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-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d0a2336539b45ccbf1ab591a226384a | CC#CCn1c(Cl)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC | C(C)OC(CN1C(N(C(C=2N(C(=NC12)Cl)CC#CC)=O)CCC1=CC=CC=C1)=O)=O.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCC1=CC=CC=C1)=O)CC(=O)OCC | Cl[c:6]1[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:22]2[c:21]([n:20]1)[n:36]([CH2:37][C:38](=[O:39])[O:40][CH2:41][CH3:42])[c:34](=[O:35])[n:25]([CH2:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:23]2=[O:24].[NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:... | CC#CCn1c(Cl)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c2nc(N3CCNCC3)[nH]c2c(=O)n1CCc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]#[C:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]#[C:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 86.9 | [{"value": 86.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCC1=CC=CC=C1)=O)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of [7-(2-butynyl)-8-chloro-1-(2-phenylethyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]acetic acid ethyl ester (273 mg) and piperazine-1-carboxylic acid tert-butyl ester (360 mg) was heated in an oil bath of 150° C. for 30 minutes. The reaction mixture was purified by silica gel column chromatography using 20–30... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1.c1ccccc1 | HCl | null | 150 | null | CC#CCn1c(Cl)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ae045dfb96b445facc711999bb05522 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)O | Cl.C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCC1=CC=CC=C1)=O)CC(=O)OCC.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCC1=CC=CC=C1)=O)CC(=O)O | CC[O:40][C:38]([CH2:37][n:36]1[c:21]2[n:20][c:6]([N:7]3[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]3)[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:22]2[c:23](=[O:24])[n:25]([CH2:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]1=[O:35])=[O:39]>>[CH3:1][C:2]#[C:3][CH2:4]... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c2nc(N3CCNCC3)[nH]c2c(=O)n1CCc1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 91.8 | [{"value": 91.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCC1=CC=CC=C1)=O)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 4-[7-(2-butynyl)-3-ethoxycarbonylmethyl-1-(2-phenylethyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (190 mg), ethanol (3 ml), and 1N aqueous sodium hydroxide solution (0.5 ml) was stirred with heating in an oil bath of 50° C. for 2 hours. 1N aqueous hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1.c1ccccc1 | Other | C(C)O | 50 | null | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)OCC>C(C)O>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05af923f27e44bcd82fbacfe45c061f1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN=[N+]=[N-])c(=O)n2C>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCN=[N+]=[N-])=O)C.O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCN)=O)C | [N-]=[N+]=[N:28][CH2:27][CH2:26][n:25]1[c:23](=[O:24])[c:22]2[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:6]([N:7]3[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]3)[n:20][c:21]2[n:31]([CH3:32])[c:29]1=[O:30]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN=[N+]=[N-])c(=O)n2C | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN)c(=O)n2C | null | null | O1CCCC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 74.7 | [{"value": 74.7, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCN)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[1-(2-Azidoethyl)-7-(2-butynyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.17 g) was dissolved in tetrahydrofuran (3.5 ml), and water (0.23 ml) and triphenylphosphine (0.13 g) were added to the solution. After the mixture was stirred at room temperature overni... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | Other | O1CCCC1 | null | 8 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN=[N+]=[N-])c(=O)n2C>O1CCCC1>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCN)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-469fd5b0efd24e2eb3d5f6ee45439c61 | CI.Cn1c(=O)c2c(ncn2-c2ccccc2C(O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O.S=C=S>>CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C | CI.[H-].[Na+].C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C(O)C1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C.C(=S)=S>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C(OC(=S)SC)C1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C | I[CH3:1].[OH:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1-[n:13]1[cH:14][n:15][c:16]2[c:17]1[c:18](=[O:19])[n:20]([CH3:21])[c:22](=[O:23])[n:24]2[CH3:25])[CH:26]1[CH2:27][N:28]([C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37][N:38]1[C:39](=[O:40])[O:41][C:42]([CH3:43])([CH3:44])[CH3:45].[S:2... | CI.Cn1c(=O)c2c(ncn2-c2ccccc2C(O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O.S=C=S | CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C | null | null | O1CCCC1.O.C(C)(=O)OCC | Acylation | OtherReaction | c7dbbaabeba4030ac13d21dbea2d065e6ae27d66135e28ce4afa6269505c204f | 8561a960f931e5a14f0c8246c71006c703df6abcd58e014f5406ceb13cbbe0b8 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2CC2CNCCN2)[nH]1 | I-[CH3;D1;+0:1].[#7:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[c:6].[S;D1;H0:7]=[C;H0;D2;+0:8]=[S;H0;D1;+0:9]>>[#7:2]-[C:3]-[C:4](-[c:6])-[O;H0;D2;+0:5]-[C;H0;D3;+0:8](=[S;D1;H0:7])-[S;H0;D2;+0:9]-[CH3;D1;+0:1] | null | [] | null | null | 20 | MINUTE | Sodium hydride (60% oleaginous) was added to a solution of 2-[[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-phenyl]hydroxymethyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (low polarity) (0.214 g) in tetrahydrofuran (10 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether.Thiocarbonyl.Monosulfide | null | null | c1ccccc1.c1ncc2[nH]cnc2n1.C1C[NH]CC[NH]1 | HI | O1CCCC1.O.C(C)(=O)OCC | null | 0.333333 | CI.Cn1c(=O)c2c(ncn2-c2ccccc2C(O)C2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O.S=C=S>O1CCCC1.O.C(C)(=O)OCC>CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16033799dbbf4bf0af540394b12d32de | CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C>>Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C(OC(=S)SC)C1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C.C(CCC)[SnH](CCCC)CCCC.N(=NC(C#N)(C)C)C(C#N)(C)C>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C | CSC(=S)O[CH:16]([c:15]1[c:10](-[n:9]2[c:5]3[c:3](=[O:4])[n:2]([CH3:1])[c:39](=[O:40])[n:37]([CH3:38])[c:6]3[n:7][cH:8]2)[cH:11][cH:12][cH:13][cH:14]1)[CH:17]1[CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28][N:29]1[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36]>>[CH3:1][n:2... | CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C | Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 4a66c27853427274b272243a753c9056b0872c3b53082a3e92fbfe42b48d2aca | b7a5234770726d9df7bf8a7a8600249246518d52f4a289b48469a444ad416279 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2CC2CNCCN2)[nH]1 | C-S-C(=S)-O-[CH;D3;+0:1](-[C:2](-[C:3]-[#7:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13])-[c:14](:[c:15]):[c:16]>>[#7:4]-[C:3]-[C:2](-[CH2;D2;+0:1]-[c:14](:[c:15]):[c:16])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13] | 83.7 | [{"value": 83.7, "product": "C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[1-[2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-phenyl]-1-methylsulfanylthiocarbonyloxymethyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (low polarity) (0.175 g), tributyltin hydride (0.25 g), and 2,2′-azobis(isobutyronitrile) (0.010 g) were dissolved in toluene (5 ml) under nitrogen atmosphere,... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Thiocarbonyl.Monosulfide | null | null | null | c1ncc2nc[nH]c2n1.c1ccccc1.C1C[NH]CC[NH]1 | Other | C1(=CC=CC=C1)C | null | null | CSC(=S)OC(c1ccccc1-n1cnc2c1c(=O)n(C)c(=O)n2C)C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC(C)(C)C>C1(=CC=CC=C1)C>Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab99aab08c6b4fb0ae2b6f9fa5a52a16 | Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O>>Cn1c(=O)c2c(nc3n2-c2ccccc2CC2CNCCN32)n(C)c1=O | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.CN1C(N(C(C2=C1N=C1N3C(CC4=C(N21)C=CC=C4)CNCC3)=O)C)=O | CC(C)(C)OC(=O)[N:19]1[CH2:18][CH:17]([CH2:16][c:15]2[c:10](-[n:9]3[c:5]4[c:3](=[O:4])[n:2]([CH3:1])[c:25](=[O:26])[n:23]([CH3:24])[c:6]4[n:7][cH:8]3)[cH:11][cH:12][cH:13][cH:14]2)[N:22](C(=O)OC(C)(C)C)[CH2:21][CH2:20]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]3[n:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C... | Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O | Cn1c(=O)c2c(nc3n2-c2ccccc2CC2CNCCN32)n(C)c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 603730c751d479d06b06dd4cfbe9ece0d6ac9b32e8c6c5a726ee664fb6aa9be1 | 98954e35dd97aa5fdb6b2d6cc2d26f8aaed3dcf612f871e78a8e228b88dc1fd5 | O=c1[nH]c(=O)c2c(nc3n2-c2ccccc2CC2CNCCN32)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[C:4])-[N;H0;D3;+0:5](-C(=O)-O-C(-C)(-C)-C)-[C:6]-[C:7]-1.[C;D1;H3:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]2:[#7;a:14](-[c:15]):[cH;D2;+0:16]:[#7;a:17]:[c:18]:1:2>>[C:4]-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-[N;H0;D3;+0:5]-1-[c;H0;D3;+0:16]1:[#7;a:17]:[c:18]2:[#7;a:9]... | null | [] | null | null | 30 | MINUTE | 2-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)benzyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.055 g) was dissolved in trifluoroacetic acid (0.5 ml), the mixture was stirred for 30 minutes, and the solvent was removed by distillation at reduced pressure. The residue was dissolved in N,N-dimeth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Tertiary amine | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | c1ccc2c(c1)CC1CNCCN1c1nc3ncncc3n12 | c1ccc2c(c1)CC1CNCCN1c1nc3ncncc3n12 | HO- | null | null | 0.5 | Cn1c(=O)c2c(ncn2-c2ccccc2CC2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)n(C)c1=O>>Cn1c(=O)c2c(nc3n2-c2ccccc2CC2CNCCN32)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05e81e29142c4ae0868982a133fee016 | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=Cc1ccccc1B(O)O>>CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O | CC(C(=O)OCN1C(N(C(C=2NC=NC12)=O)COC(C(C)(C)C)=O)=O)(C)C.C(=O)C1=C(C=CC=C1)B(O)O.N1=CC=CC=C1>>CC(C(=O)OCN1C(N(C=2N=CN(C2C1=O)C1=C(C=CC=C1)C=O)COC(C(C)(C)C)=O)=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][nH:16]2)[n:25]([CH2:26][O:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[c:34]1=[O:35].OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH:23]=[O:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9... | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=Cc1ccccc1B(O)O | CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 193a52be698a8cc7c00a0e51f250e81e1eef3fc7f6e6eee9787e052516f6fde7 | e0368246531386f86cd0aa9da1423eb47f529b782fb229563cefe1166d6ba4f5 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2)[nH]1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].[C:8]-[#7;a:9]1:[c:10]:[#7;a:11](-[C:12]):[c:13](=[O;D1;H0:14]):[c:15]2:[nH;D2;+0:16]:[c:17]:[#7;a:18]:[c:19]:1:2>>[C:8]-[#7;a:9]1:[c:10]:[#7;a:11](-[C:12]):[c:13](=[O;D1;H0:14]):[c:15]2:[c:19]:1:[#7;a:18]:[c:17]:[n;H0;D3;+0:16]:2-[c;H0;D3;+0:1](:[c:2... | 31.7 | [{"value": 31.7, "product": "CC(C(=O)OCN1C(N(C=2N=CN(C2C1=O)C1=C(C=CC=C1)C=O)COC(C(C)(C)C)=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 37 | HOUR | 2,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (10.2 g), 2-formylphenylboronic acid (8.04 g), and copper(II) acetate (7.30 g) were suspended in N,N-dimethylformamide (50 ml), pyridine (4.34 ml) was added thereto, and the mixture was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C=O)C.C(C)(=O)OCC | null | 37 | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=Cc1ccccc1B(O)O>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C=O)C.C(C)(=O)OCC>CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4827b0d3f5684e7292dc522efb21c879 | CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl>>CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O | CC(C(=O)OCN1C(N(C=2N=CN(C2C1=O)C1=C(C=CC=C1)C=O)COC(C(C)(C)C)=O)=O)(C)C.ClN1C(CCC1=O)=O>>ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:17]2-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[CH:24]=[O:25])[n:26]([CH2:27][O:28][C:29](=[O:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]1=[O:36].O=C1CCC(=O)N1[Cl:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[... | CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl | CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | 14c81eccfe7222df9f154a6d36de877a8f4fe32e30972af529ae83dcf968a138 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2)[nH]1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]1:[#7;a:4]:[cH;D2;+0:5]:[#7;a:6](-[c:7]):[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:2]:[c:3]1:[#7;a:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[#7;a:6](-[c:7]):[c:8]:1:[c:9]:[#7;a:10] | 74.7 | [{"value": 74.7, "product": "ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2,2-Dimethylpropionic acid [1-(2,2-dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.50 g) and N-chlorosuccinimide (896 mg) were dissolved in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2nc[nH]c2n1.C1CCNC1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl>CN(C=O)C.C(C)(=O)OCC>CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15d6af6873dd481bba186ab0b176bf15 | CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1 | ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | Cl[c:12]1[n:13][c:14]2[c:15]([c:16](=[O:17])[n:18]([CH2:19][O:20][C:21](=[O:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[c:27](=[O:28])[n:29]2[CH2:30][O:31][C:32](=[O:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[n:38]1-[c:39]1[cH:40][cH:41][cH:42][cH:43][c:44]1[CH:45]=[O:46].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1... | CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e9344fb5b31533e2c38d57778c7c82c0aa2d752545a4dd76e010d9a664cd15dc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:14]-[C:15]-[#7:10]-[C:11]-[C:12]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 75.3 | [{"value": 75.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 10 | MINUTE | 2,2-Dimethylpropionic acid [8-chloro-1-(2,2-dimethyl-propionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.0 g) and piperazine-1-carboxylic acid tert-butyl ester (2.15 g) were mixed, and the mixture was stirred at 150° C. for 1 hour and 10 minutes. The reaction mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2nc[nH]c2n1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ncc2nc[nH]c2n1 | C1C[NH]CC[NH]1.c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | 150 | 0.166667 | CC(C)(C)C(=O)OCn1c(=O)c2c(nc(Cl)n2-c2ccccc2C=O)n(COC(=O)C(C)(C)C)c1=O.CC(C)(C)OC(=O)N1CCNCC1>C(Cl)(Cl)Cl>CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43a4a930cbcd4fe4bd46bc76aade3211 | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | O1CCCC1.CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.O1CCCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | O=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]2)[n:24][c:25]2[c:26]1[c:27](=[O:28])[n:29]([CH2:30][O:31][C:32](=[O:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[c:38](=[O:39])[n:40]2[CH2:41][O:42][C:43](=[O:44])[... | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | Methyltriphenylphosphonium bromide (3.52 g) was dissolved in tetrahydrofuran (20 ml), potassium tert-butoxide (948 mg) was added to the solution, and the mixture was stirred at room temperature for 1 hour. A solution of 4-[1,3-bis(2,2-dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2C=O)CC1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbb5d32f258e4e769350aaf68d59b9a5 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | [H-].[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O | CC(C)(C)C(=O)OC[n:26]1[c:25]2[n:24][c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[n:9](-[c:8]3[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]3)[c:40]2[c:38](=[O:39])[n:29]([CH2:30][O:31][C:32](=[O:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[c:27]1=[O:28]>>[CH2:... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | null | null | O1CCCC1.C(Cl)(Cl)Cl.CO | Reduction | OtherReaction | 640a644854d0d424f3b2f603152cc1a7aea1cadf590f863f6706eb0b62b24502 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5](-[c:6]):[c:7]:2:[c:8]:[#7;a:9](-[C:10]):[c:11]:1=[O;D1;H0:12]>>[C:10]-[#7;a:9]1:[c:8]:[c:7]2:[#7;a:5](-[c:6]):[c:4]:[#7;a:3]:[c:2]:2:[nH;D2;+0:1]:[c:11]:1=[O;D1;H0:12] | 87.4 | [{"value": 87.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | MINUTE | 4-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (704 mg) was dissolved in tetrahydrofuran (7 ml) and methanol (14 ml), sodium hydride (51 mg) was added to the solution, and the mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.C(Cl)(Cl)Cl.CO | null | 0.283333 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>O1CCCC1.C(Cl)(Cl)Cl.CO>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adf3dc29b84349008f1bd7593bcf1b04 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O)CC(=O)OCC | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]2)[n:24][c:25]2[c:26]1[c:27](=[O:28])[n:29]([CH2:30][O:31][C:32](=[O:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[c:38](=[O:39])[nH:40]2.Br[CH2:41][C:42](=[O:4... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7d358008569a510febb7dbae9ae69699ebd741f56473500303ef0889f4be2b21 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[c:11]):[c:12]:[#7;a:13]:[c:14]:2:[nH;D2;+0:15]:[c:16]:1=[O;D1;H0:17]>>[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[c:11]):[c:12]:[#7;a:13]:[c:14]:2:[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]):[c:16]:1=[O;D1;H0:17... | null | [] | null | null | 14 | HOUR | 4-[1-(2,2-Dimethylpropionyloxymethyl)-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (80 mg) was dissolved in N,N-dimethylformamide (2 ml), ethyl bromoacetate (19 μl) and potassium carbonate (22 mg) were added to the solution, and the mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 14 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr>CN(C=O)C.C(C)(=O)OCC>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea04dafa420d4f0d9abd859d79b64910 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC | [H-].[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O)CC(=O)OCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)C=C)=O)=O)CC(=O)OCC | CC(C)(C)C(=O)OC[n:29]1[c:27](=[O:28])[c:26]2[n:9](-[c:8]3[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]3)[c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[n:24][c:25]2[n:32]([CH2:33][C:34](=[O:35])[O:36][CH2:37][CH3:38])[c:30]1=[O:31]>>[CH2:1]=[CH:2][c:3]1[cH... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC | null | null | O1CCCC1.CO.C(C)(=O)OCC | Reduction | OtherReaction | df8a3c8b7aa7d10b48c9fb6d61e80538577be49615529cea0e9d9fc23715d092 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]2:[#7;a:5](-[c:6]):[c:7]:[#7;a:8]:[c:9]:2:[#7;a:10](-[C:11]-[C:12](-[#8:13])=[O;D1;H0:14]):[c:15]:1=[O;D1;H0:16]>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]-[#7;a:10]1:[c:9]2:[#7;a:8]:[c:7]:[#7;a:5](-[c:6]):[c:4]:2:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:15]:1=[O;D1;... | 82.1 | [{"value": 82.1, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)C=C)=O)=O)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | 4-[1-(2,2-Dimethylpropionyloxymethyl)-3-ethoxycarbonylmethyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (89 mg) was dissolved in tetrahydrofuran (1 ml) and methanol (2 ml), sodium hydride (7 mg) was added to the solution, and the mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.CO.C(C)(=O)OCC | null | 3.5 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CC(=O)OCC>O1CCCC1.CO.C(C)(=O)OCC>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95e6c1ed76d642f8aca0012bb640c73c | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC.CI>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)C=C)=O)=O)CC(=O)OCC.CI.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)C)=O)CC(=O)OCC | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]2)[n:24][c:25]2[c:26]1[c:27](=[O:28])[nH:29][c:31](=[O:32])[n:33]2[CH2:34][C:35](=[O:36])[O:37][CH2:38][CH3:39].I[CH3:30]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC.CI | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 011a6d20d1a2cde13aab96bd8efb9a0393d2f8a89a318e20bc7624b0300657a4 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7;a:6]1:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10](-[c:11]):[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16]:1=[O;D1;H0:17]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7;a:6]1:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10](-[c:11]):[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH3;D1;+0:1]):[c:16... | 77.9 | [{"value": 77.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)C)=O)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 13 | HOUR | 4-[3-Ethoxycarbonylmethyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (60 mg) was dissolved in N,N-dimethylformamide (2 ml), methyl iodide (17 μl) and potassium carbonate (17 mg) were added to the solution, and the mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HI | CN(C=O)C.C(C)(=O)OCC | null | 13 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OCC.CI>CN(C=O)C.C(C)(=O)OCC>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff900d9875734a6a9c281ddf5fcf81de | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC>>C=Cc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)C)=O)CC(=O)OCC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.C(C)OC(CN1C(N(C(C=2N(C(=NC12)N1CCNCC1)C1=C(C=CC=C1)C=C)=O)C)=O)=O | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([c:10]2[n:9](-[c:8]3[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]3)[c:19]3[c:18]([n:17]2)[n:26]([CH2:27][C:28](=[O:29])[O:30][CH2:31][CH3:32])[c:24](=[O:25])[n:22]([CH3:23])[c:20]3=[O:21])[CH2:16][CH2:15]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC | C=Cc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 4-[3-Ethoxycarbonylmethyl-1-methyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (8 mg) was dissolved in trifluoroacetic acid and the solution was concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 2.68 mg ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | null | null | null | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC>>C=Cc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2CC(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d5c834b6634d45bfba14c26c79f7b31d | Cc1ccc(O)cc1.Nc1ccccc1[N+](=O)[O-]>>Cc1ccc(O)c(N=Nc2ccccc2[N+](=O)[O-])c1 | CCC(CC)COC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)N(C)CC[NH+](C)C.[Cl-].N(=O)OS(O)(=O)=O.[N+](=O)([O-])C1=C(N)C=CC=C1.C1=CC(=CC=C1O)C.CCC(CC)COC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)N(C)CC[NH+](C)C.[Cl-]>>[N+](=O)([O-])C1=C(C=CC=C1)N=NC1=C(C=CC(=C1)C)O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][cH:19]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[N+:16](=[O:17])[O-:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([N:8]=[N:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[N+:16](=[O:17])[O-:18])[cH:19]1 | Cc1ccc(O)cc1.Nc1ccccc1[N+](=O)[O-] | Cc1ccc(O)c(N=Nc2ccccc2[N+](=O)[O-])c1 | null | null | O.S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | 4dfa1e0075917e3f76a2c771d85af2eb7328e8c1dacc2fef053ab9d7871727bb | 369e32a405523c63be3b198dc14b1fa8567bb17806d598f8dc85ecca177f9307 | c1ccc(N=Nc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H1:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H1:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[#7:11]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]:[c:10] | null | [] | 50 | CELSIUS | 15 | MINUTE | A mixture of 2-nitroaniline (27.63 g, 0.2 mol), para-cresol (10.81 g, 0.10 mol), Hostapur® SAS93 (1.55), Triton X-100® [polyethylene(10) isooctylphenyl ether] (2.45 g) and water (100 mL) is heated to 50° C. The reaction mixture is rapidly stirred at this temperature for 15 minutes and then the rapidly stirred resultant... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O.S(O)(O)(=O)=O | 50 | 0.25 | Cc1ccc(O)cc1.Nc1ccccc1[N+](=O)[O-]>O.S(O)(O)(=O)=O>Cc1ccc(O)c(N=Nc2ccccc2[N+](=O)[O-])c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54712e92bae34a0a8db4cc695beda680 | CC(C)(C)[Si](C)(C)Cl.CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1 | C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2N1)=O.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O | Cl[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([n:11][cH:12][n:13]2[C@H:14]2[CH2:15][C@H:16]([OH:17])[C@@H:18]([CH2:19][OH:20])[O:28]2)[c:29](=[O:30])[nH:31]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([n:11][cH:12]... | CC(C)(C)[Si](C)(C)Cl.CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 | CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 74.7 | [{"value": 74.0, "product": "C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.7, "product": "C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 8 | HOUR | N2-isobutyryl-2′-deoxyguanosine (20.5 g) was dissolved in 200 ml of DMF. After 18.5 g of imidazole was dissolved in the resultant solution by addition, 21.4 g of tert-butyldimethylsilyl chloride was then added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction us... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ncc2[nH]cnc2n1.C1CCOC1 | HCl | CN(C)C=O | null | 8 | CC(C)(C)[Si](C)(C)Cl.CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=O>CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c98c3a80fa4e45bcbe3bfa72698996ee | CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(=O)[nH]c(NC(=O)C(C)C)nc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | C(O)([O-])=O.[Na+].COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1.C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O>>C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O | [OH:8][C@H:9]1[CH2:10][C@H:11]([n:12]2[cH:13][n:14][c:15]3[c:16](=[O:17])[nH:18][c:19]([NH:20][C:21](=[O:22])[CH:23]([CH3:24])[CH3:25])[n:26][c:27]23)[O:28][C@@H:29]1[CH2:30][O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38].Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:54][cH:53]1)([c:39]1[cH:40][c... | CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1 | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(=O)[nH]c(NC(=O)C(C)C)nc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 5ab68839e2c0c36dcda93f3c0a707140e3d24e3e006f5c14702a7b8884a9a81e | 26c50c761bd192b9bbaacc80ceb1f72503dc7c2f688b52834534ac0a03b55cce | O=c1[nH]cnc2c1ncn2[C@H]1C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)CO1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]>>[#8:11]-[C:12]-[C:13](-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10])-[C:15] | 698.5 | [{"value": 78.0, "product": "C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 698.5, "product": "C(C(C)C)(=O)NC=1NC(C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC... | 40 | CELSIUS | null | null | N2-isobutyryl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyguanosine (19.8 g) was dissolved in 100 ml of anhydrous pyridine. 4,4′-dimethoxytrityl chloride (1.66 g) was added to the resultant solution and 140 ml of anhydrous pyridine was further added, follow by stirring at 40° C. After the reaction completed, the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | 40 | null | CC(C)C(=O)Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)c(=O)[nH]1.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>N1=CC=CC=C1>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(=O)[nH]c(NC(=O)C(C)C)nc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5a4db9a237d4cf9997ec58c3924f4fb | CC(C)(C)[Si](C)(C)Cl.O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1)c1ccccc1>>CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O | [Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1.C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2N=CN1>>C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][C@H:10]1[O:11][C@@H:12]([n:13]2[cH:14][n:15][c:16]3[c:17]([NH:18][C:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[n:27][cH:28][n:29][c:30]23)[CH2:31][C@@H:32]1[OH:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C@H... | CC(C)(C)[Si](C)(C)Cl.O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1)c1ccccc1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | O=C(Nc1ncnc2c1ncn2[C@H]1CCCO1)c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | 8 | HOUR | N6-benzoyl-2′-deoxyadenosine (20.95 g) was dissolved in 200 ml of DMF. Imidazole (15.7 g) was dissolved to the resultant solution by addition. Then, 20.8 g of tert-butyldimethylsilyl chloride was added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction using chlo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | C1CCOC1.c1ccccc1.c1ncnc2[nH]cnc12 | HCl | CN(C)C=O | null | 8 | CC(C)(C)[Si](C)(C)Cl.O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1)c1ccccc1>CN(C)C=O>CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-18c7ff5220a5423189fd868f41a6727a | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1.COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1.C(O)([O-])=O.[Na+]>>C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1 | [OH:8][C@H:9]1[CH2:10][C@H:11]([n:12]2[cH:13][n:14][c:15]3[c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[n:26][cH:27][n:28][c:29]23)[O:30][C@@H:31]1[CH2:32][O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40].Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:56][cH:55]1)([c:41]1... | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1 | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 5ab68839e2c0c36dcda93f3c0a707140e3d24e3e006f5c14702a7b8884a9a81e | 26c50c761bd192b9bbaacc80ceb1f72503dc7c2f688b52834534ac0a03b55cce | O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)CO1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]>>[#8:11]-[C:12]-[C:13](-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10])-[C:15] | 63.1 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=... | 45 | CELSIUS | null | null | N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine (16.1 g) was dissolved in 100 ml of anhydrous pyridine. 4,4′-dimethoxytrityl chloride (12.8 g) and anhydrous pyridine (140 ml) were further added, follow by stirring at 45° C. After the reaction completed, the reaction mixture was neutralized by sodium hydroge... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCOC1.c1ccccc1.c1ncnc2[nH]cnc12.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | 45 | null | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)C[C@@H]1O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>N1=CC=CC=C1>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02a4ff65175446a9b2d8b8655bce1c71 | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1>>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO)(c2ccccc2)c2ccc(OC)cc2)cc1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO[Si](C)(C)C(C)(C)C)O3)C2N=CN1>>C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO)O3)C2N=CN1 | CC(C)(C)[Si](C)(C)[O:33][CH2:32][C@@H:31]1[C@@H:9]([O:8][C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:49][cH:48]2)([c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[c:40]2[cH:41][cH:42][c:43]([O:44][CH3:45])[cH:46][cH:47]2)[CH2:10][C@H:11]([n:12]2[cH:13][n:14][c:15]3[c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23]... | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1 | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](OC(c2ccccc2)(c2ccccc2)c2ccccc2)CO1)c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 100 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](CO)O3)C2N=CN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "C(C1=CC=CC=C1)(=O)NC=1C=2N=CN([C@H]3C[C@H](OC(C4=CC=C(C=C4)OC)(C4=CC=C(C=C4)OC)C4=CC=CC=C4)[C@@H](C... | null | null | 8 | HOUR | N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-3′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine (16.2 g) was dissolved in 200 ml of dry THF. A THF solution (31 ml) of tetrabutylammonium fluoride was added to the resultant solution and 100 ml of dry THF was further added, followed by stirring at room temperature. After 8 hours,... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.C1CCOC1.c1ccccc1.c1ncnc2[nH]cnc12.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 8 | COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO[Si](C)(C)C(C)(C)C)(c2ccccc2)c2ccc(OC)cc2)cc1>C1CCOC1>COc1ccc(C(O[C@H]2C[C@H](n3cnc4c(NC(=O)c5ccccc5)ncnc43)O[C@@H]2CO)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-417447cdb51a438bb0b0932df74ca360 | CC(=O)OCCBr.CCn1c(=O)[nH]c2ncn(Cc3ccc(OC)cc3)c2c1=O>>CCn1c(=O)c2c(ncn2Cc2ccc(OC)cc2)n(CCOC(C)=O)c1=O | C(C)N1C(NC=2N=CN(C2C1=O)CC1=CC=C(C=C1)OC)=O.C([O-])([O-])=O.[K+].[K+].C(C)(=O)OCCBr>>C(C)(=O)OCCN1C(N(C(C=2N(C=NC12)CC1=CC=C(C=C1)OC)=O)CC)=O | Br[CH2:21][CH2:22][O:23][C:24]([CH3:25])=[O:26].[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([n:8][cH:9][n:10]2[CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]2)[nH:20][c:27]1=[O:28]>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([n:8][cH:9][n:10]2[CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:1... | CC(=O)OCCBr.CCn1c(=O)[nH]c2ncn(Cc3ccc(OC)cc3)c2c1=O | CCn1c(=O)c2c(ncn2Cc2ccc(OC)cc2)n(CCOC(C)=O)c1=O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[nH;D2;+0:12]:[c:13](=[O;D1;H0:14]):[#7;a:15](-[C:16]):[c:17]:[c:18]:1:2>>[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:18]:1:[c:17]:[#7;a:15](-[C:16]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C... | 75 | [{"value": 75.0, "product": "C(C)(=O)OCCN1C(N(C(C=2N(C=NC12)CC1=CC=C(C=C1)OC)=O)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | Acetonitrile was added to a mixture of Compound 5A (about 1.0 mole), anhydrous potassium carbonate (about 1.5 moles) and tetrabutylammonium hydrogen sulfate (about 0.05 mole). 2-bromoethyl acetate (about 1.5 moles) was added in three separate portions (0.72 mole in the beginning, another 0.45 mole after about 2 hours o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N | null | 7 | CC(=O)OCCBr.CCn1c(=O)[nH]c2ncn(Cc3ccc(OC)cc3)c2c1=O>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N>CCn1c(=O)c2c(ncn2Cc2ccc(OC)cc2)n(CCOC(C)=O)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e4fce7737e24aebbe5a46ccc285cb6d | CCn1c(=O)c2c(nc(Br)n2Cc2ccc(OC)c(Br)c2)n(CCOC(C)=O)c1=O.N[C@@H]1CCC[C@H]1O>>CCn1c(=O)c2c(nc(NC3CCCC3O)n2Cc2ccc(OC)c(Br)c2)n(CCO)c1=O | [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.BrC1=NC=2N(C(N(C(C2N1CC1=CC(=C(C=C1)OC)Br)=O)CC)=O)CCOC(C)=O.Cl.N[C@H]1[C@@H](CCC1)O.C([O-])(O)=O.[Na+].Cl.N[C@H]1[C@@H](CCC1)O>>CCN1C(=O)C2=C(N=C(N2CC3=CC(=C(C=C3)OC)Br)NC4CCCC4O)N(C1=O)CCO | CC(=O)[O:31][CH2:30][CH2:29][n:28]1[c:7]2[c:6]([c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:32]1=[O:33])[n:17]([CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH3:24])[c:25]([Br:26])[cH:27]1)[c:9](Br)[n:8]2.[NH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[OH:16]>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[c:7]([n:8][c:9]([NH:10][CH... | CCn1c(=O)c2c(nc(Br)n2Cc2ccc(OC)c(Br)c2)n(CCOC(C)=O)c1=O.N[C@@H]1CCC[C@H]1O | CCn1c(=O)c2c(nc(NC3CCCC3O)n2Cc2ccc(OC)c(Br)c2)n(CCO)c1=O | null | null | O.CO.CN(C(C)=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 3f5a6a497ea9d80a6bc5e13a61301a854ae9c711f0d3b07c7e15d9b1d01480a9 | 03164802232677317a7efd0e24d53056dbf9714f8e35a1ee2da95661003b43d6 | O=c1[nH]c(=O)c2c(nc(NC3CCCC3)n2Cc2ccccc2)[nH]1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]-[C:6]-[O;H0;D2;+0:7]-C(-C)=O):[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[#7;a:12]:1-[C:13].[NH2;D1;+0:14]-[C@@H;D3;+0:15]1-[C:16]-[C:17]-[C:18]-[C@H;D3;+0:19]-1-[O;D1;H1:20]>>[C:13]-[#7;a:12]1:[c:11]2:[c:10]:[#7;a:9]:[c:8]:[#7;a:4](-[C:5]-[C:6]-[OH;D1;+0:7]):[c:3]:2:[#7;a:2]:[c;H... | 85 | [{"value": 85.0, "product": "CCN1C(=O)C2=C(N=C(N2CC3=CC(=C(C=C3)OC)Br)NC4CCCC4O)N(C1=O)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 7A (about 1 mole) was combined with (R,R)-2-amino-1-cyclopentanol hydrochloride (Compound 8A, about 1.2 moles) and sodium bicarbonate (about 3 moles). To this reaction mixture was added N,N-dimethylacetamide (“DMA”), and the reaction mixture was agitated at about 135–140° C. for about 15–17 hours until complet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Primary alcohol.Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1CCCC1.c1ccccc1 | HBr | O.CO.CN(C(C)=O)C | null | null | CCn1c(=O)c2c(nc(Br)n2Cc2ccc(OC)c(Br)c2)n(CCOC(C)=O)c1=O.N[C@@H]1CCC[C@H]1O>O.CO.CN(C(C)=O)C>CCn1c(=O)c2c(nc(NC3CCCC3O)n2Cc2ccc(OC)c(Br)c2)n(CCO)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52b64d49f97e460aaf28e0d6614f1d05 | COC(=O)Cl.CON1C(=O)[C@H](N)Cc2ccccc21>>COC(=O)N[C@@H]1Cc2ccccc2N(OC)C1=O | ClC(=O)OC.CON1C([C@@H](CC2=CC=CC=C12)N)=O.C([O-])(O)=O.[Na+]>>CON1C([C@@H](CC2=CC=CC=C12)NC(OC)=O)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@@H:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[N:14]([O:15][CH3:16])[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[N:14]([O:15][CH3:16])[C:17]1=[O:18] | COC(=O)Cl.CON1C(=O)[C@H](N)Cc2ccccc21 | COC(=O)N[C@@H]1Cc2ccccc2N(OC)C1=O | null | null | O.C(Cl)(Cl)Cl.CCCCC | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C1CCc2ccccc2N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#8:5]-[#7:6](-[c:7])-[C:8](=[O;D1;H0:9])-[C:10](-[NH2;D1;+0:11])-[C:12]>>[#8:5]-[#7:6](-[c:7])-[C:8](=[O;D1;H0:9])-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4])-[C:12] | 99 | [{"value": 99.0, "product": "CON1C([C@@H](CC2=CC=CC=C12)NC(OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "CON1C([C@@H](CC2=CC=CC=C12)NC(OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of methyl chloroformate (42.8 g, 0.453 mol) in chloroform (50 ml) was added to a mixture of (R)-1,2,3,4-tetrahydro-1-methoxy-2-oxo-3-quinolinamine 1 (M. Kawase, T. Kitamura, Y. Kilugawa, J. Org. Chem., 54, 1989 3394–3403)(0.15 mol) and sodium bicarbonate (50.4 g, 0.600 mol) in chloroform (250 ml) and water (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2c(c1)CCC[NH]2 | HCl | O.C(Cl)(Cl)Cl.CCCCC | null | 8 | COC(=O)Cl.CON1C(=O)[C@H](N)Cc2ccccc21>O.C(Cl)(Cl)Cl.CCCCC>COC(=O)N[C@@H]1Cc2ccccc2N(OC)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d343a18f0d5d4b3e83df4a271cf4b5d1 | CCCI.CCCN[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1>>CCCN(CCC)[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1 | ICCC.C(CC)N[C@H]1CN2C3=C(C=CC=C3C1)N(C2=O)OC.ICCC.C([O-])([O-])=O.[K+].[K+]>>C(CC)N([C@H]1CN2C3=C(C=CC=C3C1)N(C2=O)OC)CCC | I[CH2:5][CH2:6][CH3:7].[CH3:1][CH2:2][CH2:3][NH:4][C@@H:8]1[CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]([c:17](=[O:18])[n:19]3[O:20][CH3:21])[CH2:22]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C@@H:8]1[CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]([c:17](=[O:18])[n:19]3[O:20][CH3:21])[CH2:2... | CCCI.CCCN[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1 | CCCN(CCC)[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]c2cccc3c2n1CCC3 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[#7;a:4]-[C:5]-[C:6](-[NH;D2;+0:7]-[C:8]-[C:9])-[C:10]>>[#7;a:4]-[C:5]-[C:6](-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:10] | 90 | [{"value": 90.0, "product": "C(CC)N([C@H]1CN2C3=C(C=CC=C3C1)N(C2=O)OC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "C(CC)N([C@H]1CN2C3=C(C=CC=C3C1)N(C2=O)OC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 3, a mixture of (R)-5-Propylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (8b, 0.93 g, 3.56 mmol), 1-iodopropane (3.05 g, 17.9 mmol), and potassium carbonate (1.97 g, 14.3 mmol) in acetonitrile (25 ml) was heated at reflux under nitrogen for 17 hours. 1-Iodopropan... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cc2c3c(c1)ncn3CCC2 | HI | C(C)#N | null | null | CCCI.CCCN[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1>C(C)#N>CCCN(CCC)[C@@H]1Cc2cccc3c2n(c(=O)n3OC)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26e379d5dcb345a5aaef6391ab1e77f6 | COC(=O)Cl.N[C@H](Cc1ccccc1)C(=O)O>>COC(=O)N[C@H](Cc1ccccc1)C(=O)O | [OH-].[Na+].Cl.ClC(=O)OC.N[C@H](CC1=CC=CC=C1)C(=O)O.[OH-].[Na+]>>COC(=O)N[C@@H](C(=O)O)CC1=CC=CC=C1 | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[OH:16]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[OH:16] | COC(=O)Cl.N[C@H](Cc1ccccc1)C(=O)O | COC(=O)N[C@H](Cc1ccccc1)C(=O)O | null | null | O1CCCC1.O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | 113.9 | [{"value": 113.9, "product": "COC(=O)N[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of D-phenylalanine (25.00 g, 0.151 mol) and sodium hydroxide (6.05 g, 0.151 mol) in water (170 ml) and tetrahydrofuran (225 ml) was cooled to −15° C., and a solution of methyl chloroformate (18.6 g, 0.197 mol) in tetrahydrofuran (50 ml) was added dropwise. When the addition was ˜half complete, a solution of ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | O1CCCC1.O | null | 2 | COC(=O)Cl.N[C@H](Cc1ccccc1)C(=O)O>O1CCCC1.O>COC(=O)N[C@H](Cc1ccccc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9fab0b95071347f8b60fa53a156419c7 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(=O)CC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 54 | [{"value": 54.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Clopidogrel base (5.01 g, leq.) was dissolved in methylethyl ketone (MEK) (39.5 mL). Eighty percent aqueous sulfuric acid (0.74 mL, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and half of the amount of... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)CC | null | null | O=S(=O)(O)O>CC(=O)CC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a8a7e4d77f14818b71be6d65c5464e0 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(=O)CC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 82 | [{"value": 82.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 67 | HOUR | Clopidogrel base (4.27 g, 1 eq.) was dissolved in methylethyl ketone (MEK) (33.7 ml). Eighty percent aqueous sulfuric acid (1.03 ml, 1.1 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this tempe... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)CC | null | 67 | O=S(=O)(O)O>CC(=O)CC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30d8debe6dd34c569a3ba14a104ccb1b | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | ClCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 30 | [{"value": 30.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Clopidogrel base (3.73 g, leq.) was dissolved in dichloromethane (29.4 mL). Eighty percent aqueous sulfuric acid (0.55 ml, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a precipitate was formed. Then, the solution was cooled to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCl | null | null | O=S(=O)(O)O>ClCCl>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7401e0220750462db219600f520c35aa | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | ClCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 48 | [{"value": 48.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Clopidogrel base (4.37 g, 1 eq.) was dissolved in dichloromethane (34.5 mL). Eighty percent aqueous sulfuric acid (1.06 mL, 1.1 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a turbid solution was formed. Then, the solution was cooled to room temp... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCl | null | 16 | O=S(=O)(O)O>ClCCl>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32168cbcc4634df6ae32c9a9b1ce0afe | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 82 | [{"value": 82.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Clopidogrel base (4.29 g, 1 eq.) was dissolved in toluene (33.8 mL). Eighty percent aqueous sulfuric acid (1.04 mL, 1.1 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 3 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an add... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C1(=CC=CC=C1)C | null | 16 | O=S(=O)(O)O>C1(=CC=CC=C1)C>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b9e0f91bee940479df50ee03db26c63 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 56 | [{"value": 56.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Clopidogrel base (4.24 g, leq.) was dissolved in chloroform (33.4 mL). Eighty percent aqueous sulfuric acid (0.62 mL, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a precipitate was formed. Then, the solution was cooled to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)(Cl)Cl | null | null | O=S(=O)(O)O>C(Cl)(Cl)Cl>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19e8796c29e342a39995c84f04d3a2f2 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 88 | [{"value": 88.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Clopidogrel base (4.37 g, leq.) was dissolved in chloroform (34.5 mL). Eighty percent aqueous sulfuric acid (1.06 ml, 1.1 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a precipitate was formed. Then, the solution was cooled to room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)(Cl)Cl | null | 16 | O=S(=O)(O)O>C(Cl)(Cl)Cl>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3b54ffe4ed14f94b2630339c1c540ca | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 49 | [{"value": 49.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Clopidogrel base (4.03 g, 1 eq.) was dissolved in ethyl acetate (31.8 mL). Eighty percent aqueous sulfuric acid (0.59 mL, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 3 hours during which a sticky precipitate was formed. Then, the solution was cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | null | 16 | O=S(=O)(O)O>C(C)(=O)OCC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47881f4596bd4cffabd3e61aec361380 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 66 | [{"value": 66.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Clopidogrel base (5.31 g, leq.) was dissolved in ethyl acetate (41.9 mL). Eighty percent aqueous sulfuric acid (1.29 mL, 1.1 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a massive precipitate was formed. Then, the solution was cooled to room tem... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | null | 3 | O=S(=O)(O)O>C(C)(=O)OCC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b818c555a26422ca7684099ad68aa00 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)(C)OC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 52 | [{"value": 52.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (4.39 g, leq.) was dissolved in tert-butylmethyl ether (MTBE) (34.6 ml). Eighty percent aqueous sulfuric acid (0.64 ml, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 3 hours during which a sticky precipitate was formed. Then, the solution was co... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)(C)OC | null | 2 | O=S(=O)(O)O>C(C)(C)(C)OC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86d7792015834df69da12ccbb57a5238 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 48 | [{"value": 48.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (4.17 g, leq.) was dissolved in 1,4-Dioxane (32.9 mL). Eighty percent aqueous sulfuric acid (0.61 ml, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours during which a massive precipitate was formed. Then, the solution was cooled to room temp... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCOCC1 | null | 2 | O=S(=O)(O)O>O1CCOCC1>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b576c48cd9f74a05ae8ae061f693d5bb | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 78 | [{"value": 78.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Clopidogrel base (3.42 g) was dissolved in acetone (27 mL). Aqueous sulfuric acid (20%, 4.57 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for additional 1.5 hours. Then the solvent w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)C | null | 1.5 | O=S(=O)(O)O>CC(=O)C>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-228f057bae954144b16d8660a2593903 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 82 | [{"value": 82.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (2.88 g) was dissolved in acetone (23 mL). Aqueous sulfuric acid (20%, 2.56 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for an additional 2 hours. Then the solvent ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)C | null | 2 | O=S(=O)(O)O>CC(=O)C>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42f2b151a28f46b786c53e833f1688e2 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)(C)OC.C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 56 | [{"value": 56.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Clopidogrel base (3.85 g) was dissolved in absolute ethanol (30.4 mL). Eighty percent aqueous sulfuric acid (0.56 mL) was added to the solution. The reaction mixture was heated to reflex temperature for 2 hours. Then, the solution was cooled to room temperature and the solvent was evaporated to dryness under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)(C)OC.C(C)O | null | null | O=S(=O)(O)O>C(C)(C)(C)OC.C(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac280c140bb948b98b2c2e9fe6e65d9d | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(CCC)O.C(C)(C)(C)OC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 60 | [{"value": 60.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Clopidogrel base (4.28 g) was dissolved in 1-butanol (16.9 ml). Eighty percent aqueous sulfuric acid (0.63 ml) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and the solvent was evaporated to dryness under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(CCC)O.C(C)(C)(C)OC | null | null | O=S(=O)(O)O>C(CCC)O.C(C)(C)(C)OC>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e29829a0079844738f99dbb5e4014801 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 71 | [{"value": 71.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (2.96 g) was dissolved in isopropanol (45 mL). Aqueous sulfuric acid (98%, 0.50 ml) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an additional 2 hours to obtai... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 2 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85ed19cd08aa4fefbfe32f1b899cbf4e | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 80 | [{"value": 80.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (2.91 g) was dissolved in isopropanol (IPA) (44 ml). Ninety eight percent aqueous sulfuric acid (0.32 ml) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an addit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 2 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e34d4f4189c4b309cb8319fcb6e162d | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 58 | [{"value": 58.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Clopidogrel base (2.93 g) was dissolved in isopropanol (45 ml). Sixty percent aqueous sulfuric acid (0.99 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an additional 2.5 hou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 2.5 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-92dc22b5901547448a58e8410fb8ef3b | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 24 | [{"value": 24.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Clopidogrel base (2.98 g) was dissolved in isopropanol (45 mL). Sixty percent aqueous sulfuric acid (0.67 ml) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for additional 2 hours to... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 2 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f2df6e7a6be40a9a2b6c14fa466eb0c | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 40 | [{"value": 40.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | Clopidogrel base (2.85 g) was dissolved in isopropanol (43 mL). Forty percent aqueous sulfuric acid (1.67 mL) was added to the solution at 20° C. The reaction mixture was heated to reflex temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for additional 3.5 hours ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 3.5 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b809176d5b3942438dee231ec3fc784f | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 13 | [{"value": 13.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | Clopidogrel base (2.95 g) was dissolved in isopropanol (45 ml). Forty percent aqueous sulfuric acid (1.15 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an additional 3.5 hou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 3.5 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54d89a4f8a55464d88343966b45eea5b | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 33 | [{"value": 33.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Clopidogrel base (2.89 g) was dissolved in isopropanol (44 mL). Eighty percent aqueous sulfuric acid (0.42 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for an additional 5 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 5 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ac6d6779bed4433a60a395433fd4f17 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 84 | [{"value": 84.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Clopidogrel base (2.96 g) was dissolved in isopropanol (IPA) (45 mL). Eighty percent aqueous sulfuric acid (0.65 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for an additional ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | 1.5 | O=S(=O)(O)O>C(C)(C)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-79a88380673f4a60829378d6d2f0f878 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O.COC(C)(C)C>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 87 | [{"value": 87.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Clopidogrel base (2.98 g) was dissolved in 2-butanol (23 mL). Ninety eight percent aqueous sulfuric acid (0.50 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for an additional 3 hours.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(CC)O | null | 3 | O=S(=O)(O)O>CC(CC)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e10d3fa053c0492dba9696b145cfbfd8 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O.C(C)OCC>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | CC(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 55 | [{"value": 55.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Clopidogrel base (2.94 g) was dissolved in 2-butanol (23 mL). Ninety eight percent aqueous sulfuric acid (0.43 mL) was added to the solution at 20° C. The reaction mixture was heated to reflex temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for additional 1.5 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(CC)O | null | 1.5 | O=S(=O)(O)O>CC(CC)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70a1d2b862e2446f9dbfd0405e0a6f96 | O=S(=O)(O)O>>O=S(=O)(O)O | COC(=O)[C@H](C=1C=CC=CC1Cl)N2CCC3=C(C=CS3)C2.S(O)(O)(=O)=O.CC(C)(C)OC>>COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O | [O:22]=[S:23](=[O:24])([OH:25])[OH:26]>>[O:22]=[S:23](=[O:24])([OH:25])[OH:26] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 69 | [{"value": 69.0, "product": "COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Clopidogrel base (2.86 g, 1 eq.) was dissolved in 1-Propanol (22.6 mL). Eighty percent aqueous sulfuric acid (0.59 mL, 0.66 eq.) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. Then, the solution was cooled to room temperature and stirred at this temperature for ad... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(CC)O | null | 16 | O=S(=O)(O)O>C(CC)O>O=S(=O)(O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4226d2232fe4b14a19c35ee9bd4e93f | Brc1cnc2ccccc2c1.C#CCO>>OCC#Cc1cnc2ccccc2c1 | BrC=1C=NC2=CC=CC=C2C1.C(C#C)O.C(C)N(CC)CC.C(C)N(CC)CC>>N1=CC(=CC2=CC=CC=C12)C#CCO | Br[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1.[OH:1][CH2:2][C:3]#[CH:4]>>[OH:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | Brc1cnc2ccccc2c1.C#CCO | OCC#Cc1cnc2ccccc2c1 | null | [Cu]I | C(=O)(O)[O-].[Na+] | C-C Coupling | Sonogashira alkyne_aryl halide | 1e174391e4a252d3fd1450e5e0322e210429c2a497011bc6a30357bb5bc3eef3 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 88.3 | [{"value": 88.3, "product": "N1=CC(=CC2=CC=CC=C12)C#CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 2-L three-necked flask previously purged with nitrogen was charged 3-bromoquinoline (118.77 g, 570 mmol), propargyl alcohol (71.9 g, 1.28 mol, 2.25 equiv), triethylamine (1500 mL), copper(I) iodide (3.62, 19 mmol, 0.033 equiv) and dichlorobis(triphenyl-phosphine) palladium(II) (6.67 g, 9.5 mmol). The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | [Cu]I.C(=O)(O)[O-].[Na+] | null | null | Brc1cnc2ccccc2c1.C#CCO>[Cu]I.C(=O)(O)[O-].[Na+]>OCC#Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47b9e37a882e47ecb16f8a0de6198a24 | OCC#Cc1cnc2ccccc2c1>>OC/C=C/c1cnc2ccccc2c1 | [H-].COCCO[Al+]OCCOC.[Na+].[H-].N1=CC(=CC2=CC=CC=C12)C#CCO>>N1=CC(=CC2=CC=CC=C12)/C=C/CO | [OH:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[OH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | OCC#Cc1cnc2ccccc2c1 | OC/C=C/c1cnc2ccccc2c1 | null | null | C1CCOC1 | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc2ncccc2c1 | [O;D1;H1:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[O;D1;H1:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | null | null | 1 | HOUR | To a dry, jacketed 250-mL three-necked round-bottom flask was charged sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al, 70% wt. solution in toluene, 11.0 g, 38.1 mmol, 1.39 eq) and anhydrous THF (20 mL). To this precooled (0–2° C.) and magnetically stirred solution was added a THF (50 mL) solution of the 3-(3-quinol... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2ncccc2c1 | null | C1CCOC1 | null | 1 | OCC#Cc1cnc2ccccc2c1>C1CCOC1>OC/C=C/c1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad72a4378b3b4b24a50d107af25b2797 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[O-] | C(C)(=O)OCC.CCCCCCC.[OH-].[Na+].N1=CC(=CC2=CC=CC=C12)C=CCO.C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C>>N1=CC(=CC2=CC=CC=C12)C=CCO.C(OC(C)(C)C)([O-])=O | CC(C)(C)OC(=O)[O:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O-:8] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C | CC(C)(C)OC(=O)[O-] | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(Cl)Cl | Miscellaneous | OtherReaction | ed733215f442ec38ffb8ac8e3ce0777b9978fcccda2fe55610efa73305a71ba0 | 5ef46932d9a1fe5669b3d06c14ca4f5627ea1d329652fc6287924421b334d6e3 | null | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | null | [] | null | null | null | null | To a 500-mL three-necked round-bottom flask equipped with an overhead mechanical stirrer was charged 3-(3-quinolyl)-2-propen-1-ol (13.03 g, 70.43 mmol) as a mixture of cis- and trans-isomers (81% cis, and 19% trans), di-tert butyl dicarbonate (16.91 g, 77.48 mmol, 1.11 equiv), tetra n-butylammonium hydrogen sulfate (74... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Boc | Carbonic Acid | null | null | null | HO- | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(Cl)Cl | null | null | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(Cl)Cl>CC(C)(C)OC(=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-044e5cc4fd5e4afc9a7e9c694199cff7 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[O-] | N1=CC(=CC2=CC=CC=C12)C#CCO.C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.[OH-].[Na+]>>N1=CC(=CC2=CC=CC=C12)C#CCO.C(C)(C)(C)OC([O-])=O | CC(C)(C)OC(=O)[O:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O-:8] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C | CC(C)(C)OC(=O)[O-] | null | null | O.C(Cl)Cl | Miscellaneous | OtherReaction | ed733215f442ec38ffb8ac8e3ce0777b9978fcccda2fe55610efa73305a71ba0 | 5ef46932d9a1fe5669b3d06c14ca4f5627ea1d329652fc6287924421b334d6e3 | null | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | null | [] | null | null | 4 | HOUR | To a dry 1-L three-necked round-bottom flask equipped with a nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (15.81 g, 86.39 mmol), di-tert-butyl dicarbonate (22.48 g, 103 mmol, 1.19 equiv), n-tetrabutyl ammonium hydrogen sulfate (0.86 g, 2.54 mmol, 0.029 equiv) and methylene chloride (300 ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Boc | Carbonic Acid | null | null | null | HO- | O.C(Cl)Cl | null | 4 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C>O.C(Cl)Cl>CC(C)(C)OC(=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b409aa7fda1e49bbb7bfb0b9464b3638 | OCC#Cc1cnc2ccccc2c1>>OCC=Cc1cnc2ccccc2c1 | N1=CC(=CC2=CC=CC=C12)C#CCO.C(C)(C)(C)OC([O-])=O>>N1=CC(=CC2=CC=CC=C12)C=CCO.C(C)(C)(C)OC([O-])=O | [OH:9][CH2:10][C:11]#[C:12][c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1>>[OH:9][CH2:10][CH:11]=[CH:12][c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1 | OCC#Cc1cnc2ccccc2c1 | OCC=Cc1cnc2ccccc2c1 | null | [Pd].[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | C(C)(C)O | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc2ncccc2c1 | [O;D1;H1:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[O;D1;H1:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | null | null | null | null | To a 250-mL single-necked round-bottom flask was charged the 3-(3-quinolyl)-2-propyn-1-ol t-butyl carbonate (1.52 g, 5.37 mmol), isopropanol (30 mL) and 5% palladium on calcium carbonate poisoned with lead (Lindlar's catalyst, 75 mg, 0.049 equiv). The suspension was stirred (rapidly) magnetically and the atmosphere abo... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2ncccc2c1 | null | [Pd].[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)(C)O | null | null | OCC#Cc1cnc2ccccc2c1>[Pd].[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)(C)O>OCC=Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f83c87bc9b8c4febad52cb8f24326a21 | Brc1cnc2ccccc2c1.C=CC(=O)OCC>>CCOC(=O)C=Cc1cnc2ccccc2c1 | CN(C=O)C.BrC=1C=NC2=CC=CC=C2C1.C(C=C)(=O)OCC.C([O-])(O)=O.[Na+].BrC=1C=NC2=CC=CC=C2C1>>N1=CC(=CC2=CC=CC=C12)C=CC(=O)OCC | Br[c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[cH:17]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[cH:17]1 | Brc1cnc2ccccc2c1.C=CC(=O)OCC | CCOC(=O)C=Cc1cnc2ccccc2c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(=O)OCC | C-C Coupling | Heck terminal vinyl | a87d881b4c1880689693d296001ccd251ba98c523b412e68ce627333ac531f30 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH2;D1;+0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 65 | [{"value": 65.0, "product": "N1=CC(=CC2=CC=CC=C12)C=CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 30 | MINUTE | The 3-bromoquinoline (300 g, 1.44 mmol), ethyl acrylate (168 g, 1.68 mmol), palladium(II) acetate (32.3 g, 144 mmol), tetrabutylammonium bromide (478 g 1.44 mol), and sodium bicarbonate (483.9 g, 5.76 mol) were combined in a 5-L round-bottom flask with overhead stirring and 3 L dimethyl formamide (anhydrous). The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)OCC | 90 | 0.5 | Brc1cnc2ccccc2c1.C=CC(=O)OCC>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)OCC>CCOC(=O)C=Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c892151205ac4c359da3777a59ad165c | O=C([O-])C=Cc1cnc2ccccc2c1>>OCC=Cc1cnc2ccccc2c1 | N1=CC(=CC2=CC=CC=C12)C=CC(=O)[O-].[H-].C(C(C)C)[Al+]CC(C)C>>N1=CC(=CC2=CC=CC=C12)C=CCO | O=[C:2]([O-:1])[CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[OH:1][CH2:2][CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | O=C([O-])C=Cc1cnc2ccccc2c1 | OCC=Cc1cnc2ccccc2c1 | null | null | C(Cl)Cl | Reduction | OtherReaction | 3ee00ae8302f5a9cabfd43f47c90c2bc696c7c0e2b77ca13873c453d0520692e | c2c13922fe3c9358e6ba38897f2383764691ea247b267e6643408d03716a3879 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[O-;H0;D1:2])-[C:3]=[C:4]-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[C:4]=[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 62 | [{"value": 62.0, "product": "N1=CC(=CC2=CC=CC=C12)C=CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "N1=CC(=CC2=CC=CC=C12)C=CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -57 | CELSIUS | 30 | MINUTE | The 3-(3-quinolyl)-2-propenoate (141 g, 0.621 moles) was dissolved in 2.0 L anhydrous methylene chloride in a 5-L round-bottom flask with overhead stirring and cooled to −57° C. with isopropanol/dry ice bath. Diisobutylaluminum hydride (1.55 L, 1.0 M in methylene chloride) was added in a slow stream, keeping the temper... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccc2ncccc2c1 | Other | C(Cl)Cl | -57 | 0.5 | O=C([O-])C=Cc1cnc2ccccc2c1>C(Cl)Cl>OCC=Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-108b40c914184cc48154e402484aabce | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=Cc1cc2ccccc2nc1I>>C=CC(O)c1cnc2ccccc2c1.CC(C)(C)OC(=O)[O-] | C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.IC1=NC2=CC=CC=C2C=C1C=O.C(=C)[Mg]Br.[Cl-].[NH4+].[Li+].CCC[CH2-]>>N1=CC(=CC2=CC=CC=C12)C(C=C)O.C(C)(C)(C)OC([O-])=O | CC(C)(C)OC(=O)[O:22][C:20]([O:19][C:16]([CH3:15])([CH3:17])[CH3:18])=[O:21].I[c:6]1[c:5]([CH:3]=[O:4])[cH:14][c:13]2[c:8]([n:7]1)[cH:9][cH:10][cH:11][cH:12]2>>[CH2:1]=[CH:2][CH:3]([OH:4])[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1.[CH3:15][C:16]([CH3:17])([CH3:18])[O:19][C:20](=[O:21])[O-:22] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=Cc1cc2ccccc2nc1I | C=CC(O)c1cnc2ccccc2c1.CC(C)(C)OC(=O)[O-] | null | null | CC(C)(C)OC.C1CCOC1 | C-C Coupling | OtherReaction | c37b84f8c11ce4454b903ce99294ae1ca011988fca379ee616427f283b4bed0c | 19cb132516618b7155a282cb13664293728ad4558cd3dc48c98aa6ff43004e7a | c1ccc2ncccc2c1 | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].I-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12](-[CH;D2;+0:13]=[O;H0;D1;+0:14]):[c:15]>>[C;D1;H2:16]=[C:17]-[CH;D3;+0:13](-[OH;D1;+0:14])-[c:12](:[c:15]):[cH;D2;+0:9]:[#7;a:10]:[c:11].[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-... | null | [] | null | null | 1 | HOUR | To a solution of 2-iodo-3-quinoline carboxaldehyde (3 g, 10.6 mmol) in THF (25 ml) at −5° C., vinylmagnesium bromide (1 M solution, 10. 8 ml, 10.8 mmol) was added. It was stirred at that temperature until the starting material disappears, which takes about one hour. N-butyllithium (8.5 ml, 2.5 M soln, 21.2 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Anhydride.Aldehyde.Carbonic Ester.Carbonic Ester.Boc | Carbonic Acid.Secondary alcohol.Vinyl | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HI | CC(C)(C)OC.C1CCOC1 | null | 1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=Cc1cc2ccccc2nc1I>CC(C)(C)OC.C1CCOC1>C=CC(O)c1cnc2ccccc2c1.CC(C)(C)OC(=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68927fb1a4ea43b9a8e0239686c36b4d | CC=O.O=Cc1cnc2ccccc2c1>>O=CC=Cc1cnc2ccccc2c1 | C(C)(=O)OC(C)=O.[OH-].[Na+].N1=CC(=CC2=CC=CC=C12)C=O.C(C)=O.C(C)(=O)OC>>N1=CC(=CC2=CC=CC=C12)C=CC=O | [O:1]=[CH:2][CH3:3].O=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[O:1]=[CH:2][CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | CC=O.O=Cc1cnc2ccccc2c1 | O=CC=Cc1cnc2ccccc2c1 | null | null | O.CO | C-C Coupling | OtherReaction | 154f038b7f5648ae5349abff8a924c982177f620bdfb6a2f53d7ca0fce37c68d | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | c1ccc2ncccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[CH3;D1;+0:7]-[C:8]=[O;D1;H0:9]>>[O;D1;H0:9]=[C:8]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | -10 | CELSIUS | 30 | MINUTE | To a 500-mL round-bottom flask, equipped with mechanical stirrer, dropping funnel and temperature bath was charged 30.9 g (0.2 mol) quinoline 3-carboxaldehyde and acetaldehyde (50 mL). The mixture was cooled to −10° C. and a solution of sodium hydroxide (500 mg) in methanol (8 mL) was added dropwise keeping the tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | null | null | c1ccc2ncccc2c1 | HO- | O.CO | -10 | 0.5 | CC=O.O=Cc1cnc2ccccc2c1>O.CO>O=CC=Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d067d67eb604ce780e28de10f9cd37b | O=CC=Cc1cnc2ccccc2c1>>OCC=Cc1cnc2ccccc2c1 | [Cl-].[NH4+].[BH4-].[Na+].N1=CC(=CC2=CC=CC=C12)C=CC=O.C(C)(=O)OC(C)C>>N1=CC(=CC2=CC=CC=C12)C=CCO | [O:1]=[CH:2][CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[OH:1][CH2:2][CH:3]=[CH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | O=CC=Cc1cnc2ccccc2c1 | OCC=Cc1cnc2ccccc2c1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc2ncccc2c1 | [#7;a:1]:[c:2]:[c:3]-[C:4]=[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[#7;a:1]:[c:2]:[c:3]-[C:4]=[C:5]-[CH2;D2;+0:6]-[OH;D1;+0:7] | 65.4 | [{"value": 65.4, "product": "N1=CC(=CC2=CC=CC=C12)C=CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "N1=CC(=CC2=CC=CC=C12)C=CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 90 | MINUTE | A mixture of 3-(3-quinolyl)propenal (10 g, 54.6 mmol) in methanol (50 mL) was cooled to 0° C. and to this mixture, sodium borohydride (1.03 g, 27 mmol) was charged in small portions keeping the temperature below 10° C. After the addition was complete, the mixture was stirred at 23° C. for 90 min. until the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2ncccc2c1 | null | CO | 23 | 1.5 | O=CC=Cc1cnc2ccccc2c1>CO>OCC=Cc1cnc2ccccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-977be506a4914aa1a39f7b8627dcf552 | O=C(Cl)N(C1CCCCC1)C1CCCCC1.OCC#Cc1cnc2ccccc2c1>>O=C(OCC#Cc1cnc2ccccc2c1)N(C1CCCCC1)C1CCCCC1 | [NH4+].[Cl-].CC(C)([O-])C.[K+].N1=CC(=CC2=CC=CC=C12)C#CCO.C1(CCCCC1)N(C(=O)Cl)C1CCCCC1>>C1(CCCCC1)N(C(=O)OCC#CC=1C=NC2=CC=CC=C2C1)C1CCCCC1 | Cl[C:2](=[O:1])[N:17]([CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1.[OH:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1>>[O:1]=[C:2]([O:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[N... | O=C(Cl)N(C1CCCCC1)C1CCCCC1.OCC#Cc1cnc2ccccc2c1 | O=C(OCC#Cc1cnc2ccccc2c1)N(C1CCCCC1)C1CCCCC1 | null | null | CC(C)(C)OC.C1CCOC1 | Protection | Schotten-Baumann to ester | 597fa7ba4ca169ec9e1d3b8730fbab27757ccde00143c31019a679c09b7b2b7f | 562b6a5118cb63cbe5ff058f35135dc3f085de8b8ec7fa4ac4de518324eb826a | O=C(OCC#Cc1cnc2ccccc2c1)N(C1CCCCC1)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5] | null | [] | 0 | CELSIUS | 2 | HOUR | To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (1 g, 5.4 mmol) in THF (10 ml) and the solution was cooled to 0° C. Potassium t-butoxide (0.67 g, 5.9 mmol) was then added followed by dicyclohexylcarbamoyl chloride (1.32 g, 5.4 mmol). Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary alcohol | Carbamic ester | null | null | c1ccc2ncccc2c1.C1CCCCC1.C1CCCCC1 | HCl | CC(C)(C)OC.C1CCOC1 | 0 | 2 | O=C(Cl)N(C1CCCCC1)C1CCCCC1.OCC#Cc1cnc2ccccc2c1>CC(C)(C)OC.C1CCOC1>O=C(OCC#Cc1cnc2ccccc2c1)N(C1CCCCC1)C1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d58dd4469bd14d00b3e47bcff1963e73 | O=C(Cl)N(c1ccccc1)c1ccccc1.OCC#Cc1cnc2ccccc2c1>>O=C(OCC#Cc1cnc2ccccc2c1)N(c1ccccc1)c1ccccc1 | [NH4+].[Cl-].CC(C)([O-])C.[K+].N1=CC(=CC2=CC=CC=C12)C#CCO.C1(=CC=CC=C1)N(C(=O)Cl)C1=CC=CC=C1>>C1(=CC=CC=C1)N(C(=O)OCC#CC=1C=NC2=CC=CC=C2C1)C1=CC=CC=C1 | Cl[C:2](=[O:1])[N:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[OH:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1>>[O:1]=[C:2]([O:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[N:17]([c:18]1... | O=C(Cl)N(c1ccccc1)c1ccccc1.OCC#Cc1cnc2ccccc2c1 | O=C(OCC#Cc1cnc2ccccc2c1)N(c1ccccc1)c1ccccc1 | null | null | CC(C)(C)OC.C1CCOC1 | Protection | Schotten-Baumann to ester | 597fa7ba4ca169ec9e1d3b8730fbab27757ccde00143c31019a679c09b7b2b7f | 562b6a5118cb63cbe5ff058f35135dc3f085de8b8ec7fa4ac4de518324eb826a | O=C(OCC#Cc1cnc2ccccc2c1)N(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[c:5].[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[c:5] | null | [] | 0 | CELSIUS | 2 | HOUR | To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (5 g, 27 mmol) in THF (50 ml) and the solution was cooled to 0° C. Potassium t-butoxide (3.6 g, 32 mmol) was then added followed by diphenylcarbamoyl chloride (6.9 g, 29.7 mmol). The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary alcohol | Carbamic ester | null | null | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HCl | CC(C)(C)OC.C1CCOC1 | 0 | 2 | O=C(Cl)N(c1ccccc1)c1ccccc1.OCC#Cc1cnc2ccccc2c1>CC(C)(C)OC.C1CCOC1>O=C(OCC#Cc1cnc2ccccc2c1)N(c1ccccc1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bbde859250e14d4b9eae21d11a8ee9d3 | CC(C)N(C(=O)Cl)C(C)C.OCC#Cc1cnc2ccccc2c1>>CC(C)N(C(=O)OCC#Cc1cnc2ccccc2c1)C(C)C | C(C)(C)N(C(=O)Cl)C(C)C.N1=CC(=CC2=CC=CC=C12)C#CCO.N1=CC(=CC2=CC=CC=C12)C#CCO.[NH4+].[Cl-].CC(C)([O-])C.[K+]>>C(C)(C)N(C(=O)OCC#CC=1C=NC2=CC=CC=C2C1)C(C)C | Cl[C:5]([N:4]([CH:2]([CH3:1])[CH3:3])[CH:21]([CH3:22])[CH3:23])=[O:6].[OH:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1>>[CH3:1][CH:2]([CH3:3])[N:4]([C:5](=[O:6])[O:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1)[CH:21]([CH3:22])... | CC(C)N(C(=O)Cl)C(C)C.OCC#Cc1cnc2ccccc2c1 | CC(C)N(C(=O)OCC#Cc1cnc2ccccc2c1)C(C)C | null | null | CC(C)(C)OC.C1CCOC1 | Protection | Schotten-Baumann to ester | 597fa7ba4ca169ec9e1d3b8730fbab27757ccde00143c31019a679c09b7b2b7f | 562b6a5118cb63cbe5ff058f35135dc3f085de8b8ec7fa4ac4de518324eb826a | c1ccc2ncccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;a:6]:[c:7]:[c:8]-[C:9]#[C:10]-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5] | null | [] | 0 | CELSIUS | 2 | HOUR | To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (2 g, 10.8 mmol) (Scheme 1, Compound (3)) in THF (20 ml) and the solution was cooled to 0° C. Potassium t-butoxide (1.34 g, 11.9 mmol) was then added followed by diisopropylcarbamoyl chlor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary alcohol | Carbamic ester | null | null | c1ccc2ncccc2c1 | HCl | CC(C)(C)OC.C1CCOC1 | 0 | 2 | CC(C)N(C(=O)Cl)C(C)C.OCC#Cc1cnc2ccccc2c1>CC(C)(C)OC.C1CCOC1>CC(C)N(C(=O)OCC#Cc1cnc2ccccc2c1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4216f66d9d54bd8abacf998327fe60b | CI.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1>>Cn1c(=O)cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc21 | [N+](=O)([O-])C=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F.[OH-].[K+].CI>>CN1C(C=C(C2=CC(=CC=C12)[N+](=O)[O-])C(F)(F)F)=O | I[CH3:1].[nH:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19]12>>[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19]12 | CI.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1 | Cn1c(=O)cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8b34fe134eb750cc9638be1186f4b7fb81aa2af5327ea2fbd8cdd88c39c64638 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1ccc2ccccc2[nH]1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[c:3](:[c:4]):[nH;D2;+0:5]:[c:6](:[c:7]):[c:8]>>[CH3;D1;+0:1]-[n;H0;D3;+0:5](:[c:6](:[c:7]):[c:8]):[c:3](=[O;D1;H0:2]):[c:4] | 57.6 | [{"value": 57.0, "product": "CN1C(C=C(C2=CC(=CC=C12)[N+](=O)[O-])C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "CN1C(C=C(C2=CC(=CC=C12)[N+](=O)[O-])C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Nitro-4-trifluoromethyl-1H-quinolin-2-one (2.50 g, 9.7 mmol) was methylated with KOH (5.46 g, 97.3 mmol) & MeI (6.1 mL, 97.3 mmol), as to give 1-methyl-6-nitro-4-trifluoromethyl-1H-quinolin-2-one (1.52 g, 57%): δH (CDCl3)=3.80 (s, 3H), 7.20 (s, 1H), 7.55 (d, 1H), 8.50 (dd, 1H), 8.75 (d, 1H). An EtOAc (50 mL) solution... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HI | null | null | null | CI.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1>>Cn1c(=O)cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b782ccaa18914a638b92100784315792 | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.O=C=Nc1ccccc1>>Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=O)Nc3ccccc3)ccc21 | NC=1C=C2C(=CC(N(C2=CC1)C)=O)C(F)(F)F.C1(=CC=CC=C1)N=C=O.N1=CC=CC=C1>>CN1C(C=C(C2=CC(=CC=C12)NC(=O)NC1=CC=CC=C1)C(F)(F)F)=O | [CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([NH2:14])[cH:24][cH:25][c:26]12.[C:15](=[O:16])=[N:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([NH:14][C:15](=[O:16])[NH:17][c:18]3[cH:19][cH:20][... | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.O=C=Nc1ccccc1 | Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=O)Nc3ccccc3)ccc21 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ccc2[nH]c(=O)ccc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 80.3 | [{"value": 80.0, "product": "CN1C(C=C(C2=CC(=CC=C12)NC(=O)NC1=CC=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "CN1C(C=C(C2=CC(=CC=C12)NC(=O)NC1=CC=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 6-amino-1-methyl-4-trifluoromethyl-1H-quinolin-2-one (Preparation 1, 48 mg, 200 μmol) in anhydrous DMF (2 mL) was treated with PhNCO (33 μL, 300 μmol) & pyridine (16 μL, 20 μmol). The mixture was stirred for 16 h & then partitioned between EtOAc (30 mL) & H2O (20 mL). The organic layer was washed with H2O... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2ncccc2c1.c1ccccc1 | null | CN(C)C=O | null | 16 | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.O=C=Nc1ccccc1>CN(C)C=O>Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=O)Nc3ccccc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5fba2f7f0da44f38995cecb0aa6fbeb1 | Cc1ccc(CCN=C=S)cc1.Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21>>Cc1ccc(CCNC(=S)Nc2ccc3c(c2)c(C(F)(F)F)cc(=O)n3C)cc1 | N1=CC=CC=C1.CC1=CC=C(CCN=C=S)C=C1.NC=1C=C2C(=CC(N(C2=CC1)C)=O)C(F)(F)F>>CN1C(C=C(C2=CC(=CC=C12)NC(=S)NCCC1=CC=C(C=C1)C)C(F)(F)F)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]=[C:9]=[S:10])[cH:28][cH:29]1.[NH2:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](=[O:25])[n:26]2[CH3:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][C:9](=[S:10])[NH:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17... | Cc1ccc(CCN=C=S)cc1.Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21 | Cc1ccc(CCNC(=S)Nc2ccc3c(c2)c(C(F)(F)F)cc(=O)n3C)cc1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=c1ccc2cc(NC(=S)NCCc3ccccc3)ccc2[nH]1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 20 | [{"value": 20.0, "product": "CN1C(C=C(C2=CC(=CC=C12)NC(=S)NCCC1=CC=C(C=C1)C)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | 6-Amino-1-methyl-4-trifluoromethyl-1H-quinolin-2-one (Preparation 1, 200 μL of a 0.2 M solution in NMP, 40 μmol) was treated with pyridine (20 μL of a 0.2 M solution in NMP, 4 μmol) & 4-methylphenethyl isothiocyanate (240 μL of a 0.2 M solution in NMP, 48 μmol). After 7 d, the mixture was concentrated, then the residue... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccc2ncccc2c1 | null | CN1CCCC1=O | null | 168 | Cc1ccc(CCN=C=S)cc1.Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21>CN1CCCC1=O>Cc1ccc(CCNC(=S)Nc2ccc3c(c2)c(C(F)(F)F)cc(=O)n3C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fa46e21f870488d806783ecc0222d0f | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.S=C=NCCc1ccc(Cl)cc1>>Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=S)NCCc3ccc(Cl)cc3)ccc21 | NC=1C=C2C(=CC(N(C2=CC1)C)=O)C(F)(F)F.ClC1=CC=C(C=C1)CCN=C=S>>ClC1=CC=C(C=C1)CCNC(=S)NC=1C=C2C(=CC(N(C2=CC1)C)=O)C(F)(F)F | [CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([NH2:14])[cH:27][cH:28][c:29]12.[C:15](=[S:16])=[N:17][CH2:18][CH2:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]2[cH:12][c:13]([NH:14][C:15](=[S:16])[NH:1... | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.S=C=NCCc1ccc(Cl)cc1 | Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=S)NCCc3ccc(Cl)cc3)ccc21 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=c1ccc2cc(NC(=S)NCCc3ccccc3)ccc2[nH]1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 40 | [{"value": 40.0, "product": "ClC1=CC=C(C=C1)CCNC(=S)NC=1C=C2C(=CC(N(C2=CC1)C)=O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 6-amino-1-methyl-4-trifluoromethyl-1H-quinolin-2-one (Preparation 1, 200 μL of a 0.2 M solution in NMP, 40 μmol) with 2-(4-chlorophenyl)ethyl isothiocyanate (240 μL of a 0.2 M solution in NMP, 48 μmol), by the procedure outlined for Example 492, furnished the title compound (7.1 mg, 40%): RT=1.95 min; m/z (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccc2ncccc2c1.c1ccccc1 | null | CN1CCCC1=O | null | null | Cn1c(=O)cc(C(F)(F)F)c2cc(N)ccc21.S=C=NCCc1ccc(Cl)cc1>CN1CCCC1=O>Cn1c(=O)cc(C(F)(F)F)c2cc(NC(=S)NCCc3ccc(Cl)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70ccfe0370df4d57ac11e4966ad1c4e0 | Nc1nc2ccc([N+](=O)[O-])cc2s1>>Nc1ccc2nc(N)sc2c1 | NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].[H][H]>>NC=1SC2=C(N1)C=CC(=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH2:8])[s:9][c:10]2[cH:11]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH2:8])[s:9][c:10]2[cH:11]1 | Nc1nc2ccc([N+](=O)[O-])cc2s1 | Nc1ccc2nc(N)sc2c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2scnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 99.3 | [{"value": 99.0, "product": "NC=1SC2=C(N1)C=CC(=C2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "NC=1SC2=C(N1)C=CC(=C2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-Amino-6-nitrobenzothiazole (500 mg, 2.56 mmol) was dissolved in methanol (20 mL) and 10% palladium on carbon (50 mg) was added as a slurry in methanol (1 mL). The atmosphere was replaced with hydrogen and the suspension was stirred overnight. The catalyst was removed by suction filtration and the solvent evaporated t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2scnc2c1 | Other | [Pd].CO | null | 8 | Nc1nc2ccc([N+](=O)[O-])cc2s1>[Pd].CO>Nc1ccc2nc(N)sc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-951fd2859fd144deb086a5a97529b901 | Nc1ccc2c(c1)CCC2.O=CO>>O=CNc1ccc2c(c1)CCC2 | NC=1C=C2CCCC2=CC1.C(=O)O.Cl.CN(CCCN=C=NCC)C.C(C)(C)N(CC)C(C)C>>C(=O)NC=1C=C2CCCC2=CC1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][CH2:12]2.O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][CH2:12]2 | Nc1ccc2c(c1)CCC2.O=CO | O=CNc1ccc2c(c1)CCC2 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2c(c1)CCC2 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 93.3 | [{"value": 93.0, "product": "C(=O)NC=1C=C2CCCC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "C(=O)NC=1C=C2CCCC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-aminoindane (7.53 g, 56.5 mmol) in DMF (100 mL) was added formic acid (2.2 mL, 58.3 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (10.94 g, 57 mmol) and diisopropylethylamine (19.7 mL, 0.11 mol). The resulting solution was stirred overnight and then partitioned between saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCC2 | HO- | CN(C)C=O | null | 8 | Nc1ccc2c(c1)CCC2.O=CO>CN(C)C=O>O=CNc1ccc2c(c1)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7aab29217ca490d8d969149d8fdcd45 | CCOC(=O)C(=NO)C(=O)CCl.NC(=S)c1ccccc1>>CCOC(=O)C(=NO)c1csc(-c2ccccc2)n1 | ClCC(C(C(=O)OCC)=NO)=O.C(C1=CC=CC=C1)(=S)N>>N(O)=C(C(=O)OCC)C=1N=C(SC1)C1=CC=CC=C1 | O=[C:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7][OH:8])[CH2:10]Cl.[S:11]=[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[NH2:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[N:7][OH:8])[c:9]1[cH:10][s:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19]1 | CCOC(=O)C(=NO)C(=O)CCl.NC(=S)c1ccccc1 | CCOC(=O)C(=NO)c1csc(-c2ccccc2)n1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1ccc(-c2nccs2)cc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[#7:4]-[O;D1;H1:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[NH2;D1;+0:10]-[C;H0;D3;+0:11](=[S;H0;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:3](=[#7:4]-[O;D1;H1:5])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:12]:[c;H0;D3;+0:11](-[c;H0;... | 107.9 | [{"value": 107.9, "product": "N(O)=C(C(=O)OCC)C=1N=C(SC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of ethyl γ-chloro-α-oximinoacetoacetate (2.10 g, 10.8 mmol) and thiobenzamide (1.49 g, 10.8 mmol) in dry benzene (15 mL) was heated to reflux. After 4 hours, the reaction mixture was poured onto NaHCO3 (sat., aq., 50 mL); The resulting mixture was extracted with ethyl acetate (2×50 mL); and the combined extr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1.c1ccccc1 | HCl | C1=CC=CC=C1 | null | 4 | CCOC(=O)C(=NO)C(=O)CCl.NC(=S)c1ccccc1>C1=CC=CC=C1>CCOC(=O)C(=NO)c1csc(-c2ccccc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b719000289c949c1b73f29564e672469 | CO.Nc1ccc(C(=O)O)cn1>>COC(=O)c1ccc(N)nc1 | NC1=NC=C(C(=O)O)C=C1.S(O)(O)(=O)=O.CO>>NC1=NC=C(C(=O)OC)C=C1 | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[n:10][cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[n:10][cH:11]1 | CO.Nc1ccc(C(=O)O)cn1 | COC(=O)c1ccc(N)nc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[C;D1;H3:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 30 | [{"value": 30.0, "product": "NC1=NC=C(C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 6-aminonicotinic acid (2.0 g, 14.5 mmol) and sulfuric acid (2 mL) in methanol (125 mL) was heated at reflux overnight. The solution was cooled, the methanol evaporated and the residue was taken up in water (100 mL) and made basic with NaHCO3 (s), causing a white solid to precipitate. The mixture was ext... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccncc1 | HO- | null | null | null | CO.Nc1ccc(C(=O)O)cn1>>COC(=O)c1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5df7c6a4559e4c7fadd29da15281fbc1 | O=C(O)c1cccnc1Cl>>COC(=O)c1cccnc1Cl | C(=O)(O)[O-].[Na+].ClC1=C(C(=O)O)C=CC=N1.S(O)(O)(=O)=O.O>>ClC1=C(C(=O)OC)C=CC=N1 | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[Cl:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[Cl:11] | O=C(O)c1cccnc1Cl | COC(=O)c1cccnc1Cl | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[C;D1;H3:7] | 40 | [{"value": 40.0, "product": "ClC1=C(C(=O)OC)C=CC=N1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-chloronicotinic acid (1.61 g, 10.2 mmol) and sulfuric acid (0.5 mL) in methanol (30 mL) was stirred at reflux overnight. The solution was poured into water (100 mL) and neutralised with NaHCO3 (s) before being extracted with 1:1 hexane/ethyl acetate (3×40 mL). The solvents were dried (MgSO4) and evapora... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccncc1 | Other | CO | null | null | O=C(O)c1cccnc1Cl>CO>COC(=O)c1cccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9b586bba5e9a41db8c92d9207fc46e12 | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl>>CCOC(=O)C(=NO)c1csc(CC)n1 | ClCC(C(C(=O)OCC)=NO)=O.C(CC)(=S)N>>N(O)=C(C(=O)OCC)C=1N=C(SC1)CC | [S:11]=[C:12]([CH2:13][CH3:14])[NH2:15].O=[C:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7][OH:8])[CH2:10]Cl>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[N:7][OH:8])[c:9]1[cH:10][s:11][c:12]([CH2:13][CH3:14])[n:15]1 | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl | CCOC(=O)C(=NO)c1csc(CC)n1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1cscn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[#7:4]-[O;D1;H1:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C;D1;H3:10]-[C:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[S;H0;D1;+0:14]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:3](=[#7:4]-[O;D1;H1:5])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:14]:[c;H0;D3;+0:12](-[C:11]-[C;D1;H3:10]):[n;H0;D2;+0... | 35.3 | [{"value": 35.3, "product": "N(O)=C(C(=O)OCC)C=1N=C(SC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of ethyl γ-chloro-α-oximinoacetoacetate (2.00 g, 10.3 mmol) and thiopropionamide (0.92 g, 10.3 mmol) in dry benzene (15 mL) was heated to reflux. After 4 hours, the reaction mixture was poured onto NaHCO3 (sat. aq., 50 mL), The resulting mixture was extracted with ethyl acetate (2×50 mL), and the combined ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1 | HCl | C1=CC=CC=C1 | null | 4 | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl>C1=CC=CC=C1>CCOC(=O)C(=NO)c1csc(CC)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4908647c9fd043d7b326254adfe97735 | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl>>CCOC(=O)C(=NO)c1csc(CC)n1 | ClCC(C(C(=O)OCC)=NO)=O.C(CC)(=S)N>>N(O)=C(C(=O)OCC)C=1N=C(SC1)CC | [S:11]=[C:12]([CH2:13][CH3:14])[NH2:15].O=[C:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7][OH:8])[CH2:10]Cl>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[N:7][OH:8])[c:9]1[cH:10][s:11][c:12]([CH2:13][CH3:14])[n:15]1 | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl | CCOC(=O)C(=NO)c1csc(CC)n1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1cscn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[#7:4]-[O;D1;H1:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C;D1;H3:10]-[C:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[S;H0;D1;+0:14]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:3](=[#7:4]-[O;D1;H1:5])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:14]:[c;H0;D3;+0:12](-[C:11]-[C;D1;H3:10]):[n;H0;D2;+0... | 35.3 | [{"value": 35.3, "product": "N(O)=C(C(=O)OCC)C=1N=C(SC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl γ-chloro-α-oximinoacetoacetate (2.00 g, 10.3 mmol) and thiopropionamide (0.92 g, 10.3 mmol) in dry benzene (15 mL) was heated at reflux. After 4 hours the reaction mixture was poured onto NaHCO3 (sat. aq., 50 mL), The resulting mixture was extracted with ethyl acetate (2×50 mL), and the combined ext... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1 | HCl | C1=CC=CC=C1 | null | null | CCC(N)=S.CCOC(=O)C(=NO)C(=O)CCl>C1=CC=CC=C1>CCOC(=O)C(=NO)c1csc(CC)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f6398d85ae1e499096b7dc403b7c24e0 | C=CC(=O)OCC(CC)CCCC>>CCCCC(CC)C(=O)O | C(C=C)(=O)OCC(CCCC)CC.C([O-])([O-])=O.[Cs+].[Cs+]>>CCCCC(CC)C(=O)O | C(C(C[O:10][C:8]([CH:5]=[CH2:6])=[O:9])[CH2:4][CH2:3][CH2:2][CH3:1])[CH3:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[C:8](=[O:9])[OH:10] | C=CC(=O)OCC(CC)CCCC | CCCCC(CC)C(=O)O | null | null | C(C)#N | Miscellaneous | OtherReaction | 7bb1c6a47ceff39dbfe124fd8262f8cabbf022e9f3f42a469d88b73802e7ca41 | e688aeafd627b2d2fb9627b228ddfee0f20a7656c4b9b14ac8ece839b175abbe | null | [C:1]-[C:2]-[CH2;D2;+0:3]-C(-C-[CH3;D1;+0:4])-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:8](-[CH2;D2;+0:9]-[CH3;D1;+0:4])-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5] | 399.2 | [{"value": 88.0, "product": "CCCCC(CC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 399.2, "product": "CCCCC(CC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of TMIT (1.0 g, 6.33 mmol), 2-ethylhexyl acrylate (1.16 g, 6.33 mmol) and cesium carbonate (1.0 g, 3.3 mmol) in acetonitrile (15 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered to separate solid cesium carbonate and solvent was evaporated from the filtrate to obtain the product... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Carboxylic acid | null | null | null | Other | C(C)#N | null | 24 | C=CC(=O)OCC(CC)CCCC>C(C)#N>CCCCC(CC)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e54e313d973542d5b345a9880f543028 | C=CC(=O)OCC(CC)CCCC.CCCCC(CC)C(=O)O>>CC(=O)CC(C)C.CC(C)=O.CCC(C)=O.O=C1CCCCC1 | CCCCC(CC)C(=O)O.C(C=C)(=O)OCC(CCCC)CC.C([O-])([O-])=O.[Cs+].[Cs+]>>CC(=O)C.C(C(C)C)C(=O)C.C(C)C(=O)C.C1(CCCCC1)=O | C([CH:2]([CH2:1]O[C:18](=[O:17])[CH:23]=[CH2:22])[CH2:4][CH2:5][CH2:6][CH3:8])[CH3:19].[O:3]=[C:15]([CH:14]([CH2:13][CH3:12])[CH2:20][CH2:21][CH2:7][CH3:10])[OH:16]>>[CH3:1][C:2](=[O:3])[CH2:4][CH:5]([CH3:6])[CH3:7].[CH3:8][C:9]([CH3:10])=[O:11].[CH3:12][CH2:13][C:14]([CH3:15])=[O:16].[O:17]=[C:18]1[CH2:19][CH2:20][CH2... | C=CC(=O)OCC(CC)CCCC.CCCCC(CC)C(=O)O | CC(=O)CC(C)C.CC(C)=O.CCC(C)=O.O=C1CCCCC1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | fd4745e6d70d8f0443751cecf30ddbdcc0bd81f584e0728f9c641d8772c5bad6 | ca7529c6d5fb6e28032a33cd0c34ce7963c71f4e51fd214696a939d1402658f7 | O=C1CCCCC1 | [C;D1;H3:1]-[C:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[OH;D1;+0:10].[CH2;D1;+0:11]=[CH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-[CH2;D2;+0:15]-[CH;D3;+0:16](-C-[CH3;D1;+0:17])-[C:18]-[CH2;D2;+0:19]-[CH2;D2;+0:20]-[CH3;D1;+0:21]>>[C;D1;H3:1]-[C:2]-[C;H... | 99 | [{"value": 99.0, "product": "CC(=O)C.C(C(C)C)C(=O)C.C(C)C(=O)C.C1(CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A procedure similar to that of Example 2 was used for the reaction with 2-EHA. Starting from the TAIT product described in the preceding paragraph (1.0 g, ca. 4.5 mmol), 2-ethylhexyl acrylate (0.82 g, 4.5 mmol) and cesium carbonate (0.75 g, 2.25 mmol) in acetonitrile (20 mL), the product was isolated as a yellow oil an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Vinyl | Ketone.Ketone.Ketone.Ketone | null | C1CCCCC1 | C1CCCCC1 | null | C(C)#N | null | null | C=CC(=O)OCC(CC)CCCC.CCCCC(CC)C(=O)O>C(C)#N>CC(=O)CC(C)C.CC(C)=O.CCC(C)=O.O=C1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-052671d368d5428ab7a7b87c87dd57b7 | C=CC(=O)OCC(CC)CCCC>>CCCCC(CC)C(=O)O | C(C=C)(=O)OCC(CCCC)CC.C([O-])([O-])=O.[Cs+].[Cs+]>>CCCCC(CC)C(=O)O | C(C(C[O:10][C:8]([CH:5]=[CH2:6])=[O:9])[CH2:4][CH2:3][CH2:2][CH3:1])[CH3:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[C:8](=[O:9])[OH:10] | C=CC(=O)OCC(CC)CCCC | CCCCC(CC)C(=O)O | null | null | CCCCCC | Miscellaneous | OtherReaction | 7bb1c6a47ceff39dbfe124fd8262f8cabbf022e9f3f42a469d88b73802e7ca41 | e688aeafd627b2d2fb9627b228ddfee0f20a7656c4b9b14ac8ece839b175abbe | null | [C:1]-[C:2]-[CH2;D2;+0:3]-C(-C-[CH3;D1;+0:4])-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:8](-[CH2;D2;+0:9]-[CH3;D1;+0:4])-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5] | 8,029.1 | [{"value": 86.0, "product": "CCCCC(CC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8029.1, "product": "CCCCC(CC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of TMIT (2.37 g, 15 mmol), 2-ethylhexyl acrylate (2.76 g, 15 mmol) and cesium carbonate (0.12 g, 0.38 mmol, 2.5 mole % based on acrylate) was heated in a sand bath at 100–120 ° C. for 2 h, while the progress of the reaction was being followed by IR spectroscopy. The reaction mixture was cooled to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Carboxylic acid | null | null | null | Other | CCCCCC | null | null | C=CC(=O)OCC(CC)CCCC>CCCCCC>CCCCC(CC)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd257e48db34464b8c956bd6616382ef | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CSc1ccc2cc(C)[nH]c2c1>>CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1 | CC=1NC2=CC(=CC=C2C1)SC.O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)SC)C | CC(C)(C)OC(=O)O[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([CH3:9])[nH:10][c:18]2[cH:19]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([CH3:9])[n:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]2[cH:19]1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CSc1ccc2cc(C)[nH]c2c1 | CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1 | null | CN(C)C=1C=CN=CC1 | CC#N | Acylation | Boc amine protection with Boc anhydride | 59b538532b052ee63d6e8c6fd2ceac74caf9447c270a35d5982b50412a6732f0 | ba6477f131c4ae5c5d3bddeb26f4fd18d7127f5da39407a22603c0ae12b886c7 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[nH;D2;+0:14]:1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[n;H0;D3;+0:14]1:[c:12](:[c:13]):[c:11]:[c:10]:[c:9]:1-[C;D1;H3:8] | null | [] | null | null | null | null | 2-Methyl-6-methylthioindole (13.9 g) prepared according to Allais A. et al. Eur. J. Med. Chem.—Chim. Ther. (1975), 10(2), 187–99, was dissolved in CH3CN (150 mL) followed by the addition of (BOC)2O (18 g) with 480 mg DMAP. After 5 h the mixture was evaporated to dryness and the resulting 2-methyl-6-methylsulfanyl-indol... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Boc.Boc | Ether.Boc | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | HO- | CN(C)C=1C=CN=CC1.CC#N | null | null | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CSc1ccc2cc(C)[nH]c2c1>CN(C)C=1C=CN=CC1.CC#N>CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3e61d42c900447d958fe32e9fec35c7 | CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1>>Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)SC)C.OOS(=O)[O-].[K+].CO.O>>C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)S(=O)(=O)C)C | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([S:8][CH3:9])[cH:12][c:13]2[n:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][c:13]2[n:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1 | Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C | null | null | null | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc2[nH]ccc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[S;H0;D2;+0:5]-[C;D1;H3:6]):[c:7]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:8])=[O;D1;H0:9]):[c:7] | null | [] | null | null | null | null | The product of step 1 (20.3 g) was treated with 135 g OXONE™ in 300 mL 1:1 MeOH/water for 2 h. The mixture was partitioned between methylene chloride and water, the organic layer was separated, washed, dried, and evaporated to dryness to yield 6-methanesulfonyl-2-methyl-indole-1-carboxylic acid tert-butyl ester (16 g) ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccc2cc[nH]c2c1 | null | null | null | null | CSc1ccc2cc(C)n(C(=O)OC(C)(C)C)c2c1>>Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a767b45ee400491aa014c4ceb48dbe06 | Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C>>Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1 | C(C)(C)(C)OC(=O)N1C(=CC2=CC=C(C=C12)S(=O)(=O)C)C.C(=O)(C(F)(F)F)O>>CS(=O)(=O)C1=CC=C2C=C(NC2=C1)C | CC(C)(C)OC(=O)[n:14]1[c:2]([CH3:1])[cH:3][c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][c:13]21>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][c:13]2[nH:14]1 | Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 3ccb08daaf21d271cf107ee1f39fc83392e4e5d2cdab9bb060bd71daac89b2f3 | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7]>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:4]:[c:2](:[c:3]):[nH;D2;+0:1]:1 | null | [] | null | null | 8 | HOUR | The above product of step 2 was dissolved in 100 mL methylene chloride and treated with 12 mL TFA. After stirring overnight, the volatiles were removed and the product crystallized from 10:1 methylene chloride/MeOH. In this way 8.0 g of 6-methanesulfonyl-2-methyl-1H-indole was obtained.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1ccc2cc[nH]c2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl | null | 8 | Cc1cc2ccc(S(C)(=O)=O)cc2n1C(=O)OC(C)(C)C>C(Cl)Cl>Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-528a8c9dd1f74cc2a0a17ba4243f5107 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)cc1>>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1 | C1=CC=C(C=C1)I(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F.CS(=O)(=O)C1=CC=C2C=C(NC2=C1)C.FC1=CC=C(C=C1)S>>FC1=CC=C(C=C1)SC1=C(NC2=CC(=CC=C12)S(=O)(=O)C)C | [CH3:1][c:2]1[nH:3][c:4]2[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]2[cH:14]1.[SH:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]2[c:14]1[S:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)cc1 | Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1 | null | null | FC(C(C(F)(F)F)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | 6d0ae58eb1269904d7dda169c1c9a22d9d8065e25d20aca85acf2d11bcd1657c | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | c1ccc(Sc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[SH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[S;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 43.2 | [{"value": 43.2, "product": "FC1=CC=C(C=C1)SC1=C(NC2=CC(=CC=C12)S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 6-methanesulfonyl-2-methyl-1H-indole (207 mg, 1 mmol) in 6 mL of hexafluoroisopropanol was treated with 4-fluorothiophenol (2 mmol) followed by addition of PIFA (1.5 mmol). The dark colored solution was stirred for 30 minutes followed by partitioning between EtOAc and water. Purification by TLC (2:1 hexan... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | FC(C(C(F)(F)F)O)(F)F | null | 0.5 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)cc1>FC(C(C(F)(F)F)O)(F)F>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75e9fdcbd15d450b90e60bf40947cf41 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.O=Cc1ccc(Br)cc1>>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Cc1ccc(Br)cc1 | [SiH](CC)(CC)CC.CS(=O)(=O)C1=CC=C2C=C(NC2=C1)C.BrC1=CC=C(C=O)C=C1.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>BrC1=CC=C(CC2=C(NC3=CC(=CC=C23)S(=O)(=O)C)C)C=C1 | [CH3:1][c:2]1[nH:3][c:4]2[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]2[cH:14]1.O=[CH:15][c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]2[c:14]1[CH2:15][c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.O=Cc1ccc(Br)cc1 | Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Cc1ccc(Br)cc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 6f6cce4aab73ee59c23ac064427a037ebc27409d1dc32dbc2e0b3f5346069911 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[c:10](:[c:11]):[cH;D2;+0:12]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[c:10](:[c:11]):[c;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 64.2 | [{"value": 64.2, "product": "BrC1=CC=C(CC2=C(NC3=CC(=CC=C23)S(=O)(=O)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of 6-methanesulfonyl-2-methyl-1H-indole (112 mg), prepared as described in Example 1 Step 3, in 9 ml CH2Cl2 was treated with p-bromo-benzaldehyde (100 mg) and 0.2 ml TMS-OTf. After cooling to 0° C., 0.26 ml of Et3SiH was added. The solution was stirred for 30 minutes followed by partitioning between EtOAc an... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | Other | C(Cl)Cl | 0 | 0.5 | Cc1cc2ccc(S(C)(=O)=O)cc2[nH]1.O=Cc1ccc(Br)cc1>C(Cl)Cl>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Cc1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-523b1051d6cf45ca941f7f0badcea3ce | COC(=O)c1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)c(F)c1>>COC(=O)c1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1F | C1=CC=C(C=C1)I(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F.C(=O)(OC)C=1NC2=CC(=CC=C2C1)S(=O)(=O)C.FC1=C(C=CC(=C1)F)S>>COC(=O)C=1NC2=CC(=CC=C2C1SC1=C(C=C(C=C1)F)F)S(=O)(=O)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[nH:6][c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15][c:16]2[cH:17]1.[SH:18][c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]1[F:26]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[nH:6][c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15][c:16]2[c:17]1[S:18][c:19]1[cH:20][c... | COC(=O)c1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)c(F)c1 | COC(=O)c1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1F | null | null | FC(C(C(F)(F)F)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | 6d0ae58eb1269904d7dda169c1c9a22d9d8065e25d20aca85acf2d11bcd1657c | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | c1ccc(Sc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1.[SH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-[S;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | 88 | [{"value": 88.0, "product": "COC(=O)C=1NC2=CC(=CC=C2C1SC1=C(C=C(C=C1)F)F)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-carbomethoxy-6-methylsulfonylindole (750 mg, 2.8 mmol), in 10 mL hexafluoroisopropanol was treated with 2,4-difluorothiophenol (7.5 mmol) followed by addition of PIFA (5.6 mmol). The dark colored solution was stirred overnight then partitioned between methylene chloride and water. After concentration of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | FC(C(C(F)(F)F)O)(F)F | null | 8 | COC(=O)c1cc2ccc(S(C)(=O)=O)cc2[nH]1.Fc1ccc(S)c(F)c1>FC(C(C(F)(F)F)O)(F)F>COC(=O)c1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccc(F)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f50514f92a8942ea84682d04f1ea7827 | CC(=O)CCl.Oc1ccc(F)cc1>>CC(=O)COc1ccc(F)cc1 | FC1=CC=C(C=C1)O.C(=O)([O-])[O-].[K+].[K+].ClCC(C)=O>>FC1=CC=C(OCC(C)=O)C=C1 | Cl[CH2:4][C:2]([CH3:1])=[O:3].[OH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | CC(=O)CCl.Oc1ccc(F)cc1 | CC(=O)COc1ccc(F)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 8 | HOUR | To a mixture of para-fluorophenol (15 g) and K2CO3 (18.5 g) in 100 mL acetone were added chloroacetone (10.4 mL) and of KI (22 g). After heating at reflux for 18 h the reaction mixture was cooled down and left at RT overnight. The reaction mixture was filtered, washed with acetone, and evaporated to dryness. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1 | HCl | CC(=O)C | null | 8 | CC(=O)CCl.Oc1ccc(F)cc1>CC(=O)C>CC(=O)COc1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-698f412e4a8d4e62afb33c8aea4ddfd7 | CS(=O)(=O)c1cccc(N)c1.NN>>CS(=O)(=O)c1cccc(NN)c1 | [OH-].[Na+].Cl.NN.CS(=O)(=O)C=1C=C(C=CC1)N.N(=O)[O-].[Na+]>>CS(=O)(=O)C=1C=C(C=CC1)NN | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:12]1.N[NH2:11]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][NH2:11])[cH:12]1 | CS(=O)(=O)c1cccc(N)c1.NN | CS(=O)(=O)c1cccc(NN)c1 | null | null | Cl.O | Miscellaneous | OtherReaction | bff6efaab43fcaa1734c9c2b1bb92dedefa785fd0e1362752739094a114b1a2d | edabab25c27777c2204ef93ae7e0a2367d16ed129319c92fb41548ddcbd38608 | c1ccccc1 | N-[NH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a solution of 3-methanesulphonyl-phenylamine (2.5 g) in 6 mL HCl was added a solution of NaNO2 in 5 mL of H2O at −5° to 0° C. After stirring for 30 min the resulted diazonium salt was poured into a cold solution (−10° to −15° C.) of stannous chloride in 6 ml HCl. The mixture of resulted hydrazine hydrochloride in HC... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | null | null | CS(=O)(=O)c1cccc(N)c1.NN>Cl.O>CS(=O)(=O)c1cccc(NN)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-610953b7741c49478a542ec730931570 | CC(=O)COc1ccc(F)cc1.CS(=O)(=O)c1cccc(NN)c1>>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Oc1ccc(F)cc1 | CS(=O)(=O)C=1C=C(C=CC1)NN.FC1=CC=C(OCC(C)=O)C=C1.P(Cl)(Cl)Cl>>FC1=CC=C(OC2=C(NC3=CC(=CC=C23)S(=O)(=O)C)C)C=C1 | O=[C:2]([CH3:1])[CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.N[NH:3][c:4]1[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][c:6]([S:7]([CH3:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]2[c:14]1[O:15][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1 | CC(=O)COc1ccc(F)cc1.CS(=O)(=O)c1cccc(NN)c1 | Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Oc1ccc(F)cc1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | f7004f13d83fee2783d4405fc57f46a9ac4daac0e3d626cdfc660b16a341e646 | 0dd0032584e8b699a0d6138c5791ba9322ca70e5c435edc5f54b9d71f78dbd00 | c1ccc(Oc2c[nH]c3ccccc23)cc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[#8:10]-[c:11]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[#8:10]-[c:11] | 5.2 | [{"value": 5.2, "product": "FC1=CC=C(OC2=C(NC3=CC(=CC=C23)S(=O)(=O)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To the solution of (3-methanesulfonyl-phenyl)-hydrazine (1.35 g) and 1-(4-fluoro-phenoxy)-propan-2-one (1.01 g) in benzene at RT was added equimolar amount of PCl3. The reaction mixture was stirred at RT for 1 hour and the solvent was removed in vacuo. The residue was purified by Biotage chromatography, eluted with 10–... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ether | Ether | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | 1 | CC(=O)COc1ccc(F)cc1.CS(=O)(=O)c1cccc(NN)c1>C1=CC=CC=C1>Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Oc1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30fdb0db690a400e91fadac5b22e9af3 | CS(=O)(=O)Cl.CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(CO)[nH]c2c1>>CS(=O)(=O)Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccccc1Cl | CN(C)C=O.CCN(CC)CC.ClC1=C(C=CC=C1)SC1=C(NC2=CC(=CC=C12)S(=O)(=O)C)CO.CS(=O)(=O)Cl>>ClC1=C(C=CC=C1)SC1=C(NC2=CC(=CC=C12)S(=O)(=O)C)CS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].O[CH2:5][c:6]1[nH:7][c:8]2[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16][c:17]2[c:18]1[S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[Cl:26]>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[nH:7][c:8]2[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16][c:17]2[c:18]1[S:19... | CS(=O)(=O)Cl.CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(CO)[nH]c2c1 | CS(=O)(=O)Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccccc1Cl | null | null | C(Cl)Cl | Acylation | OtherReaction | 0ac8a603953c98c1814574689e0056190c62616c176b8b4c31c7acd96ef43528 | 7d02e147285bb417922c236d16ce79bf71b54bc3f6dc1c2237422f2069c2cc63 | c1ccc(Sc2c[nH]c3ccccc23)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | 10 | MINUTE | [3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indol-2-yl]-methanol (1 mmole) (as prepared in Example 5) was dissolved in 2 mL CH2Cl2 and treated with 0.3 mL NEt3 followed by 0.08 ml MsCl. After stirring 10 min. 3 mL DMF was added followed by 0.5 g NaSO2Me. The mixture was stirred overnight. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfone | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.166667 | CS(=O)(=O)Cl.CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(CO)[nH]c2c1>C(Cl)Cl>CS(=O)(=O)Cc1[nH]c2cc(S(C)(=O)=O)ccc2c1Sc1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ae93c12a81d411fb6521d083ccbeaea | CS(=O)(=O)c1ccc2c(Sc3ccccc3)c(CO)[nH]c2c1.O=C(Cl)C(=O)Cl>>CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(C=O)[nH]c2c1 | C(C)N(CC)CC.CS(=O)(=O)C1=CC=C2C(=C(NC2=C1)CO)SC1=CC=CC=C1.CS(=O)C.C(C(=O)Cl)(=O)Cl>>ClC1=C(C=CC=C1)SC1=C(NC2=CC(=CC=C12)S(=O)(=O)C)C=O | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([S:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:18]([CH2:19][OH:20])[nH:21][c:22]2[cH:23]1.O=C(Cl)C(=O)[Cl:17]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([S:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18]([CH:19]=[O:20])[nH:21][c... | CS(=O)(=O)c1ccc2c(Sc3ccccc3)c(CO)[nH]c2c1.O=C(Cl)C(=O)Cl | CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(C=O)[nH]c2c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 977131743567ce3e393f5f6884a1bc719dbe0b0f509fce2ae235f5e2d86155b1 | d4f6de1ccba455daea3295211e2abcf26570ce1f4d081f21ccb444a5cef35368 | c1ccc(Sc2c[nH]c3ccccc23)cc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].[OH;D1;+0:2]-[CH2;D2;+0:3]-[c:4](:[#7;a:5]:[c:6]):[c:7]-[#16:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](-[#16:8]-[c:7]:[c:4](-[CH;D2;+0:3]=[O;H0;D1;+0:2]):[#7;a:5]:[c:6]):[c:10] | null | [] | null | null | null | null | A solution of alcohol [3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indol-2-yl]-methanol (75 mg) (prepared as described in Example 5) in CH2Cl2 (5 ml) was added to a solution of DMSO (0.2 ml) and oxalyl chloride (0.1 ml) that had been prepared at −78°. After 15 min triethylamine (0.45 ml) was added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Aromatic halide.Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)c1ccc2c(Sc3ccccc3)c(CO)[nH]c2c1.O=C(Cl)C(=O)Cl>C(Cl)Cl>CS(=O)(=O)c1ccc2c(Sc3ccccc3Cl)c(C=O)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c5a13dd0dcf440dbcd2da5397634bd9 | C/C(=N\[Si](C)(C)C)O[Si](C)(C)C.N#Cc1ccc([N+](=O)[O-])cc1.O=S(=O)(Cl)c1cccs1>>O=S(=O)(NCC(CO)c1ccccc1)c1cccs1 | [N+](=O)([O-])C1=CC=C(C=C1)C#N.CN1CCOCC1.S1C(=CC=C1)S(=O)(=O)Cl.C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C>>OCC(CNS(=O)(=O)C=1SC=CC1)C1=CC=CC=C1 | C[Si](C)(C)/[N:4]=[C:6](\[CH3:5])[O:8][Si](C)(C)C.N#C[c:9]1[cH:10][cH:11][c:12]([N+](=O)[O-])[cH:13][cH:14]1.Cl[S:2](=[O:1])(=[O:3])[c:15]1[cH:16][cH:17][cH:18][s:19]1>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH:6]([CH2:7][OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][s:19]1 | C/C(=N\[Si](C)(C)C)O[Si](C)(C)C.N#Cc1ccc([N+](=O)[O-])cc1.O=S(=O)(Cl)c1cccs1 | O=S(=O)(NCC(CO)c1ccccc1)c1cccs1 | null | null | O.CC(C)(C)OC.C1CCOC1 | Acylation | OtherReaction | 266d72bb5a41bebd7073d5c50c7d2737ca37a3157db4c9a314755a78e9640642 | b3d053a1893b5f94ac79bc8d06f67773b7e3aea3d0b8779497cdc92075ed3b0c | O=S(=O)(NCCc1ccccc1)c1cccs1 | C-[Si](-C)(-C)/[N;H0;D2;+0:1]=[C;H0;D3;+0:2](\[CH3;D1;+0:3])-[O;H0;D2;+0:4]-[Si](-C)(-C)-C.Cl-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8](:[c:9]):[#16;a:10]:[c:11].N#C-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c;H0;D3;+0:15](-[N+](=O)-[O-]):[c:16]:[c:17]:1>>[O;D1;H0:6]=[S;H0;D4;+0:5](=[O;D1;H0:7])(-[NH;D2;+0:1]-[CH2;D2;+0:3... | 83 | [{"value": 83.0, "product": "OCC(CNS(=O)(=O)C=1SC=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | A three-necked round bottom flask equipped with a thermocouple, a nitrogen inlet, and a mechanical stirrer was charged with (R)-3-[N-(1-hydroxymethyl-2-phenylethyl)amino]methyl]-4-nitrobenzenecarbonitrile (25 g, 0.08 moles), THF (20 ml), and N-methyl morpholine (NMM) (17.8 mL, 2.0 eq). To this mixture was added N,O-bis... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitro group.Sulfonyl halide.Silyl protective group.Silyl protective group | Sulfonamide.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HCl | O.CC(C)(C)OC.C1CCOC1 | 25 | null | C/C(=N\[Si](C)(C)C)O[Si](C)(C)C.N#Cc1ccc([N+](=O)[O-])cc1.O=S(=O)(Cl)c1cccs1>O.CC(C)(C)OC.C1CCOC1>O=S(=O)(NCC(CO)c1ccccc1)c1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4cfd76072bfd4a1c94c3b2d643eab6cf | CC(C)(O)C(=O)[O-].ClCC1CO1>>CC(C)(O)C(=O)OCC1CO1 | OC(C(=O)[O-])(C)C.[Na+].C(Cl)C1CO1>>OC(C(=O)OCC1CO1)(C)C | [CH3:1][C:2]([CH3:3])([OH:4])[C:5](=[O:6])[O-:7].Cl[CH2:8][CH:9]1[CH2:10][O:11]1>>[CH3:1][C:2]([CH3:3])([OH:4])[C:5](=[O:6])[O:7][CH2:8][CH:9]1[CH2:10][O:11]1 | CC(C)(O)C(=O)[O-].ClCC1CO1 | CC(C)(O)C(=O)OCC1CO1 | null | [Cl-].C[N+](C)(C)C | O | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | C1CO1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1 | null | [] | 120 | CELSIUS | 1.5 | HOUR | Into a 200 mL three-necked flask equipped with a stirrer and reflux tube was charged 37.83 g (0.3 mol) of sodium 2-hydroxyisobutyrate, 138.7 g (1.5 mol) of epichlorohydrin, 0.25 g of tetramethylammonium chloride and pure water at room temperature under normal pressure, and heated at temperatures from room temperature t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | C1CO1 | Other | [Cl-].C[N+](C)(C)C.O | 120 | 1.5 | CC(C)(O)C(=O)[O-].ClCC1CO1>[Cl-].C[N+](C)(C)C.O>CC(C)(O)C(=O)OCC1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-399cca0fbbf6451b89afcb477ad98cfd | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S>>CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | CS(=O)(=O)Cl.C(C)(=S)[O-].[K+].[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.C(C)N(CC)CC>>C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | O[CH2:5][C:6]1=[CH:7][CH2:8][C@H:9]2[C:10]3=[CH:11][CH:12]=[C:13]4[CH2:14][C@@H:15]([O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][C@H:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[C@:34]4([CH3:35])[C@H:36]3[CH2:37][CH2:38][C@:39]12[CH3:40].[CH3:1][C:2]([O-:3])=[... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.CCCCCC.CS(=O)C | Acylation | OtherReaction | f0ef48ecf2991802b01fab2c99f81aa4ec5b243bec9eedcaaebf72a3cffee580 | e483c239103a312878e017a96b05cdd3919bff7fb9afe11e6eb3dea046fbf05c | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | O-[CH2;D2;+0:1]-[C:2](=[C:3]-[C:4])-[C:5].[C;D1;H3:6]-[C;H0;D3;+0:7](-[O-;H0;D1:8])=[S;H0;D1;+0:9]>>[C:5]-[C:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[C;H0;D3;+0:7](-[C;D1;H3:6])=[O;H0;D1;+0:8])=[C:3]-[C:4] | 88.3 | [{"value": 88.0, "product": "C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.3, "product": "C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](... | null | null | 20 | MINUTE | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (4.00 g, 7.34 mmol) in tetrahydrofuran (70 ml), was added triethylamine (4.10 ml, 29.4 mmol), followed by the dropwise addition of methanesulfonyl chloride (1.70 ml, 22.0 mmol) at −10° C. and stirring for 20 min. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Thiocarbonyl | Carbo-thioester | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HO- | O1CCCC1.CCCCCC.CS(=O)C | null | 0.333333 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S>O1CCCC1.CCCCCC.CS(=O)C>CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-068d92d58af1432dad376d55043050cc | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CBr)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S>>CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CBr)O[Si](C)(C)C(C)(C)C.C(C)(=S)[O-].[K+]>>C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | Br[CH2:5][C:6]1=[CH:7][CH2:8][C@H:9]2[C:10]3=[CH:11][CH:12]=[C:13]4[CH2:14][C@@H:15]([O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][C@H:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[C@:34]4([CH3:35])[C@H:36]3[CH2:37][CH2:38][C@:39]12[CH3:40].[CH3:1][C:2]([O-:3])=... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CBr)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S | CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | CCCCCC.CC(=O)C | Acylation | OtherReaction | 1f876542c8a2de0f0c93c1e55257e1922650fd69ea48617e41a961445109d4b2 | 00ab4047825d93b84a3dc255ab210414ba88fbe19a5ef7a3657605acca13230b | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2](=[C:3]-[C:4])-[C:5].[C;D1;H3:6]-[C;H0;D3;+0:7](-[O-;H0;D1:8])=[S;H0;D1;+0:9]>>[C:5]-[C:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[C;H0;D3;+0:7](-[C;D1;H3:6])=[O;H0;D1;+0:8])=[C:3]-[C:4] | 64 | [{"value": 64.0, "product": "C(C)(=O)SCC=1[C@]2(C)[C@@H](CC1)C1=CC=C3C[C@H](C[C@@H]([C@]3(C)[C@H]1CC2)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (100 mg, 0.183 mmol), triphenylphosphine (96.0 mg, 0.366 mmol) and imidazole (49.8 mg, 0.732 mmol) in dichloromethane (2 ml), was added N-bromosuccinimide (65.1 mg, 0.366 mmol) at 0° C., followed by stirring at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiocarbonyl | Carbo-thioester | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | Br- | CCCCCC.CC(=O)C | null | 0.5 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CBr)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC([O-])=S>CCCCCC.CC(=O)C>CC(=O)SCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9cc781dd66fd4b36b6a7e6f6c86e2e78 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCBr>>CC[Si](CC)(CC)OC(C)(C)CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.[H-].[Na+].C1COCCOCCOCCOCCO1.BrCCCC(C)(O[Si](CC)(CC)CC)C>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | [OH:15][CH2:16][C:17]1=[CH:18][CH2:19][C@H:20]2[C:21]3=[CH:22][CH:23]=[C:24]4[CH2:25][C@@H:26]([O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][C@H:36]([O:37][Si:38]([CH3:39])([CH3:40])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@:45]4([CH3:46])[C@H:47]3[CH2:48][CH2:49][C@:50]12[CH3:51].Br[CH2:14][... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCBr | CC[Si](CC)(CC)OC(C)(C)CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]=[C:6](-[C:7]-[OH;D1;+0:8])-[C:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:7]-[C:6](=[C:5]-[C:4])-[C:9] | 100 | [{"value": 100.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (200 mg, 0.367 mmol), sodium hydride (60% in oil, 45 mg, 1.125 mmol) and 15-crown-5 (80 mg, 0.363 mmol) in tetrahydrofuran (1 ml), was added 1-bromo-4-methyl-4-(triethylsilyloxy)pentane (220 mg, 0.745 mmol) at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1.O.C(C)(=O)OCC | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCBr>O1CCCC1.O.C(C)(=O)OCC>CC[Si](CC)(CC)OC(C)(C)CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e7c0aaac82b48a196a7fd936bac8e10 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>>CCC(CC)(CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.BrCCCC(CC)(O[Si](CC)(CC)CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C | [OH:9][CH2:10][C:11]1=[CH:12][CH2:13][C@H:14]2[C:15]3=[CH:16][CH:17]=[C:18]4[CH2:19][C@@H:20]([O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]([O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[C@:39]4([CH3:40])[C@H:41]3[CH2:42][CH2:43][C@:44]12[CH3:45].Br[CH2:8][CH... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC | CCC(CC)(CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]=[C:6](-[C:7]-[OH;D1;+0:8])-[C:9]>>[C:4]-[C:5]=[C:6](-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9] | 98.4 | [{"value": 98.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCC(CC)(O[Si](CC)(CC)CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (400 mg, 0.734 mmol), 1-bromo-4-ethyl-4-(triethylsilyloxy)hexane (475 mg, 1.47 mmol), sodium hydride (60% in oil, 88 mg, 2.20 mmol), 15-crown-5 (162 mg, 0.735 mmol) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure simi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(CCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-51ebe64bd2154f2b9412ca6ccc7b36e4 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCCBr>>CC[Si](CC)(CC)OC(C)(C)CCCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.BrCCCCC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | [OH:16][CH2:17][C:18]1=[CH:19][CH2:20][C@H:21]2[C:22]3=[CH:23][CH:24]=[C:25]4[CH2:26][C@@H:27]([O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][C@H:37]([O:38][Si:39]([CH3:40])([CH3:41])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@:46]4([CH3:47])[C@H:48]3[CH2:49][CH2:50][C@:51]12[CH3:52].Br[CH2:15][... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCCBr | CC[Si](CC)(CC)OC(C)(C)CCCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]=[C:6](-[C:7]-[OH;D1;+0:8])-[C:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:7]-[C:6](=[C:5]-[C:4])-[C:9] | 95.1 | [{"value": 95.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCCCCC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]1... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (200 mg, 0.367 mmol), 1-bromo-5-triethylsilyloxy-5-methylhexane (227 mg, 0.734 mmol), sodium hydride (60% in oil, 44 mg, 1.10 mmol), 15-crown-5 (81 mg, 0.368 mmol) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure sim... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)CCCCBr>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)CCCCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bdea4a72c64b44bfae57265ad669ee45 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C#CCBr>>CC[Si](CC)(CC)OC(C)(C)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.BrCC#CC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC#CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | [OH:15][CH2:16][C:17]1=[CH:18][CH2:19][C@H:20]2[C:21]3=[CH:22][CH:23]=[C:24]4[CH2:25][C@@H:26]([O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][C@H:36]([O:37][Si:38]([CH3:39])([CH3:40])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@:45]4([CH3:46])[C@H:47]3[CH2:48][CH2:49][C@:50]12[CH3:51].Br[CH2:14][... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C#CCBr | CC[Si](CC)(CC)OC(C)(C)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8]-[OH;D1;+0:9])-[C:10]>>[C:5]-[C:6]=[C:7](-[C:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4])-[C:10] | 66 | [{"value": 66.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)COCC#CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]1... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (200 mg, 0.367 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-2-pentyne (216 mg, 0.741 mmol), sodium hydride (60% in oil, 44 mg, 1.10 mmol) 15-crown-5 (81 mg, 0.368 mmol) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure si... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C#CCBr>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)C#CCOCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d73a24bb858946d1bbd1c0ffe34a20a8 | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>>CC[Si](CC)(CC)OC(C)(C)C/C=C/OCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO)O[Si](C)(C)C(C)(C)C.Br\C=C\CC(C)(C)O[Si](CC)(CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO\C=C\CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C | [OH:15][CH2:16][C:17]1=[CH:18][CH2:19][C@H:20]2[C:21]3=[CH:22][CH:23]=[C:24]4[CH2:25][C@@H:26]([O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][C@H:36]([O:37][Si:38]([CH3:39])([CH3:40])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@:45]4([CH3:46])[C@H:47]3[CH2:48][CH2:49][C@:50]12[CH3:51].Br/[CH:14]=... | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br | CC[Si](CC)(CC)OC(C)(C)C/C=C/OCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C | null | null | O1CCCC1 | Acylation | Williamson Ether Synthesis | 6ea2ecb1a9662f756e9e0abf21897ef5086f34c2e732d2ef2696caeea95650ca | d81e0d3b4d57ff7b2f3fcadb65b1e8eb90864aba075c535b9ef521dca07670ef | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4].[C:5]-[C:6]=[C:7](-[C:8]-[OH;D1;+0:9])-[C:10]>>[C:5]-[C:6]=[C:7](-[C:8]-[O;H0;D2;+0:9]/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4])-[C:10] | 100 | [{"value": 100.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3[C@@]12C)CO\\C=C\\CC(C)(C)O[Si](CC)(CC)CC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C([C@@]4(C)CC[C@@H]3... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (400 mg, 0.734 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2E)-pentene (431 mg, 1.47 mmol), sodium hydride (60% in oil, 88 mg, 2.20 mmol), 15-crown-5 (162 mg, 0.735 mmol) and tetrahydrofuran (1 ml) were subjected to reaction using a procedur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(C)[Si](C)(C)O[C@@H]1CC2=CC=C3[C@H](CC[C@]4(C)C(CO)=CC[C@@H]34)[C@@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1.CC[Si](CC)(CC)OC(C)(C)C/C=C/Br>O1CCCC1>CC[Si](CC)(CC)OC(C)(C)C/C=C/OCC1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-181ba1521ec749ff9911042772875c44 | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>>CCC(CC)(CCCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | [Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)O)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C.BrCCCC(CC)(O[Si](CC)(CC)CC)CC.[H-].[Na+].C1COCCOCCOCCOCCO1>>[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCCC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C | [OH:9][C:10]([CH3:11])([CH3:12])[C:13]1=[CH:14][CH2:15][C@H:16]2[C:17]3=[CH:18][CH:19]=[C:20]4[CH2:21][C@@H:22]([O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][C@H:32]([O:33][Si:34]([CH3:35])([CH3:36])[C:37]([CH3:38])([CH3:39])[CH3:40])[C@:41]4([CH3:42])[C@H:43]3[CH2:44][CH2:45][C@:46]12[CH... | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC | CCC(CC)(CCCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9ef84a8c80411e848c10c5384ce78141e473ad5db44b97f46285876278d6d001 | 004868630acb495c3cf864467df50d8e3d3bf839809342ad5aeae72f8c34f6c8 | C1=CC2CC[C@H]3C(=CC=C4CCCCC43)[C@@H]2C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]=[C:6](-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[OH;D1;+0:10])-[C:11]>>[C:4]-[C:5]=[C:6](-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:11] | 100.2 | [{"value": 100.0, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCCC(CC)(O[Si](CC)(CC)CC)CC)[C@]4(CC[C@@H]3[C@@]12C)C)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](CC2=CC=C3[C@@H]4CC=C(C(C)(C)OCCCC(CC)... | null | null | null | null | 1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.175 mmol), 1-bromo-4-ethyl-4-(triethylsilyloxy)hexane (225 mg, 0.696 mmol), sodium hydride (60% in oil, 42 mg, 1.05 mmol), 15-crown-5 (38 mg, 0.173 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure simi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary alcohol | Ether | null | null | C1=C[C@H]2CC[C@H]3C(=CC=C4CCCC[C@@H]43)[C@@H]2C1 | HBr | O1CCCC1 | null | null | CC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C.CCC(CC)(CCCBr)O[Si](CC)(CC)CC>O1CCCC1>CCC(CC)(CCCOC(C)(C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)O[Si](CC)(CC)CC |
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