C2C(NC=NC2=CC1OCCCN1CCN(CC1)C)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:2... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCNCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | After repetition of the previous reaction, a mixture of 6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]-3,4-dihydroquinazolin-4-one (2.15 g), thionyl chloride (25 ml) and DMF (0.18 ml) was stirred and heated to reflux for 2 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped twice with to... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6dece205276a4b6fab876c8abbd09338 | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.FC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>FC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([F:9])[c:10]([NH2:11])[c:34]2[c:35]1[O:36][CH2:37][O:38]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[c:29]([O:30][CH3:31])[cH:32][c:33]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([... | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 78 | [{"value": 78.0, "product": "FC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "FC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | 4-Chloro-6-methoxy-7-(3-morpholin-4ylpropoxy)quinazoline (201 mg, 0.60 mmol) and 5-fluoro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (140 mg, 0.63 mmol) in DMF (3 ml) were cooled in an ice-water bath then treated dropwise, under an atmosphere of nitrogen, with a solution of sodium bis(trimethylsilyl)amide (1.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | 1.5 | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0bb6e202603404c829e87cd57f5bc37 | Nc1c(F)ccc2c1OCO2>>Nc1c(F)cc(I)c2c1OCO2 | FC1=C(C2=C(OCO2)C=C1)N.I(=O)(=O)Cl.I(=O)(=O)Cl.C(C1=CC=CC=C1)[N+](C)(C)C.C([O-])([O-])=O.[Ca+2]>>NC1=C(C=C(C=2OCOC21)I)F | [NH2:1][c:2]1[c:3]([F:4])[cH:5][cH:6][c:8]2[c:9]1[O:10][CH2:11][O:12]2>>[NH2:1][c:2]1[c:3]([F:4])[cH:5][c:6]([I:7])[c:8]2[c:9]1[O:10][CH2:11][O:12]2 | Nc1c(F)ccc2c1OCO2 | Nc1c(F)cc(I)c2c1OCO2 | null | null | ClCCl.CO | Functional Group Addition | Aromatic iodination | 6ba82dee4826ea9605d6e45f3fbe0149be15f482d7d85b7cfe266d92504d953d | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc2c(c1)OCO2 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1>>[I;D1;H0:9]-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 57.1 | [{"value": 57.0, "product": "NC1=C(C=C(C=2OCOC21)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.1, "product": "NC1=C(C=C(C=2OCOC21)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Fluoro-1,3-benzodioxol-4-amine (1.1 g, 7.10 mmol), benzyltrimethylammonium dichloroiodate (2.7 g, 7.76 mmol) and calcium carbonate (0.92 g, 9.2 mmol) in a mixture of dichloromethane (10 ml) and methanol (5 ml) were stirred at room temperature for 3 hr. The mixture was filtered through Celite and then evaporated to a ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | Other | ClCCl.CO | null | 3 | Nc1c(F)ccc2c1OCO2>ClCCl.CO>Nc1c(F)cc(I)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d15ad3c88c042edbba2f2e018d07877 | COCC#Cc1cc(F)cc2c1OC(N)O2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1>>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCS(=O)(=O)CC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCS(CC1)(=O)=O.FC1=CC2=C(OC(O2)N)C(=C1)C#CCOC.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)F)OC)=O | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([F:9])[cH:10][c:36]2[c:37]1[O:38][CH:39]([NH2:11])[O:40]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][S:26](=[O:27])(=[O:28])[CH2:29][CH2:30]3)[c:31]([O:32][CH3:33])[cH:34][c:35]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][... | COCC#Cc1cc(F)cc2c1OC(N)O2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCS(=O)(=O)CC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 8d8d958541a668a8e4a7b9c38e8c19a2d704e8170d6ab4859e11cd0ae2f5309f | 073f62a3818e3c589c6cf905d1f7b64adb426c91fc96c232669654b3fe83ad5b | O=S1(=O)CCN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[F;D1;H0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]1:[c:14]-[#8:15]-[CH;D3;+0:16](-[NH2;D1;+0:17])-[#8:18]-1>>[F;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13]1:[c:14]... | 87 | [{"value": 87.0, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)F)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-7-[3-(1,1-dioxidothiomorpholin-4-yl)propoxy]-6-methoxyquinazoline (150 mg, 0.39 mmol), 5-fluoro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxolamine (91 mg, 0.41 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 0.82 ml) in DMF (2.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary amine | Ether.Ether.Secondary amine | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | c1ccc2ncncc2c1.C1CSCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCC#Cc1cc(F)cc2c1OC(N)O2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1>CN(C)C=O>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCS(=O)(=O)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91553e00759a490f9aba0023e4e56409 | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C(C)=O)CC1>>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)Cl)OC.FC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)F)OC | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([F:9])[c:10]([NH2:11])[c:37]2[c:38]1[O:39][CH2:40][O:41]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][N:26]([C:27]([CH3:28])=[O:29])[CH2:30][CH2:31]3)[c:32]([O:33][CH3:34])[cH:35][c:36]12>>[CH3:1][O:2][CH2:3][C:4]... | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C(C)=O)CC1 | COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 72 | [{"value": 72.0, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the, method described in the example 4 using 7-[3-(4-acetylpiperazin-1-yl)propoxy]-4-chloro-6-methoxyquinazoline (150 mg, 0.40 mmol), 5-fluoro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (97 mg, 0.43 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 0.83 ml) in DMF (2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C(C)=O)CC1>CN(C)C=O>COCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dda3c0e7a704bc8979c8831a11755f0 | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:35]2[c:36]1[O:37][CH2:38][O:39]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[c:30]([O:31][CH3:32])[cH:33][c:34]12>>[CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:... | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 33.3 | [{"value": 33.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (165 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The crude... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8bf547caa3d74fd2af9026660ec1851e | COCCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COCCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.FC1=C(C2=C(OCO2)C(=C1)C#CCCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>FC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([F:10])[c:11]([NH2:12])[c:35]2[c:36]1[O:37][CH2:38][O:39]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[c:30]([O:31][CH3:32])[cH:33][c:34]12>>[CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7... | COCCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COCCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 57.6 | [{"value": 57.0, "product": "FC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "FC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-fluoro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (154 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.25 ml) in DMF (3 ml). The crude... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCCC#Cc1cc(F)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COCCC#Cc1cc(F)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98a753213cf941e28486fe2eb805ad86 | CCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>CCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][CH2:2][O:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:35]2[c:36]1[O:37][CH2:38][O:39]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[c:30]([O:31][CH3:32])[cH:33][c:34]12>>[CH3:1][CH2:2][O:3][CH2:4][C:5]#[C:6][c:... | CCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | CCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 79.7 | [{"value": 79.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-(3-ethoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (165 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The crude... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | CCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>CCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7463d5ac6fc3463687627bcc22aaefab | COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COCCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]#[C:8][c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:37]2[c:38]1[O:39][CH2:40][O:41]2.Cl[c:15]1[n:16][cH:17][n:18][c:19]2[cH:20][c:21]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[c:32]([O:33][CH3:34])[cH:35][c:36]12>>[CH3:1][O:2][CH2:3][CH2:4]... | COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COCCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 77.6 | [{"value": 77.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-[3-(2-methoxyethoxy)prop-1-yn-1-yl]-1,3-benzodioxol-4-amine (185 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COCCOCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da4f073e48274596bac6afd0de47976e | C#CCOCCOC.Nc1c(Cl)cc(I)c2c1OCO2>>COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)I)N.COCCOCC#C.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)N | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]#[CH:8].I[c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]2[c:16]1[O:17][CH2:18][O:19]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]#[C:8][c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]2[c:16]1[O:17][CH2:18][O:19]2 | C#CCOCCOC.Nc1c(Cl)cc(I)c2c1OCO2 | COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 86 | [{"value": 86.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCCOC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 5-Chloro-7-iodo-1,3-benzodioxol-4-amine (1.0 g, 3.36 mmol) and 3-(2-methoxyethoxy)prop-1-yne (766 mg, 6.72 mmol) in ethyl acetate (12 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, and then treated with bis(triphenylphosphine) palladium(II) dichloride (236 mg, 10 mol %) followed by copper(I) iodide (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 2.5 | C#CCOCCOC.Nc1c(Cl)cc(I)c2c1OCO2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>COCCOCC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7964d59c0c7649a787bd8ee1409aa931 | CC(C)OCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][O:16][CH:17]([CH3:18])[CH3:19])[c:20]2[c:21]1[O:22][CH2:23][O:24]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[cH:29][c:28]2[n:27][cH:26][n:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[... | CC(C)OCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 66.1 | [{"value": 66.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-(3-isopropoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (174 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | CC(C)OCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e90b30b417e14c0da8c9a12b575ea345 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2>>COc1cc2c(Nc3c(Cl)cc(C#CCOCC4CC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[cH:30][c:29]2[n:28][cH:27][n:26]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][O:16][CH2:17][CH:18]2[CH2:19][CH2:20]2)[c:21]2[c:22]1[O:23][CH2:24][O:25]2>>[CH3:1][O:2][c:3]1[cH:4... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2 | COc1cc2c(Nc3c(Cl)cc(C#CCOCC4CC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | C(#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2)COCC1CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 72 | [{"value": 72.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-[3-(cyclopropylmethoxy)prop-1-yn-1-yl]-1,3-benzodioxol-4-amine (182 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | C1CC1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCOCC4CC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff6d403082bb4c9caf5ce5a3e20fbcf0 | C#CCOCC1CC1.Nc1c(Cl)cc(I)c2c1OCO2>>Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)I)N.C(C#C)OCC1CC1.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)N | [CH:7]#[C:8][CH2:9][O:10][CH2:11][CH:12]1[CH2:13][CH2:14]1.I[c:6]1[cH:5][c:3]([Cl:4])[c:2]([NH2:1])[c:16]2[c:15]1[O:19][CH2:18][O:17]2>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7]#[C:8][CH2:9][O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[c:15]2[c:16]1[O:17][CH2:18][O:19]2 | C#CCOCC1CC1.Nc1c(Cl)cc(I)c2c1OCO2 | Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cccc2c1OCO2)COCC1CC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 90.4 | [{"value": 90.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOCC1CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 5-Chloro-7-iodo-1,3-benzodioxol-4-amine (1.0 g, 3.36 mmol) and [(prop-2-yn-1-yloxy)methyl]cyclopropane (739 mg, 6.72 mmol) in ethyl acetate (12 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine) palladium(II) dichloride (236 mg, 10 mol %) followed by copper(I) io... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | C1CC1.c1ccc2c(c1)OCO2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 4 | C#CCOCC1CC1.Nc1c(Cl)cc(I)c2c1OCO2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>Nc1c(Cl)cc(C#CCOCC2CC2)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6491e3b2764442018e042adba2734313 | CC(=O)N1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.C(C)(=O)N1CCNCC1>>C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC | [NH:24]1[CH2:25][CH2:26][N:27]([C:28]([CH3:29])=[O:30])[CH2:31][CH2:32]1.Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:39]4[c:38]3[O:42][CH2:41][O:40]4)[c:37]2[cH:36][c:33]1[O:34][CH3:35]>>[CH3:1][O:2][CH2:... | CC(=O)N1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 82.6 | [{"value": 82.0, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (192 mg, 0.38 mmol) and 1-acetylpiperazine (244 mg, 1.9 mmol) in 2-methoxyethanol (4 ml) were stirred and heated at 100° for 12 hr. then quenched in water and extracted with dichloromethane. The combined extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | CC(=O)N1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cc1be49569b4380ba972522b23e8531 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OCC1CCNCC1>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(CO)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.N1CCC(CC1)CO>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)CO | Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34].[NH:24]1[CH2:25][CH2:26][CH:27]([CH2:28][OH:29])[CH2:30][CH2:31]1>>[CH3:1][O:2][CH2:3][CH2:... | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OCC1CCNCC1 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(CO)CC4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCCCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 80 | [{"value": 80.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 13 using N-[5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (192 mg, 0.38 mmol) and 4-piperidinemethanol (220 mg, 1.9 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OCC1CCNCC1>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(CO)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-705e201ed1f54150bae5b932266b0257 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2>>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N4CCOCC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)N2CCOCC2)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)N1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH2:37][CH2:38][CH2:39][N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)[cH:34][c:33]2[n:32][cH:31][n:30]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][NH:16][C:17](=[O:18])[N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[c:25]2[c:26]1[O:27][CH2:28][O:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2 | COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N4CCOCC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(NCC#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2)N1CCOCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 72.1 | [{"value": 72.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | This was prepared by the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), N-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]morpholine-4-carboxamide (220 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | C1COCC[NH]1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N4CCOCC4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-899fcc4891e9410c93e903e7568e6b17 | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.C1COCCN1>>C#CCNC(=O)N1CCOCC1 | N1CCOCC1.C(C#C)NC(OC1=CC=C(C=C1)[N+](=O)[O-])=O>>C(C#C)NC(=O)N1CCOCC1 | O=[N+]([O-])c1ccc(O[C:5]([NH:4][CH2:3][C:2]#[CH:1])=[O:6])cc1.[NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1 | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.C1COCCN1 | C#CCNC(=O)N1CCOCC1 | null | null | ClCCl | Acylation | OtherReaction | 09154e896c7157b7f9689a575f751f2c9525c214676349059c8525cde3edb5ef | fc4b793bbeca2541e0488e7b2269d1dcbab20357be7785ff606aacdf4ebd8736 | C1COCCN1 | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5]#[C;D1;H1:6]):c:c:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H1:6]#[C:5]-[C:4]-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-1 | 92.6 | [{"value": 92.0, "product": "C(C#C)NC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "C(C#C)NC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Morpholine (510 mg, 5.86 mmol) and 4-nitrophenyl prop-2-yn-1-ylcarbamate (800 mg (80% purity), 2.91 mmol) in dichloromethane (10 ml) were stirred at room temperature for 4 hours and then the reaction solution was purified directly by chromatography on silica using ethyl acetate as eluent to give N-prop-2-yn-1-ylmorphol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Secondary amine | Urea | c1ccccc1.C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HO- | ClCCl | null | null | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.C1COCCN1>ClCCl>C#CCNC(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fcb2972fcc543b897ea9b26af6fc289 | C#CCNC(=O)N1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2>>Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)I)N.C(C#C)NC(=O)N1CCOCC1.C(C)(C)NC(C)C>>NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)N2CCOCC2)Cl | [CH:7]#[C:8][CH2:9][NH:10][C:11](=[O:12])[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.I[c:6]1[cH:5][c:3]([Cl:4])[c:2]([NH2:1])[c:20]2[c:19]1[O:23][CH2:22][O:21]2>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7]#[C:8][CH2:9][NH:10][C:11](=[O:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[c:19]2[c:20]1[O:21][CH2:22][O... | C#CCNC(=O)N1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2 | Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C(NCC#Cc1cccc2c1OCO2)N1CCOCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 78 | [{"value": 78.0, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)N2CCOCC2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)N2CCOCC2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Chloro-7-iodo-1,3-benzodioxol-4-amine (600 mg, 2.02 mmol) and N-prop-2-yn-1-ylmorpholine-4-carboxamide (406 mg, 2.42 mmol) in ethyl acetate (10 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, and then treated with bis(triphenylphosphine) palladium(II) dichloride (140 mg, 10 mol %) followed by copper... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | C1COCC[NH]1.c1ccc2c(c1)OCO2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 3 | C#CCNC(=O)N1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>Nc1c(Cl)cc(C#CCNC(=O)N2CCOCC2)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6b67a06e69049aeaa8b8415d1396d21 | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(N(C)C)=O | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][NH:16][C:17](=[O:18])[N:19]([CH3:20])[CH3:21])[c:22]2[c:23]1[O:24][CH2:25][O:26]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH2:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[cH:31][c:30]2[n:29][cH:28][n:27]1>>[CH3:1][O:2][c:3... | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 72.1 | [{"value": 72.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), N′-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N,N-dimethylurea (193 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7148a8bdb98f4432be05718119742861 | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.CNC>>C#CCNC(=O)N(C)C | CNC.C(C#C)NC(OC1=CC=C(C=C1)[N+](=O)[O-])=O>>CN(C(=O)NCC#C)C | O=[N+]([O-])c1ccc(O[C:5]([NH:4][CH2:3][C:2]#[CH:1])=[O:6])cc1.[NH:7]([CH3:8])[CH3:9]>>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[N:7]([CH3:8])[CH3:9] | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.CNC | C#CCNC(=O)N(C)C | null | null | ClCCl.C1CCOC1 | Acylation | OtherReaction | e2d977a702ed644c57a3c6a03e066457d8dc73a51640ae48afb0cf24b6adf835 | fc4b793bbeca2541e0488e7b2269d1dcbab20357be7785ff606aacdf4ebd8736 | null | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5]#[C;D1;H1:6]):c:c:1.[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H1:6]#[C:5]-[C:4]-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9] | 79 | [{"value": 79.0, "product": "CN(C(=O)NCC#C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethylamine (3.0 ml of a 2.0M solution in THF, 6.0 mmol) and 4-nitrophenyl prop-2-yn-1-ylcarbamate (800 mg (80% purity), 2.91 mmol) in dichloromethane (7 ml) were stirred at room temperature for 4 hr. then the reaction solution purified by chromatography on silica using ethyl acetate as eluent to give N,N-dimethyl-N′... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Secondary amine | Urea | c1ccccc1 | null | null | HO- | ClCCl.C1CCOC1 | null | null | C#CCNC(=O)Oc1ccc([N+](=O)[O-])cc1.CNC>ClCCl.C1CCOC1>C#CCNC(=O)N(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3e05626616943cbb19396b2669793c4 | C#CCNC(=O)N(C)C.NC1(Cl)C=C(I)C2=C(C1)OCO2>>CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 | ClC1(CC2=C(OCO2)C(=C1)I)N.CN(C(=O)NCC#C)C.C(C)(C)NC(C)C>>NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][C:8]#[CH:9].I[C:10]1=[CH:11][C:12]([Cl:13])([NH2:15])[CH2:14][C:16]2=[C:17]1[O:18][CH2:19][O:20]2>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][C:8]#[C:9][c:10]1[cH:11][c:12]([Cl:13])[c:14]([NH2:15])[c:16]2[c:17]1[O:18][CH2:19][O:20]2 | C#CCNC(=O)N(C)C.NC1(Cl)C=C(I)C2=C(C1)OCO2 | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 2b0a3772e410de844c94c47be109f4ca55f5272dd9761ac50f8feff83778b70b | 5db9710764a7249fb1da8c25bd3dc2425f54f0a9f9f87614d5671906363e7f87 | c1ccc2c(c1)OCO2 | I-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C;H0;D4;+0:3](-[Cl;D1;H0:4])(-[NH2;D1;+0:5])-[CH2;D2;+0:6]-[C;H0;D3;+0:7]2=[C;H0;D3;+0:8]-1-[#8:9]-[C:10]-[#8:11]-2.[C:12]-[C:13]#[CH;D1;+0:14]>>[C:12]-[C:13]#[C;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[Cl;D1;H0:4]):[c;H0;D3;+0:6](-[NH2;D1;+0:5]):[c;H0;D3;+0:7]2:[c;H0;D... | 68.4 | [{"value": 68.0, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Chloro-7-iodo-1,3-benzodioxol-5-amine (682 mg, 2.29 mmol) and N,N-dimethyl-N′-prop-2-yn-1-ylurea (289 mg, 2.29 mmol) in ethyl acetate (10 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine) palladium(II) dichloride (161 mg, 10 mol %) followed by copper(I) iodide... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Alkenyl halide.Ether.Ether.Primary amine.Alkyne | Aromatic halide.Ether.Ether.Primary amine.Alkyne | C1=CC2=C(CC1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 3 | C#CCNC(=O)N(C)C.NC1(Cl)C=C(I)C2=C(C1)OCO2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13976471972b4cabb87c6b6d9052a3b2 | CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>CNC(=O)NCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)NC)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)NC | [CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][C:7]#[C:8][c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:37]2[c:38]1[O:39][CH2:40][O:41]2.Cl[c:15]1[n:16][cH:17][n:18][c:19]2[cH:20][c:21]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[c:32]([O:33][CH3:34])[cH:35][c:36]12>>[CH3:1][NH:2][C:3](=[O:4]... | CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | CNC(=O)NCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 61 | [{"value": 61.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCNC(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), N-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N′-methylurea (170 mg, 0.60 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The crude pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>CNC(=O)NCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-406e541964b44e17bdd87d62440fc6cf | C#CCNC(=O)NC.Nc1c(Cl)cc(I)c2c1OCO2>>CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)I)N.CNC(=O)NCC#C.C(C)(C)NC(C)C>>NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)NC)Cl | [CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][C:7]#[CH:8].I[c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]2[c:16]1[O:17][CH2:18][O:19]2>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][C:7]#[C:8][c:9]1[cH:10][c:11]([Cl:12])[c:13]([NH2:14])[c:15]2[c:16]1[O:17][CH2:18][O:19]2 | C#CCNC(=O)NC.Nc1c(Cl)cc(I)c2c1OCO2 | CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 37.4 | [{"value": 37.0, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)NC)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "NC1=C(C=C(C2=C1OCO2)C#CCNC(=O)NC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Chloro-7-iodo-1,3-benzodioxol-4-amine (500 mg, 1.68 mmol) and N-methyl-N′-prop-2-yn-1-ylurea (226 mg, 2.02 mmol) in ethyl acetate (10 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine) palladium(II) dichloride (118 mg, 10 mol %) followed by copper(I) iodide (32... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 3 | C#CCNC(=O)NC.Nc1c(Cl)cc(I)c2c1OCO2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>CNC(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a7a7712521d45429ef2571406f77e4e | CN1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CN1CCNCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C | [NH:24]1[CH2:25][CH2:26][N:27]([CH3:28])[CH2:29][CH2:30]1.Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:37]4[c:36]3[O:40][CH2:39][O:38]4)[c:35]2[cH:34][c:31]1[O:32][CH3:33]>>[CH3:1][O:2][CH2:3][CH2:4][C:5]#... | CN1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 68 | [{"value": 68.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 13 using N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 1-methylpiperazine (198 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatography on... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | CN1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c883de606af43868ac1be7d94f5896d | CNC.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(C)C)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CNC>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(C)C | [NH:24]([CH3:25])[CH3:26].Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:33]4[c:32]3[O:36][CH2:35][O:34]4)[c:31]2[cH:30][c:27]1[O:28][CH3:29]>>[CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[... | CNC.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(C)C)c(OC)cc23)c2c1OCO2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 77 | [{"value": 77.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and dimethylamine (5 ml of a 33% solution in ethanol) were stirred and heated under reflux at 90° for 30 min. before evaporating the solution. A further 5 ml of dimethylamine solution were ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | C(C)O | null | null | CNC.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>C(C)O>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(C)C)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b8ef117e3524324a8958ace0a4d1733 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.COCCNCCOC>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(CCOC)CCOC)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.COCCNCCOC>>COCCN(CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC)CCOC | Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:39]4[c:38]3[O:42][CH2:41][O:40]4)[c:37]2[cH:36][c:33]1[O:34][CH3:35].[NH:24]([CH2:25][CH2:26][O:27][CH3:28])[CH2:29][CH2:30][O:31][CH3:32]>>[CH3:1][O:2][CH2:3][... | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.COCCNCCOC | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(CCOC)CCOC)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 66 | [{"value": 66.0, "product": "COCCN(CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC)CCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "COCCN(CCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCCOC)Cl)OC)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 13 using N-[5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and bis(2-methoxyethyl)amine (264 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromato... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.COCCNCCOC>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN(CCOC)CCOC)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-386a9cd81d134e42be1324060dfa8a44 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=CN1CCNCC1>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.C(=O)N1CCNCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C=O | Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34].[NH:24]1[CH2:25][CH2:26][N:27]([CH:28]=[O:29])[CH2:30][CH2:31]1>>[CH3:1][O:2][CH2:3][CH2:4]... | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=CN1CCNCC1 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 64 | [{"value": 64.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 13 using N-[5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 1-formylpiperazine (226 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=CN1CCNCC1>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b83045e29e547b7bec799a4143f6340 | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF.ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF | [CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:38]2[c:39]1[O:40][CH2:41][O:42]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][N:27]([CH2:28][CH2:29][F:30])[CH2:31][CH2:32]3)[c:33]([O:34][CH3:35])[cH:36][c:37]12>>[CH3:1][O:2][CH2... | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 60 | [{"value": 60.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.9, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 4 using 4-chloro-7-{3-[4-(2-fluoroethyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline (200 mg, 0.52 mmol), 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (146 mg, 0.57 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.10 ml) in DMF (3 ml). The cru... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1>CN(C)C=O>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-319d7e7bc5a547a9ad5d7b42063f980a | COc1cc2c(Cl)ncnc2cc1O.OCCCN1CCN(CCF)CC1>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.ClC1=NC=NC2=CC(=C(C=C12)OC)O.FCCN1CCN(CC1)CCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[OH:14].O[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH2:22][CH2:23][F:24])[CH2:25][CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20]... | COc1cc2c(Cl)ncnc2cc1O.OCCCN1CCN(CCF)CC1 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1 | null | null | ClCCl.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ncc2ccc(OCCCN3CCNCC3)cc2n1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 48 | [{"value": 48.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Diisopropylazodicarboxylate (921 mg, 4.56 mmol) was added portionwise, at room temperature, to a stirred suspension of 4-chloro-6-methoxyquinazolin-7-ol (800 mg, 3.80 mmol), 3-[4-(2-fluoroethyl)piperazin-1-yl]propan-1-ol (794 mg, 4.18 mmol) and triphenylphosphine (1.4 g, 5.34 mmol) in THF (20 ml). The reaction was stir... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HO- | ClCCl.C1CCOC1 | null | 1 | COc1cc2c(Cl)ncnc2cc1O.OCCCN1CCN(CCF)CC1>ClCCl.C1CCOC1>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(CCF)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c9b87ce15c1466892dafb25794e12aa | CC(C)(C)OC(=O)N1CCNCC1.FCCBr>>CC(C)(C)OC(=O)N1CCN(CCF)CC1 | BrCCF.C([O-])([O-])=O.[K+].[K+].BrCCF.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)CCF | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:15][CH2:16]1.Br[CH2:12][CH2:13][F:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][F:14])[CH2:15][CH2:16]1 | CC(C)(C)OC(=O)N1CCNCC1.FCCBr | CC(C)(C)OC(=O)N1CCN(CCF)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[F;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#7:4]-[C:5]-[C:6]-1 | 57 | [{"value": 57.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CCF", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium carbonate (1.85 g, 13.4 mmol) and 1-bromo-2-fluoroethane (440 μl, 5.9 mmol) were added to a solution of tert-butyl-1-piperazinecarboxylate (1 g, 5.4 mmol) in acetonitrile (12 ml). The reaction mixture was stirred at 65?C for 3.5 hours after which time more 1-bromo-2-fluoroethane (160 μl, 2.1 mmol) was added. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HBr | C(C)#N | null | null | CC(C)(C)OC(=O)N1CCNCC1.FCCBr>C(C)#N>CC(C)(C)OC(=O)N1CCN(CCF)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-891d5ca82acf457981726b9d1a8dfc7e | CC(C)(C)OC(=O)N1CCN(CCF)CC1.O=C(O)C(F)(F)F>>FCCN1CCNCC1.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F | FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N1CCN(CC1)CCF>>OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FCCN1CCNCC1 | C[C:20](C)(C)[O:19][C:18]([N:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][F:1])[CH2:9][CH2:8]1)=[O:17].[O:10]=[C:11]([OH:12])[C:13]([F:14])([F:21])[F:23]>>[F:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1.[O:10]=[C:11]([OH:12])[C:13]([F:14])([F:15])[F:16].[O:17]=[C:18]([OH:19])[C:20]([F:21])([F:22])[F:23] | CC(C)(C)OC(=O)N1CCN(CCF)CC1.O=C(O)C(F)(F)F | FCCN1CCNCC1.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F | null | null | C(Cl)Cl | Functional Group Addition | OtherReaction | 63e75daca4f4e76fadebef53e5e157c706073976758fa02f89818055e5e42d40 | ae802c34808856bdd715b87a3e9abed66d27e47fe6cd05110d395ff832686723 | C1CNCCN1 | C-[C;H0;D4;+0:1](-C)(-C)-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1.[F;D1;H0:11]-[C;H0;D4;+0:12](-[F;H0;D1;+0:13])(-[F;H0;D1;+0:14])-[C:15](=[O;D1;H0:16])-[O;D1;H1:17]>>[#7:8]1-[C:7]-[C:6]-[NH;D2;+0:5]-[C:10]-[C:9]-1.[F;D1;H0:11]-[C;H0;D4;+0:12](-[F;D1;H0:18])(-[F;D1;H... | 96 | [{"value": 96.0, "product": "OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FCCN1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FCCN1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | Trifluoroacetic acid (3 ml, 17.5 mmol) was added to a solution of 4-(2-fluoroethyl)-piperazine-1-carboxylic acid tert-butyl ester (350 mg, 1.5 mmol) in methylene chloride (12 ml). The reaction mixture was stirred at ambient temperature for 40 minutes, before the solvent was evaporated under high vacuum. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carbamic ester.Ether.Boc | Trifluoro group.Trifluoro group.Carboxylic acid.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | null | C(Cl)Cl | null | 0.666667 | CC(C)(C)OC(=O)N1CCN(CCF)CC1.O=C(O)C(F)(F)F>C(Cl)Cl>FCCN1CCNCC1.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dadf50e5032348668ad75358a0b5fbde | FCCN1CCNCC1.OCCCBr>>OCCCN1CCN(CCF)CC1 | BrCCCO.C([O-])([O-])=O.[K+].[K+].OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.FCCN1CCNCC1>>FCCN1CCN(CC1)CCCO | [NH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][F:11])[CH2:12][CH2:13]1.Br[CH2:4][CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][F:11])[CH2:12][CH2:13]1 | FCCN1CCNCC1.OCCCBr | OCCCN1CCN(CCF)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 91 | [{"value": 91.0, "product": "FCCN1CCN(CC1)CCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "FCCN1CCN(CC1)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 4 | HOUR | 3-Bromopropan-1-ol (581 mg, 4.18 mmol) and potassium carbonate (2.88 g, 20.9 mmol) were added to a solution of 1-(2-fluoroethyl)-piperazine diTFA salt (1.5 g, 4.18 mmol) in acetonitrile (11 ml). The reaction mixture was stirred at 85° C. for 4 hours and then loaded directly onto a column and eluted with a mixture of me... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HBr | C(C)#N | 85 | 4 | FCCN1CCNCC1.OCCCBr>C(C)#N>OCCCN1CCN(CCF)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f8cfe34e4c84f5096edd5b2bb9fa917 | COC1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(OC)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.COC1CCNCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)OC | [NH:24]1[CH2:25][CH2:26][CH:27]([O:28][CH3:29])[CH2:30][CH2:31]1.Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34]>>[CH3:1][O:2][CH2:3][CH2:4... | COC1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(OC)CC4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCCCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 80 | [{"value": 80.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCC(CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 13 using N-[5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 4-methoxypiperidine (246 mg, 2.14 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CC[NH]CC1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | COC1CCNCC1.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC(OC)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfa75bdb4e6845028a04bef467c823d7 | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>COc1cc2ncnc(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)c2cc1OC | ClC1=NC=NC2=CC(=C(C=C12)OC)OC.NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCNC(N(C)C)=O | [NH2:10][c:11]1[c:12]([Cl:13])[cH:14][c:15]([C:16]#[C:17][CH2:18][NH:19][C:20](=[O:21])[N:22]([CH3:23])[CH3:24])[c:25]2[c:26]1[O:27][CH2:28][O:29]2.Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][c:30]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[c:12]([Cl:1... | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | COc1cc2ncnc(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 77.1 | [{"value": 77.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCNC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCNC(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-6,7-dimethoxyquinazoline (160 mg, 0.71 mmol), N′-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N,N-dimethylurea (232 mg, 0.78 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.5 ml) in DMF (3 ml). The crude product was purified... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>CN(C)C=O>COc1cc2ncnc(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-343f7a7d141f4104bcc5e97ba57373f9 | CN1CCNCC1=O.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CN1C(CNCC1)=O>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | [NH:24]1[CH2:25][CH2:26][N:27]([CH3:28])[C:29](=[O:30])[CH2:31]1.Cl[CH2:23][CH2:22][CH2:21][O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14][c:13]([NH:12][c:11]3[c:9]([Cl:10])[cH:8][c:7]([C:6]#[C:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34]>>[CH3:1][O:2][CH2:3][CH2:4... | CN1CCNCC1=O.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5](-[C;D1;H3:4])-[C:10](=[O;D1;H0:11])-[C:9]-1 | 72 | [{"value": 72.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | This was prepared by the method described in example 13 using N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 1-methylpiperazin-2-one (226 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | CN1CCNCC1=O.COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>COCCO>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e33abe0006cc49f8b4c1967b0f21ae7b | C#CCN1CCCC1=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCN4CCCC4=O)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C(C#C)N1C(CCC1)=O.C(C)(C)NC(C)C>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN1C(CCC1)=O | [CH:13]#[C:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][C:20]1=[O:21].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH2:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)[cH:31][c:30]3[n:29][cH:28][n:27]2)[c:23]2[c:22]1[O:26][CH2:25][O:24]2>>[CH3:1][O:2][c:3]1... | C#CCN1CCCC1=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCN4CCCC4=O)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C1CCCN1CC#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 40 | [{"value": 40.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN1C(CCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.3, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 46 | HOUR | N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4ylpropoxy)quinazolin-4-amine (250 mg, 0.42 mmol) and 1-prop-2-yn-1-ylpyrrolidin-2-one (103 mg, 0.84 mmol) in ethyl acetate (8 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine) palladium(II) dichl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | C1CC[NH]C1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC | null | 46 | C#CCN1CCCC1=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#CCN4CCCC4=O)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7af1041f67345d5aa8f4e3ab4fc4cc9 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2>>COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)I)N>>ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([I:13])[c:14]2[c:15]1[O:16][CH2:17][O:18]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9]([Cl:10])[cH:11][c:12]([... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2 | COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4ylpropoxy)quinazolin-4-amine was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (1.0 g, 2.96 mmol), 5-chloro-7-iodo-1,3-benzodioxol-4-amine (0.97 g, 3.26 mmol) and sodium bis(trimethylsil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1c(Cl)cc(I)c2c1OCO2>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.