dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5927c1ce0634c51b3eac27254c6f6f0 | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1>>c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)Br.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1 | Br[c:19]1[cH:18][cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([O:6][CH2:5][c:4]4[cH:3][cH:2][cH:1][cH:35][cH:34]4)[cH:33][cH:32]3)[c:31]2[cH:30]1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:20]1[cH:21][cH:22][c:23]([CH:24]2[O:25][CH2:26][CH2:27][O:28]2)[o:29]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7... | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:[#7;a:8]):[c:9]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:10]1:[#8;a:11]:[c:12]:[c:13]:[c:14]:1>>[#7;a:8]:[c:7]:[c:6]1:[c:9]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[#8;a:11]:[c:12]:[c:13]:[c:14]:2):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | 62.1 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure B from (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (1.5 g, 3.7 mmol) and 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)-furan (1.9 g, 4.42 mmol) dissolved in dioxan (30 ml) and heated at reflux under nitrogen for 6 hr. The solvent was removed from the cooled reaction under vacuum, and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccc2ncncc2c1.c1ccoc1.C1COCO1 | HBr.Sn | O1CCOCC1 | null | null | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1>O1CCOCC1>c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0606d7ad44d468bb930ce3610f78c51 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:27]1[cH:28][cH:29][c:30]([CH:31]2[O:32][CH2:33][CH2:34][O:35]2)[o:36]1.I[c:26]1[c:2]([F:1])[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23]3)[c:24]2[cH:25]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][cH:6][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | null | null | CN(C)C=O | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[c:9]:[#7;a:10]):[c:11](:[#7;a:12]):[c:13]:[c:14]:1-[F;D1;H0:15]>>[#7;a:12]:[c:11]1:[c:13]:[c:14](-[F;D1;H0:15]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[c:7]:[c:8]:1:[c:9]:[#7;... | null | [] | 100 | CELSIUS | 4 | HOUR | Prepared according to Procedure B from a solution of (4-benzyloxyphenyl)-(6-iodo-7-fluoro-quinazolin-4-yl)-amine hydrochloride (508 mg, 1 mmole), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (645 mg, 1.5 mmole), diisopropylethyl amine (650 mg, 5 mmole), and dichlorobis(triphenylphosphine) palladium (140 mg, 0.2 mmole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccoc1.C1COCO1 | HI.Sn | CN(C)C=O | 100 | 4 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>CN(C)C=O>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1dfe55d6d4ca4231abe5f419b1190ebd | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1>>CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2N=C(SC2)CCN)Cl)C=CC1.CS(=O)(=O)CC(=O)O.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2N=C(SC2)CCNC(CS(=O)(=O)C)=O)Cl)C=CC1 | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]3[n:18][cH:19][n:20][c:21]([NH:22][c:23]4[cH:24][cH:25][c:26]([O:27][CH2:28][c:29]5[cH:30][cH:31][cH:32][c:33]([F:34])[cH:35]5)[c:36]([Cl:37])[cH:38]4)[c:39]3[cH:40]2)[cH:41][s:42]1>>[CH3:1][S:2](=[O:... | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5cscn5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | (4-(3-Fluorobenzyloxy)-3-chlorophenyl)-(6-(2-(2-aminoethyl)-thiazol-4-yl)-quinazolin-4-yl)-amine (0.229 mmol) was reacted with methanesulfonyl acetic acid (0.252 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.252 mmol) in DMF as outlined in procedure (I) to provide the title compound after pur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1>CN(C)C=O>CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3adab48748f4173ae882f024d04c9c0 | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | C(C)(C)N(C(C)C)CC.FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2OC(=CC2)CCN)Cl)C=CC1.CS(=O)(=O)CC(=O)O.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2OC(=CC2)CCNC(CS(=O)(=O)C)=O)Cl)C=CC1 | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]3[n:19][cH:20][n:21][c:22]([NH:23][c:24]4[cH:25][cH:26][c:27]([O:28][CH2:29][c:30]5[cH:31][cH:32][cH:33][c:34]([F:35])[cH:36]5)[c:37]([Cl:38])[cH:39]4)[c:40]3[cH:41]2)[o:42]1>>[CH3:1][S:2](=[O... | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | Preparation according to Procedure (I) utilizing (4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(5-(2-aminoethyl)-furan-2-yl)-quinazolin-4-yl)-amine (26 mg, 0.0537 mmol), methanesulfonylacetic acid (22.2 mg, 0.161 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (30.0 mg, 0.161 mmol) and N,N-diisopropyleth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91c0f806f9d948f08723f0ec1e264516 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1>>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F.Cl>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C1=CC=C(O1)C=O)F | C1C[O:2][CH:3]([c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][c:10]4[c:11]([NH:12][c:13]5[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]6[cH:20][cH:21][cH:22][cH:23][cH:24]6)[cH:25][cH:26]5)[n:27][cH:28][n:29][c:30]4[cH:31][c:32]3[F:33])[o:34]2)O1>>[O:2]=[CH:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([NH:12][c:13]4[cH:14][c... | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | [c:1]:[c:2](-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1):[#8;a:5]:[c:6]>>[O;H0;D1;+0:4]=[CH;D2;+0:3]-[c:2](:[c:1]):[#8;a:5]:[c:6] | 61 | [{"value": 61.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C1=CC=C(O1)C=O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | Prepared according to Procedure C from a stirred solution of (4-benzyloxyphenyl)-(6-(5-(1,3-dioxolan-2-yl)-furan-2-yl)-7-fluoro-quinazolin-4-yl)-amine (0.51 grams, 1.1 mmol) in 20 ml of THF was added 5 ml of 1 N HCl. After stirring for 90 minutes, the resultant suspension was filtered and washed with diethyl ether (200... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccc2ncncc2c1 | HO- | C1CCOC1 | null | 1.5 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1>C1CCOC1>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45684ba680524dc8a3e6288bf2186d8c | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>>O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 | ClC1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1.C(CCC)[Sn](C1=CC(=CO1)C=O)(CCCC)CCCC>>FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3=CC(=CO3)C=O)C=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[o:5][cH:4][c:3]([CH:2]=[O:1])[cH:33]1.Cl[c:7]1[cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][c:22]([F:23])[cH:24]4)[cH:25][cH:26]3)[n:27][cH:28][n:29][c:30]2[cH:31][n:32]1>>[O:1]=[CH:2][c:3]1[cH:4][o:5][c:6](-[c:7]2[cH:8][c:9]3[c:1... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | ae92753133f40dafb22d85bdbe2fa24b7eeb98432119f995c0a0fbd50f7dd9fc | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4cnc(-c5ccco5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11](:[#7;a:12]):[c:13](:[c:14]:[#7;a:15]):[c:16]:1>>[#7;a:15]:[c:14]:[c:13]1:[c:16]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:2):[#7;a:... | null | [] | null | null | null | null | (6-Chloropyrido[3,4-d]pyrimidin-4-yl)-(4-(3-fluorobenzyloxy)-phenyl)-amine (1 g) and 5-(tributylstannyl)-furan-3-carbaldehyde (J. Org. Chem. (1992), 57(11), 3126–31) (1.84 g) in dioxan (35 ml) were reacted together as in Procedure B. The solvent was evaporated and the residue suspended in dichloromethane. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl.Sn | O1CCOCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>O1CCOCC1>O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bddbc54a05334636880860c92f604f72 | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)OCC)C=C2)Cl)C=CC1.[OH-].[Na+]>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1 | CC[O:3][C:2](=[O:1])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[c:32]([Cl:33])[cH:34]4)[c:35]3[cH:36]2)[o:37]1>>[O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c... | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]:[#8;a:7]>>[#8;a:7]:[c:6]-[C:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": "FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure H utilizing ethyl 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoate (0.50 g) and aqueous sodium hydroxide (2M, 2 mL) in THF (6 mL) to afford the title compound (0.46 g). Electrospray MS m/z 516 (MH+).
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C1CCOC1>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3f605577d1c43ee9bbbf9de025ccc38 | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | C(C)(C)N(CC)C(C)C.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1.Cl.C1(=CC=CC=C1)S(=O)(=O)CCN.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)C3=CC=CC=C3)C=C2)Cl)C=CC1 | [NH2:37][CH2:38][CH2:39][S:40](=[O:41])(=[O:42])[c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1.O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4... | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | null | null | C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[#8;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8;a:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | null | null | Prepared according to Procedure (I) utilizing 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoic acid (0.25 g, 0.45 mmol), 2-(phenylsulfonyl)-ethylamine hydrochloride (0.30 g, 1.36 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.26 g, 1.36 mmol) and diisopropyleth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)#N | null | null | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C(C)#N>O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-169f17b97cc946d1845b2df31bc05560 | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.C(CC)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)CCC)C=C2)Cl)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O[C:10](=[O:11])[CH:12]=[CH:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]3[n:22][cH:23][n:24][c:25]([NH:26][c:27]4[cH:28][cH:29][c:30]([O:31][CH2:32][c:33]5[cH:34][cH:35][cH:36][c:37]([F:38])[cH:39]5)[c:40]([Cl:41])[cH:42]4)[c:43]3[cH:44]2)[o... | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[#8;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8;a:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7] | 18.3 | [{"value": 18.3, "product": "FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)CCC)C=C2)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure I utilizing 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoic acid (0.23 g, 0.42 mmol), carbonyldiimidazole (0.21 g, 1.27 mmol), and n-propanesulfonylethylamine (0.16 g, 0.85 mmol) in DMF to afford the title compound (0.05 g) after purification by chrom... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>CN(C)C=O>CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f5ff89040334acd8782a5d92f29c318 | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 | CCN(CC)CC.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=O)C=C2)Cl)C=CC1.[BH4-].[Na+].Cl.C1(=CC=CC=C1)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCCS(=O)(=O)C2=CC=CC=C2)Cl)C=CC1 | [O:1]=[S:2](=[O:3])([CH2:4][CH2:5][NH2:6])[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.O=[CH:7][c:38]1[cH:37][cH:36][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]3[cH:35]2)[o:39... | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 | null | null | C1CCOC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)CC=CO1)c1ccccc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:10]:[c:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D2;+0:4... | null | [] | null | null | null | null | The title compound and its hydrochloride salt are prepared according to Procedure D utilizing 5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde (0.317 mmol, 0.15 g), Phenylsulfonylethyl amine hydrochloride salt (0.475 mmol, 0.105 g) in the presence of Et3N (0.51 mmol, 0.067 mL) and NaBH4 (0.79... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1.c1ccccc1 | Other | C1CCOC1.CO | null | null | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C1CCOC1.CO>O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a76109751687407ea2a7cb9ad6f5339a | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1>>CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 | FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3=CC=C(O3)C=O)C=CC1.C(CC)S(=O)(=O)CCN.C(OC)COC>>FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3(OC=CC3)CNCCS(=O)(=O)CCC)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O=[CH:10][c:40]1[cH:39][cH:38][c:11](-[c:12]2[cH:13][c:14]3[c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]5[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]5)[cH:30][cH:31]4)[n:32][cH:33][n:34][c:35]3[cH:36][n:37]2)[o:41]1>>[CH3:1][CH2:2][CH2:3][S:... | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1 | CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | C1=COC(c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[#7;a:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:2):[c:13]:[#7;a:14]):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:14]:[c:13]:[c:11]1:[c:12]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D... | null | [] | null | null | null | null | 5-(4-(4-(3-Fluorobenzyloxy)-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-2-carbaldehyde (0.31 mmol) and 2-n-propanesulphonyl-ethyl amine (0.94 mmol) were reacted together in dimethoxyethane as in Procedure D. 1H NMR (DMSO) 11.25 (bs, 1H); 9.88 (bs, 1H); 9.49 (s, 1H); 9.20 (s, 1H); 8.80 (s, 1H); 7.85 (d, 2H); 7.44 (m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1.C1=COCC1 | Other | null | null | null | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1>>CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-732a120e519747e2961a90e4717ce1f7 | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 | ClC=1C=C(NC2=NC=NC3=CC=C(C=C23)C2=CC=C(O2)C=O)C=CC1OCC1=CC(=CC=C1)F.C(CC)S(=O)(=O)CCN.C(OC)COC>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCCS(=O)(=O)CCC)Cl)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O=[CH:10][c:41]1[cH:40][cH:39][c:11](-[c:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]3[cH:38]2)[o:42]1>>[CH3:1][CH2:2][... | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | C1=COC(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:10]:[c:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D2;+0:4... | null | [] | null | null | null | null | 5-(4-{3-Chloro-4-[(3-fluorobenzyl)oxy]anilino}-6-quinazolinyl)-2-furaldehyde (0.32 mmol) and 2-n-propanesulphonyl-ethyl amine (0.95 mmol) were reacted together in dimethoxyethane as in Procedure D. 1H NMR (DMSO) 11.85 (bs, 1H); 9.94 (bs, 2H); 9.67 (s, 1H); 8.95 (s, 1H); 8.45 (d, 1H); 8.08 (s, 1H); 8.00 (d, 1H); 7.84 (d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1 | Other | null | null | null | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-427ae6f2ee94471aadc99a98f30484bb | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O | CCN(CC)CC.C1CCOC1.CO.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=O)C=C2)Cl)C=CC1.[BH4-].[Na+].Cl.C(C)(C)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCC(C(C)C)=S(=O)=O)Cl)C=CC1 | [CH3:1][CH:2]([CH3:3])[S:40]([CH2:4][CH2:5][NH2:6])(=[O:41])=[O:42].O=[CH:7][c:38]1[cH:37][cH:36][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]3[cH:35]2)[o:39]1>>[CH3:1][CH:2](... | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b0080e890ae8315d1f84c0b390aa75b246afaa192e612173d63a6c36d407d62 | 3a41577e0815d59ec9dddd142d8f2f1930fdd79f0bb05d3ed5a99ff7d1cf5106 | C1=COC(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C;D1;H3:16]-[CH;D3;+0:17](-[C;D1;H3:18])-[S;H0;D4;+0:19](=[O;D1;H0:20])(=[O;D1;H0:21])-[CH2;D2;+0:22]-[C:23]-[NH2;D1;+0:24]>>[#7;a:10]:[c:9]1:[c:8... | null | [] | null | null | null | null | The title compound and its hydrochloride salt are prepared according to Procedure D utilizing 5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde (0.317 mmol, 0.15 g), Isopropylsulfonylethyl amine hydrochloride salt (0.475 mmol, 0.105 g) in the presence of Et3N (0.95 mmol, 0.13 mL) and NaBH4 (1.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Sulfone | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1 | Other | null | null | null | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2bfe43fcebe4adc8c2978aa82da026e | CCOC(=O)COc1ccc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)cc1C>>Cc1cc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)ccc1OCC(=O)O | Cl.CC1=C(OCC(=O)OCC)C=CC(=C1)SCC1=C(N=C(S1)C1=CC(=C(C=C1)C(F)(F)F)F)C.[Li+].[OH-].O>>CC1=C(OCC(=O)O)C=CC(=C1)SCC1=C(N=C(S1)C1=CC(=C(C=C1)C(F)(F)F)F)C | CC[O:31][C:29]([CH2:28][O:27][c:26]1[c:2]([CH3:1])[cH:3][c:4]([S:5][CH2:6][c:7]2[s:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[c:18]([F:19])[cH:20]3)[n:21][c:22]2[CH3:23])[cH:24][cH:25]1)=[O:30]>>[CH3:1][c:2]1[cH:3][c:4]([S:5][CH2:6][c:7]2[s:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:... | CCOC(=O)COc1ccc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)cc1C | Cc1cc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)ccc1OCC(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(SCc2cnc(-c3ccccc3)s2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | A solution of Example 2a (1 mmol) in THF (10 mL) was treated with 1N LiOH in water (2 mL, 2 mmol), and stirred 16 h at room temperature (when reactions were slow, the temperature was elevated to 50° C.). The solution was neutralized with 1N HCl (2 mL, 2 mmol) and the organic solvent evaporated to afford an aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cscn1.c1ccccc1 | Other | C1CCOC1 | null | 16 | CCOC(=O)COc1ccc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)cc1C>C1CCOC1>Cc1cc(SCc2sc(-c3ccc(C(F)(F)F)c(F)c3)nc2C)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8501356412b4821bc14f268d1131b78 | CC(=O)CCl.CI.N#CCC(=O)c1ccc(Cl)cc1.S=C=S>>CSc1sc(C(C)=O)c(-c2ccc(Cl)cc2)c1C#N | CI.ClC1=CC=C(C=C1)C(CC#N)=O.C(=O)([O-])[O-].[K+].[K+].ClCC(C)=O.C(=S)=S>>C(C)(=O)C1=C(C(=C(S1)SC)C#N)C1=CC=C(C=C1)Cl | Cl[CH2:5][C:6]([CH3:7])=[O:8].I[CH3:1].O=[C:9]([c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1)[CH2:17][C:18]#[N:19].[S:2]=[C:3]=[S:4]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]([CH3:7])=[O:8])[c:9](-[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[c:17]1[C:18]#[N:19] | CC(=O)CCl.CI.N#CCC(=O)c1ccc(Cl)cc1.S=C=S | CSc1sc(C(C)=O)c(-c2ccc(Cl)cc2)c1C#N | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 92724f62e81d5afee611b59f950a1fd25262f2d4f83ceb8648b891e81a43c5cb | d3180b15549cb0989dba1ec9c0cee0751286f457e05c4b8dde90548d463bacd1 | c1ccc(-c2ccsc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].I-[CH3;D1;+0:5].O=[C;H0;D3;+0:6](-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[S;H0;D1;+0:15]=[C;H0;D2;+0:16]=[S;H0;D1;+0:17]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[s;H0;D2;+0:17]:[c;H0;D3;+0:16](-[S;H0;D2;+0:15]-[CH3;D1;+0:5... | null | [] | null | null | 10 | MINUTE | 3-(4-Chloro-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 min... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Ketone.Monosulfide | null | c1ccsc1 | c1ccsc1.c1ccccc1 | HCl.I- | CN(C)C=O | null | 0.166667 | CC(=O)CCl.CI.N#CCC(=O)c1ccc(Cl)cc1.S=C=S>CN(C)C=O>CSc1sc(C(C)=O)c(-c2ccc(Cl)cc2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5067be8faaa479d8cc0710e9fd56529 | CC(=O)CCl.CI.Cc1ccc(C(=O)CC#N)cc1.S=C=S>>CSc1sc(C(C)=O)c(-c2ccc(C)cc2)c1C#N | CI.CC1=CC=C(C=C1)C(CC#N)=O.C(=O)([O-])[O-].[K+].[K+].ClCC(C)=O.C(=S)=S>>C(C)(=O)C1=C(C(=C(S1)SC)C#N)C1=CC=C(C=C1)C | Cl[CH2:5][C:6]([CH3:7])=[O:8].I[CH3:1].O=[C:9]([c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH2:17][C:18]#[N:19].[S:2]=[C:3]=[S:4]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]([CH3:7])=[O:8])[c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]2)[c:17]1[C:18]#[N:19] | CC(=O)CCl.CI.Cc1ccc(C(=O)CC#N)cc1.S=C=S | CSc1sc(C(C)=O)c(-c2ccc(C)cc2)c1C#N | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 92724f62e81d5afee611b59f950a1fd25262f2d4f83ceb8648b891e81a43c5cb | d3180b15549cb0989dba1ec9c0cee0751286f457e05c4b8dde90548d463bacd1 | c1ccc(-c2ccsc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].I-[CH3;D1;+0:5].O=[C;H0;D3;+0:6](-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[S;H0;D1;+0:15]=[C;H0;D2;+0:16]=[S;H0;D1;+0:17]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[s;H0;D2;+0:17]:[c;H0;D3;+0:16](-[S;H0;D2;+0:15]-[CH3;D1;+0:5... | null | [] | null | null | 10 | MINUTE | 3-(4-Methyl-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 min... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Ketone.Monosulfide | null | c1ccsc1 | c1ccsc1.c1ccccc1 | HCl.I- | CN(C)C=O | null | 0.166667 | CC(=O)CCl.CI.Cc1ccc(C(=O)CC#N)cc1.S=C=S>CN(C)C=O>CSc1sc(C(C)=O)c(-c2ccc(C)cc2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fab1cf601eeb4f96bf3c58d1ce626549 | CC(=O)CC(C)=O.CI.N#CCCl.S=C=S>>CSc1sc(C#N)c(C)c1C(C)=O | ClCC#N.CI.CC(CC(C)=O)=O.C(=O)([O-])[O-].[K+].[K+].C(=S)=S>>C(C)(=O)C=1C(=C(SC1SC)C#N)C | O=[C:8]([CH3:9])[CH2:10][C:11]([CH3:12])=[O:13].I[CH3:1].Cl[CH2:5][C:6]#[N:7].[S:2]=[C:3]=[S:4]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[c:10]1[C:11]([CH3:12])=[O:13] | CC(=O)CC(C)=O.CI.N#CCCl.S=C=S | CSc1sc(C#N)c(C)c1C(C)=O | null | null | O.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 92724f62e81d5afee611b59f950a1fd25262f2d4f83ceb8648b891e81a43c5cb | d3180b15549cb0989dba1ec9c0cee0751286f457e05c4b8dde90548d463bacd1 | c1ccsc1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].I-[CH3;D1;+0:4].O=[C;H0;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])=[O;D1;H0:10].[S;H0;D1;+0:11]=[C;H0;D2;+0:12]=[S;H0;D1;+0:13]>>[C;D1;H3:9]-[C:8](=[O;D1;H0:10])-[c;H0;D3;+0:7]1:[c;H0;D3;+0:12](-[S;H0;D2;+0:11]-[CH3;D1;+0:4]):[s;H0;D2;+0:13]:[c;H0;D3;+0:1](-[C:2]#[N;D1;H... | null | [] | 0 | CELSIUS | 10 | MINUTE | To a slurry of 2,4-pentanedione (20 mmol) and K2CO3 (3 equivalents, 60 mmol) in DMF (10 mL) was added CS2 (1.2 equivalents, 24 mmol) and the resulting mixture stirred for 10 minutes. The mixture was cooled to 0° C. then chloroacetonitrile (1.0 equivalent, 20 mmol) was added and the reaction stirred 1 hour then warmed t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Ketone.Monosulfide | null | c1ccsc1 | c1ccsc1 | HCl.I- | O.CN(C)C=O | 0 | 0.166667 | CC(=O)CC(C)=O.CI.N#CCCl.S=C=S>O.CN(C)C=O>CSc1sc(C#N)c(C)c1C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-415fb75af4324233a0dbe7387235e9d9 | COC(OC)N(C)C.CSc1sc(C#N)c(C)c1C(C)=O>>CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C | C(C)(=O)C=1C(=C(SC1SC)C#N)C.CN(C)C(OC)OC>>CN(C=CC(=O)C=1C(=C(SC1SC)C#N)C)C | CO[CH:14](OC)[N:15]([CH3:16])[CH3:17].[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[c:10]1[C:11](=[O:12])[CH3:13]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[c:10]1[C:11](=[O:12])[CH:13]=[CH:14][N:15]([CH3:16])[CH3:17] | COC(OC)N(C)C.CSc1sc(C#N)c(C)c1C(C)=O | CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C | null | null | C(C)#N | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | c1ccsc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[#16;a:5]:[c:6]:[c:7]-[C:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[#16;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:10])-[CH;D2;+0:9]=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4] | null | [] | null | null | null | null | To a solution of 4-acetyl-3-methyl-5-methylsulfanyl-thiophene-2-carbonitrile (10 mmol) in acetonitrile (5 mL) was added DMF-DMA (2 mL) and the resulting mixture heated at reflux for 18 hours. The reaction was concentrated and the residue triturated with diethyl ether (20 mL). The suspension was filtered and washed with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccsc1 | HO- | C(C)#N | null | null | COC(OC)N(C)C.CSc1sc(C#N)c(C)c1C(C)=O>C(C)#N>CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2810a450ddcc4664936267dcc3b490d2 | CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C.N=C(N)Nc1ccccc1>>CSc1sc(C#N)c(C)c1-c1ccnc(Nc2ccccc2)n1 | CN(C=CC(=O)C=1C(=C(SC1SC)C#N)C)C.C1(=CC=CC=C1)NC(=N)N>>CC1=C(SC(=C1C1=NC(=NC=C1)NC1=CC=CC=C1)SC)C#N | CN(C)[CH:13]=[CH:12][C:11](=O)[c:10]1[c:3]([S:2][CH3:1])[s:4][c:5]([C:6]#[N:7])[c:8]1[CH3:9].[NH2:14][C:15]([NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)=[NH:23]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:... | CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C.N=C(N)Nc1ccccc1 | CSc1sc(C#N)c(C)c1-c1ccnc(Nc2ccccc2)n1 | null | null | CO.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(Nc2nccc(-c3ccsc3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5](-[#16:6]):[#16;a:7]:[c:8](-[C:9]#[N;D1;H0:10]):[c:11]:1-[C;D1;H3:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](=[NH;D1;+0:15])-[#7:16]-[c:17]>>[#16:6]-[c:5]1:[#16;a:7]:[c:8](-[C:9]#[N;D1;H0:10]):[c:11](-[C;D1;H3:12]):[c;H0;D3;+0:4]:1-[c;H0;D3;+0:3]1:[cH;D2... | null | [] | null | null | null | null | To a solution of 4-(3-dimethylamino-acryloyl)-3-methyl-5-methylsulfanyl-thiophene-2-carbonitrile (0.2 mmol) in acetonitrile (0.25 mL) was added N-phenyl guanidine (1 equivalent, 0.2 mmol) and the reaction heated at reflux for 24 hours. The resulting mixture was cooled to room temperature then diluted with methanol (3 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccsc1.c1cncnc1.c1ccccc1 | HO- | CO.C(C)#N | null | null | CSc1sc(C#N)c(C)c1C(=O)C=CN(C)C.N=C(N)Nc1ccccc1>CO.C(C)#N>CSc1sc(C#N)c(C)c1-c1ccnc(Nc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8a2a8b23e3b40ccab14cf61318616f3 | CC#N.CCOC(=O)c1cccnc1>>N#CCC(=O)c1cccnc1 | C(C)#N.C(C1=CN=CC=C1)(=O)OCC.[H-].[Na+]>>O=C(CC#N)C=1C=NC=CC1 | [N:1]#[C:2][CH3:3].CCO[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1>>[N:1]#[C:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1 | CC#N.CCOC(=O)c1cccnc1 | N#CCC(=O)c1cccnc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[CH3;D1;+0:8]-[C:9]#[N;D1;H0:10]>>[N;D1;H0:10]#[C:9]-[CH2;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | 90 | CELSIUS | null | null | To a solution of ethyl nicotinate (30.24 g, 0.20 mol) in toluene (anhydrous, 200 mL) was added NaH (18.64 g, 0.47 mol, 60% in mineral oil). The resulting suspension was heated at 90° C. and acetonitrile (anhydrous, 24.74 ml, 0.47 mol) was added into this suspension via syringe under nitrogen and the reaction was heated... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1 | HO- | C1(=CC=CC=C1)C | 90 | null | CC#N.CCOC(=O)c1cccnc1>C1(=CC=CC=C1)C>N#CCC(=O)c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2ea8994468d4030884c9f6a18eafa8c | CCC(=O)CBr.CI.N#CCC(=O)c1cccnc1.S=C=S>>CCC(=O)c1sc(SC)c(C)c1-c1cccnc1 | CI.O=C(CC#N)C=1C=NC=CC1.C(=S)=S.[NH4+].[Cl-].BrCC(CC)=O>>CC=1C(=C(SC1SC)C(CC)=O)C=1C=NC=CC1 | Br[CH2:5][C:3]([CH2:2][CH3:1])=[O:4].I[CH3:9].N#[C:11][CH2:10][C:12](=O)[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1.[S:6]=[C:7]=[S:8]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[s:6][c:7]([S:8][CH3:9])[c:10]([CH3:11])[c:12]1-[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1 | CCC(=O)CBr.CI.N#CCC(=O)c1cccnc1.S=C=S | CCC(=O)c1sc(SC)c(C)c1-c1cccnc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 4e5d2763cafc01f0a56d01ab6b5e75b0cec28c085c9662fd968fcb01976b0ffb | 33243d4c8e055f81b07b347e7105495befcada1bf8e96825d6f989b0c9e9712a | c1cncc(-c2ccsc2)c1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].I-[CH3;D1;+0:5].N#[C;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1.[S;H0;D1;+0:15]=[C;H0;D2;+0:16]=[S;H0;D1;+0:17]>>[C:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[s;H0;D2;+0:15]:[c;H0;D3;+0:16](-[S;H0;D2;+0:17]-[CH3;D1;+0:5]):... | 32.1 | [{"value": 32.1, "product": "CC=1C(=C(SC1SC)C(CC)=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | To a solution of 3-oxo-3-pyridin-3-yl-propionitrile (11.9 mmol) in DMF (100 mL) was added CS2 (0.90 ml, 15.0 mmol) at 0° C. The reaction was stirred at 0° C. for 45 minutes under nitrogen then 1-bromo-butan-2-one (1.79 g, 11.8 mmol) was added via a syringe at 0° C. The reaction was stirred for another 30 minutes then m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Nitrile | Ketone.Monosulfide | null | c1ccsc1 | c1ccsc1.c1ccncc1 | HBr.I- | CN(C)C=O | 0 | 0.75 | CCC(=O)CBr.CI.N#CCC(=O)c1cccnc1.S=C=S>CN(C)C=O>CCC(=O)c1sc(SC)c(C)c1-c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6b1f13036c244b682cb1d3247b19d66 | N#CN.Nc1cccc(OCc2ccccc2)c1>>N=C(N)Nc1cccc(OCc2ccccc2)c1 | [OH-].[Na+].N#CN.C(C1=CC=CC=C1)OC=1C=C(C=CC1)N.Cl>>C(C1=CC=CC=C1)OC=1C=C(C=CC1)NC(=N)N | [N:1]#[C:2][NH2:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | N#CN.Nc1cccc(OCc2ccccc2)c1 | N=C(N)Nc1cccc(OCc2ccccc2)c1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | a0cbddf5d7d81fe92104447f1edef14329807abeadc66f8268b3c04bddc38ea2 | 9b168a0be416143e92b99e2902110a4569d3f9f31721e83b72aa42867628c64d | c1ccc(COc2ccccc2)cc1 | [N;D1;H2:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H2:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 98.4 | [{"value": 98.4, "product": "C(C1=CC=CC=C1)OC=1C=C(C=CC1)NC(=N)N", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of 3-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (35 ml, 210.00 mmol) was added. ... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | null | O1CCOCC1 | 80 | null | N#CN.Nc1cccc(OCc2ccccc2)c1>O1CCOCC1>N=C(N)Nc1cccc(OCc2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c2f6a5a2ec34decaf8e5a51310a14b6 | N=C(N)Nc1cccc(OCc2ccccc2)c1>>N=C(N)Nc1cccc(O)c1 | C(C1=CC=CC=C1)OC=1C=C(C=CC1)NC(=N)N>>OC=1C=C(C=CC1)NC(=N)N | c1ccc(C[O:10][c:9]2[cH:8][cH:7][cH:6][c:5]([NH:4][C:2](=[NH:1])[NH2:3])[cH:11]2)cc1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1 | N=C(N)Nc1cccc(OCc2ccccc2)c1 | N=C(N)Nc1cccc(O)c1 | null | [Pd] | CCO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 8 | HOUR | To a solution of N-(3-benzyloxy-phenyl)guanidine (5.0 g, 20.6 mmol) in EtOH (150 mL) was added palladium on carbon (10%, wet, 50% water, 0.5 g)). The mixture was stirred under hydrogen atmosphere overnight. The reaction was filtered through a plug of celite and the filtrate concentrated in vacuo with toluene azeotropin... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CCO | null | 8 | N=C(N)Nc1cccc(OCc2ccccc2)c1>[Pd].CCO>N=C(N)Nc1cccc(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a70559842d214e9992445c087f09443a | CSc1sc(-c2cc(Nc3cccc(O)c3)ccc2C)c(-c2cccnc2)c1C#N.OCCCBr>>CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N | C(=O)([O-])[O-].[K+].[K+].OC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C.BrCCCO>>OCCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C | [CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:20]3)[cH:21][cH:22][c:23]2[CH3:24])[c:25](-[c:26]2[cH:27][cH:28][cH:29][n:30][cH:31]2)[c:32]1[C:33]#[N:34].Br[CH2:16][CH2:17][CH2:18][OH:19]>>[CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c... | CSc1sc(-c2cc(Nc3cccc(O)c3)ccc2C)c(-c2cccnc2)c1C#N.OCCCBr | CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Nc2cccc(-c3sccc3-c3cccnc3)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "OCCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "OCCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[5-(3-hydroxyphenylamino)-2-methyl-phenyl]-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile (330 mg, 0.77 mmol) in DMF (anhydrous, 5 mL) was added 3-bromo-propan-1-ol (214 mL, 1.54 mmol). The reaction was stirred at 70° C. in the presence of excess K2CO3 overnight then cooled to ambient tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccsc1.c1ccccc1.c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | null | null | CSc1sc(-c2cc(Nc3cccc(O)c3)ccc2C)c(-c2cccnc2)c1C#N.OCCCBr>CN(C)C=O>CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68ea0f9f7b8643a29e9da64ecd7da0c0 | CS(=O)(=O)Cl.CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N>>CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N | O.CS(=O)(=O)Cl.OCCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C.CCN(CC)CC>>C(#N)C=1C(=C(SC1SC)C=1C=C(C=CC1C)NC=1C=C(OCCCOS(=O)(=O)C)C=CC1)C=1C=NC=CC1 | Cl[S:20]([CH3:21])(=[O:22])=[O:23].[CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[cH:24]3)[cH:25][cH:26][c:27]2[CH3:28])[c:29](-[c:30]2[cH:31][cH:32][cH:33][n:34][cH:35]2)[c:36]1[C:37]#[N:38]>>[CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][c:8... | CS(=O)(=O)Cl.CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N | CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(Nc2cccc(-c3sccc3-c3cccnc3)c2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 10 | MINUTE | To a solution of 5-{5-[3-(3-hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile (370 mg, 0.76 mmol) in DCM (10 mL) was added Et3N (155 mg, 0.15 mmol) followed by MsCl (130 mg, 1.15 mmol). The resulting mixture was stirred at ambient temperature for 10 min under nitrog... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccsc1.c1ccccc1.c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | 0.166667 | CS(=O)(=O)Cl.CSc1sc(-c2cc(Nc3cccc(OCCCO)c3)ccc2C)c(-c2cccnc2)c1C#N>C(Cl)Cl>CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9388568c90274f3dbf1e9cde00a3a358 | CNC.CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N>>CSc1sc(-c2cc(Nc3cccc(OCCCN(C)C)c3)ccc2C)c(-c2cccnc2)c1C#N | O.C(#N)C=1C(=C(SC1SC)C=1C=C(C=CC1C)NC=1C=C(OCCCOS(=O)(=O)C)C=CC1)C=1C=NC=CC1.CNC.C(C)N(CC)CC>>CN(CCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C)C | [NH:19]([CH3:20])[CH3:21].CS(=O)(=O)O[CH2:18][CH2:17][CH2:16][O:15][c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][c:8]2[cH:7][c:6](-[c:5]3[s:4][c:3]([S:2][CH3:1])[c:34]([C:35]#[N:36])[c:27]3-[c:28]3[cH:29][cH:30][cH:31][n:32][cH:33]3)[c:25]([CH3:26])[cH:24][cH:23]2)[cH:22]1>>[CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][c:8]([... | CNC.CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N | CSc1sc(-c2cc(Nc3cccc(OCCCN(C)C)c3)ccc2C)c(-c2cccnc2)c1C#N | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc(Nc2cccc(-c3sccc3-c3cccnc3)c2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 95 | [{"value": 95.0, "product": "CN(CCCOC=1C=C(C=CC1)NC=1C=CC(=C(C1)C1=C(C(=C(S1)SC)C#N)C=1C=NC=CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of methanesulfonic acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl ester (20 mg, 0.035 mmol) in DCM (1 mL) was added excess dimethylamine and excess triethylamine. The reaction was stirred at ambient temperature for 3 hours then water (2 ml) was... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccsc1.c1ccccc1.c1ccccc1.c1ccncc1 | MsOH.HO- | C(Cl)Cl | null | 3 | CNC.CSc1sc(-c2cc(Nc3cccc(OCCCOS(C)(=O)=O)c3)ccc2C)c(-c2cccnc2)c1C#N>C(Cl)Cl>CSc1sc(-c2cc(Nc3cccc(OCCCN(C)C)c3)ccc2C)c(-c2cccnc2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d1a6d861cf4a468590e8aa366704d9ac | CCOC(=O)C(C#N)C(=O)C1CCCCC1>>N#CCC(=O)C1CCCCC1 | C(C)OC(C(C(=O)C1CCCCC1)C#N)=O>>C1(CCCCC1)C(CC#N)=O | CCOC(=O)[CH:3]([C:2]#[N:1])[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1>>[N:1]#[C:2][CH2:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1 | CCOC(=O)C(C#N)C(=O)C1CCCCC1 | N#CCC(=O)C1CCCCC1 | null | null | CS(=O)C.O | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | C1CCCCC1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4](-[C:5])=[O;D1;H0:6]>>[C:5]-[C:4](=[O;D1;H0:6])-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3] | null | [] | null | null | null | null | A solution of 2-cyano-3-cyclohexyl-3-oxo-propionic acid ethyl ester in DMSO:water (10:1) was stirred at 120° C. for 2 hours. The reaction mixture was partitioned between ether and 1N HCl, the organic phase was dried with MgSO4 and the solvent removed under reduced pressure.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | C1CCCCC1 | HO- | CS(=O)C.O | null | null | CCOC(=O)C(C#N)C(=O)C1CCCCC1>CS(=O)C.O>N#CCC(=O)C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-183102cc420b4877ac00ee09af6bc6a9 | CC(=O)CCl.CI.N#CCC(=O)C1CCCCC1.S=C=S>>CSc1sc(C(C)=O)c(C2CCCCC2)c1C#N | IC.ClCC(C)=O.C1(CCCCC1)C(CC#N)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.C(=S)=S>>C(C)(=O)C1=C(C(=C(S1)SC)C#N)C1CCCCC1 | Cl[CH2:5][C:6]([CH3:7])=[O:8].I[CH3:1].O=[C:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:16][C:17]#[N:18].[S:2]=[C:3]=[S:4]>>[CH3:1][S:2][c:3]1[s:4][c:5]([C:6]([CH3:7])=[O:8])[c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[c:16]1[C:17]#[N:18] | CC(=O)CCl.CI.N#CCC(=O)C1CCCCC1.S=C=S | CSc1sc(C(C)=O)c(C2CCCCC2)c1C#N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 92724f62e81d5afee611b59f950a1fd25262f2d4f83ceb8648b891e81a43c5cb | d3180b15549cb0989dba1ec9c0cee0751286f457e05c4b8dde90548d463bacd1 | c1cc(C2CCCCC2)cs1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].I-[CH3;D1;+0:5].O=[C;H0;D3;+0:6](-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9])-[C:10](-[C:11])-[C:12].[S;H0;D1;+0:13]=[C;H0;D2;+0:14]=[S;H0;D1;+0:15]>>[C:11]-[C:10](-[c;H0;D3;+0:6]1:[c;H0;D3;+0:7](-[C:8]#[N;D1;H0:9]):[c;H0;D3;+0:14](-[S;H0;D2;+0:13]-[CH3;D1;+0:5]):[s;H0;D2;+0:15]:[c... | null | [] | null | null | 2 | HOUR | To a solution of 3-cyclohexyl-3-oxo-propionitrile in DMF:CS2 (1:1) was added K2CO3 at 0° C. and the reaction mixture stirred at ambient temperature for 2 hours. To the resulting reaction mixture was added chloroacetone (1 equivalent) and the reaction mixture stirred at ambient temperature for 3 hours. Iodomethane was t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Ketone.Monosulfide | null | c1ccsc1 | c1ccsc1.C1CCCCC1 | HCl.I- | null | null | 2 | CC(=O)CCl.CI.N#CCC(=O)C1CCCCC1.S=C=S>>CSc1sc(C(C)=O)c(C2CCCCC2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05feb69e36f74c72a511e7d41bd5b6b6 | CSc1sc(C(=O)C(C)=CN(C)C)c(C2CCCCC2)c1C#N.N=C(N)Nc1cccc([N+](=O)[O-])c1>>CSc1sc(-c2nc(Nc3cccc([N+](=O)[O-])c3)ncc2C)c(C2CCCCC2)c1C#N | [N+](=O)([O-])C=1C=C(C=CC1)NC(=N)N.C1(CCCCC1)C=1C(=C(SC1C(C(=CN(C)C)C)=O)SC)C#N.CN(C)C(OC)OC>>[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)C1=C(C(=C(S1)SC)C#N)C1CCCCC1)C | CN(C)[CH:20]=[C:21]([C:6](=O)[c:5]1[s:4][c:3]([S:2][CH3:1])[c:30]([C:31]#[N:32])[c:23]1[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)[CH3:22].[NH:7]=[C:8]([NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1)[NH2:19]>>[CH3:1][S:2][c:3]1[s:4][c:5](-[c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH... | CSc1sc(C(=O)C(C)=CN(C)C)c(C2CCCCC2)c1C#N.N=C(N)Nc1cccc([N+](=O)[O-])c1 | CSc1sc(-c2nc(Nc3cccc([N+](=O)[O-])c3)ncc2C)c(C2CCCCC2)c1C#N | null | null | CCOC(=O)C.CN(C)C=O.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(Nc2nccc(-c3sccc3C3CCCCC3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C;D1;H3:3])-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5]1:[#16;a:6]:[c:7]:[c:8]:[c:9]:1-[C:10].[NH2;D1;+0:11]-[C;H0;D3;+0:12](=[NH;D1;+0:13])-[#7:14]-[c:15]>>[C:10]-[c:9]1:[c:8]:[c:7]:[#16;a:6]:[c;H0;D3;+0:5]:1-[c;H0;D3;+0:4]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:12](-[#7:14]-[c:15]):[n;H0;D2;+0:11]:[... | 42 | [{"value": 42.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)C1=C(C(=C(S1)SC)C#N)C1CCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile (0.5 g, 1.7 mmol) in toluene (3 ml) was added DMF-DMA and the reaction was heated at 90° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The crude product was combined ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccsc1.c1cncnc1.c1ccccc1.C1CCCCC1 | HO- | CCOC(=O)C.CN(C)C=O.C1(=CC=CC=C1)C | 90 | null | CSc1sc(C(=O)C(C)=CN(C)C)c(C2CCCCC2)c1C#N.N=C(N)Nc1cccc([N+](=O)[O-])c1>CCOC(=O)C.CN(C)C=O.C1(=CC=CC=C1)C>CSc1sc(-c2nc(Nc3cccc([N+](=O)[O-])c3)ncc2C)c(C2CCCCC2)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49d09abfa3ef48e594e043221a405f61 | CCN(CC)CCBr.CSc1sc(-c2nc(Nc3cccc(N)c3)ncc2C)c(C2CCCCC2)c1C#N>>CCN(CC)CCNc1cccc(Nc2ncc(C)c(-c3sc(SC)c(C#N)c3C3CCCCC3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)C1=C(C(=C(S1)SC)C#N)C1CCCCC1)C.C(C)N(CCBr)CC.Br.CC(C)([O-])C.[Na+]>>C1(CCCCC1)C=1C(=C(SC1C1=NC(=NC=C1C)NC1=CC(=CC=C1)NCCN(CC)CC)SC)C#N | Br[CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].[NH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][cH:17][c:18]([CH3:19])[c:20](-[c:21]3[s:22][c:23]([S:24][CH3:25])[c:26]([C:27]#[N:28])[c:29]3[CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[n:36]2)[cH:37]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH... | CCN(CC)CCBr.CSc1sc(-c2nc(Nc3cccc(N)c3)ncc2C)c(C2CCCCC2)c1C#N | CCN(CC)CCNc1cccc(Nc2ncc(C)c(-c3sc(SC)c(C#N)c3C3CCCCC3)n2)c1 | null | null | CO.C1CCOC1.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(Nc2nccc(-c3sccc3C3CCCCC3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 33 | [{"value": 33.0, "product": "C1(CCCCC1)C=1C(=C(SC1C1=NC(=NC=C1C)NC1=CC(=CC=C1)NCCN(CC)CC)SC)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-[2-(3-aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile (20 mg, 45.91 micromol) and N,N-diethyl-2-aminobromoethane.HBr (12 mg, 45.91 micromol) in THF was added sodium t-butoxide (9 mg, 91.82 micromol) and the reaction was stirred at ambient temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1cncnc1.c1ccsc1.C1CCCCC1 | HBr | CO.C1CCOC1.C(Cl)Cl | null | 8 | CCN(CC)CCBr.CSc1sc(-c2nc(Nc3cccc(N)c3)ncc2C)c(C2CCCCC2)c1C#N>CO.C1CCOC1.C(Cl)Cl>CCN(CC)CCNc1cccc(Nc2ncc(C)c(-c3sc(SC)c(C#N)c3C3CCCCC3)n2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0f346fd6672465c92d63410e95e866a | NC(=S)Nc1ccccn1.O=CC(Br)=CO>>O=Cc1cnc(Nc2ccccn2)s1 | C(C)(=O)[O-].[Na+].N1=C(C=CC=C1)NC(=S)N.BrC(C=O)=CO>>N1=C(C=CC=C1)NC=1SC(=CN1)C=O | [NH2:5][C:6]([NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1)=[S:14].O[CH:4]=[C:3](Br)[CH:2]=[O:1]>>[O:1]=[CH:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[s:14]1 | NC(=S)Nc1ccccn1.O=CC(Br)=CO | O=Cc1cnc(Nc2ccccn2)s1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | d367ec81c78cfdb7b0d7f48767ce6383ba777d900fbe8c3da2c52ddd5f67387a | 87248dadd5ff4ef5750cb08be6268a97d7af6d31ebcf094ec726591896924988 | c1ccc(Nc2nccs2)nc1 | Br-[C;H0;D3;+0:1](-[C:2]=[O;D1;H0:3])=[CH;D2;+0:4]-O.[#7;a:5]:[c:6]-[#7:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10]>>[#7;a:5]:[c:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[cH;D2;+0:4]:[c;H0;D3;+0:1](-[C:2]=[O;D1;H0:3]):[s;H0;D2;+0:10]:1 | 52 | [{"value": 52.0, "product": "N1=C(C=CC=C1)NC=1SC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "N1=C(C=CC=C1)NC=1SC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 1.5 | HOUR | To a solution of 1-(2-pyridyl)-2-thiourea (765 mg, 5.0 mmol) in acetone (14 mL) was added slowly 2-bromo-3-hydroxypropenal (755 mg, 5.0 mmol, for preparation see J. Org. Chem. 28, 3243, 1963) in acetone (14 mL) over a period of 5 min. After stirring for 1.5 h, a precipitate formed. The solids were separated, washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Aldehyde.Thiourea.Enol | Aldehyde | null | c1cscn1 | c1cscn1.c1ccncc1 | HBr | CC(=O)C | 75 | 1.5 | NC(=S)Nc1ccccn1.O=CC(Br)=CO>CC(=O)C>O=Cc1cnc(Nc2ccccn2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e536b4f293e4a9abaef797cf8c29f57 | O=C(O)c1ccc(F)cc1F.O=[N+]([O-])O>>O=C(O)c1cc([N+](=O)[O-])c(F)cc1F | FC1=C(C(=O)O)C=CC(=C1)F.[N+](=O)(O)[O-]>>FC1=C(C(=O)O)C=C(C(=C1)F)[N+](=O)[O-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:10]([F:11])[cH:12][c:13]1[F:14].O[N+:7](=[O:8])[O-:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([F:11])[cH:12][c:13]1[F:14] | O=C(O)c1ccc(F)cc1F.O=[N+]([O-])O | O=C(O)c1cc([N+](=O)[O-])c(F)cc1F | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[F;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | 98 | [{"value": 98.0, "product": "FC1=C(C(=O)O)C=C(C(=C1)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a suspension of 2,4-difluorobenzoic acid (9.985 g, 63.2 mmol) in concentrated sulfuric acid (30 mL) at 0° C. was added fuming nitric acid (30 mL) over 30 min. The mixture was allowed to warm to RT and stirred for an additional 16 h. The homogeneous mixture was poured onto ice and extracted with ethyl acetate. The or... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 16 | O=C(O)c1ccc(F)cc1F.O=[N+]([O-])O>S(O)(O)(=O)=O>O=C(O)c1cc([N+](=O)[O-])c(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f6298eabc42429f85799e265714a6cf | O=C(O)c1cc([N+](=O)[O-])c(F)cc1F>>Nc1cc(C(=O)O)c(F)cc1F | FC1=C(C(=O)O)C=C(C(=C1)F)[N+](=O)[O-]>>FC1=C(C(=O)O)C=C(C(=C1)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]([F:9])[cH:10][c:11]1[F:12]>>[NH2:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]([F:9])[cH:10][c:11]1[F:12] | O=C(O)c1cc([N+](=O)[O-])c(F)cc1F | Nc1cc(C(=O)O)c(F)cc1F | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.6 | [{"value": 97.0, "product": "FC1=C(C(=O)O)C=C(C(=C1)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "FC1=C(C(=O)O)C=C(C(=C1)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2,4-difluoro-5-nitrobenzoic acid (0.998 g, 4.91 mmol) in ethanol (50 mL) was added 10% palladium on charcoal (107 mg) and the mixture was hydrogenated at 30 psi. After 2 h, the mixture was degassed, filtered and the filtrate was concentrated in vacuo to afford 2,4-difluoro-5-aminobenzoic acid (0.83 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | 2 | O=C(O)c1cc([N+](=O)[O-])c(F)cc1F>[Pd].C(C)O>Nc1cc(C(=O)O)c(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b2bf3783bd943be8a72c6dd87d5cd4d | CN.Nc1cc(C(=O)O)c(F)cc1F>>CNC(=O)c1cc(N)c(F)cc1F | CN.FC1=C(C(=O)O)C=C(C(=C1)F)N.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O>>NC=1C(=CC(=C(C(=O)NC)C1)F)F | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11][c:12]1[F:13]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11][c:12]1[F:13] | CN.Nc1cc(C(=O)O)c(F)cc1F | CNC(=O)c1cc(N)c(F)cc1F | null | null | C(C)(=O)OCC.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 41 | [{"value": 41.0, "product": "NC=1C(=CC(=C(C(=O)NC)C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.8, "product": "NC=1C(=CC(=C(C(=O)NC)C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2,4-difluoro-5-aminobenzoic acid (1.73 g, 10.0 mmol) in DMF (40 mL) were successively added EDCI (1.62 g, 12.0 mmol), HOBt (2.30 g, 12.0 mmol) and methylamine (6.0 mL, 12.0 mmol, 2 M in MeOH) in that order at RT. After stirring for 2 h, the reaction mixture was diluted with ethyl acetate (100 mL) and w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)OCC.CN(C)C=O | null | 2 | CN.Nc1cc(C(=O)O)c(F)cc1F>C(C)(=O)OCC.CN(C)C=O>CNC(=O)c1cc(N)c(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67fc0467b9744c9cae8a4d6ce0d4b91d | O=C(O)c1ccc(F)c([N+](=O)[O-])c1>>Nc1cc(C(=O)O)ccc1F | [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1F>>NC=1C=C(C(=O)O)C=CC1F | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1[F:11]>>[NH2:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1[F:11] | O=C(O)c1ccc(F)c([N+](=O)[O-])c1 | Nc1cc(C(=O)O)ccc1F | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | A mixture of 3-nitro-4-fluorobenzoic acid (1.85 g, 10.0 mmol) in MeOH (10 mL) and 5% Pd/C (100 mg) was stirred under an atmosphere of hydrogen and for 6 h. The catalyst was removed by filtration, washed with methanol and the volatiles were removed in vacuo to give compound 8A, 3-amino-4-fluorobenzoic acid, as a light y... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 6 | O=C(O)c1ccc(F)c([N+](=O)[O-])c1>[Pd].CO>Nc1cc(C(=O)O)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f887d35ea77b46e1a21c1bb7e91e381a | O=Cc1cnc(Nc2ccccn2)s1>>OCc1cnc(Nc2ccccn2)s1 | N1=C(C=CC=C1)NC=1SC(=CN1)C=O.[BH4-].[K+]>>N1=C(C=CC=C1)NC=1SC(=CN1)CO | [O:1]=[CH:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[s:14]1>>[OH:1][CH2:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[s:14]1 | O=Cc1cnc(Nc2ccccn2)s1 | OCc1cnc(Nc2ccccn2)s1 | null | null | CN(C)C=O.C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(Nc2nccs2)nc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1 | 93 | [{"value": 93.0, "product": "N1=C(C=CC=C1)NC=1SC(=CN1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "N1=C(C=CC=C1)NC=1SC(=CN1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(pyridin-2-ylamino)thiazole-5-carbaldehyde (410 mg, 2 mmol) in ethanol (15 mL) and DMF (5 mL) was added potassium borohydride (120 mg). The resulting mixture was stirred at RT for 1 h, quenched with 10% sulfuric acid solution and concentrated in vacuo. The residue was extracted with methanol and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1cscn1.c1ccncc1 | null | CN(C)C=O.C(C)O | null | 1 | O=Cc1cnc(Nc2ccccn2)s1>CN(C)C=O.C(C)O>OCc1cnc(Nc2ccccn2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a2b72a6f89d4c19be519c1cb751c4ae | CS(=O)(=O)Cl.Nc1cc(C(=O)NC2CC2)ccc1F>>CS(=O)(=O)Nc1cc(C(=O)NC2CC2)ccc1F | CS(=O)(=O)Cl.C1(CC1)NC(C1=CC(=C(C=C1)F)N)=O>>C1(CC1)NC(C1=CC(=C(C=C1)F)NS(=O)(=O)C)=O | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][CH:12]2[CH2:13][CH2:14]2)[cH:15][cH:16][c:17]1[F:18]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][CH:12]2[CH2:13][CH2:14]2)[cH:15][cH:16][c:17]1[F:18] | CS(=O)(=O)Cl.Nc1cc(C(=O)NC2CC2)ccc1F | CS(=O)(=O)Nc1cc(C(=O)NC2CC2)ccc1F | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NC1CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | N-cyclopropyl-4-fluoro-3-methanesulfonylaminobenzamide was prepared by treatment of N-cyclopropyl-4-fluoro-3-aminobenzamide (prepared by a procedure similar to Example 1) with methanesulfonyl chloride in the presence of pyridine by standard procedure.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC1 | HCl | N1=CC=CC=C1 | null | null | CS(=O)(=O)Cl.Nc1cc(C(=O)NC2CC2)ccc1F>N1=CC=CC=C1>CS(=O)(=O)Nc1cc(C(=O)NC2CC2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-291beb463c0d4332921ff3a2d84bcb76 | ClCc1cnc(Nc2ccccn2)s1.O=C(O)c1cccc(S)c1>>O=C(O)c1cccc(SCc2cnc(Nc3ccccn3)s2)c1 | Cl.ClCC1=CN=C(S1)NC1=NC=CC=C1.SC=1C=C(C(=O)O)C=CC1.[H-].[Na+].S(=O)(=O)(O)[O-].[K+]>>N1=C(C=CC=C1)NC=1SC(=CN1)CSC=1C=C(C(=O)O)C=CC1 | Cl[CH2:10][c:11]1[cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]2)[s:22]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([SH:9])[cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([S:9][CH2:10][c:11]2[cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][n:21]3)[s:22]2)[cH:23]1 | ClCc1cnc(Nc2ccccn2)s1.O=C(O)c1cccc(S)c1 | O=C(O)c1cccc(SCc2cnc(Nc3ccccn3)s2)c1 | null | null | null | Heteroatom Alkylation and Arylation | S-alkylation of thiols | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(SCc2cnc(Nc3ccccn3)s2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | null | [] | null | null | 10 | MINUTE | A mixture of 3-mercaptobenzoic acid (308 mg, 2 mmol) and sodium hydride (60% in oil, 160 mg, 4 mmol) was stirred at RT under argon for 10 min and then cooled to 0° C. and (5-chloromethyl-thiazol-2-yl)pyridin-2-yl-amine hydrochloride salt (262 mg, 1 mmol) was added. The resulting reaction mixture was stirred at 0° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1cscn1.c1ccncc1 | HCl | null | null | 0.166667 | ClCc1cnc(Nc2ccccn2)s1.O=C(O)c1cccc(S)c1>>O=C(O)c1cccc(SCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27b9e1260647442584ff0f4565e0531d | NC1CC1.O=C(O)c1ccc(F)c(O)c1>>O=C(NC1CC1)c1ccc(F)c(O)c1 | OC=1C=C(C(=O)O)C=CC1F.C1(CC1)N.C(C)N(CC)CC.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C>>OC=1C=C(C(=O)NC2CC2)C=CC1F | [NH2:3][CH:4]1[CH2:5][CH2:6]1.O[C:2](=[O:1])[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([OH:13])[cH:14]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([OH:13])[cH:14]1 | NC1CC1.O=C(O)c1ccc(F)c(O)c1 | O=C(NC1CC1)c1ccc(F)c(O)c1 | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]1-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | 61.5 | [{"value": 61.5, "product": "OC=1C=C(C(=O)NC2CC2)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "OC=1C=C(C(=O)NC2CC2)C=CC1F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 3-hydroxy-4-fluorobenzoic acid (1.56 g, 10 mmol), cyclopropylamine (0.6 g, 10.5 mmol), triethylamine (1.02 g, 10 mmol) and HOBt (0.3 g, 2 mol) in DMF (10 mL) was added EDCI (2.0 g, 10.5 mmol) at RT. The mixture was stirred at RT overnight. The mixture was diluted with water and extracted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC1.c1ccccc1 | HO- | O.CN(C)C=O | null | 8 | NC1CC1.O=C(O)c1ccc(F)c(O)c1>O.CN(C)C=O>O=C(NC1CC1)c1ccc(F)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87002b9f196d4b4bafaff983bc899b02 | ClCc1cnc(Nc2ccccn2)s1.O=C(NC1CC1)c1ccc(F)c(O)c1>>O=C(NC1CC1)c1ccc(F)c(OCc2cnc(Nc3ccccn3)s2)c1 | Cl.ClCC1=CN=C(S1)NC1=NC=CC=C1.OC=1C=C(C(=O)NC2CC2)C=CC1F.OS(=O)(=O)[O-].[K+]>>C1(CC1)NC(C1=CC(=C(C=C1)F)OCC1=CN=C(S1)NC1=NC=CC=C1)=O | Cl[CH2:14][c:15]1[cH:16][n:17][c:18]([NH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][n:25]2)[s:26]1.[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([OH:13])[cH:27]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([O:13][CH2:14][c:15]2[cH:16][n:17][c:18]([NH:19... | ClCc1cnc(Nc2ccccn2)s1.O=C(NC1CC1)c1ccc(F)c(O)c1 | O=C(NC1CC1)c1ccc(F)c(OCc2cnc(Nc3ccccn3)s2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CC1)c1cccc(OCc2cnc(Nc3ccccn3)s2)c1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 33 | [{"value": 33.0, "product": "C1(CC1)NC(C1=CC(=C(C=C1)F)OCC1=CN=C(S1)NC1=NC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "C1(CC1)NC(C1=CC(=C(C=C1)F)OCC1=CN=C(S1)NC1=NC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of NaR (16 mg, 60% in oil) in DMF (1 mL) was added a solution of 3-hydroxy-4-fluoro-N-cyclopropylbenzamide (58.5 mg, 0.3 mmol) in DMF (1 mL) at RT. After 10 min, (5-chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride (Example 10A) (52.4 mg, 0.2 mmol) was added. The mixture was stirred at RT for 1 h... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1CC1.c1ccccc1.c1cscn1.c1ccncc1 | HCl | CN(C)C=O | null | 0.166667 | ClCc1cnc(Nc2ccccn2)s1.O=C(NC1CC1)c1ccc(F)c(O)c1>CN(C)C=O>O=C(NC1CC1)c1ccc(F)c(OCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b66a4138f5a24ea6bea939d006b10a7b | C=CCC(OCC)OCC.O=C(NC1CC1)c1ccc(F)c(Br)c1>>CCOC(CCCc1cc(C(=O)NC2CC2)ccc1F)OCC | C(C)OC(CC=C)OCC.B1C2CCCC1CCC2.C(=O)([O-])[O-].[Na+].[Na+].BrC=1C=C(C(=O)NC2CC2)C=CC1F>>C1(CC1)NC(C1=CC(=C(C=C1)F)CCCC(OCC)OCC)=O | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH:6]=[CH2:7])[O:21][CH2:22][CH3:23].Br[c:8]1[cH:9][c:10]([C:11](=[O:12])[NH:13][CH:14]2[CH2:15][CH2:16]2)[cH:17][cH:18][c:19]1[F:20]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][CH2:7][c:8]1[cH:9][c:10]([C:11](=[O:12])[NH:13][CH:14]2[CH2:15][CH2:16]2)[cH:17][cH:18][c:19]1[F:20])[O:21][CH... | C=CCC(OCC)OCC.O=C(NC1CC1)c1ccc(F)c(Br)c1 | CCOC(CCCc1cc(C(=O)NC2CC2)ccc1F)OCC | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CCO.C(C)(=O)OCC.C1=CC=CC=C1 | C-C Coupling | OtherReaction | 2d4a44695e29e4a9ab430c3b66736ad86dd99247e7216f16f3ca137abca78747 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | O=C(NC1CC1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[F;D1;H0:8]):[c:9].[C:10]-[C:11]-[CH;D2;+0:12]=[CH2;D1;+0:13]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:13]-[CH2;D2;+0:12]-[C:11]-[C:10]):[c:7](-[F;D1;H0:8]):[c:9] | 93.4 | [{"value": 93.0, "product": "C1(CC1)NC(C1=CC(=C(C=C1)F)CCCC(OCC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "C1(CC1)NC(C1=CC(=C(C=C1)F)CCCC(OCC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A solution of 3-butenal diethyl acetal (144 mg, 1 mmol) and 9-BBN (0.5 M in THF, 2.2 mL, 1.1 mmol) was stirred at RT for 1 h. The mixture was concentrated and to the residue were added benzene (2 mL), EtOH (1 mL), aqueous Na2CO3 solution (2M, 1 mL), 3-bromo-4-fluoro-N-cyclopropylbenzamide (127 mg, 0.5 mmol) and Pd(Ph3P... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCO.C(C)(=O)OCC.C1=CC=CC=C1 | 80 | 2 | C=CCC(OCC)OCC.O=C(NC1CC1)c1ccc(F)c(Br)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCO.C(C)(=O)OCC.C1=CC=CC=C1>CCOC(CCCc1cc(C(=O)NC2CC2)ccc1F)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e587e61d27f4401dbb3291711c0d358c | Cc1ccnc(N)c1.O=C(N=C=S)c1ccccc1>>Cc1ccnc(NC(=S)NC(=O)c2ccccc2)c1 | NC1=NC=CC(=C1)C.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NC1=NC=CC(=C1)C | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[cH:19]1.[C:8](=[S:9])=[N:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][C:8](=[S:9])[NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1 | Cc1ccnc(N)c1.O=C(N=C=S)c1ccccc1 | Cc1ccnc(NC(=S)NC(=O)c2ccccc2)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)Nc1ccccn1)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7](-[c:8])-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[S;D1;H0:11]>>[O;D1;H0:6]=[C:7](-[c:8])-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[S;D1;H0:11])-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 2-amino-4-methylpyridine (1.08 g, 10 mmol) and benzoyl isothiocyanate (1.63 g, 10 mmol) in acetone ( 15 mL) was stirred at RT for 1.5 h. The precipitate formed was filtered and washed with acetone to afford 1 -benzoyl-3-[4-methylpyridin-2-yl]-thiourea as a solid. This material was stirred with 2 N NaOH so... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccncc1.c1ccccc1 | null | CC(=O)C | null | null | Cc1ccnc(N)c1.O=C(N=C=S)c1ccccc1>CC(=O)C>Cc1ccnc(NC(=S)NC(=O)c2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e1d32d3e8fb4e439de64c8c1b26c148 | Cc1ccnc(NC(N)=S)c1.O=CC(Br)C=O>>Cc1ccnc(Nc2ncc(C=O)s2)c1 | CC1=CC(=NC=C1)NC(=S)N.BrC(C=O)C=O.C(C)(=O)[O-].[Na+]>>CC1=CC(=NC=C1)NC=1SC(=CN1)C=O | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][C:8]([NH2:9])=[S:14])[cH:15]1.O=[CH:10][CH:11](Br)[CH:12]=[O:13]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([CH:12]=[O:13])[s:14]2)[cH:15]1 | Cc1ccnc(NC(N)=S)c1.O=CC(Br)C=O | Cc1ccnc(Nc2ncc(C=O)s2)c1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7dca2436bf473ad25062e40b44470b498baa7e51887d9d41aefc51478f129aa7 | 89ff6b282554dec8511816adfb1d0a94512f0bd22287f34dda54fcd769a38d0d | c1ccc(Nc2nccs2)nc1 | Br-[CH;D3;+0:1](-[C:2]=[O;D1;H0:3])-[CH;D2;+0:4]=O.[#7;a:5]:[c:6]-[#7:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10]>>[#7;a:5]:[c:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[cH;D2;+0:4]:[c;H0;D3;+0:1](-[C:2]=[O;D1;H0:3]):[s;H0;D2;+0:10]:1 | 80 | [{"value": 80.0, "product": "CC1=CC(=NC=C1)NC=1SC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "CC1=CC(=NC=C1)NC=1SC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of (4-methylpyridin-2-yl)-thiourea (334 mg, 2 mmol), 2-bromomalonaldehyde (302 mg, 2 mmol) and sodium acetate (250 mg, 3.0 mmol) in acetic acid (5 mL) was stirred at 100° C. for 3 h. The mixture was cooled to RT and diluted with water and the precipitate formed was collected, washed with water and dried to af... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Thiourea | Aldehyde | null | c1cscn1 | c1ccncc1.c1cscn1 | HBr | O.C(C)(=O)O | 100 | 3 | Cc1ccnc(NC(N)=S)c1.O=CC(Br)C=O>O.C(C)(=O)O>Cc1ccnc(Nc2ncc(C=O)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-137bd54ea5d047a4b72c7657d212dda8 | Cc1ccnc(Nc2ncc(C=O)s2)c1.Nc1cc(C(=O)NC2CC2)c(F)cc1F>>Cc1ccnc(Nc2ncc(CNc3cc(C(=O)NC4CC4)c(F)cc3F)s2)c1 | CC1=CC(=NC=C1)NC=1SC(=CN1)C=O.NC=1C(=CC(=C(C(=O)NC2CC2)C1)F)F>>C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC=CC(=C1)C)F)F)=O | O=[CH:12][c:11]1[cH:10][n:9][c:8]([NH:7][c:6]2[n:5][cH:4][cH:3][c:2]([CH3:1])[cH:29]2)[s:28]1.[NH2:13][c:14]1[cH:15][c:16]([C:17](=[O:18])[NH:19][CH:20]2[CH2:21][CH2:22]2)[c:23]([F:24])[cH:25][c:26]1[F:27]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([CH2:12][NH:13][c:14]3[cH:15][c:16]([C:17](=[O... | Cc1ccnc(Nc2ncc(C=O)s2)c1.Nc1cc(C(=O)NC2CC2)c(F)cc1F | Cc1ccnc(Nc2ncc(CNc3cc(C(=O)NC4CC4)c(F)cc3F)s2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NC1CC1)c1cccc(NCc2cnc(Nc3ccccn3)s2)c1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | null | [] | null | null | null | null | 2-(4-Methylpyridin-2-ylamino)-thiazole-5-carbaldehyde was treated with 5-amino-N-cyclopropyl-2,4-difluorobenzamide (for preparation see Example 18) in a manner similar to Example 1 to afford the title compound. LC/MS; (M+H)+=416.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1cscn1.c1ccccc1.C1CC1 | Other | null | null | null | Cc1ccnc(Nc2ncc(C=O)s2)c1.Nc1cc(C(=O)NC2CC2)c(F)cc1F>>Cc1ccnc(Nc2ncc(CNc3cc(C(=O)NC4CC4)c(F)cc3F)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c09aa937df8b486caaee08ce9bc04f1a | Nc1cc(C(=O)NC2CC2)c(F)cc1F.O=Cc1cnc(Nc2ccccn2)s1>>O=C(NC1CC1)c1cc(NCc2cnc(Nc3ccccn3)s2)c(F)cc1F | N1=C(C=CC=C1)NC=1SC(=CN1)C=O.NC=1C(=CC(=C(C(=O)NC2CC2)C1)F)F.C(C)[SiH](CC)CC>>C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC=CC=C1)F)F)=O | [O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][c:9]([NH2:10])[c:24]([F:25])[cH:26][c:27]1[F:28].O=[CH:11][c:12]1[cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]2)[s:23]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18]... | Nc1cc(C(=O)NC2CC2)c(F)cc1F.O=Cc1cnc(Nc2ccccn2)s1 | O=C(NC1CC1)c1cc(NCc2cnc(Nc3ccccn3)s2)c(F)cc1F | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NC1CC1)c1cccc(NCc2cnc(Nc3ccccn3)s2)c1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 47.3 | [{"value": 47.0, "product": "C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC=CC=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC=CC=C1)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A mixture of 2-[pyridin-2-ylamino]-thiazole-5-carbaldehyde (41.0 mg, 0.2 mmol) and 5-amino-N-cyclopropyl-2,4-difluorobenzamide (46.6 mg, 0.22 mmol) in TFA/DCM (1:1, 1 mL) was stirred at RT for 10 min and triethylsilane (0.1 mL) was added. The mixture was stirred for 1 h, then concentrated and the residue was neutralize... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CC1.c1ccccc1.c1cscn1.c1ccncc1 | Other | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | 0.166667 | Nc1cc(C(=O)NC2CC2)c(F)cc1F.O=Cc1cnc(Nc2ccccn2)s1>C(=O)(C(F)(F)F)O.C(Cl)Cl>O=C(NC1CC1)c1cc(NCc2cnc(Nc3ccccn3)s2)c(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-446464081e0447db9f4ca083cb4217ae | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1>>CCOC(=O)c1ccc(NC(=S)NC(=O)c2ccccc2)nc1 | NC1=NC=C(C(=O)OCC)C=C1.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(NC1=NC=C(C(=O)OCC)C=C1)=S | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:22][cH:23]1.[C:11](=[S:12])=[N:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[S:12])[NH:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][cH:23]1 | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1 | CCOC(=O)c1ccc(NC(=S)NC(=O)c2ccccc2)nc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)Nc1ccccn1)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7](-[c:8])-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[S;D1;H0:11]>>[O;D1;H0:6]=[C:7](-[c:8])-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[S;D1;H0:11])-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)(=O)NC(NC1=NC=C(C(=O)OCC)C=C1)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(C1=CC=CC=C1)(=O)NC(NC1=NC=C(C(=O)OCC)C=C1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 6-amino-nicotinate (830 mg, 5 mmol) and benzoyl isothiocyanate (830 mg, 5.1 mmol) in acetone was refluxed for 2 h. The mixture was concentrated to thin slurry and methanol was added. The solid was filtered, washed with methanol and dried to afford ethyl 6-(3-benzoyl-thioureido)-nicotinate (1.35 g, 8... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccncc1.c1ccccc1 | null | CC(=O)C | null | null | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1>CC(=O)C>CCOC(=O)c1ccc(NC(=S)NC(=O)c2ccccc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1ddbc472b3f4e66b63e1ab615f44a28 | NC(=S)Nc1ccc(C(=O)O)cn1.O=CC(Br)C=O>>O=Cc1cnc(Nc2ccc(C(=O)O)cn2)s1 | N(C(=S)N)C1=NC=C(C(=O)O)C=C1.BrC(C=O)C=O.C(C)(=O)[O-].[Na+]>>C(=O)C1=CN=C(S1)NC1=NC=C(C(=O)O)C=C1 | [NH2:5][C:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][n:16]1)=[S:17].O=[CH:4][CH:3](Br)[CH:2]=[O:1]>>[O:1]=[CH:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][n:16]2)[s:17]1 | NC(=S)Nc1ccc(C(=O)O)cn1.O=CC(Br)C=O | O=Cc1cnc(Nc2ccc(C(=O)O)cn2)s1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7dca2436bf473ad25062e40b44470b498baa7e51887d9d41aefc51478f129aa7 | 89ff6b282554dec8511816adfb1d0a94512f0bd22287f34dda54fcd769a38d0d | c1ccc(Nc2nccs2)nc1 | Br-[CH;D3;+0:1](-[C:2]=[O;D1;H0:3])-[CH;D2;+0:4]=O.[#7;a:5]:[c:6]-[#7:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10]>>[#7;a:5]:[c:6]-[#7:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[cH;D2;+0:4]:[c;H0;D3;+0:1](-[C:2]=[O;D1;H0:3]):[s;H0;D2;+0:10]:1 | 96.3 | [{"value": 96.0, "product": "C(=O)C1=CN=C(S1)NC1=NC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "C(=O)C1=CN=C(S1)NC1=NC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 20 | MINUTE | A mixture of 6-thioureido-nicotinic acid (197 mg, 1 mmol), 2-bromomalonaldehyde (166 mg, 1.1 mmol) and sodium acetate (100 mg) in acetic acid (2 mL) was stirred at 100° C. for 20 min. The mixture was then cooled to RT, diluted with water and the precipitates were collected. The solid was washed with water, then methano... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Thiourea | Aldehyde | null | c1cscn1 | c1cscn1.c1ccncc1 | HBr | O.C(C)(=O)O | 100 | 0.333333 | NC(=S)Nc1ccc(C(=O)O)cn1.O=CC(Br)C=O>O.C(C)(=O)O>O=Cc1cnc(Nc2ccc(C(=O)O)cn2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dcdd4dc25d754501bcc4494e4162c584 | Nc1cc(C(=O)O)ccc1F.O=Cc1cnc(Nc2ccccn2)s1>>O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | N1=C(C=CC=C1)NC=1SC(=CN1)C=O.N1=C(C=CC=C1)NC=1SC(=CN1)C=O.NC=1C=C(C(=O)O)C=CC1F.C(C)[SiH](CC)CC>>FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([NH2:10])[cH:24]1.O=[CH:11][c:12]1[cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]2)[s:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([NH:10][CH2:11][c:12]2[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][n:22]3)[s:23... | Nc1cc(C(=O)O)ccc1F.O=Cc1cnc(Nc2ccccn2)s1 | O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(NCc2cnc(Nc3ccccn3)s2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 91.3 | [{"value": 91.0, "product": "FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a suspension of 2-(pyridin-2-ylamino)-thiazole-5-carbaldehyde (1.0 g, 4.90 mmol, compound 1A) in methylene chloride (20 mL) at RT 3-amino-4-fluorobenzoic acid (0.95 g, 4.90 mmol) TFA (5 mL) and triethylsilane (1.71 mg, 14.7 mmol) were added. The above reaction mixture was stirred at RT for 4 h, then concentrated in ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1cscn1.c1ccncc1 | Other | C(Cl)Cl | null | 4 | Nc1cc(C(=O)O)ccc1F.O=Cc1cnc(Nc2ccccn2)s1>C(Cl)Cl>O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4666dd45d7d6434b83112ed5ee7716cf | NCC1CC1.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>>O=C(NCC1CC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | CN(C)[P+](N(C)C)(N(C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1.C1(CC1)CN>>C1(CC1)CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O | [NH2:3][CH2:4][CH:5]1[CH2:6][CH2:7]1.O[C:2](=[O:1])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]2[cH:17][n:18][c:19]([NH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][n:26]3)[s:27]2)[cH:28]1>>[O:1]=[C:2]([NH:3][CH2:4][CH:5]1[CH2:6][CH2:7]1)[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]2[cH:17][n... | NCC1CC1.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | O=C(NCC1CC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | null | null | CCOC(=O)C.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC1CC1)c1cccc(NCc2cnc(Nc3ccccn3)s2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "C1(CC1)CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "C1(CC1)CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid (35 mg, 0.10 mmol) in DMF (1 mL) at RT, cyclopropylmethyl amine (14 mg 0.20 mmol) was added followed by the addition of BOP reagent (53 mg, 0.12 mmol). The above reaction mixture was stirred for 2 h, diluted with EtOAc (10 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC1.c1ccccc1.c1cscn1.c1ccncc1 | HO- | CCOC(=O)C.CN(C)C=O | null | 2 | NCC1CC1.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>CCOC(=O)C.CN(C)C=O>O=C(NCC1CC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55368fddc085434994f442da384179d4 | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1>>CCOC(=O)c1ccc(NC(N)=S)nc1 | [O-]CC.[Na+].C(C)OC(C1=CN=C(C=C1)N)=O.C(C1=CC=CC=C1)(=O)N=C=S>>C(C)OC(C1=CN=C(C=C1)NC(=S)N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:14][cH:15]1.O=C(c1ccccc1)[N:12]=[C:11]=[S:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11]([NH2:12])=[S:13])[n:14][cH:15]1 | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1 | CCOC(=O)c1ccc(NC(N)=S)nc1 | null | null | C1CCOC1.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f3d5ee7043d8a577adb0512143500efe5d39c77c08b3b6f4076866a4340782f8 | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | c1ccncc1 | O=C(-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[S;D1;H0:3])-c1:c:c:c:c:c:1.[NH2;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[S;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 77 | [{"value": 77.0, "product": "C(C)OC(C1=CN=C(C=C1)NC(=S)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C(C)OC(C1=CN=C(C=C1)NC(=S)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 16 | HOUR | A mixture of ethyl-6-amino-nicotinate (2.5 g, 15 mmol) and benzoyl isothiocyanate (2.45 g, 15 mmol) in THF (20 mL) was heated at 40° C. for 4 h. To this mixture at RT, was added sodium ethoxide (2.04 g, 30 mmol) in ethanol (10 mL). After stirring the resulting mixture at RT for 16 h, the volatiles were removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | c1ccccc1 | null | c1ccncc1 | HO- | C1CCOC1.C(C)O | 40 | 16 | CCOC(=O)c1ccc(N)nc1.O=C(N=C=S)c1ccccc1>C1CCOC1.C(C)O>CCOC(=O)c1ccc(NC(N)=S)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-462377d8589748f69115599778a6a316 | NC1CC1.O=S(=O)(Cl)c1ccc(F)cc1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F | [N+](=O)(O)[O-].OS(=O)(=O)O.FC1=CC=C(C=C1)S(=O)(=O)Cl.CCN(C(C)C)C(C)C.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C1(CC1)N>>C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)[N+](=O)[O-] | [NH2:10][CH:11]1[CH2:12][CH2:13]1.Cl[S:7]([c:6]1[cH:5][cH:4][c:16]([F:17])[cH:15][cH:14]1)(=[O:8])=[O:9].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH:11]2[CH2:12][CH2:13]2)[cH:14][cH:15][c:16]1[F:17] | NC1CC1.O=S(=O)(Cl)c1ccc(F)cc1.O=[N+]([O-])O | O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F | null | null | null | Acylation | OtherReaction | fe28fa047d6580144c1fd6bccfd9d7748f60096250347000afeb67088e0fb21a | 6ae27a13224b9908951fb5c816e381af007926604da63265bdb54d62bd2b3ca5 | O=S(=O)(NC1CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[F;D1;H0:8]):[cH;D2;+0:9]:[c:10]:1.O-[N+;H0;D3:11](-[O;-;D1;H0:12])=[O;D1;H0:13].[NH2;D1;+0:14]-[C:15]1-[C:16]-[C:17]-1>>[F;D1;H0:8]-[c:7]1:[c:6]:[c:5]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[C:15]2-[C:16]-[C:17]-2):[c:10]:... | 92 | [{"value": 92.0, "product": "C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of fuming nitric acid (8 mL) and conc. H2SO4 (16 mL), was added 4-fluorobenzenesulfonyl chloride (1.3 g, 6.7 mmol) in small portions. The mixture was stirred at RT for 2 h. and then poured onto crushed ice (60 g) and extracted with dichloromethane (2×). The organic layer was washed with brine, dried over ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Primary amine.Sulfonyl halide | Sulfonamide.Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | HCl | null | null | 2 | NC1CC1.O=S(=O)(Cl)c1ccc(F)cc1.O=[N+]([O-])O>>O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-742bd07a01d3417fa9f833046b9b7c41 | O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F>>Nc1cc(S(=O)(=O)NC2CC2)ccc1F | C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)[N+](=O)[O-]>>C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[NH:8][CH:9]2[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]1[F:15]>>[NH2:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[NH:8][CH:9]2[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]1[F:15] | O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F | Nc1cc(S(=O)(=O)NC2CC2)ccc1F | null | [Pd] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(NC1CC1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.5 | [{"value": 95.0, "product": "C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "C1(CC1)NS(=O)(=O)C1=CC(=C(C=C1)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of N-cyclopropyl-4-fluoro-3-nitrobenzenesulfonamide (520 mg, 2 mmol) and Pd/C (10%, 100 mg) in EtOH was hydrogenated (1 atm) overnight. The mixture was filtered through a short pad of celite and concentrated in vacuo to afford N-cyclopropyl-4-fluoro-3-aminobenzenesulfonamide (440 mg, 95%) as an ivory solid.... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC1 | Other | [Pd].CCO | null | null | O=[N+]([O-])c1cc(S(=O)(=O)NC2CC2)ccc1F>[Pd].CCO>Nc1cc(S(=O)(=O)NC2CC2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-998102171ea145578b3da40483685ff2 | NCC(F)(F)CN.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>>NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1.FC1=C(C=C(C(=O)O)C=C1)NCC1=CN=C(S1)NC1=NC=CC=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.FC(CN)(CN)F.CCN(C(C)C)C(C)C>>NCC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(F)F | [NH2:1][CH2:2][C:3]([F:4])([F:5])[CH2:6][NH2:7].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([NH:16][CH2:17][c:18]2[cH:19][n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][cH:27][n:28]3)[s:29]2)[cH:30]1>>[NH2:1][CH2:2][C:3]([F:4])([F:5])[CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([NH:1... | NCC(F)(F)CN.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | null | null | C1CCOC1.CN(C)C=O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(NCc2cnc(Nc3ccccn3)s2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65 | [{"value": 65.0, "product": "NCC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "NCC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a mixture of 4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid (compound 52A, 21 mg, 0.06 mmol) and HATU (38 mg, 0.1 mmol) in DMF (0.2 ml) and THF (0.4 ml), were added 2,2-difluoro-1,3-propanediamine (ref. Tetrahedron, 8617, 1994) (60 mg, 0.54 mmol) and DIPEA (26 mg, 0.2 mmol). The resulting... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cscn1.c1ccncc1 | HO- | C1CCOC1.CN(C)C=O.C(Cl)Cl | null | 18 | NCC(F)(F)CN.O=C(O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>C1CCOC1.CN(C)C=O.C(Cl)Cl>NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15517eb9e2224d3691c2bd14be7ee22b | C1=COCC1.NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>>O=C(NCC(F)(F)CN1CCOCC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].NCC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(F)F.O1CCC=C1.O=[O+][O-]>>FC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(CN1CCOCC1)F | [CH:10]1=[CH:11][O:12][CH2:13][CH2:14]1.[O:1]=[C:2]([NH:3][CH2:4][C:5]([F:6])([F:7])[CH2:8][NH2:9])[c:15]1[cH:16][cH:17][c:18]([F:19])[c:20]([NH:21][CH2:22][c:23]2[cH:24][n:25][c:26]([NH:27][c:28]3[cH:29][cH:30][cH:31][cH:32][n:33]3)[s:34]2)[cH:35]1>>[O:1]=[C:2]([NH:3][CH2:4][C:5]([F:6])([F:7])[CH2:8][N:9]1[CH2:10][CH2... | C1=COCC1.NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | O=C(NCC(F)(F)CN1CCOCC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 | null | null | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 41f6bf4ac9637dac121babd0026be2aefe2aeb3a73d13a37c9d2a42a059c056b | b4ab165450d2654d4f73a97412c3ce5b9408acf1ff05a45dc947ed5467e94717 | O=C(NCCCN1CCOCC1)c1cccc(NCc2cnc(Nc3ccccn3)s2)c1 | [#8:1]1-[C:2]-[CH2;D2;+0:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[N;H0;D3;+0:8]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[#8:1]-[C:2]-[CH2;D2;+0:3]-1 | 51.2 | [{"value": 51.0, "product": "FC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(CN1CCOCC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.2, "product": "FC(CNC(C1=CC(=C(C=C1)F)NCC1=CN=C(S1)NC1=NC=CC=C1)=O)(CN1CCOCC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of dihydrofuran (35 mg, 0.5 mmol) in MeOH (1.5 mL) was treated with ozone at −78° C. until the solution turned blue. Argon was streamed through the solution to remove excess ozone. The solution was warmed to 0° C., and N-(3-Amino-2,2-difluoro-propyl)-4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-ami... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Ether.Tertiary amine | C1=COCC1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccccc1.c1cscn1.c1ccncc1 | null | CO.C(Cl)Cl | 0 | null | C1=COCC1.NCC(F)(F)CNC(=O)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1>CO.C(Cl)Cl>O=C(NCC(F)(F)CN1CCOCC1)c1ccc(F)c(NCc2cnc(Nc3ccccn3)s2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e55bfd629be1418da8d3424c0022d3ce | CN1CCNCC1.O=C(NC1CC1)c1cc(NCc2cnc(Nc3cccc(Br)n3)s2)c(F)cc1F>>CN1CCN(c2cccc(Nc3ncc(CNc4cc(C(=O)NC5CC5)c(F)cc4F)s3)n2)CC1 | BrC1=CC=CC(=N1)NC=1SC(=CN1)CNC=1C(=CC(=C(C(=O)NC2CC2)C1)F)F.CN1CCNCC1>>C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC(=CC=C1)N1CCN(CC1)C)F)F)=O | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:34][CH2:35]1.Br[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([CH2:16][NH:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[NH:23][CH:24]4[CH2:25][CH2:26]4)[c:27]([F:28])[cH:29][c:30]3[F:31])[s:32]2)[n:33]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([N... | CN1CCNCC1.O=C(NC1CC1)c1cc(NCc2cnc(Nc3cccc(Br)n3)s2)c(F)cc1F | CN1CCN(c2cccc(Nc3ncc(CNc4cc(C(=O)NC5CC5)c(F)cc4F)s3)n2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(NC1CC1)c1cccc(NCc2cnc(Nc3cccc(N4CCNCC4)n3)s2)c1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 55 | [{"value": 55.0, "product": "C1(CC1)NC(C1=C(C=C(C(=C1)NCC1=CN=C(S1)NC1=NC(=CC=C1)N1CCN(CC1)C)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 5-{[2-(6-bromo-pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-N-cyclopropyl-2,4-difluoro-benzamide (96 mg, 0.20 mmol) in neat N-methyl piperazine (0.4 mL) was heated to 120° C. in a sealed tube for 5 h. The reaction mixture was cooled to RT, diluted with methylene chloride (5 mL), and washed with water (2×5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1.c1cscn1.c1ccccc1.C1CC1 | HBr | C(Cl)Cl | 120 | null | CN1CCNCC1.O=C(NC1CC1)c1cc(NCc2cnc(Nc3cccc(Br)n3)s2)c(F)cc1F>C(Cl)Cl>CN1CCN(c2cccc(Nc3ncc(CNc4cc(C(=O)NC5CC5)c(F)cc4F)s3)n2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3fb6b76b3db46f8b97331384f535130 | C=CCOC(=O)Nc1cn(C)c(C(=O)OCC)c1OC>>C=CCOC(=O)Nc1cn(C)c(C(=O)O)c1OC | CN1C(=C(C(=C1)NC(=O)OCC=C)OC)C(=O)OCC.[OH-].[Na+].C(C)O>>CN1C(=C(C(=C1)NC(=O)OCC=C)OC)C(=O)O | CC[O:15][C:13]([c:12]1[n:10]([CH3:11])[cH:9][c:8]([NH:7][C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[c:16]1[O:17][CH3:18])=[O:14]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10]([CH3:11])[c:12]([C:13](=[O:14])[OH:15])[c:16]1[O:17][CH3:18] | C=CCOC(=O)Nc1cn(C)c(C(=O)OCC)c1OC | C=CCOC(=O)Nc1cn(C)c(C(=O)O)c1OC | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc[nH]c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 71.5 | [{"value": 71.0, "product": "CN1C(=C(C(=C1)NC(=O)OCC=C)OC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "CN1C(=C(C(=C1)NC(=O)OCC=C)OC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | A mixture of 0.93 g (3.3 mmol) of ethyl 1-methyl-4-[(allyloxycarbonyl)amino]-3-methoxy-1H-pyrrole-2-carboxylate (prepared according to the method described in K. Narkunan, M. A. Ciufolini, Synthesis, 2000, 673–676), 3.3 ml of a 2 molar sodium hydroxide aqueous solution and 3.3 ml of ethanol is stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1 | Other | O | null | 120 | C=CCOC(=O)Nc1cn(C)c(C(=O)OCC)c1OC>O>C=CCOC(=O)Nc1cn(C)c(C(=O)O)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6cbca41f26745508b2a75aeede61ad4 | COC(=O)Nc1noc(C(=O)OC)c1OC>>COC(=O)Nc1noc(C(=O)O)c1OC | COC(=O)C1=C(C(=NO1)NC(=O)OC)OC.[OH-].[Na+].Cl>>COC(=O)NC1=NOC(=C1OC)C(=O)O | C[O:12][C:10]([c:9]1[o:8][n:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[c:13]1[O:14][CH3:15])=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][o:8][c:9]([C:10](=[O:11])[OH:12])[c:13]1[O:14][CH3:15] | COC(=O)Nc1noc(C(=O)OC)c1OC | COC(=O)Nc1noc(C(=O)O)c1OC | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cnoc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]:[#7;a:6]>>[#7;a:6]:[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 84,537.9 | [{"value": 86.0, "product": "COC(=O)NC1=NOC(=C1OC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84537.9, "product": "COC(=O)NC1=NOC(=C1OC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 1 | HOUR | A mixture of 2.50 g (0.011 mmol) of methyl-3-(methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylate (prepared according to the method described in W. Kloetzer, J. Schantz, Monatsh. Chem., 1965, 102–115) and 1.30 g of powdered sodium hydroxide dissolved in 9 ml of water is heated at 90° C. for 3 hours. After cooling, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnoc1 | Other | O | 90 | 1 | COC(=O)Nc1noc(C(=O)OC)c1OC>O>COC(=O)Nc1noc(C(=O)O)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a333f75678774bb6bf82775dc7ec01b8 | COc1cc[n+]([O-])cc1C>>COc1ccncc1C | CC=1C=[N+](C=CC1OC)[O-]>>CC=1C=NC=CC1OC | [O-][n+:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]([CH3:9])[cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[CH3:9] | COc1cc[n+]([O-])cc1C | COc1ccncc1C | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | 8660dc08f9c4d3b8c6814ee1b12714454b2bd6ddbe4d55cbaaeb274a83637cea | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccncc1 | [O-]-[n+;H0;D3:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[n;H0;D2;+0:1]:[c:4]:[c:5] | 90.2 | [{"value": 90.0, "product": "CC=1C=NC=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "CC=1C=NC=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4 g (28.8 mmol) 3-methyl-4-methoxy pyridine N-oxide (prepared according to the method described in Kohl, Bernhard et al; J. Med. Chem.; 1992; 1049–1057) and 1.1 mg of 5% palladium on charcoal in 50 ml of methanol is hydrogenated at 20 atms at room temperature for 12 hours (2*6 hours). Filtration through ce... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | Other | [Pd].CO | null | null | COc1cc[n+]([O-])cc1C>[Pd].CO>COc1ccncc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-082f5c4b45dc497e883bc6aabeb2e2b5 | COc1ccncc1C.O=[N+]([O-])O>>COc1c(C)cncc1[N+](=O)[O-] | [N+](=O)(O)[O-].CC=1C=NC=CC1OC.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[K+].[K+]>>CC=1C=NC=C(C1OC)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][cH:9]1.O=[N+:10]([OH:11])[O-:12]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12] | COc1ccncc1C.O=[N+]([O-])O | COc1c(C)cncc1[N+](=O)[O-] | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | cb3ba0bb7f4ff246f608a5c967bfb512792a47826af0eb60d49c2f2aea6e8ead | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccncc1 | O=[N+;H0;D3:1](-[O;-;D1;H0:2])-[OH;D1;+0:3].[#8:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[cH;D2;+0:10]:1>>[#8:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c;H0;D3;+0:10]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;H0;D1;+0:3] | 30 | [{"value": 30.0, "product": "CC=1C=NC=C(C1OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 30 ml of 100% nitric acid is added to 150 ml of 98% sulphuric acid with stirring and cooling. To this solution is added dropwise 3.2 g (26 mmol) of 3-methyl-4-methoxy pyridine. The mixture is stirred at 80° C. for 2.5 hours, cooled down and added cautiously to a mixture of 400 g of crushed ice and 300 g of potassium ca... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | null | COc1ccncc1C.O=[N+]([O-])O>S(O)(O)(=O)=O>COc1c(C)cncc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50f3cbc31d9d4e928a22ec21cd756ab4 | Cc1cc(=O)c(C(=O)O)c(C)o1.N>>Cc1cc(O)c(C(=O)O)c(C)n1 | CC=1OC(=CC(C1C(=O)O)=O)C.N>>CC1=C(C(=O)O)C(=CC(=N1)C)O | o1[c:2]([CH3:1])[cH:3][c:4](=[O:5])[c:6]([C:7](=[O:8])[OH:9])[c:10]1[CH3:11].[NH3:12]>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[c:10]([CH3:11])[n:12]1 | Cc1cc(=O)c(C(=O)O)c(C)o1.N | Cc1cc(O)c(C(=O)O)c(C)n1 | null | null | Cl | Miscellaneous | OtherReaction | 7f06c5731034c550730d18c134b1d257487952bd0129e807a2d0f0cb7bba2f39 | 6dd67d2d062ecf3a4bfbb86c40e45739a873f777b0585faa974e3874e3a0b559 | c1ccncc1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:o:[c;H0;D3;+0:3](-[C;D1;H3:4]):[c:5]:[c;H0;D3;+0:6](=[O;H0;D1;+0:7]):[c:8]:1-[C:9](=[O;D1;H0:10])-[O;D1;H1:11].[NH3;D0;+0:12]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:3](-[C;D1;H3:4]):[c:5]:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c:8]:1-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | 69 | [{"value": 69.0, "product": "CC1=C(C(=O)O)C(=CC(=N1)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 10 g (59.5 mmol) of 2,6-dimethyl-4-oxo-4H-pyran-3-carboxylic acid (prepared according to the method described in Collie, J. Chem. Soc.; 1907; 787) is stirred in 100 ml of 28% aqueous ammonia at room temperature overnight. The residue is diluted with little aqueous HCl, and the solid is filtered off. There is obtained 6... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic alcohol | c1cccoc1 | c1ccncc1 | c1ccncc1 | HO- | Cl | null | null | Cc1cc(=O)c(C(=O)O)c(C)o1.N>Cl>Cc1cc(O)c(C(=O)O)c(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72534ca11d814b16ab1a292f213777db | Cc1cc(O)c(C(=O)O)c(C)n1.O=[N+]([O-])O>>Cc1nc(C)c([N+](=O)[O-])c(O)c1C(=O)O | [N+](=O)(O)[O-].CC1=C(C(=O)O)C(=CC(=N1)C)O>>CC1=C(C(=O)O)C(=C(C(=N1)C)[N+](=O)[O-])O | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[cH:6][c:10]([OH:11])[c:12]1[C:13](=[O:14])[OH:15].O[N+:7](=[O:8])[O-:9]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([OH:11])[c:12]1[C:13](=[O:14])[OH:15] | Cc1cc(O)c(C(=O)O)c(C)n1.O=[N+]([O-])O | Cc1nc(C)c([N+](=O)[O-])c(O)c1C(=O)O | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | cb3ba0bb7f4ff246f608a5c967bfb512792a47826af0eb60d49c2f2aea6e8ead | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccncc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]):[c:12](-[O;D1;H1:13]):[cH;D2;+0:14]:1>>[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]):[c:12](-[O;D1;H1:13]):[c;H0;D3;+0:14]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | 77 | [{"value": 77.0, "product": "CC1=C(C(=O)O)C(=C(C(=N1)C)[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 20 ml of 90% nitric acid is added to 100 ml of 98% sulphuric acid with stirring and cooling. To this solution is added portion-wise 6.9 g (41.1 mmol) of 2,6-dimethyl-4-hydroxy-nicotinic acid. The mixture is stirred at 80° C. for 1 hour, cooled down and added cautiously 300 g of crushed ice. The resulting suspension is ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | null | Cc1cc(O)c(C(=O)O)c(C)n1.O=[N+]([O-])O>S(O)(O)(=O)=O>Cc1nc(C)c([N+](=O)[O-])c(O)c1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4a9dca21e40463ab3e70a50648798e9 | COC(=O)c1c[nH]cc(C(=O)OC)c1=O.O=S(Cl)Cl>>COC(=O)c1cncc(C(=O)OC)c1Cl | COC(=O)C1=CNC=C(C1=O)C(=O)OC.CN(C)C=O.S(=O)(Cl)Cl>>COC(C1=CN=CC(=C1Cl)C(=O)OC)=O | O=[c:14]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][nH:7][cH:8][c:9]1[C:10](=[O:11])[O:12][CH3:13].O=S(Cl)[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]1[Cl:15] | COC(=O)c1c[nH]cc(C(=O)OC)c1=O.O=S(Cl)Cl | COC(=O)c1cncc(C(=O)OC)c1Cl | null | null | null | Functional Group Interconversion | OtherReaction | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]):[c:8]:[nH;D2;+0:9]:[c:10]:[c:11]:1-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C;D1;H3:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[c:11]1:[c:10]:[n;H0;D2;+0:9]:[c:8]:[c:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]):[c;H0;D3;+0:2]:1-[Cl;H0;D... | 41 | [{"value": 41.0, "product": "COC(C1=CN=CC(=C1Cl)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 16.38 g (77.6 mmol) of 4-oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester (prepared according to the method described in S. Zupancic, Heterocycles; 2000; 2033–2042) and 0.5 ml of DMF in 150 ml of thionyl chloride is heated at reflux for 2 hours. Excess thionyl chloride is removed under vacuum ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | null | null | null | COC(=O)c1c[nH]cc(C(=O)OC)c1=O.O=S(Cl)Cl>>COC(=O)c1cncc(C(=O)OC)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a45cdf4188e45cba8817e064590da3d | COC(=O)c1cncc(C(=O)OC)c1Cl.C[O-]>>COC(=O)c1cncc(C(=O)OC)c1OC | COC(C1=CN=CC(=C1Cl)C(=O)OC)=O.C[O-].[Na+]>>COC(C1=CN=CC(=C1OC)C(=O)OC)=O | Cl[c:14]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][n:7][cH:8][c:9]1[C:10](=[O:11])[O:12][CH3:13].[O-:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]1[O:15][CH3:16] | COC(=O)c1cncc(C(=O)OC)c1Cl.C[O-] | COC(=O)c1cncc(C(=O)OC)c1OC | null | null | CO.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 600484490705932a09b3fac6538a42c6f3fc156ab44a4ea0bbd020dd3eafd6ff | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c:7]:[#7;a:8]:[c:9]:[c:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14].[C;D1;H3:15]-[O-;H0;D1:16]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c:10]1:[c:9]:[#7;a:8]:[c:7]:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:16]-[... | null | [] | null | null | 10 | MINUTE | To a solution of 6.3 g (27.5 mmol) of methyl-4-chloro-5-methoxycarbonyl-nicotinate in 100 ml of THF is added 6.48 ml (35 mmol) of a 5.4 m solution of sodium methoxide in methanol. The mixture is stirred for 10 minutes and evaporated. 100 ml of a 0.25M aqueous HCl is added to the residue. The solution is made basic with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CO.C1CCOC1 | null | 0.166667 | COC(=O)c1cncc(C(=O)OC)c1Cl.C[O-]>CO.C1CCOC1>COC(=O)c1cncc(C(=O)OC)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e8c5e49e9bb4710b4cc40f382d88cd5 | COC(=O)c1cncc(C(=O)OC)c1OC>>COC(=O)c1cncc(C(=O)O)c1OC | [OH-].[Na+].COC(C1=CN=CC(=C1OC)C(=O)OC)=O>>COC1=C(C=NC=C1C(=O)O)C(=O)OC | C[O:12][C:10]([c:9]1[cH:8][n:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:13]1[O:14][CH3:15])=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13]1[O:14][CH3:15] | COC(=O)c1cncc(C(=O)OC)c1OC | COC(=O)c1cncc(C(=O)O)c1OC | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 57 | [{"value": 57.0, "product": "COC1=C(C=NC=C1C(=O)O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.0, "product": "COC1=C(C=NC=C1C(=O)O)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5,3 g (23.5 mmol) of methyl-4-methoxy-5-methoxycarbonyl-nicotinate in 150 ml of methanol and 50 m. of water is added a solution of 0.94 g (23,5 mmol) of sodium hydroxide in 10 ml of water. The resulting mixture is stirred at room temperature overnight. The methanol is removed under vacuum, the aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | CO.O | null | 8 | COC(=O)c1cncc(C(=O)OC)c1OC>CO.O>COC(=O)c1cncc(C(=O)O)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-422e54a7b8534818a58e13cc907fb18e | O=Cc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1>>N#Cc1ccc(Oc2ccc(Cl)c(Cl)c2)c(C=O)c1 | BrC=1C=CC(=C(C=O)C1)OC1=CC(=C(C=C1)Cl)Cl.CN(C)C=O>>C(#N)C=1C=CC(=C(C=O)C1)OC1=CC(=C(C=C1)Cl)Cl | Br[c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]2)[c:16]([CH:17]=[O:18])[cH:19]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]2)[c:16]([CH:17]=[O:18])[cH:19]1 | O=Cc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1 | N#Cc1ccc(Oc2ccc(Cl)c(Cl)c2)c(C=O)c1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(Oc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7]>>[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7] | null | [] | null | null | null | null | Under N2 in a flame-dried 3-neck round bottomed flask fitted with a reflux condenser and magnetic stirrer, a mixture of 5-bromo-2-(3,4-dichlorophenoxy)-benzaldehyde (3.0 g, 8.7 mmol), zinc (II) cyanide (1.5 g, 13 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.5 g, 1.3 mmol) in anhydrous DMF (145 ml) was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | O=Cc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>N#Cc1ccc(Oc2ccc(Cl)c(Cl)c2)c(C=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cea5963e61c54fcea99b57a43cf1be79 | COc1ccc(F)cc1OC>>COc1cc(F)c(C=O)cc1OC | FC=1C=C(C(=CC1)OC)OC.COC(Cl)Cl>>COC1=CC(=C(C=O)C=C1OC)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:10][c:11]1[O:12][CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1[O:12][CH3:13] | COc1ccc(F)cc1OC | COc1cc(F)c(C=O)cc1OC | null | [Ti](Cl)(Cl)(Cl)Cl | C(Cl)Cl | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | null | [] | 0 | CELSIUS | null | null | In a flame-dried, round-bottomed flask fitted with a magnetic stirrer and N2 inlet was placed 4-fluoroveratrole (0.78 g, 5.0 mmol, Aldrich Chemical Co.) in 20 ml of anhydrous CH2Cl2. After cooling to 0° C., titanium (IV) chloride (0.91 ml, 1.57 g, 8.3 mmol) was added, followed after 10 min. by a,a-dichloromethyl methyl... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl | 0 | null | COc1ccc(F)cc1OC>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>COc1cc(F)c(C=O)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46b34f726ee24169b4da1dd46149cf32 | N#Cc1cc(F)ccc1F.Oc1ccc(Cl)c(Cl)c1>>N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | ClC=1C=C(C=CC1Cl)O.C([O-])([O-])=O.[K+].[K+].FC1=C(C#N)C=C(C=C1)F>>ClC=1C=C(OC2=C(C#N)C=C(C=C2)F)C=CC1Cl | F[c:9]1[c:3]([C:2]#[N:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1.[OH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1 | N#Cc1cc(F)ccc1F.Oc1ccc(Cl)c(Cl)c1 | N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:2]:[c:3] | null | [] | 105 | CELSIUS | null | null | A flame-dried flask containing N2 inlet and magnetic stirrer was charged with 2.9 g (18 mmol) of 3,4-dichlorophenol, 6.2 g (45 mmol) of potassium carbonate and 50 mL of anhydrous DMF. With stirring, 2.08 g (15 mmol) of 2,5-difluorobenzonitrile (Aldrich Chem. Co.) was added and the mixture was heated overnight at 105° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C)C=O | 105 | null | N#Cc1cc(F)ccc1F.Oc1ccc(Cl)c(Cl)c1>CN(C)C=O>N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa247d297f624cf2b98f0abe5ea5ce3a | O=C(O)c1cc(F)ccc1I.Oc1ccc(Cl)c(Cl)c1>>O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | C([O-])([O-])=O.[Cs+].[Cs+].FC=1C=CC(=C(C(=O)O)C1)I.FC=1C=CC(=C(C(=O)O)C1)I.Cl.ClC=1C=C(C=CC1Cl)O>>ClC=1C=C(OC2=C(C(=O)O)C=C(C=C2)F)C=CC1Cl | I[c:10]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6]([F:7])[cH:8][cH:9]1.[OH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1 | O=C(O)c1cc(F)ccc1I.Oc1ccc(Cl)c(Cl)c1 | O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | null | FC(S(=O)(=O)[O-])(F)F.[Cu+2].FC(S(=O)(=O)[O-])(F)F | CCOC(=O)C.O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | null | [] | null | null | 5 | MINUTE | Under N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer were placed 6.37 g (19.55 mmol) of cesium carbonate and 3.2 g (19.55 mmol) of 3,4-dichlorophenol (both from Aldrich Chem. Co., Milwaukee, Wis.) in 60 mL of anhydrous toluene. After stirring the mixture for 5 min., 89 mg (0.24 mmol) o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | FC(S(=O)(=O)[O-])(F)F.[Cu+2].FC(S(=O)(=O)[O-])(F)F.CCOC(=O)C.O.C1(=CC=CC=C1)C | null | 0.083333 | O=C(O)c1cc(F)ccc1I.Oc1ccc(Cl)c(Cl)c1>FC(S(=O)(=O)[O-])(F)F.[Cu+2].FC(S(=O)(=O)[O-])(F)F.CCOC(=O)C.O.C1(=CC=CC=C1)C>O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3006829c64043e1abcf88cb05d868f9 | O=Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>>O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | ClC=1C=C(OC2=C(C=O)C=C(C=C2)F)C=CC1Cl.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>ClC=1C=C(OC2=C(C(=O)O)C=C(C=C2)F)C=CC1Cl | [O:1]=[CH:2][c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1 | O=Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | null | null | CC(=O)C | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | c1ccc(Oc2ccccc2)cc1 | [O;D1;H0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[O;D1;H1:6])-[c:3](:[c:4]):[c:5] | null | [] | 25 | CELSIUS | 1 | HOUR | Alternatively, a solution of 4.28 g (15 mmol) of 2-(3,4-dichloro-phenoxy)-5-fluorobenzaldehyde (Preparation no. 5) in 25 mL of acetone was cooled to 5–10° C. and treated via syringe with 5.8 mL (15.6 mmol) of 2.67 M Jones reagent*. After 1 hr at this temperature, the reaction was quenched with 8 mL of isopropanol, allo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CC(=O)C | 25 | 1 | O=Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>CC(=O)C>O=C(O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6742d79d77984fc691d8b3b1f13cd6df | CNC(=O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>>CNCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | ClC=1C=C(OC2=C(C(=O)NC)C=C(C=C2)F)C=CC1Cl>>ClC=1C=C(OC2=C(CNC)C=C(C=C2)F)C=CC1Cl | O=[C:3]([NH:2][CH3:1])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1 | CNC(=O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | CNCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(Oc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:3]-[#7:2]-[CH2;D2;+0:1]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Under N2, a mixture of 0.313g (1.0 mmol) of 2-(3,4-dichlorophenoxy)-5-fluoro-N-methyl benzamide in 5.0 mL of anhydrous tetrahydrofuran (THF) was treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M BH3 in THF (Aldrich Chem. Co.). and the mixture was heated to reflux for a total of 48 hr. The reaction was quenched by the... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | null | CNC(=O)c1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>O1CCCC1>CNCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ab977e35bee4c779b1417e43a933a78 | N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>>NCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | ClC=1C=C(OC2=C(C#N)C=C(C=C2)F)C=CC1Cl>>ClC=1C=C(OC2=C(CN)C=C(C=C2)F)C=CC1Cl | [N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[NH2:1][CH2:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1 | N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | NCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(Oc2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A flame-dried flask containing N2 inlet and magnetic stirrer was charged with 3.0 mL of 2.0 M borane methyl sulfide complex in THF (6.0 mmol, Aldrich Chem. Co.), followed by an additional 10 mL of anhydrous THF at room temperature. While stirring, 0.562 g (2.0 mmol) of 2-(3,4-dichlorophenoxy)-5-fluoro-benzonitrile (tit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | null | N#Cc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1>C1CCOC1>NCc1cc(F)ccc1Oc1ccc(Cl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d441d990f8a04c2088accbd3027bf473 | COc1ccccc1O.O=C(Cl)Cl>>COc1ccccc1OC(=O)Cl | COC1=C(C=CC=C1)O.CN(C1=CC=CC=C1)C.C(=O)(Cl)Cl.CN(C)C=O>>ClC(=O)OC1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].Cl[C:10](=[O:11])[Cl:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][C:10](=[O:11])[Cl:12] | COc1ccccc1O.O=C(Cl)Cl | COc1ccccc1OC(=O)Cl | null | null | ClC1=CC=CC=C1.C1(=CC=CC=C1)C | Acylation | Schotten-Baumann to ester | d7df561744c5e12a4c33bd41e504e10e21081938decb9a35cb2c144bb7567959 | a1901b75cf036b519179815322102c350ea735396706569df72d320157c257c6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 50 | [{"value": 50.0, "product": "ClC(=O)OC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methoxyphenol (2 g, 16.1 mmol), N,N-dimethylaniline (1.95 g, 16.1 mmol), phosgene (8.34 mL of a 1.93 M solution in toluene, 16.1 mmol) and a catalytic amount of DMF in chlorobenzene (5 mL) was stirred in a pressure tube for 2 h at 80° C. The organic layer was separated and concentrated in vacuo. The res... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic alcohol | Acyl halide.Ether | null | null | c1ccccc1 | HCl | ClC1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | COc1ccccc1O.O=C(Cl)Cl>ClC1=CC=CC=C1.C1(=CC=CC=C1)C>COc1ccccc1OC(=O)Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3378496704a04e2a9685d0d6d1f3e5fe | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)c([N+](=O)[O-])c1>>NS(=O)(=O)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | S(=O)(=O)(Cl)Cl.N1=CC=CC=C1.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])S(=O)(=O)Cl.C(=O)(C(F)(F)F)O>>[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])S(=O)(=O)N | Cl[S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)c([N+](=O)[O-])c1 | NS(=O)(=O)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | C1CCOC1.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 76fbc3582e2f63736dd65176b79ffad31881adfa34415872457e21307ad3c8dc | 8d9fe3486c870d18f12e4e21ee2410d7c9641745d38b34bc61fa11f384cef528 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[N;D1;H2:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 15 | HOUR | A solution of Part A compound (1.01 g, 2.37 mmol) and TFA (8 mL) in CH2Cl2 (30 mL) was stirred at RT for 4.5 h. The solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 and filtered through a pad of solid K2CO3. The filtrate was concentrated in vacuo to give the corresponding crude amine. To a so... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | null | C1CCOC1.C(Cl)Cl | null | 15 | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)c([N+](=O)[O-])c1>C1CCOC1.C(Cl)Cl>NS(=O)(=O)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b4e7c8c64764d9385bb00888530814d | COc1ccc(C)c(N)c1>>COc1ccc(C)c(F)c1 | N(=O)[O-].[Na+].COC=1C=CC(=C(N)C1)C.Cl.[H+].[B-](F)(F)(F)F>>FC=1C=C(C=CC1C)OC | N[c:8]1[c:6]([CH3:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:8]([F:9])[cH:10]1 | COc1ccc(C)c(N)c1 | COc1ccc(C)c(F)c1 | null | null | O | Functional Group Interconversion | Primary amine to fluoride | f4fea6a3c7b007f3829d29d893f3499a4094808c0f3b2211f4c3483919a690d8 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[F;D1;H0:7]):[c:2]:[c:3] | 31 | [{"value": 31.0, "product": "FC=1C=C(C=CC1C)OC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A mixture of 5-methoxy-2-methyl aniline (5.0 g; 36 mmol), HCl (7.6 mL of a 12 M solution; 91 mmol) and H2O (11 mL) was heated at 60° C. for 15 min until complete dissolution had occurred. The reaction was cooled to 0° C. and an aqueous solution of NaNO2 (2.5 g; 36 mmol) was added dropwise (internal temperature ≦7° C.).... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | 0 | 0.333333 | COc1ccc(C)c(N)c1>O>COc1ccc(C)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be3ba95f315f4cc39d451cc115a70d5d | COc1ccc(C)c(F)c1>>Cc1ccc(O)cc1F | FC=1C=C(C=CC1C)OC.B(Br)(Br)Br>>FC=1C=C(C=CC1C)O | C[O:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([F:9])[cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[F:9] | COc1ccc(C)c(F)c1 | Cc1ccc(O)cc1F | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75.2 | [{"value": 75.0, "product": "FC=1C=C(C=CC1C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "FC=1C=C(C=CC1C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 10 | MINUTE | To a −70° C. solution of 3-fluoro-4-methyl anisole (1.62 g; 11.6 mmol) in CH2Cl2 (10 mL) was added dropwise BBr3 (10 mL; 12 mmol). The reaction mixture was stirred at −70° C. for 10 min, then allowed to warm to 0° C. and stirred at 0° C. for 2 h. The reaction was allowed to warm to RT and concentrated in vacuo and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | -70 | 0.166667 | COc1ccc(C)c(F)c1>C(Cl)Cl>Cc1ccc(O)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03e350e0a3fc454085162cb70907dbec | Cc1ccc(N)cc1Br>>Cc1ccc(O)cc1Br | N(=O)[O-].[Na+].BrC=1C=C(N)C=CC1C.OS(=O)(=O)O>>BrC=1C=C(C=CC1C)O | N[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([Br:9])[cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[Br:9] | Cc1ccc(N)cc1Br | Cc1ccc(O)cc1Br | null | null | O | Functional Group Interconversion | OtherReaction | 5476e3e4f8e8862ba087972a35863ca0b6ebf27577a68b3ac2018e9a7004c864 | ed7617b9cd113fcbf3232da782e35483fef55189a64648ab4bdbc41767cd9a80 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 34 | [{"value": 34.0, "product": "BrC=1C=C(C=CC1C)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a 0° C. mixture of 3-bromo-4-methyl aniline (5 g; 27 mmol) and H2SO4 (5.5 mL of a 16 M solution) in H2O (7.5 mL) was added dropwise a solution of aqueous NaNO2 (1.93 g; 28 mmol in 7.5 mL H2O). The reaction was stirred at 0° C. for 30 min, then was heated at 50° C. for 2 h, then was cooled to RT and extracted with Et... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | 0 | 0.5 | Cc1ccc(N)cc1Br>O>Cc1ccc(O)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e28654bbf10d4c98af4bbd8e07de6718 | COc1ccc(N)cc1Cl>>COc1ccc(O)cc1Cl | ClC=1C=C(N)C=CC1OC.OS(=O)(=O)O.N(=O)[O-].[Na+]>>ClC=1C=C(C=CC1OC)O | N[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]([Cl:10])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[Cl:10] | COc1ccc(N)cc1Cl | COc1ccc(O)cc1Cl | null | null | O | Functional Group Interconversion | OtherReaction | 5476e3e4f8e8862ba087972a35863ca0b6ebf27577a68b3ac2018e9a7004c864 | ed7617b9cd113fcbf3232da782e35483fef55189a64648ab4bdbc41767cd9a80 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 30 | [{"value": 30.0, "product": "ClC=1C=C(C=CC1OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 0° C. solution of 3-chloro-4-methoxy aniline (1.0 g; 6.4 mmol) in 1:1 H2O:conc. H2SO4 (100 mL) was added very slowly a solution of NaNO2 (0.5 g; 7.6 mmol) in H2O (10 mL). Thick yellow fumes were emitted, and the black solution was then heated to reflux for 30 min. The mixture was extracted with EtOAc (4×50 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | null | null | COc1ccc(N)cc1Cl>O>COc1ccc(O)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a38c84e2ef9f48209dd841a26f28b318 | COc1ccc(C(C)=O)cc1F>>COc1ccc(O)cc1F | FC=1C=C(C=CC1OC)C(C)=O.ClC1=CC(=CC=C1)C(=O)OO.O[Li].O.O>>FC=1C=C(C=CC1OC)O | CC(=O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]([F:10])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[F:10] | COc1ccc(C(C)=O)cc1F | COc1ccc(O)cc1F | null | null | CO.C(Cl)Cl | Miscellaneous | OtherReaction | f22418696d888ed4a416b794e7f8ce83eabcab0b82ac566511aba78020aafa9b | 90cbc93f90c6cebb3b72cd095340683bd11073d8d0096986acad0977f99a5f52 | c1ccccc1 | C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 72.7 | [{"value": 72.0, "product": "FC=1C=C(C=CC1OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.7, "product": "FC=1C=C(C=CC1OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3′-fluoro-4′-methoxyacetophenone (10 g; 59 mmol) and m-chloroperbenzoic acid (50% purity; 30 g; 89 mmol) in CH2Cl2 (300 mL) was stirred at RT overnight. The solution was washed with saturated aqueous Na2CO3, then filtered through a pad of SiO2 (CH2Cl2 as eluent) and finally chromatographed (SiO2; hex:EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CO.C(Cl)Cl | null | null | COc1ccc(C(C)=O)cc1F>CO.C(Cl)Cl>COc1ccc(O)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1defd81fa024523893967969113599f | CCOC(=O)C1CCN(c2ccccn2)CC1>>O=C(O)C1CCN(c2ccccn2)CC1 | [OH-].[Na+].C(C)OC(=O)C1CCN(CC1)C1=NC=CC=C1>>N1(CCC(CC1)C(=O)O)C1=NC=CC=C1 | CC[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[CH2:14][CH2:15]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[CH2:14][CH2:15]1 | CCOC(=O)C1CCN(c2ccccn2)CC1 | O=C(O)C1CCN(c2ccccn2)CC1 | null | null | O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(N2CCCCC2)nc1 | 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] | 89.3 | [{"value": 89.3, "product": "N1(CCC(CC1)C(=O)O)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | Sodium hydroxide solution (5M, 24.8 ml, 0.12 mol) was added drop wise to a solution of 3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl-4-carboxylic acid ethyl ester (5.8 g, 24 mmol)(see reference Farmaco, 1993, 48(10), 1439) in 1,4-dioxane (100 ml). The mixture was stirred at room temperature for 72 hours and then evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccncc1 | Other | O1CCOCC1 | null | 72 | CCOC(=O)C1CCN(c2ccccn2)CC1>O1CCOCC1>O=C(O)C1CCN(c2ccccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e299013dbfd48c1bf2a6e7afd13ee69 | CCCC(=O)NN.O=C(O)C1CCN(c2ncccn2)CC1>>CCCC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 | O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C.C(CCC)(=O)NN.N1=C(N=CC=C1)N1CCC(CC1)C(=O)O>>C(CCC)(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=N1 | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][NH2:7].O[C:8](=[O:9])[CH:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][cH:16][cH:17][cH:18][n:19]2)[CH2:20][CH2:21]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][NH:7][C:8](=[O:9])[CH:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][cH:16][cH:17][cH:18][n:19]2)[CH2:20][CH2:21]1 | CCCC(=O)NN.O=C(O)C1CCN(c2ncccn2)CC1 | CCCC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 | null | null | ClCCl.C(O)([O-])=O.[Na+] | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | c1cnc(N2CCCCC2)nc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[NH2;D1;+0:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[#7:9]-[C:7](-[C:6])=[O;D1;H0:8])-[C:5] | 62 | [{"value": 62.0, "product": "C(CCC)(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 1-pyrimidin-2-yl-piperidine-4-carboxylic acid (3.0 g, 14.5 mmol)(see reference U.S. Pat. No. 4,826,843), 1-hydroxybenzotriazole hydrate (1.96 g, 14.5 mmol) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (2.78 g, 14.5 mmol) in dichloromethane (100 ml) was stirred for 10 minutes. Butyric acid... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | C1CC[NH]CC1.c1cncnc1 | HO- | ClCCl.C(O)([O-])=O.[Na+] | null | 18 | CCCC(=O)NN.O=C(O)C1CCN(c2ncccn2)CC1>ClCCl.C(O)([O-])=O.[Na+]>CCCC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ada1b54a83b344aea2f34e86236cf6ac | CCCCC(=O)NN.CN1CCCC1=O>>CCCCC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 | C(C(=O)Cl)(=O)Cl.C(CCCC)(=O)NN.CN1C(CCC1)=O.Cl>>C(CCCC)(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][NH2:8].[C:9]1(=[O:10])[CH2:11][CH2:12][CH2:13][N:14]1[CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][NH:8][C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[CH2:21][CH2:22]1 | CCCCC(=O)NN.CN1CCCC1=O | CCCCC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 | null | CN(C=O)C | ClCCl.O | Aromatic Heterocycle Formation | OtherReaction | 330243bedeb882e5b85e2ef349bf62a4a21e3be603b110a86ce9e72ac3a0cfa7 | b7ce3bfffaf245fc7d46fae4b46eeee8d5c3b068244c209a1a8a20461e9a0594 | c1ccc(N2CCCCC2)nc1 | [CH3;D1;+0:1]-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6]-1=[O;D1;H0:7].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH2;D1;+0:12]>>[#7;a:13]:[c:14](-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[CH;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:12]-[#7:11]-[C:9](-[C:8])=[O;D1;H0:10])-[C:15]-[CH2;D2;+0:1]-1):[c:16] | 30.6 | [{"value": 30.6, "product": "C(CCCC)(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The carboxylic acid from Preparation 1 (1.5 g, 7.3 mmol) was suspended in dichloromethane (40 ml) containing N,N-dimethylformamide (2 drops) and oxalyl chloride (1.27 ml, 14 mmol) in dichloromethane (5 ml) was added drop wise. The mixture was stirred for 5 hours at room temperature and then was evaporated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Tertiary amide | Acylhydrazine.Acylhydrazine.Tertiary amine | C1CC[NH]C1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | Other | CN(C=O)C.ClCCl.O | null | 5 | CCCCC(=O)NN.CN1CCCC1=O>CN(C=O)C.ClCCl.O>CCCCC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c0cc20436e440c9a6f5ae1c9ddc1270 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O=C(O)C1CCN(c2ncccn2)CC1.On1nnc2ccccc21>>CC(C)CC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 | C(C)(C)N(CC)C(C)C.N1=C(N=CC=C1)N1CCC(CC1)C(=O)O.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>CC(CC(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=N1)C | CC(C)N(C(C)C)[CH2:2][CH3:1].CN(CCC[N:7]=[C:5]=NC[CH3:4])[CH3:3].[OH:6][C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][cH:17][cH:18][cH:19][n:20]2)[CH2:21][CH2:22]1.On1c2ccccc2n[n:8]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][NH:8][C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][cH:17][cH:18... | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O=C(O)C1CCN(c2ncccn2)CC1.On1nnc2ccccc21 | CC(C)CC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 | null | null | ClCCl | Acylation | OtherReaction | 215ca6adcf50fabf1ca73f61d1a1b65921eff27cca25fa153ceac7404d74a695 | f39112c84b19a65b244b986e038cda736ca182c10c46675a2c8c606dc5dd70b2 | c1cnc(N2CCCCC2)nc1 | C-C(-C)-N(-[CH2;D2;+0:1]-[C;D1;H3:2])-C(-C)-C.C-N(-[CH3;D1;+0:3])-C-C-C-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=N-C-[CH3;D1;+0:6].O-n1:[n;H0;D2;+0:7]:n:c2:c:c:c:c:c:2:1.[C:8]-[C:9](-[C;H0;D3;+0:10](=[O;D1;H0:11])-[OH;D1;+0:12])-[C:13]>>[C:8]-[C:9](-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:7]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1... | 46.4 | [{"value": 46.4, "product": "CC(CC(=O)NNC(=O)C1CCN(CC1)C1=NC=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | The residue was added to a mixture of 1-pyrimidin-2-yl-piperidine-4-carboxylic acid (6.6 g, 31.7 mmol) (see reference U.S. Pat. No. 4,826,843), 1-hydroxybenzotriazole hydrate (4.28 g, 31.7 mmol) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (6.09 g, 31.7 mmol) in dichloromethane (50 ml). Diisopropyleth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine.Tertiary amine | Acylhydrazine.Acylhydrazine | c1ccc2[nH]nnc2c1 | null | C1CC[NH]CC1.c1cncnc1 | HO- | ClCCl | null | 72 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O=C(O)C1CCN(c2ncccn2)CC1.On1nnc2ccccc21>ClCCl>CC(C)CC(=O)NNC(=O)C1CCN(c2ncccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6db3128a3104baab6ac26020f6aaa80 | Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)o1.NCc1ccccc1>>Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)n1Cc1ccccc1 | C(C)(C)(C)OC(=O)N1CCC(CC1)C=1OC(=NN1)C.C(C1=CC=CC=C1)N.C(C1=CC=CC=C1)N>>C(C)(C)(C)OC(=O)N1CCC(CC1)C1=NN=C(N1CC1=CC=CC=C1)C | o1[c:2]([CH3:1])[n:3][n:4][c:5]1[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1.[NH2:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][c:2]1[n:3][n:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:1... | Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)o1.NCc1ccccc1 | Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)n1Cc1ccccc1 | null | [Cl-].[Mg+2].[Cl-] | null | Miscellaneous | OtherReaction | 06fefb205a4853de5c4e4a339b564c57a94b95a37d2e8ba13cde385235751498 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(Cn2cnnc2C2CCNCC2)cc1 | [C:1]-[C:2](-[c;H0;D3;+0:3]1:[#7;a:4]:[#7;a:5]:[c;H0;D3;+0:6](-[C;D1;H3:7]):o:1)-[C:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[C:1]-[C:2](-[c;H0;D3;+0:3]1:[#7;a:4]:[#7;a:5]:[c;H0;D3;+0:6](-[C;D1;H3:7]):[n;H0;D3;+0:9]:1-[C:10]-[c:11])-[C:8] | 70.4 | [{"value": 70.4, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C1=NN=C(N1CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 4-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (5 g, 18.7 mmol) (see reference WO 0039125), benzylamine (2.5 ml, 22 mmol) and magnesium chloride (100 mg) were heated at 150° C. for 1 hour, a further quantity of benzylamine (2.5 ml, 22 mmol) was added and the mixture was heated at 150° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nnco1 | c1nc[nH]n1 | c1nc[nH]n1.C1CC[NH]CC1.c1ccccc1 | HO- | [Cl-].[Mg+2].[Cl-] | 150 | null | Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)o1.NCc1ccccc1>[Cl-].[Mg+2].[Cl-]>Cc1nnc(C2CCN(C(=O)OC(C)(C)C)CC2)n1Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-082ae31a954c4fd782ac740e11e1b426 | CCOC(=O)C1CCN(c2ccccn2)CC1.NN>>NNC(=O)C1CCN(c2ccccn2)CC1 | C(C)OC(=O)C1CCN(CC1)C1=NC=CC=C1.O.NN>>N1(CCC(CC1)C(=O)NN)C1=NC=CC=C1 | CCO[C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[CH2:15][CH2:16]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[CH2:15][CH2:16]1 | CCOC(=O)C1CCN(c2ccccn2)CC1.NN | NNC(=O)C1CCN(c2ccccn2)CC1 | null | null | CO | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc(N2CCCCC2)nc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[N;D1;H2:6])-[C:5] | 52.1 | [{"value": 52.1, "product": "N1(CCC(CC1)C(=O)NN)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,4,5,6-Tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (1 g, 4.3 mmol)(see reference Farmaco, 1993, 48(10), 1439) was dissolved in methanol (20 ml) containing hydrazine hydrate (620 μl, 20 mmol) and was heated under reflux for 18 hours. The mixture was cooled to room temperature and evaporated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1CC[NH]CC1.c1ccncc1 | HO- | CO | null | null | CCOC(=O)C1CCN(c2ccccn2)CC1.NN>CO>NNC(=O)C1CCN(c2ccccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ff387fd184f4f2e8c6f2f73124e8925 | CC(C)(C)OC(=O)CC(=O)[O-].CCN(CC)CC.CCN=C=NCCCN(C)C.NN.On1nnc2ccccc21>>CC(C)(C)OC(=O)CC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 | NN.C(CC(=O)[O-])(=O)OC(C)(C)C.O.ON1N=NC2=C1C=CC=C2.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C>>C(C)(C)(C)OC(CC(NNC(=O)C1CCN(CC1)C1=NC=CC=C1)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[O-:14].CCN(CC)[CH2:25][CH3:26].CCN=[C:13]=N[CH2:16][CH2:17]CN(C)C.[NH2:11][NH2:12].O[n:24]1n[n:18][c:19]2[c:15]1[cH:23][cH:22][cH:21][cH:20]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[NH:11][NH:12][C:13](=[O:14])[CH:15]1[... | CC(C)(C)OC(=O)CC(=O)[O-].CCN(CC)CC.CCN=C=NCCCN(C)C.NN.On1nnc2ccccc21 | CC(C)(C)OC(=O)CC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 | null | null | ClCCl | Acylation | OtherReaction | 218fb3dba8d13ccce98134ecb8828b747347ea3778276dec468f47513d29c75f | 3fad08901541c1cd325bdbd2f7fc0a2b1a9fea4f7b0b174a7a0579d4fd9c0253 | c1ccc(N2CCCCC2)nc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-C-N=[C;H0;D2;+0:3]=N-[CH2;D2;+0:4]-[CH2;D2;+0:5]-C-N(-C)-C.O-[n;H0;D3;+0:6]1:n:[n;H0;D2;+0:7]:[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:2:1.[C;D1;H3:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[#8:18]-[C:19](=[O;D1;H0:20])-[C:21]-[C;H0;D3;+0:22](-[O-;H0;D1:... | null | [] | null | null | 5 | HOUR | A mixture of the hydrazine from preparation 35 (2.2 g, 10 mmol), tert-butyl malonate (1.6 g, 10 mmol), 1-hydroxybenzotriazole hydrate (2.02 g, 15 mmol), triethylamine (4.8 ml, 20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g, 12.5 mmol) in dichloromethane (50 ml) was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Tertiary amine.Tertiary amine | Acylhydrazine.Acylhydrazine.Tertiary amine | c1ccc2[nH]nnc2c1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HO- | ClCCl | null | 5 | CC(C)(C)OC(=O)CC(=O)[O-].CCN(CC)CC.CCN=C=NCCCN(C)C.NN.On1nnc2ccccc21>ClCCl>CC(C)(C)OC(=O)CC(=O)NNC(=O)C1CCN(c2ccccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f803006c536d4840968facd6e79dd9ea | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CI>>CO[C@@H]1CCN(C(=O)OC(C)(C)C)C1 | C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O.[H-].[Na+].CI>>C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OC | [OH:2][C@@H:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1.I[CH3:1]>>[CH3:1][O:2][C@@H:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CI | CO[C@@H]1CCN(C(=O)OC(C)(C)C)C1 | null | null | O.O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | C1CCNC1 | I-[CH3;D1;+0:1].[#7:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]>>[#7:2]-[C:3]-[C:4](-[O;H0;D2;+0:5]-[CH3;D1;+0:1])-[C:6] | null | [] | 0 | CELSIUS | 18 | HOUR | (3R)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (12.5 g, 66.70 mmol) was dissolved in tetrahydrofuran (334 ml) and the reaction mixture cooled to 0° C. in an ice bath. The reaction mixture was treated with sodium hydride (2.20 g, 80% dispersion in mineral oil, 73.3 mmol) and allowed to warm to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | C1CC[NH]C1 | HI | O.O1CCCC1 | 0 | 18 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CI>O.O1CCCC1>CO[C@@H]1CCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e967219ebc4429ab10775cd7daa89c4 | CC(C)(C)OC(=O)N1CCC(C(=O)NN)CC1.O=C(Cl)CCl>>CC(C)(C)OC(=O)N1CCC(C(=O)NNC(=O)CCl)CC1 | ClCC(=O)Cl.C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)NN.CN1CCOCC1>>C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)NNC(CCl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[NH:14][NH2:15])[CH2:20][CH2:21]1.Cl[C:16](=[O:17])[CH2:18][Cl:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[NH:14][NH:15][C:16](=[O:17])[CH2:18][Cl:19])[CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCC(C(=O)NN)CC1.O=C(Cl)CCl | CC(C)(C)OC(=O)N1CCC(C(=O)NNC(=O)CCl)CC1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[NH2;D1;+0:9]>>[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4] | null | [] | null | null | 4 | HOUR | 4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (see reference WO 9703986 A1 19970206)(25 g, 103 mmol) was dissolved in dichloromethane (300 ml) and 4-methylmorpholine (12.5 ml, 113 mmol) was added. The mixture was cooled using an ice bath and chloroacetyl chloride (8.2 ml, 103 mmol) was added drop wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | C1CC[NH]CC1 | HCl | ClCCl | null | 4 | CC(C)(C)OC(=O)N1CCC(C(=O)NN)CC1.O=C(Cl)CCl>ClCCl>CC(C)(C)OC(=O)N1CCC(C(=O)NNC(=O)CCl)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f19733c657e4b04b7ed2ac578424390 | C=O.COCCNCc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1>>COCCN(C)Cc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1 | C(C1=CC=CC=C1)N1C(=NN=C1C1CCN(CC1)C1=NC=CC=C1)CNCCOC.C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C1=CC=CC=C1)N1C(=NN=C1C1CCN(CC1)C1=NC=CC=C1)CN(C)CCOC | O=[CH2:6].[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:7][c:8]1[n:9][n:10][c:11]([CH:12]2[CH2:13][CH2:14][N:15]([c:16]3[cH:17][cH:18][cH:19][cH:20][n:21]3)[CH2:22][CH2:23]2)[n:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[CH2:7][c:8]1[n:9][n:10][c:11]([CH:12]2[CH2:13][CH2:14]... | C=O.COCCNCc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1 | COCCN(C)Cc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(Cn2cnnc2C2CCN(c3ccccn3)CC2)cc1 | O=[CH2;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4](-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]):[#7;a:9]>>[#7;a:2]:[#7;a:3]:[c:4](-[C:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7]-[C:8]):[#7;a:9] | null | [] | null | null | null | null | The amine from example 43 (50 mg, 0.12 mmol), formaldehyde (37% aq, 40 μl, 0.49 mmol) and sodium triacetoxyborohydride (51 mg, 0.24 mmol) in dichloromethane (1 ml) was stirred vigorously at room temperature for 21 hours. The reaction mixture was partitioned between dichloromethane and aqueous sodium carbonate solution,... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1nc[nH]n1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | Other | ClCCl | null | null | C=O.COCCNCc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1>ClCCl>COCCN(C)Cc1nnc(C2CCN(c3ccccn3)CC2)n1Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e304c46bb199409e93427fe99739240d | N#Cc1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1.[OH-]>>NC(=O)c1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1 | [OH-].[K+].C(C1=CC=CC=C1)N1C(=NN=C1CN1CCOCC1)C1CCN(CC1)C1=NC=CC=C1C#N>>C(C1=CC=CC=C1)N1C(=NN=C1CN1CCOCC1)C1CCN(CC1)C1=NC=CC=C1C(=O)N | [N:1]#[C:2][c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][n:16][c:17]([CH2:18][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[n:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1.[OH-:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[N:10]1[CH2:11][CH2:1... | N#Cc1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1.[OH-] | NC(=O)c1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1 | null | null | CC(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccc(Cn2c(CN3CCOCC3)nnc2C2CCN(c3ccccn3)CC2)cc1 | [#7:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8].[OH-;D0:9]>>[#7:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[O;H0;D1;+0:9]):[c:8] | 85.1 | [{"value": 85.1, "product": "C(C1=CC=CC=C1)N1C(=NN=C1CN1CCOCC1)C1CCN(CC1)C1=NC=CC=C1C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Powdered potassium hydroxide (95 mg, 1.68 mmol) was added to a solution of the carbonitrile of example 52 (250 mg, 0.56 mmol) in 2-Methyl-propan-2-ol (10 ml). The mixture was heated at 100° C. for 18 hr before evaporating under reduced pressure. The residue was purified by chromatography on silica gel using methanol an... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccncc1.C1CC[NH]CC1.c1nc[nH]n1.C1COCC[NH]1.c1ccccc1 | null | CC(C)(C)O | 100 | null | N#Cc1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1.[OH-]>CC(C)(C)O>NC(=O)c1cccnc1N1CCC(c2nnc(CN3CCOCC3)n2Cc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e046a0d0a6494d69abb5d050df00025d | CSC(=Nc1ccccc1F)C(C)C.NNC(=O)c1ccc(-c2ccccc2)cc1>>CC(C)c1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | CSC(C(C)C)=NC1=C(C=CC=C1)F.C1(=CC=C(C=C1)C(=O)NN)C1=CC=CC=C1>>C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)C(C)C)C1=CC=CC=C1 | CS[C:4]([CH:2]([CH3:1])[CH3:3])=[N:20][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[F:27].O=[C:7]([NH:6][NH2:5])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18]... | CSC(=Nc1ccccc1F)C(C)C.NNC(=O)c1ccc(-c2ccccc2)cc1 | CC(C)c1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 5eef0978e887821354f5f6fd4f309eeeeaaa4e491ed05d5fb96505fbc7e13105 | d400bf825bb5b42935afef9308c3fbe17169a89d58bb6ad007e2f12d1bf2f6f0 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cc2)cc1 | C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[F;D1;H0:7]):[c:8])-[C:9](-[C;D1;H3:10])-[C;D1;H3:11].O=[C;H0;D3;+0:12](-[NH;D2;+0:13]-[NH2;D1;+0:14])-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[n;H0;D2;+0:13]:[c;H0;D3;+0:12](-... | 68 | [{"value": 68.0, "product": "C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)C(C)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)C(C)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 59 | HOUR | N-(2-Fluorophenyl)-2-methylthiopropionimidate methyl ester (7.84 g) prepared in the Reference Example 1 and biphenyl-4-carboxylic acid hydrazide (5.25 g) were dissolved in N,N-dimethylformamide (50 ml), followed by addition of p-toluenesulfonic acid·monohydrate (941 mg), and stirred at 120° C. for 59 hours. After the r... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Monosulfide | null | null | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CN(C=O)C | 120 | 59 | CSC(=Nc1ccccc1F)C(C)C.NNC(=O)c1ccc(-c2ccccc2)cc1>CN(C=O)C>CC(C)c1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffac4d3930b0426da52d569c2e6fa4ff | Brc1ccccc1-n1cnnc1-c1ccc(-c2ccccc2)nc1.O=C1CCC(=O)N1Br>>Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1 | BrC1=C(C=CC=C1)N1C(=NN=C1)C=1C=CC(=NC1)C1=CC=CC=C1.C1CC(=O)N(C1=O)Br.C(O)([O-])=O.[Na+]>>BrC=1N(C(=NN1)C=1C=CC(=NC1)C1=CC=CC=C1)C1=C(C=CC=C1)Br | [Br:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[cH:9][n:11][n:12][c:13]1-[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][cH:25]1.O=C1CCC(=O)N1[Br:10]>>[Br:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[c:9]([Br:10])[n:11][n:12][c:13]1-[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c... | Brc1ccccc1-n1cnnc1-c1ccc(-c2ccccc2)nc1.O=C1CCC(=O)N1Br | Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1 | null | null | C(C)(=O)O.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 2d2115bcf199d84f752b10b51c41b56b956f63f352f0c256718d4f08e543bd2f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cn2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[#7;a:6]:[cH;D2;+0:7]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[#7;a:6]:[#7;a:5]:[c:4]:[#7;a:3]:1-[c:2] | 69 | [{"value": 69.0, "product": "BrC=1N(C(=NN1)C=1C=CC(=NC1)C1=CC=CC=C1)C1=C(C=CC=C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-[4-(2-Bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine prepared in the Production Example 2 was dissolved in a mixture solvent of carbon tetrachloride (100 ml) and acetic acid (100 ml), followed by addition of n-bromosuccinimide (5.90 g), and refluxed under heating for 3 hours. After the reaction solution was coo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nnc[nH]1.C1CCNC1 | c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1.c1ccncc1.c1ccccc1 | HO- | C(C)(=O)O.C(Cl)(Cl)(Cl)Cl | null | null | Brc1ccccc1-n1cnnc1-c1ccc(-c2ccccc2)nc1.O=C1CCC(=O)N1Br>C(C)(=O)O.C(Cl)(Cl)(Cl)Cl>Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a904a1801944e218f386ef167711319 | Cc1c(C(N)=O)cccc1[N+](=O)[O-]>>Cc1c(N)cccc1C(N)=O | CC1=C(C(=O)N)C=CC=C1[N+](=O)[O-]>>NC=1C(=C(C(=O)N)C=CC1)C | O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[c:8]([C:9]([NH2:10])=[O:11])[cH:7][cH:6][cH:5]1>>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][cH:6][cH:7][c:8]1[C:9]([NH2:10])=[O:11] | Cc1c(C(N)=O)cccc1[N+](=O)[O-] | Cc1c(N)cccc1C(N)=O | null | [C].[Pd] | O1CCCC1.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 91.2 | [{"value": 91.0, "product": "NC=1C(=C(C(=O)N)C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "NC=1C(=C(C(=O)N)C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 2-Methyl-3-nitrobenzamide (8.85 g) was dissolved in a mixture solvent of ethanol (300 ml) and tetrahydrofuran (200 ml), followed by addition of 10% palladium-carbon (800 mg). The resulting mixture was stirred under hydrogen atmosphere at ambient temperature and atmospheric pressure for 6 hours. After insoluble material... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [C].[Pd].O1CCCC1.C(C)O | null | 6 | Cc1c(C(N)=O)cccc1[N+](=O)[O-]>[C].[Pd].O1CCCC1.C(C)O>Cc1c(N)cccc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23a7463ec365497a8da5e62103007ce0 | CC(C)(C)OC(=O)NN.COCCCC(=O)O>>COCCCC(=O)NNC(=O)OC(C)(C)C | C(C)(C)(C)OC(NN)=O.COCCCC(=O)O.Cl.C(C)N=C=NCCCN(C)C>>C(C)(C)(C)OC(=O)NNC(CCCOC)=O | [NH2:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].O[C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)OC(=O)NN.COCCCC(=O)O | COCCCC(=O)NNC(=O)OC(C)(C)C | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[NH2;D1;+0:13]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[#7:12]-[C:10](=[O;D1;H0:11])-[#8:9]-[C:6](-[C;D1;H3:5])(-[C;D1;H3:7])-[C;D1;H3:8] | 57 | [{"value": 57.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | Carbazic acid tert-butyl ester (9.21 g) was dissolved in pyridine (120 ml), followed by addition of 4-methoxybutyric acid (9.06 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (20.0 g), and stirred at ambient temperature for 64 hours. After the reaction solution was concentrated under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | null | HO- | N1=CC=CC=C1 | null | 64 | CC(C)(C)OC(=O)NN.COCCCC(=O)O>N1=CC=CC=C1>COCCCC(=O)NNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f1fc4e63bcd49baab4faaaf5cb38cf8 | Cl>>Cl | COCCCC(=O)NN.Cl.C(C)(=O)OCC>>Cl.COCCCC(=O)NN | [ClH:10]>>[ClH:10] | Cl | Cl | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 89 | [{"value": 89.0, "product": "Cl.COCCCC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N′-(4-Methoxybutyryl)hydrazine carboxylic acd tert-butyl ester (9.30 g) was dissolved in ethyl acetate (50 ml), followed by addition of 4 mol/liter hydrochloric acid/ethyl acetate solution (150 ml), and stirred at ambient temperature for 2 hours. After the reaction solution was concentrated under reduced pressure, the ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | null | 2 | Cl>C(C)(=O)OCC>Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e17521f35c844b38b7cd816a96b56009 | COCCCC(=O)NN.O=C(O)c1ccc(-c2ccccc2)nc1>>COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1 | C1(=CC=CC=C1)C1=NC=C(C(=O)O)C=C1.Cl.COCCCC(=O)NN.Cl.C(C)N=C=NCCCN(C)C>>COCCCC(=O)NNC(C1=CN=C(C=C1)C1=CC=CC=C1)=O | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][cH:23]1>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][cH... | COCCCC(=O)NN.O=C(O)c1ccc(-c2ccccc2)nc1 | COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1 | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | c1ccc(-c2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH2;D1;+0:12]>>[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 65.3 | [{"value": 65.0, "product": "COCCCC(=O)NNC(C1=CN=C(C=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "COCCCC(=O)NNC(C1=CN=C(C=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | HOUR | 6-Phenylnicotinic acid (5.90 g) was dissolved in pyridine (150 ml), followed by addition of 4-methoxybutyric acid hydrazide hydrochloride salt (5.99 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (8.51 g), and stirred at 60° C. for 10 hours. After the reaction solution was cooled to ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccncc1.c1ccccc1 | HO- | N1=CC=CC=C1 | 60 | 10 | COCCCC(=O)NN.O=C(O)c1ccc(-c2ccccc2)nc1>N1=CC=CC=C1>COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27aad1f22981490b815940bdd6106842 | COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1>>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1 | COCCCC(=O)NNC(C1=CN=C(C=C1)C1=CC=CC=C1)=O>>COCCCC1=NN=C(O1)C=1C=CC(=NC1)C1=CC=CC=C1 | O=[C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[NH:7][NH:8][C:9]([c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][cH:21]1)=[O:22]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[n:7][n:8][c:9](-[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20][cH:21]2)[o:22]1 | COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1 | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1 | null | null | P(=O)(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(-c2ccc(-c3nnco3)cn2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:2):[o;H0;D2;+0:7]:1 | 65.1 | [{"value": 65.0, "product": "COCCCC1=NN=C(O1)C=1C=CC(=NC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.1, "product": "COCCCC1=NN=C(O1)C=1C=CC(=NC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | To 6-phenylnicotinic acid N′-(4-methoxybutyryl)hydrazide (6.06 g) was added phosphorus oxychloride (100 ml), and stirred at 100° C. for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure. To the resulting residue was added aqueous 1 mol/liter sod... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccncc1.c1ccccc1 | HO- | P(=O)(Cl)(Cl)Cl | 100 | 3 | COCCCC(=O)NNC(=O)c1ccc(-c2ccccc2)nc1>P(=O)(Cl)(Cl)Cl>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1220b742e04a4582a13bd0b0471941a4 | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1.Cc1c(N)cccc1C(N)=O>>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C | C(Cl)(Cl)Cl.COCCCC1=NN=C(O1)C=1C=CC(=NC1)C1=CC=CC=C1.NC=1C(=C(C(=O)N)C=CC1)C.CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C>>COCCCC1=NN=C(N1C=1C(=C(C(=O)N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1 | o1[c:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[n:7][n:8][c:9]1-[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][cH:21]1.[NH2:22][c:23]1[cH:24][cH:25][cH:26][c:27]([C:28]([NH2:29])=[O:30])[c:31]1[CH3:32]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[n:7][n:8][c:9](-[c:10]2[cH:11][cH:12][c:13](-[c:1... | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1.Cc1c(N)cccc1C(N)=O | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C | null | null | CN1C(N(CC1)C)=O | Miscellaneous | OtherReaction | 06fefb205a4853de5c4e4a339b564c57a94b95a37d2e8ba13cde385235751498 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cn2)cc1 | [C;D1;H3:1]-[c:2](:[c:3]-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[c;H0;D3;+0:7](-[NH2;D1;+0:8]):[c:9]:[c:10].[C:11]-[C:12]-[c;H0;D3;+0:13]1:[#7;a:14]:[#7;a:15]:[c;H0;D3;+0:16](-[c:17](:[c:18]):[c:19]:[#7;a:20]:[c:21]):o:1>>[C:11]-[C:12]-[c;H0;D3;+0:13]1:[#7;a:14]:[#7;a:15]:[c;H0;D3;+0:16](-[c:17](:[c:18]):[c:19]:[#7;a:20]:[c:... | 56.1 | [{"value": 56.0, "product": "COCCCC1=NN=C(N1C=1C(=C(C(=O)N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "COCCCC1=NN=C(N1C=1C(=C(C(=O)N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 16 | HOUR | 5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine (1.0 g) prepared in the Reference Example 7 was dissolved in 1,3-dimethyl-2-imidazolidinone (10 ml), followed by addition of 3-amino-2-methylbenzamide (1.53 g) prepared in the Reference Example 6 and D-10-camphorsulfonic acid (290 mg), and stirred at 200° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nnco1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CN1C(N(CC1)C)=O | 200 | 16 | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)o1.Cc1c(N)cccc1C(N)=O>CN1C(N(CC1)C)=O>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72e7e9fd9d714797ab3b1ceb025540aa | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C>>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C#N)c1C | P(=O)(Cl)(Cl)Cl.COCCCC1=NN=C(N1C=1C(=C(C(=O)N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1>>COCCCC1=NN=C(N1C=1C(=C(C#N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1 | O=[C:28]([c:27]1[cH:26][cH:25][cH:24][c:23](-[n:22]2[c:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[n:7][n:8][c:9]2-[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20][cH:21]2)[c:30]1[CH3:31])[NH2:29]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[n:7][n:8][c:9](-[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:1... | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C#N)c1C | null | null | null | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cn2)cc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | 52.3 | [{"value": 52.0, "product": "COCCCC1=NN=C(N1C=1C(=C(C#N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.3, "product": "COCCCC1=NN=C(N1C=1C(=C(C#N)C=CC1)C)C=1C=NC(=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Phosphorus oxychloride (8 ml) was added to 3-[3-(3-methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide (770 mg) prepared in the Example 4, and refluxed under heating for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1nc[nH]n1.c1ccncc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C(N)=O)c1C>>COCCCc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc(C#N)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e15683ab87d482184ed6c6ba6dd6304 | Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1.CNCCOC>>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br | COCCNC.BrC=1N(C(=NN1)C=1C=CC(=NC1)C1=CC=CC=C1)C1=C(C=CC=C1)Br>>BrC1=C(C=CC=C1)N1C(=NN=C1C=1C=NC(=CC1)C1=CC=CC=C1)N(C)CCOC | Br[c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21][cH:22]2)[n:23]1-[c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[Br:30].[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16]... | Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1.CNCCOC | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1c5140a16b98c8622dd561f15d9064ef2d9e3793a6123294dacf3a1a1e648482 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cn2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[c:5]:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C;D1;H3:13]>>[#7;a:7]:[c:6]:[c:5]-[c:4]1:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12](-[C;D1;H3:13])-[C:11]-[C:10]):[#7;a:8]:1-[c:9] | 70 | [{"value": 70.0, "product": "BrC1=C(C=CC=C1)N1C(=NN=C1C=1C=NC(=CC1)C1=CC=CC=C1)N(C)CCOC", "details": "PERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 24 | HOUR | In a sealed tube, N-(2-methoxyethyl)methylamine (3 ml) was added to 5-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine (1.0 g) prepared in the Production Example 3, and stirred at 180° C. for 13 hours and at 200° C. for 24 hours. After the reaction solution was cooled to ambient temperature, chlorofor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccncc1.c1ccccc1.c1ccccc1 | HBr | C(Cl)(Cl)Cl | 200 | 24 | Brc1ccccc1-n1c(Br)nnc1-c1ccc(-c2ccccc2)nc1.CNCCOC>C(Cl)(Cl)Cl>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5c95ac0d15845fe92f518839e0e9db3 | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br>>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1C#N | C(Cl)(Cl)Cl.BrC1=C(C=CC=C1)N1C(=NN=C1C=1C=NC(=CC1)C1=CC=CC=C1)N(C)CCOC.[OH-].[Ca+2].[OH-].CN1C(CCC1)=O>>COCCN(C)C1=NN=C(N1C1=C(C#N)C=CC=C1)C=1C=NC(=CC1)C1=CC=CC=C1 | Br[c:29]1[c:24](-[n:23]2[c:7]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])[n:8][n:9][c:10]2-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21][cH:22]2)[cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:1... | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1C#N | null | [C-]#N.[Zn+2].[C-]#N | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;a:5]):[c:6]>>[#7;a:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 63 | [{"value": 63.0, "product": "COCCN(C)C1=NN=C(N1C1=C(C#N)C=CC=C1)C=1C=NC(=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 3 | HOUR | [4-(2-Bromophenyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-3-yl]-N-(2-methoxyethyl)-N-methylamine (436 mg) prepared in the Example 7 was dissolved in N-methyl-2-pyrrolidone (5 ml), followed by addition of zinc cyanide (121 mg), calcium hydroxide (76 mg) and tetrakistriphenylphosphine palladium (326 mg), and stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1nc[nH]n1.c1ccncc1.c1ccccc1.c1ccccc1 | Br- | [C-]#N.[Zn+2].[C-]#N | 180 | 3 | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1Br>[C-]#N.[Zn+2].[C-]#N>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1ccccc1C#N |
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