dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61a55138082e4da3a2bdcb3802651dcc | Nc1cccc(-c2cc[nH]n2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4cc[nH]n4)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.N1N=C(C=C1)C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C1=NNC=C1)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][nH:20][n:21]2)[cH:22]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][nH:2... | Nc1cccc(-c2cc[nH]n2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3cccc(-c4cc[nH]n4)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cccc(-c4cc[nH]n4)c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-(1H-pyrazol-3-yl)aniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-[3-(1H-pyrazol-3-yl)phenyl]-2,4-pyrimidinediamine.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1cn[nH]c1 | HCl | null | null | null | Nc1cccc(-c2cc[nH]n2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4cc[nH]n4)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58d91c70062f4b58b92798c7b77d36b3 | Nc1cccc(-c2nnn[nH]2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4nnn[nH]4)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.N1N=NN=C1C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C1=NN=NN1)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][n:19][n:20][nH:21]2)[cH:22]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16](-[c:17]4[n:18][n:19][n:20][nH... | Nc1cccc(-c2nnn[nH]2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3cccc(-c4nnn[nH]4)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cccc(-c4nnn[nH]4)c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-(tetrazol-5-yl)aniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-[3-(tetrazol-5-yl)phenyl]-2,4-pyrimidinediamine. 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1nnn[nH]1 | HCl | null | null | null | Nc1cccc(-c2nnn[nH]2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4nnn[nH]4)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab1d74183b9d40ab8f81d708b9a2f4d4 | Nc1cccc(-c2cnco2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4cnco4)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.O1C=NC=C1C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C1=CN=CO1)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][n:19][cH:20][o:21]2)[cH:22]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16](-[c:17]4[cH:18][n:19][cH:20]... | Nc1cccc(-c2cnco2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3cccc(-c4cnco4)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cccc(-c4cnco4)c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-(1,3-oxazol-5-yl)aniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-(1,3-oxazol-5-yl)phenyl]-2,4-pyrimidinediamine.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1cocn1 | HCl | null | null | null | Nc1cccc(-c2cnco2)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cccc(-c4cnco4)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5c0c9ab76984dcf8cdf1dd76a906429 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Nc2cccc(-c3nnn[nH]3)c2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.N1N=NN=C1C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C1=NN=NN1)NC1=CC2=C(C=C1)OCCO2 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:19]([NH:20][c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][CH2:29][O:30]3)[n:18]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][n:14][n:15][nH:16]2)[cH:17]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[n:13][n:14][n:15][nH:16]3)[cH:17]2... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2nnn[nH]2)c1 | Fc1cnc(Nc2cccc(-c3nnn[nH]3)c2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc(-c2nnn[nH]2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine with 3-(tetrazol-5-yl)aniline gave 5-fluoro-N4-(3,4-ethylenedioxyphenyl)-N2-[3-(tetrazol-5-yl)phenyl]-2,4-pyrimi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnn[nH]1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Nc2cccc(-c3nnn[nH]3)c2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-303e9e9b6eab44eea3dadc4d3a142109 | COc1ccc(N)c(C)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC1=CC(=C(N)C=C1)C>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=C(C=C(C=C1)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:26]([CH3:27])[cH:28]1.Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:1... | COc1ccc(N)c(C)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine with 4-methoxy-2-methylaniline gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(4-methoxy-2-methylphenyl)-2,4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(N)c(C)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29f4d536d43d40ccaf44616415aa2e6b | COC(=O)C1Cc2cc(N)ccc2O1.Fc1ccc(Nc2nc(Cl)ncc2F)cc1F>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)F)F)F.NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>FC=1C=C(C=CC1F)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:27][cH:28][c:29]2[O:30]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([F:22])[c:23]([F:24])[cH:25]2)[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH... | COC(=O)C1Cc2cc(N)ccc2O1.Fc1ccc(Nc2nc(Cl)ncc2F)cc1F | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | 80 | CELSIUS | 48 | HOUR | A mixture of equivalent amount of 2-chloro-N4-(3,4-difluorophenyl)-5-fluoro-4-pyrimidineamine and (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran in MeOH was shaken in a sealed tube at 80° C. for 48 h, cooled to room temperature and diluted with a mixture of n-hexanes:EtOAc (1:1; v/v). The resulting solid formed wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | CO | 80 | 48 | COC(=O)C1Cc2cc(N)ccc2O1.Fc1ccc(Nc2nc(Cl)ncc2F)cc1F>CO>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d8846e216f84ffb8ad539de4005e331 | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 | NC=1C=CC2=C(CC(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)Cl)F>>ClC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:26][cH:27][c:28]2[O:29]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c... | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, the reaction of (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran with 2-chloro-N4-(4-chlorophenyl)-5-fluoro-4-pyrimidineamine gave (±)-N4-(4-chlorophenyl)-N2-(2,3-dihydro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe7e9fafd18d41d5b50c71d5549809b7 | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 | NC=1C=CC2=C(CC(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)Cl)Cl)F>>ClC=1C=C(C=CC1Cl)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:27][cH:28][c:29]2[O:30]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]2)[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([... | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, the reaction of (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran with 2-chloro-N4-(3,4-dichlorophenyl)-5-fluoro-4-pyrimidineamine gave (±)-N4-(3,4-dichlorophenyl)-N2-(2,3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4f839cbb3e245529c3bdc0219f745a4 | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 | NC=1C=CC2=C(CC(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC=1C(=NC(=CC1)OC)OC)F>>COC(=O)C1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC=2C(=NC(=CC2)OC)OC)F | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[O:32]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH3:23])[n:24][c:25]2[O:26][CH3:27])[n:28]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:1... | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, the reaction of (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran with 2-chloro-N4-(2,6-dimethoxypyridin-3-yl)-5-fluoro-4-pyrimidineamine gave (±)-N2-(2,3-dihydro-2-methox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccncc1 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-597fef4038b049b4900bf4b58031a92d | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cc5c(F)c(F)c4OCO5)n3)ccc2O1 | NC=1C=CC2=C(CC(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC1=C2C(=C(C(=C1)OCO2)F)F)F>>COC(=O)C1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC2=C1C(=C(C(=C2)OCO1)F)F)F | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:30][cH:31][c:32]2[O:33]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][c:20]3[c:21]([F:22])[c:23]([F:24])[c:25]2[O:26][CH2:27][O:28]3)[n:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:1... | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cc5c(F)c(F)c4OCO5)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2cc3ccc2OCO3)nc(Nc2ccc3c(c2)CCO3)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, the reaction of (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran with 2-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine gave (±)-N2-(2,3-dihydro-2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1cc2ccc1OCO2 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cc5c(F)c(F)c4OCO5)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd22e8a2633048b58a62af5e0ee99a54 | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 | FC=1C=C(C=CC1F)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1.Cl.CN.C(C)(C)N(CC)C(C)C>>FC=1C=C(C=CC1F)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([F:22])[c:23]([F:24])[cH:25]4)[n:26]3)[cH:27][cH:28][c:29]2[O:30]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([... | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 | CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 | null | null | O.CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])-[#8:5]-[c:6] | null | [] | 80 | CELSIUS | 24 | HOUR | A mixture of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, methylamine Hydrogen Chloride (5 equivalents) and diisopropylethylamine (5 equivalents) in MeOH was shaken in a sealed tube at 80° C. for 24 h. The resulting solution was diluted with water and the... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HO- | O.CO | 80 | 24 | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1>O.CO>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(F)c(F)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f7436e34cd844109dce748df6118393 | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 | Cl.CN.ClC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>ClC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]4)[n:25]3)[cH:26][cH:27][c:28]2[O:29]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17]... | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 | CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])-[#8:5]-[c:6] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2-(N-methylamino)carbonyl-2,3-dihydrobenzofuran-5-yl]-2,4-pyrimidinediamine, the reaction of methyl amine Hydrogen Chloride with (±)-N4-(4-chlorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine gave (±)... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd1267a9753f4c00bdff68edd17de25a | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 | Cl.CN.ClC=1C=C(C=CC1Cl)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>ClC=1C=C(C=CC1Cl)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]4)[n:26]3)[cH:27][cH:28][c:29]2[O:30]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]... | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 | CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])-[#8:5]-[c:6] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2-(N-methylamino)carbonyl-2,3-dihydrobenzofuran-5-yl]-2,4-pyrimidinediamine, the reaction of methyl amine Hydrogen Chloride with (±)-N4-(3,4-dichlorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine gave... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70ace3025ac140d9a97d79417d420648 | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 | Cl.CN.COC1=NC(=CC=C1NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1)OC>>COC1=NC(=CC=C1NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)NC)C1)OC | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH3:23])[n:24][c:25]4[O:26][CH3:27])[n:28]3)[cH:29][cH:30][c:31]2[O:32]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F... | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 | CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cncc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])-[#8:5]-[c:6] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2-(N-methylamino)carbonyl-2,3-dihydrobenzofuran-5-yl]-2,4-pyrimidinediamine, the reaction of methyl amine Hydrogen Chloride with (±)-N4-(2,6-dimethoxypyridin-3-yl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediami... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2.c1cncnc1.c1ccncc1 | HO- | null | null | null | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)nc4OC)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce997cb356ab476dafdc8b8eb855492c | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1 | Cl.CN.COC(=O)C1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC2=CC(=CC=C2)OC(F)(F)F)F>>CNC(=O)C1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC2=CC(=CC=C2)OC(F)(F)F)F | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([O:23][C:24]([F:25])([F:26])[F:27])[cH:28]4)[n:29]3)[cH:30][cH:31][c:32]2[O:33]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][... | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1 | CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;D1;H3:7])-[#8:5]-[c:6] | null | [] | null | null | null | null | In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-5-fluoro-N2-[2-(N-methylamino) carbonyl-2,3-dihydrobenzofuran-5-yl]-2,4-pyrimidinediamine, the reaction of methyl amine Hydrogen Chloride with (±)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-N4-(3-trifluoromethoxyphenyl)-2,4-pyrimidinediami... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1>>CNC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4cccc(OC(F)(F)F)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dbe1675b55f34d91a9fa14495761abe4 | Nc1cccc(O)c1.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1>>OB(O)c1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)B(O)O)F.OC=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)B(O)O | [NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]1.Cl[c:12]1[n:11][c:10]([NH:9][c:8]2[cH:7][cH:6][cH:5][c:4]([B:2]([OH:1])[OH:3])[cH:25]2)[c:23]([F:24])[cH:22][n:21]1>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]3)[n:21][cH... | Nc1cccc(O)c1.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1 | OB(O)c1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-dihydroxyborylphenyl)-4-pyrimidineamine and 3-hydroxyaniline were reacted to produce 5-Fluoro-N4-(3-dihydroxyborylphenyl)-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Nc1cccc(O)c1.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1>>OB(O)c1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-918d7475ed11438fba55bbbfd80c38e8 | Nc1ccc2c(c1)OCCO2.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1>>OBc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)B(O)O)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)BO)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2.O[B:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11](Cl)[n:23][cH:24][c:25]2[F:26])[cH:27]1>>[OH:1][BH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[O:19][CH2:... | Nc1ccc2c(c1)OCCO2.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1 | OBc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a507bea2a26352d6ab81ae36980353510c52c9fea9d1cb3898455fdd5d8b132c | f4f41afdf27c805f07d6df4034c5ca9feda3cf6e0942c11b7167f16832744466 | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].O-[B;H0;D3;+0:6](-[O;D1;H1:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H1:7]-[BH;D2;+0:6]-[c:8](:[c:9]):[c:10].[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:14] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-dihydroxyborylphenyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to produce N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-(3-hydroxyborylphenyl)-2,4-pyrimidinediam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Nc1ccc2c(c1)OCCO2.OB(O)c1cccc(Nc2nc(Cl)ncc2F)c1>>OBc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d996479622f04e73929aa3ba6a9912e7 | COc1cc(N)cc(OC)c1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1OC | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC=1C=C(N)C=C(C1OC)OC>>FC=1C(=NC(=NC1)NC1=CC(=C(C(=C1)OC)OC)OC)NC1=CC(=CC=C1)O | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:22][c:23]([O:24][CH3:25])[c:26]1[O:27][CH3:28].Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]2)[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19]... | COc1cc(N)cc(OC)c1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3,4,5-trimethoxyaniline were reacted to produce 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3,4,5-trimethoxyphenyl)-2,4-pyrimidinediamine. 1H NMR (D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1cc(N)cc(OC)c1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-baa0901f749049f2bdb881a65032f1ce | COc1cc(N)cc(OC)c1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(OC)c1OC | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC=1C=C(N)C=C(C1OC)OC>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=C(C(=C1)OC)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][c:26]([O:27][CH3:28])[c:29]1[O:30][CH3:31].Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[O:20][CH2:21][CH2:22][O:23]3)[n:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16... | COc1cc(N)cc(OC)c1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(OC)c1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3,4,5-trimethoxyaniline were reacted to produce N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3,4,5-trimethoxyphenyl)-2,4-pyrimidinedi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1cc(N)cc(OC)c1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(OC)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-436d8570f4c647568f2af00bf88f9a12 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(Cl)c(O)c(Cl)c1>>Oc1c(Cl)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC=1C=C(N)C=C(C1O)Cl>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=C(C(=C1)Cl)O)Cl | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1.[OH:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([NH2:7])[cH:26][c:27]1[Cl:28]>>[OH:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(Cl)c(O)c(Cl)c1 | Oc1c(Cl)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3,5-dichloro-4-hydroxyaniline were reacted to produce N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3,5-dichloro-4-hydroxyphenyl)-2,4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(Cl)c(O)c(Cl)c1>>Oc1c(Cl)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b27da2b1fd284e5a971dc57b1700fbee | Nc1cc(Cl)c(O)c(Cl)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cc(Cl)c(O)c(Cl)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC=1C=C(N)C=C(C1O)Cl>>FC=1C(=NC(=NC1)NC1=CC(=C(C(=C1)Cl)O)Cl)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][c:14]([Cl:15])[c:16]([OH:17])[c:18]([Cl:19])[cH:20]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:25]2)[c:23]([F:24])[cH:22][n:21]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][c:14]([Cl:15])[c:16]([OH:17])[c:18]([Cl:19])[cH:20]3)[n:21][... | Nc1cc(Cl)c(O)c(Cl)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3cc(Cl)c(O)c(Cl)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3,5-dichloro-4-hydroxyaniline were reacted to produce 5-Fluoro-N2-(3,5-dichloro-4-hydroxyphenyl)-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Nc1cc(Cl)c(O)c(Cl)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3cc(Cl)c(O)c(Cl)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9022024bd58f42e4bf19bb22e0bfbc3a | Cc1cc(O)ccc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(O)cc(N(c2ccc3c(c2)OCCO3)c2nc(N)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.Cl.NC=1C(=CC(=CC1)O)C.C(C)(C)N(CC)C(C)C>>C1OC=2C=C(C=CC2OC1)N(C1=NC(=NC=C1F)N)C1=CC(=CC(=C1)C)O | [CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][cH:7][c:27]1[NH2:22].Cl[c:21]1[n:20][c:19]([NH:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[O:15][CH2:16][CH2:17][O:18]3)[c:25]([F:26])[cH:24][n:23]1>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([N:8]([c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[O:15][CH2:16][CH2:17][O:18]3)[c:19]... | Cc1cc(O)ccc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | Cc1cc(O)cc(N(c2ccc3c(c2)OCCO3)c2nc(N)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6479e2ef96c54a05a8aed08e573f62acb47b83f93c994d142fb089edc2fb444f | 3e73feb1dca6e66ea9b3917426713f608e758767b2fa3bbf3ea155f54ecc0d2a | c1ccc(N(c2ccc3c(c2)OCCO3)c2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]:[c:9]:[#7;a:10]:1.[C;D1;H3:11]-[c:12]1:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17]:1-[NH2;D1;+0:18]>>[C;D1;H3:11]-[c:12]1:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16](-[N;H0;D3;+0:4](-[c:3]2:[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:18]):[#7;a:10]:[c:9... | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 4-amino-m-cresol hydrogenchloride salt, and diisopropylethylamine were reacted to provide N4-(3,4-ethylened... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine | Primary amine.Tertiary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1ccc2c(c1)OCCO2.c1cncnc1 | HCl | null | null | null | Cc1cc(O)ccc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(O)cc(N(c2ccc3c(c2)OCCO3)c2nc(N)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02ab450355b84cc6bbf7a660a04b3e41 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(C(F)(F)F)c1>>Fc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC=1C=C(C=C(C1)F)C(F)(F)F>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC(=C1)C(F)(F)F)F | Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[O:19][CH2:20][CH2:21][O:22]3)[n:23]1.[F:1][c:2]1[cH:3][c:4]([NH2:5])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]1>>[F:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17](... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(C(F)(F)F)c1 | Fc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-amino-5-fluorobenzotrifluoride were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(C(F)(F)F)c1>>Fc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b56275c2d044d59924851aa84ba8462 | Cc1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC=1C=C(C=C(C1)C)C(F)(F)F>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC(=C1)C(F)(F)F)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]1.Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[O:19][CH2:20][CH2:21][O:22]3)[n:23]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:... | Cc1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-amino-5-methylbenzotrifluoride were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-met... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Cc1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c2556879eae46bdab168c53fae0f310 | COc1ccc(C)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(C)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC=1C=CC(=C(N)C1)C>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=C(C=CC(=C1)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:8]([NH2:9])[cH:28]1.Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[O:23][CH2:24][CH2:25][O:26]3)[n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]3[cH:18][c... | COc1ccc(C)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(C)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 5-methoxy-2-methylaniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(5-methoxy-2-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(C)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(C)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b96fa0744867479fbb3fb171002e4b19 | Cc1ccc(F)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1ccc(F)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC1=C(N)C=C(C=C1)C>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=C(C=CC(=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([NH2:8])[cH:27]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]4[c:2... | Cc1ccc(F)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | Cc1ccc(F)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-fluoro-5-methylaniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-fluoro-5-me... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Cc1ccc(F)c(N)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1ccc(F)c(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84edd088e7ba467c81fdca3dde8b624c | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(F)c1>>Fc1cc(F)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC=1C=C(N)C=C(C1)F>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC(=C1)F)F | Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:26]1.[F:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([NH2:8])[cH:27]1>>[F:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]4[c:20]([... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(F)c1 | Fc1cc(F)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3,5-difluoroaniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3,5-difluorophenyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cc(F)cc(F)c1>>Fc1cc(F)cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16efbc4b9af346b68aefc1b9967736f1 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(SC(F)(F)F)cc1>>Fc1cnc(Nc2ccc(SC(F)(F)F)cc2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC(SC1=CC=C(N)C=C1)(F)F>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)SC(F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:19]([NH:20][c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][CH2:29][O:30]3)[n:18]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]([S:11][C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([S:11][C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(SC(F)(F)F)cc1 | Fc1cnc(Nc2ccc(SC(F)(F)F)cc2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-(trifluoromethylthio)aniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(4-trifl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(SC(F)(F)F)cc1>>Fc1cnc(Nc2ccc(SC(F)(F)F)cc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c63dd3322bde42a9bf06b1bef1070a9b | CCNC(=O)Oc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCNC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C)NC(=O)OC=1C=C(N)C=CC1>>C(C)NC(=O)OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([NH2:12])[cH:28]1.Cl[c:13]1[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([OH:25])[cH:26]2)[n:27]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([NH:12][c:13]2[n:14][cH:15][c:16]([F:17])[c:18]([NH... | CCNC(=O)Oc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CCNC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-[(N-ethylamino)carbonyloxy]aniline were reacted to provide N2-[3-[(N-ethylamino)carbonyloxy]phenyl]-5-fluoro-N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCNC(=O)Oc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCNC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78dd5374a54c48829cccbc8d379c03e3 | Fc1cnc(Cl)nc1Nc1ccc2[nH]ccc2c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4[nH]ccc4c3)n2)c1 | ClC1=NC=C(C(=N1)NC=1C=C2C=CNC2=CC1)F.OC=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC=1C=C2C=CNC2=CC1 | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[nH:19][cH:20][cH:21][c:22]3[cH:23]2)[n:24]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:25]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[nH:19][cH:20][cH:21][c:22]4[... | Fc1cnc(Cl)nc1Nc1ccc2[nH]ccc2c1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3ccc4[nH]ccc4c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4[nH]ccc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[(1H)-indol-5-yl]-4-pyrimidineamine and 3-hydroxyaniline were reacted to provide 5-fluoro-N2-(3-hydroxyphenyl)-N4-[(1H)-indol-5-yl]-2,4-pyrimidinediamin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2[nH]ccc2c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4[nH]ccc4c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5950b67943e145e2b7cc0eb5d9b99792 | CNC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1>>CNC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4cc[nH]c4c3)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC=C2C=CNC2=C1)F.CNC(=O)C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C(=O)NC)NC1=CC=C2C=CNC2=C1 | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:28]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]3[cH:22][cH:23][nH:24][c:25]3[cH:26]2)[n:27]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH:... | CNC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1 | CNC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4cc[nH]c4c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4cc[nH]c4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[(1H)indol-6-yl]-4-pyrimidineamine and 3-[(N-methylamino)carbonyl]aniline were reacted to provide 5-fluoro-N4-[(1H)indol-6-yl]-N2-[3-[(N-methylamino)car... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | CNC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1>>CNC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4cc[nH]c4c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3f198eb1b8b4d89807b552bfba93ffe | CNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.CNC(=O)C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C(=O)NC)NC1=CC(=CC=C1)O | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:26]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]2)[n:25]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH:19][cH:20][cH... | CNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-[(N-methylamino)carbonyl]aniline were reacted to provide 5-fluoro-N4-(3-hydroxyphenyl)-N2-[3-[(N-methylamino)c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d08e47503c24250b90eff6a7a506258 | CCCNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCCNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(CC)NC(=O)C=1C=C(N)C=CC1>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)C(=O)NCCC)NC1=CC(=CC=C1)O | [CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([NH2:12])[cH:28]1.Cl[c:13]1[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([OH:25])[cH:26]2)[n:27]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([NH:12][c:13]2[n:14][cH:15][c:16]([F:17])[c:18]... | CCCNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CCCNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-[(N-propylamino)carbonyl]aniline were reacted to provide 5-fluoro-N4-(3-hydroxyphenyl)-N2-[3-[(N-propylamino)c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCCNC(=O)c1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCCNC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebf80cd8648e4e4d8716ae602d06b7f2 | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)c2)CC1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C)OC(=O)C1CCN(CC1)C(=O)C=1C=C(N)C=CC1>>C(C)OC(=O)C1CCN(CC1)C(=O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:33]2)[CH2:34][CH2:35]1.Cl[c:18]1[n:19][cH:20][c:21]([F:22])[c:23]([NH:24][c:25]2[cH:26][cH:27][cH:28][c:29]([OH:30])[cH:31]2)[n:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10... | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cccc(Nc2nccc(Nc3ccccc3)n2)c1)N1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-[[4-(ethoxycarbonyl)piperidino]carbonyl]aniline were reacted to provide N2-[3-[[4-(ethoxycarbonyl)piperidino]c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC[NH]CC1.c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea3c599fac3e449ab951cac450b1ac63 | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1.Nc1cccc(O)c1>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Nc4cccc(O)c4)ncc3F)c2)CC1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)N1CCC(CC1)C(=O)OCC)F.OC=1C=C(N)C=CC1>>C(C)OC(=O)C1CCN(CC1)C(=O)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:20]1[n:19][c:18]([NH:17][c:16]2[cH:15][cH:14][cH:13][c:12]([C:10]([N:9]3[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:35][CH2:34]3)=[O:11])[cH:33]2)[c:31]([F:32])[cH:30][n:29]1.[NH2:21][c:22]1[cH:23][cH:24][cH:25][c:26]([OH:27])[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10... | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1.Nc1cccc(O)c1 | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Nc4cccc(O)c4)ncc3F)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cccc(Nc2ccnc(Nc3ccccc3)n2)c1)N1CCCCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-4-pyrimidineamine and 3-hydroxyaniline were reacted to provide N4-[3-[[4-(ethoxycarbonyl)piperidino]c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC[NH]CC1.c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1.Nc1cccc(O)c1>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Nc4cccc(O)c4)ncc3F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d059f0124904b67b3181f42b280228c | COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1Cl | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)Cl)F.OC=1C=C(N)C=CC1>>ClC=1C=C(C=CC1OC)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([Cl:25])[cH:23]2)[c:21]([F:22])[cH:20][n:19]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]3)[n:19][cH:20][c:21]2[F:2... | COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl.Nc1cccc(O)c1 | COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine and 3-hydroxyaniline were reacted to produce N4-(3-chloro-4-methoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5f695eddf634ecd9698ccdac128c34f | COc1ccc(N)cc1Cl.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(Cl)c3)n2)cc1Cl | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=CC1OC>>ClC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)Cl)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:25][c:26]1[Cl:27].Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([Cl:22])[n:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([Cl:22])[cH:23]3)[n:24]2)[cH:25][c:26]1[Cl:27] | COc1ccc(N)cc1Cl.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(Cl)c3)n2)cc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 28c96941d7a614285883e2061bf88840b6ce249cc676b79816dd71f85400d675 | a6cb82e32a2a06db7e4989e5e6dbcba52145284f9da6a6637612c4abb9630d33 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;H0;D1;+0:7]-[c:13](:[c:14]):[c:15]:[c:16](-[NH;D2;+0:8]-[c;H0;D3;+0:6]1:[#7;a:17]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:[c:3]:[c:4]:1-[F;D1;H0:5]):[c:... | null | [] | null | null | null | null | In a like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-chloro-4-methoxyaniline were reacted to provide N2,N4-Bis(3-chloro-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.90 (bs, 1H), 9.68 (bs, 1H), 8.16 (d, 1H, J=4.8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1ccc(N)cc1Cl.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(Cl)c3)n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b163f3ece0154f7d91e03eddcc3de691 | COC(=O)c1cc2cc(N)ccc2o1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2o1 | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)Cl)F.NC=1C=CC2=C(C=C(O2)C(=O)OC)C1>>ClC=1C=C(C=CC1OC)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:28][cH:29][c:30]2[o:31]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH3:23])[c:24]([Cl:25])[cH:26]2)[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16... | COC(=O)c1cc2cc(N)ccc2o1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine and 5-amino-2-(methoxycarbonyl)benzofuran were reacted to produce N4-(3-chloro-4-methoxyphenyl)-5-fluoro-N2-[2-(methoxycarbonyl)benzo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc2cc(N)ccc2o1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1bdf601c4d5406194b8c997bfe7b1da | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2O1 | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)Cl)F.NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>ClC=1C=C(C=CC1OC)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:28][cH:29][c:30]2[O:31]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH3:23])[c:24]([Cl:25])[cH:26]2)[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[... | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to produce N4-(3-chloro-4-methoxyphenyl)-5-fluoro-N2-[2,3-dihydro-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC)c(Cl)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e64155502df24db7be4226d73ba9b114 | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(F)(F)F)c(Cl)c4)n3)ccc2O1 | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC(F)(F)F)Cl)F.NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>ClC=1C=C(C=CC1OC(F)(F)F)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:31][cH:32][c:33]2[O:34]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[c:27]([Cl:28])[cH:29]2)[n:30]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][c... | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(F)(F)F)c(Cl)c4)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to produce N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)C1Cc2cc(N)ccc2O1.Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(F)(F)F)c(Cl)c4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45156532dc7048c69bab1ac57daf775f | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1>>c1ccc(-c2cccc(Nc3ccnc(Nc4cccc(-c5ccccc5)c4)n3)c2)cc1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(C=CC1)C1=CC=CC=C1>>C1(=CC=CC=C1)C=1C=C(C=CC1)NC1=NC=CC(=N1)NC1=CC(=CC=C1)C1=CC=CC=C1 | F[c:12]1[c:11](Cl)[n:29][c:15](Cl)[n:14][cH:13]1.[cH:1]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:30]2)[cH:27][cH:26][cH:25]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][cH:20][c:21](-[c:22]5[cH:23][cH:24][cH:25][cH:26][cH:... | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1 | c1ccc(-c2cccc(Nc3ccnc(Nc4cccc(-c5ccccc5)c4)n3)c2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ad804421340c8d397bef394acc806bc24dc33b51a89a1342402f97bcdfdede18 | 9e9fc68757551c84085c2512302fce7a6e64e6a8b203eba2c480626f43f05899 | c1ccc(-c2cccc(Nc3ccnc(Nc4cccc(-c5ccccc5)c4)n3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c;H0;D3;+0:6]:1-F.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[c:11](-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1):[c:18]>>[c:19]-[#7:20]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c... | null | [] | null | null | null | null | In a like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-aminobiphenyl were reacted to provide N2,N4-Bis(3-phenylphenyl)-2,4-pyrimidinediamine. LCMS: purity: 98%; MS (m/e): 415(MH+).
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1>>c1ccc(-c2cccc(Nc3ccnc(Nc4cccc(-c5ccccc5)c4)n3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1df86197f45340c8b0e610969a2dbf6d | COC(=O)c1cc(N)ccc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)ccc1OC | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC(=O)C=1C=C(N)C=CC1OC>>FC=1C(=NC(=NC1)NC1=CC(=C(C=C1)OC)C(=O)OC)NC1=CC(=CC=C1)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[O:27][CH3:28].Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]2)[n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19... | COC(=O)c1cc(N)ccc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)ccc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of 5-fluoro-N2-[3-(methylaminocarbonylmethyleneoxy)phenyl]-N4-(3-aminocarbonylphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3-methyloxycarbonyl-4-methoxyaniline were reacted to yield 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-methyloxycarbonyl-4-m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(N)ccc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3acc31f6c9b4f6bb6f45269ceb6db01 | CCN(C(C)C)C(C)C.CN.COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC>>CNC(=O)c1cc(Nc2nc(NC)ncc2F)ccc1OC | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)OC)F.Cl.CN.C(C)(C)N(CC)C(C)C>>FC=1C(=NC(=NC1)NC)NC1=CC(=C(C=C1)OC)C(=O)NC | CC(C)[N:2](C(C)C)[CH2:1]C.[NH2:12][CH3:13].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11](Cl)[n:14][cH:15][c:16]2[F:17])[cH:18][cH:19][c:20]1[O:21][CH3:22]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][CH3:13])[n:14][cH:15][c:16]2[F:17])[cH:18][cH:19][c:20]1[O:21][CH3:22] | CCN(C(C)C)C(C)C.CN.COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC | CNC(=O)c1cc(Nc2nc(NC)ncc2F)ccc1OC | null | null | O.CO | Acylation | OtherReaction | 14770569b62b5f4a045df82e0af662ffd54e1bcea26a040f8509aac956cc95a7 | f715df5c72843c4882944ba8f4439d80e84e00ce53a51637a4fab63c33c9b9c3 | c1ccc(Nc2ccncn2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10].C-[CH2;D2;+0:11]-[N;H0;D3;+0:12](-C(-C)-C)-C(-C)-C.[C;D1;H3:13]-[NH2;D1;+0:14]>>[C;D1;H3:13]-[NH;D2;+0:14]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10].[CH3;D1;+0:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:... | null | [] | 100 | CELSIUS | null | null | A mixture of 2-chloro-5-fluoro-N4-(3-methyloxycarbonyl-4-methoxyphenyl)-4-pyrimidineamine (0.15 g, 0.4 mmol), methylamine hydrochloride (0.324 g, 48 mmol) and diisopropylethylamine (0.84 mL, 48 mmol) in MeOH (2 mL) was heated in a sealed tube at 100° C. for 24 h (followed by TLC). The reaction was cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine.Tertiary amine | Secondary amide.Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | O.CO | 100 | null | CCN(C(C)C)C(C)C.CN.COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC>O.CO>CNC(=O)c1cc(Nc2nc(NC)ncc2F)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edd7f21850474a76966b2e23b6bdb9df | O=C1COc2ccc(Nc3nc(Nc4cccc(O)c4)ncc3F)cc2N1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1 | O1CC(NC2=C1C=CC(=C2)NC2=NC(=NC=C2F)NC2=CC(=CC=C2)O)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.Cl>>O1CC(NC2=C1C=CC(=C2)NC2=NC(=NC=C2F)NC2=CC(=CC=C2)O)=S | O=[C:22]1[NH:21][c:19]2[c:18]([cH:17][cH:16][c:15]([NH:14][c:13]3[c:11]([F:12])[cH:10][n:9][c:8]([NH:7][c:6]4[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]4)[n:26]3)[cH:20]2)[O:25][CH2:24]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:23])(S2)S3>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[c... | O=C1COc2ccc(Nc3nc(Nc4cccc(O)c4)ncc3F)cc2N1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | b148f0daf5047cdf5bf05243e4a3e7c25881a27a0ee2b259d0f5ec864b71d7d8 | d2920cd05bf4135748938e381b9b1f7839b4c239209f6e5ccf529257462c8544 | S=C1COc2ccc(Nc3ccnc(Nc4ccccc4)n3)cc2N1 | O=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[#8:5]-[C:6]-1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[#8:5]-[C:6]-1 | null | [] | null | null | null | null | N4-[2H-1,4-Benzoxazin-3(4H)-one-6-yl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine (800 mg, 2.18 mmol) and phosphorus pentasulfide (800 mg, 1.80 mmol) were stirred in pyridine (5 mL) at 70° C. for 2 h. The reaction solution was treated with 1N HCl solution to pH 5. The precipitation was collected with filtration... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)NCCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1cncnc1.c1ccc2c(c1)NCCO2 | Other | N1=CC=CC=C1 | null | null | O=C1COc2ccc(Nc3nc(Nc4cccc(O)c4)ncc3F)cc2N1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3827c9f2fdea4af2955fcb99f3b19258 | NCCC(=O)O.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1>>O=C1CCNC2=COc3ccc(Nc4nc(Nc5cccc(O)c5)ncc4F)cc3N12 | O1CC(NC2=C1C=CC(=C2)NC2=NC(=NC=C2F)NC2=CC(=CC=C2)O)=S.NCCC(=O)O>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC=1C=CC2=C(N3C(=CO2)NCCC3=O)C1 | O[C:2](=[O:1])[CH2:3][CH2:4][NH2:5].S=[C:6]1[CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]4)[n:25][cH:26][c:27]3[F:28])[cH:29][c:30]2[NH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][NH:5][C:6]2=[CH:7][O:8][c:9]3[cH:10][cH:11][c:12]([NH:13][c:14]4[n:15][c:... | NCCC(=O)O.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1 | O=C1CCNC2=COc3ccc(Nc4nc(Nc5cccc(O)c5)ncc4F)cc3N12 | null | null | null | Acylation | OtherReaction | 1ecdc7978443ad14df6fda360aaaf1b60b066f75097be042944821e94835305e | 29da8d958028ea3bae8918c768a4725d8a624308976674c871addece8ed51271 | O=C1CCNC2=COc3ccc(Nc4ccnc(Nc5ccccc5)n4)cc3N12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[NH2;D1;+0:5].S=[C;H0;D3;+0:6]1-[CH2;D2;+0:7]-[#8:8]-[c:9]:[c:10](:[c:11])-[NH;D2;+0:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6]2=[CH;D2;+0:7]-[#8:8]-[c:9]:[c:10](:[c:11])-[N;H0;D3;+0:12]-1-2 | null | [] | null | null | null | null | In a manner analogous to the preparation of N4-[2,4-dihydro-1-oxo-4H-imidazo[2,1-c][1,4]benzoxazin-8-yl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, N4-[2H-1,4-benzoxazin-3(4H)-thione-6-yl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine (400 mg, 1.04 mmol) and β-alanine (500 mg) gave 5-fluoro-N2-(3-hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Thioamide.Primary amine | Enamine.Enamine.Ether.Tertiary amide | c1ccc2c(c1)NCCO2 | C1=C2NCCCN2c2ccccc2O1 | C1=C2NCCCN2c2ccccc2O1.c1cncnc1.c1ccccc1 | Other | null | null | null | NCCC(=O)O.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)NC(=S)CO4)n2)c1>>O=C1CCNC2=COc3ccc(Nc4nc(Nc5cccc(O)c5)ncc4F)cc3N12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb55c9bbea04436db77ca2cd39f6e8d9 | O=C1COc2cccnc2N1>>C1=Nc2ncccc2OC1 | O1C2=C(NC(C1)=O)N=CC=C2>>O1C2=C(N=CC1)N=CC=C2 | O=[C:1]1[NH:2][c:3]2[n:4][cH:5][cH:6][cH:7][c:8]2[O:9][CH2:10]1>>[CH:1]1=[N:2][c:3]2[n:4][cH:5][cH:6][cH:7][c:8]2[O:9][CH2:10]1 | O=C1COc2cccnc2N1 | C1=Nc2ncccc2OC1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 170e6e88ada44e8090d5832b3226af778d4aafe7186ba73e624fff3b91892ec0 | 589d7a64abdf0c0a5128ac8f276986757f04b00faa61bedc30df353e57a4ab36 | C1=Nc2ncccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5](:[#7;a:6]:[c:7])-[NH;D2;+0:8]-1>>[c:7]:[#7;a:6]:[c:5]1:[c:4]-[#8:3]-[C:2]-[CH;D2;+0:1]=[N;H0;D2;+0:8]-1 | null | [] | null | null | null | null | 2H-Pyrido[3,2-b]-1,4-oxazin-3(4H)-one (1 g, 6.66 mmol) was refluxed with boron hydride methyl sulfide complex (2 mL) in THF (10 mL) for 30 min to give 2H-pyrido[3,2-b]-1,4-oxazine. In a manner analogous to the preparation of 5-fluoro-N2-(3-methylaminocarbonylmethyleneoxyphenyl)-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Substituted imine | c1cnc2c(c1)OCCN2 | C1=Nc2ncccc2OC1 | C1=Nc2ncccc2OC1 | Other | C1CCOC1 | null | null | O=C1COc2cccnc2N1>C1CCOC1>C1=Nc2ncccc2OC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa7f61a7b7004949ace683c059a25d23 | O=C1COc2cccnc2N1.O=[N+]([O-])O>>O=C1COc2ccc([N+](=O)[O-])nc2N1 | O1C2=C(NC(C1)=O)N=CC=C2.[N+](=O)(O)[O-]>>[N+](=O)([O-])C=1C=CC=2OCC(NC2N1)=O | [O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][n:12][c:13]2[NH:14]1.O[N+:9](=[O:10])[O-:11]>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[n:12][c:13]2[NH:14]1 | O=C1COc2cccnc2N1.O=[N+]([O-])O | O=C1COc2ccc([N+](=O)[O-])nc2N1 | null | null | C(C)(=O)O.C(C)(=O)OC(C)=O | Functional Group Addition | Aromatic nitration with HNO3 | 2d81659f813e9397231c2fa1c7faaad9ac402b3b24e0d6b1ab04e33a0aecc16d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1COc2cccnc2N1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#7:4]-[c:5]:[#7;a:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#7:4]-[c:5]:[#7;a:6]:[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 8 | HOUR | 2H-Pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.5 g) was dissolved in acetic acid (6 mL) and acetic anhydride (30 mL). Fuming nitric acid (3 mL) was added dropwise to the reaction solution in ice-bath. The reaction solution was stirred in ice-bath overnight. Solution was poured into crashed ice. The light yellow precipitation... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | HO- | C(C)(=O)O.C(C)(=O)OC(C)=O | null | 8 | O=C1COc2cccnc2N1.O=[N+]([O-])O>C(C)(=O)O.C(C)(=O)OC(C)=O>O=C1COc2ccc([N+](=O)[O-])nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0895affa0995477da85114bebb4a1375 | O=C1COc2ccc([N+](=O)[O-])nc2N1>>Nc1ccc2c(n1)NC(=O)CO2 | [N+](=O)([O-])C=1C=CC=2OCC(NC2N1)=O>>NC=1C=CC=2OCC(NC2N1)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([n:7]1)[NH:8][C:9](=[O:10])[CH2:11][O:12]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([n:7]1)[NH:8][C:9](=[O:10])[CH2:11][O:12]2 | O=C1COc2ccc([N+](=O)[O-])nc2N1 | Nc1ccc2c(n1)NC(=O)CO2 | null | [Pd] | Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1COc2cccnc2N1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[#7;a:4]:[c:5]-[#7:6]>>[#7:6]-[c:5]:[#7;a:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | 6-Nitro-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (1 g) was reduced under hydrogenolysis conditions using 10% Pd—C in methanol (50 mL) and 1N HCl solution (10 mL) at 50 psi for 2 h. The catalyst was filtered off and washed with methanol and 1N HCl solution. The filtrate was evaporated to give 6-amino-2H-pyrido[3,2-b]-1,4-o... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cnc2c(c1)OCCN2 | Other | [Pd].Cl.CO | null | null | O=C1COc2ccc([N+](=O)[O-])nc2N1>[Pd].Cl.CO>Nc1ccc2c(n1)NC(=O)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09d4ad56b51c41099ecc5a3debca269b | O=C1COc2ccc([N+](=O)[O-])nc2N1>>O=[N+]([O-])c1ccc2c(n1)N=CCO2 | [N+](=O)([O-])C=1C=CC=2OCC(NC2N1)=O>>[N+](=O)([O-])C=1C=CC=2OCC=NC2N1 | O=[C:11]1[NH:10][c:8]2[c:7]([cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:9]2)[O:13][CH2:12]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([n:9]1)[N:10]=[CH:11][CH2:12][O:13]2 | O=C1COc2ccc([N+](=O)[O-])nc2N1 | O=[N+]([O-])c1ccc2c(n1)N=CCO2 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 170e6e88ada44e8090d5832b3226af778d4aafe7186ba73e624fff3b91892ec0 | 589d7a64abdf0c0a5128ac8f276986757f04b00faa61bedc30df353e57a4ab36 | C1=Nc2ncccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5](:[#7;a:6]:[c:7])-[NH;D2;+0:8]-1>>[c:7]:[#7;a:6]:[c:5]1:[c:4]-[#8:3]-[C:2]-[CH;D2;+0:1]=[N;H0;D2;+0:8]-1 | null | [] | null | null | null | null | 6-Nitro-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (500 mg) was refluxed with boron hydride methyl sulfide complex (1 mL) in THF (10 mL) for 30 min to give 6-nitro-2H-pyrido[3,2-b]-1,4-oxazine. In a manner analogous to the preparation of 5-fluoro-N2-(3-methylaminocarbonylmethyleneoxyphenyl)-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Substituted imine | c1cnc2c(c1)OCCN2 | C1=Nc2ncccc2OC1 | C1=Nc2ncccc2OC1 | Other | C1CCOC1 | null | null | O=C1COc2ccc([N+](=O)[O-])nc2N1>C1CCOC1>O=[N+]([O-])c1ccc2c(n1)N=CCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db40474404cc4a829e9b456ef0aab187 | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.Nn1cccc1>>CC(C)Oc1ccc(Nc2nc(Nn3cccc3)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OC(C)C)F.NN1C=CC=C1>>FC=1C(=NC(=NC1)NN1C=CC=C1)NC1=CC=C(C=C1)OC(C)C | Cl[c:12]1[n:11][c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:24][cH:23]2)[c:21]([F:22])[cH:20][n:19]1.[NH2:13][n:14]1[cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][c:12]([NH:13][n:14]3[cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][c:21]2[F:22])[... | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.Nn1cccc1 | CC(C)Oc1ccc(Nc2nc(Nn3cccc3)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nn3cccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[#7;a:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[#7;a:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(4-isopropoxyphenyl)-4-pyrimidineamine was reacted with 1-aminopyrrole to provide 5-fluoro-N4-(4-isopropoxyphenyl)-N2-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cc[nH]c1 | HCl | null | null | null | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.Nn1cccc1>>CC(C)Oc1ccc(Nc2nc(Nn3cccc3)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-faede01aa8dd49b6a4a7845d9032ab07 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nn1cccc1>>Fc1cnc(Nn2cccc2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NN1C=CC=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NN1C=CC=C1 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:12]1.[NH2:6][n:7]1[cH:8][cH:9][cH:10][cH:11]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][n:7]2[cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]1[NH:14][c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[O:21][CH2:22][CH2:... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nn1cccc1 | Fc1cnc(Nn2cccc2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[#7;a:7](:[c:8]):[c:9]>>[c:8]:[#7;a:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine was reacted with 1-aminopyrrole to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cc[nH]c1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nn1cccc1>>Fc1cnc(Nn2cccc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a1a95a4d25540b88e44d0d9f43e2ab9 | Nn1cccc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nn3cccc3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NN1C=CC=C1>>FC=1C(=NC(=NC1)NN1C=CC=C1)NC1=CC(=CC=C1)O | [NH2:11][n:12]1[cH:13][cH:14][cH:15][cH:16]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:21]2)[c:19]([F:20])[cH:18][n:17]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][n:12]3[cH:13][cH:14][cH:15][cH:16]3)[n:17][cH:18][c:19]2[F:20])[cH:21]1 | Nn1cccc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nn3cccc3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nn3cccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[#7;a:7](:[c:8]):[c:9]>>[c:8]:[#7;a:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine was reacted with 1-aminopyrrole to provide 5-fluoro-N4-(3-hydroxyphenyl)-N2-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.95 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cc[nH]c1 | HCl | null | null | null | Nn1cccc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nn3cccc3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3db38208cd547679d9de29e181733c7 | CC(C)Oc1ccc(N)cc1.Fc1cnc(Cl)nc1Nn1cccc1>>CC(C)Oc1ccc(Nc2ncc(F)c(Nn3cccc3)n2)cc1 | ClC1=NC=C(C(=N1)NN1C=CC=C1)F.C(C)(C)OC1=CC=C(N)C=C1>>FC=1C(=NC(=NC1)NC1=CC=C(C=C1)OC(C)C)NN1C=CC=C1 | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:23][cH:24]1.Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][n:17]2[cH:18][cH:19][cH:20][cH:21]2)[n:22]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][n:17]3[cH:18][cH:19][cH:20][cH:21]3)[n:22]2... | CC(C)Oc1ccc(N)cc1.Fc1cnc(Cl)nc1Nn1cccc1 | CC(C)Oc1ccc(Nc2ncc(F)c(Nn3cccc3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nn3cccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine was reacted with 4-isopropoxyaniline to produce 5-fluoro-N2-(4-isopropoxyphenyl)-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cc[nH]c1 | HCl | null | null | null | CC(C)Oc1ccc(N)cc1.Fc1cnc(Cl)nc1Nn1cccc1>>CC(C)Oc1ccc(Nc2ncc(F)c(Nn3cccc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90e353ad12474827ae82cb1ebe146784 | Fc1cnc(Cl)nc1Nn1cccc1.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nn1cccc1 | ClC1=NC=C(C(=N1)NN1C=CC=C1)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NN1C=CC=C1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18]([NH:19][n:20]2[cH:21][cH:22][cH:23][cH:24]2)[n:17]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[O:13][CH2:14][CH2:15][O:16]2>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[O:13][CH2:14][CH2:15][O:16]3)[n:17][c:18]1[NH:19][n:20]1[cH:21][cH:22][cH:2... | Fc1cnc(Cl)nc1Nn1cccc1.Nc1ccc2c(c1)OCCO2 | Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nn1cccc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine was reacted with 3,4-ethylenedioxyaniline to produce N2-(3,4-ethylenedioxyphenyl)-5-Fluoro-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.c1cc[nH]c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nn1cccc1.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nn1cccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd4c9d70e7dc4aa598874c0c42ab236b | Fc1cnc(Cl)nc1Nn1cccc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nn3cccc3)n2)c1 | ClC1=NC=C(C(=N1)NN1C=CC=C1)F.NC=1C=C(C=CC1)O>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NN1C=CC=C1 | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][n:15]2[cH:16][cH:17][cH:18][cH:19]2)[n:20]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:21]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][n:15]3[cH:16][cH:17][cH:18][cH:19]3)[n:20]2)[cH:21]1 | Fc1cnc(Cl)nc1Nn1cccc1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nn3cccc3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nn3cccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine was reacted with 3-aminophenol to produce 5-fluoro-N2-(3-hydroxyphenyl)-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.68 (s, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cc[nH]c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nn1cccc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nn3cccc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1d63dd37c1742878f062013a6be6afd | Clc1cc(Cl)ncn1.Nc1cccc(O)c1>>Oc1cccc(Nc2cc(Cl)ncn2)c1 | ClC1=NC=NC(=C1)Cl.OC=1C=C(N)C=CC1.O>>ClC1=CC(=NC=N1)NC1=CC(=CC=C1)O | Cl[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][n:14]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:15]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][n:14]2)[cH:15]1 | Clc1cc(Cl)ncn1.Nc1cccc(O)c1 | Oc1cccc(Nc2cc(Cl)ncn2)c1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7]:1 | null | [] | null | null | null | null | The reaction of 4,6-dichloropyrimidine with excess 3-hydroxyaniline in MeOH at 800° C. for 24 h followed by dilution with water and acidification gave the crude product which was purified by silica gel column chromatography to obtain 6-chloro N4-(3-hydroxyphenyl)-4-pyrimidineamine. 1H NMR (CD3OD): δ 8.36 (d, 1H, J=1.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CO | null | null | Clc1cc(Cl)ncn1.Nc1cccc(O)c1>CO>Oc1cccc(Nc2cc(Cl)ncn2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36014a71ae2348c19cf0144bcff7d6d0 | Brc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2.OB(O)c1ccccc1>>c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.C1(=CC=CC=C1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2 | Br[c:5]1[cH:6][n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[O:16][CH2:17][CH2:18][O:19]3)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][c:26]2[c:27]([cH:28]1)[O:29][CH2:30][CH2:31][O:32]2.OB(O)[c:4]1[cH:3][cH:2][cH:1][cH:34][cH:33]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12... | Brc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2.OB(O)c1ccccc1 | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd] | COCCOC.CCOC(=O)C | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12] | null | [] | 80 | CELSIUS | null | null | A mixture of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine (20 mg, 0.044 mmol) and phenylboronic acid (6.9 mg, 0.057 mmol) in DME (1 mL) was prepared in a sealed tube and purged with N2. Tetrakis(triphenylphosphine) palladium(O) (0.002 mmol) was added, and the reaction tube sealed and heated at 80° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HBr.B | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].COCCOC.CCOC(=O)C | 80 | null | Brc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2.OB(O)c1ccccc1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd].COCCOC.CCOC(=O)C>c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-369154de1ab0432ab5b97886a4e923f5 | OB(O)c1ccco1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>c1coc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.O1C(=CC=C1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C=2OC=CC2 | OB(O)[c:4]1[o:3][cH:2][cH:1][cH:33]1.c1ccc(-[c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]4[c:14]([cH:15]3)[O:16][CH2:17][CH2:18][O:19]4)[n:20][c:21]2[NH:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[O:29][CH2:30][CH2:31][O:32]3)cc1>>[cH:1]1[cH:2][o:3][c:4](-[c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12... | OB(O)c1ccco1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | c1coc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 | null | null | null | C-C Coupling | OtherReaction | 496806d7af8ea3a310508855ff2ceeab2a90623f30ee9d9e1e5e3cf0f78375ba | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1coc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 | O-B(-O)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-c1:c:c:c:c:c:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine and furan-2-boronic acid were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-(2-furanyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.13 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccoc1.c1ccccc1.c1cncnc1 | c1ccoc1.c1cncnc1 | c1ccoc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO-.B | null | null | null | OB(O)c1ccco1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>c1coc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bd74b909423490797eed0ae38eccd0a | OB(O)c1ccc(Cl)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Clc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.ClC1=CC=C(C=C1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=C(C=C2)Cl | OB(O)[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:35][cH:34]1.c1ccc(-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:15]([cH:16]3)[O:17][CH2:18][CH2:19][O:20]4)[n:21][c:22]2[NH:23][c:24]2[cH:25][cH:26][c:27]3[c:28]([cH:29]2)[O:30][CH2:31][CH2:32][O:33]3)cc1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:... | OB(O)c1ccc(Cl)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | Clc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | null | null | null | C-C Coupling | Chlorination | ba893125520e25966ca57a6f0faee6e64c94fe3ac336cf5998684ec6dad689dc | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-c1:c:c:c:c:c:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine and 4-chlorophenylboronic acid were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-(4-chlorophenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6)... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccccc1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO-.B | null | null | null | OB(O)c1ccc(Cl)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Clc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-580e15a72edc4812b37b735868565e88 | OB(O)c1cccc(Cl)c1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Clc1cccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.ClC=1C=C(C=CC1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC(=CC=C2)Cl | OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:35]1.c1ccc(-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[O:18][CH2:19][CH2:20][O:21]4)[n:22][c:23]2[NH:24][c:25]2[cH:26][cH:27][c:28]3[c:29]([cH:30]2)[O:31][CH2:32][CH2:33][O:34]3)cc1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:1... | OB(O)c1cccc(Cl)c1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | Clc1cccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 | null | null | null | C-C Coupling | Chlorination | ba893125520e25966ca57a6f0faee6e64c94fe3ac336cf5998684ec6dad689dc | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-c1:c:c:c:c:c:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine and 3-chlorophenylboronic acid were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-(3-chlorophenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): ... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccccc1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO-.B | null | null | null | OB(O)c1cccc(Cl)c1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Clc1cccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8bdc2e638e74d23a73b1adcc13c61b2 | COC(=O)c1ccc(B(O)O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>COC(=O)c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.COC(=O)C1=CC=C(C=C1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=C(C=C2)C(=O)OC | OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:38][cH:37]1.c1ccc(-[c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][CH2:21][CH2:22][O:23]4)[n:24][c:25]2[NH:26][c:27]2[cH:28][cH:29][c:30]3[c:31]([cH:32]2)[O:33][CH2:34][CH2:35][O:36]3)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6... | COC(=O)c1ccc(B(O)O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | COC(=O)c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | null | null | null | C-C Coupling | OtherReaction | ba893125520e25966ca57a6f0faee6e64c94fe3ac336cf5998684ec6dad689dc | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-c1:c:c:c:c:c:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine and (4-methoxycarbonylphenyl)boronic acid were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-(4-methoxycarbonylphenyl)-2,4-pyrimidinediami... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccccc1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO-.B | null | null | null | COC(=O)c1ccc(B(O)O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>COC(=O)c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6aeaa66aa68c4aa5953e81211d17653e | OB(O)c1ccc(O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Oc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)Br.OC1=CC=C(C=C1)B(O)O>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=C(C=C2)O | OB(O)[c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:35][cH:34]1.c1ccc(-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:15]([cH:16]3)[O:17][CH2:18][CH2:19][O:20]4)[n:21][c:22]2[NH:23][c:24]2[cH:25][cH:26][c:27]3[c:28]([cH:29]2)[O:30][CH2:31][CH2:32][O:33]3)cc1>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:... | OB(O)c1ccc(O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | Oc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | null | null | null | C-C Coupling | OtherReaction | ba893125520e25966ca57a6f0faee6e64c94fe3ac336cf5998684ec6dad689dc | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-c1:c:c:c:c:c:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3,4-ethylenedioxyphenyl)-5-bromo-2,4-pyrimidinediamine and 4-hydroxyphenylboronic acid were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-(4-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccccc1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO-.B | null | null | null | OB(O)c1ccc(O)cc1.c1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1>>Oc1ccc(-c2cnc(Nc3ccc4c(c3)OCCO4)nc2Nc2ccc3c(c2)OCCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0c8d64f4a714626884b302fe1855503 | OB(O)c1ccccc1.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(-c3ccccc3)c(Nc3cccc(O)c3)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)Br.C1(=CC=CC=C1)B(O)O>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)C1=CC=CC=C1 | OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.Br[c:11]1[cH:10][n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:28]2)[n:27][c:18]1[NH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([OH:25])[cH:26]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18](... | OB(O)c1ccccc1.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1 | Oc1cccc(Nc2ncc(-c3ccccc3)c(Nc3cccc(O)c3)n2)c1 | null | null | null | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Nc2ncc(-c3ccccc3)c(Nc3ccccc3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine and phenylboronic acid were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-phenyl-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.85 (bs, 1H), 7.54-7.38 (m, 5H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccccc1.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(-c3ccccc3)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b594c951e9b4617acf2c8449af9926c | OB(O)c1ccc2c(c1)OCO2.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(-c3ccc4c(c3)OCO4)c(Nc3cccc(O)c3)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C2=CC=CC=C2.OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)Br.C1OC=2C=C(C=CC2O1)B(O)O>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)C1=CC2=C(C=C1)OCO2 | OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][CH2:19][O:20]2.Br[c:11]1[cH:10][n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:31]2)[n:30][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:26][c:27]([OH:28])[cH:29]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]4[... | OB(O)c1ccc2c(c1)OCO2.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1 | Oc1cccc(Nc2ncc(-c3ccc4c(c3)OCO4)c(Nc3cccc(O)c3)n2)c1 | null | null | null | C-C Coupling | Suzuki | 9533a78ae0398b6b9e084e3edece74b99cc46716836dba421d6c9648f8d75be4 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Nc2ncc(-c3ccc4c(c3)OCO4)c(Nc3ccccc3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]-[#8:13]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]-[#8:13] | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine and 3,4-methylenedioxyphenylboronic acid were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-(3,4-methylenedioxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3O... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)OCO2.c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCO2.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccc2c(c1)OCO2.Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(-c3ccc4c(c3)OCO4)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e986d123b0e545078aaa34f5e1ce8f17 | COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1>>COC(=O)c1cc(N)cc(C(=O)O)c1 | [N+](=O)([O-])C=1C=C(C=C(C(=O)OC)C1)C(=O)[O-]>>NC=1C=C(C(=O)O)C=C(C1)C(=O)OC | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][c:10]([C:11](=[O:12])[O-:13])[cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14]1 | COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1 | COC(=O)c1cc(N)cc(C(=O)O)c1 | null | [Pd] | CO | Reduction | OtherReaction | 52a7f99de94db5801d99f619b45e832fbffda7c4f32ee30c9a1b79bddd276142 | 8634c38070179766e5e7f40efed7e6c01018220fad7c2952027accf0a452ff4c | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7] | null | [] | null | null | 3 | HOUR | A suspension of mono-methyl 5-nitro-isophthalate (22.5 g, 100 mmol) and palladium on carbon (5%, 2.00 g) in methanol (100 mL) is shaken in a hydrogenation apparatus under hydrogen (50 psi) for 3 hours. The mixture is then filtered through diatomaceous earth and concentrated to give the title compound, NMR (300 MHz, CDC... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Carboxylic acid.Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 3 | COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1>[Pd].CO>COC(=O)c1cc(N)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c899b6547e174f08974c65b6dc006c10 | CCCNCCC.COC(=O)c1cc(Br)cc(C(=O)O)c1>>CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 | C(=O)(C=1NC=CN1)C=1NC=CN1.BrC=1C=C(C(=O)O)C=C(C1)C(=O)OC.C(CC)NCCC>>BrC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH3:7].O[C:8](=[O:9])[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20]1 | CCCNCCC.COC(=O)c1cc(Br)cc(C(=O)O)c1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 0.5 | HOUR | Carbonyl diimidazole (3.0 g, 18 mmol) is added to a solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (XIX, PREPARATION 2, 3.9 g, 15 mmol) in THF (30 mL). The mixture is stirred for 0.5 hours. Dipropylamine (AMINE, 4.2 mL, 30 mmol) is added to the mixture, which is then stirred for 24 hours. The solvent is then remov... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 0.5 | CCCNCCC.COC(=O)c1cc(Br)cc(C(=O)O)c1>C1CCOC1>CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cc7d72019e942889e3debee57a7b35a | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>>CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1 | BrC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.O.[OH-].[Li+]>>BrC=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC | C[O:18][C:16]([c:15]1[cH:14][c:12]([Br:13])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:19]1)=[O:17]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19]1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1 | null | null | C1CCOC1.O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 1 | HOUR | To a solution of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, PREPARATION 3, 1.4 g, 4.1 mmol) in THF/water/methanol (4/2/2, 8 mL) is added to lithium hydroxide monohydrate (0.17 g, 4.05 mmol). The mixture is stirred at 20 degrees -25 degrees C. for 1 hour and then solvent is removed under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C1CCOC1.O.CO | null | 1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>C1CCOC1.O.CO>CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-068e6c94189f4da7b89a898e231dbb0c | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.CN1CCCC1=O>>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1 | C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C[Si](N[Si](C)(C)C)(C)C.C(C)(C)N(CC)C(C)C.BrC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.CN1CCCC1=O>>NC(=O)C=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC | Br[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:22][c:17]([C:18](=[O:19])[O:20][CH3:21])[cH:16]1.C[N:14]1CCC[C:13]1=[O:15]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][c:17]([C:18](=[O:19])[O:20][CH3:21])[cH... | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.CN1CCCC1=O | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | C-C Coupling | OtherReaction | 4cdd7d11680ebfc4858694e428bd9467d58d06cb82c458985358e4e35d51ad9f | f157759dea0eed7ccdc9216bb16577a255aaad8f7f0f3cdb122addeb23d2a8ef | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11].C-[N;H0;D3;+0:12]1-C-C-C-[C;H0;D3;+0:13]-1=[O;D1;H0:14]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D3;+0:13](-[NH2;D1;+0:12])=[O;D1;H0:14]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11] | null | [] | 100 | CELSIUS | 24 | HOUR | To a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, PREPARATION 3, 0.5 g, 1.47 mmol) in dry N-methyl pyrrolidinone under a carbon monoxide atmosphere is added palladium (II) acetate (0.017 9, 0.074 mmol), 1,3-bis(diphenylphosphino)propane (0.045 g, 0.11 mmol), hexamethyldisilazane (1.0 mL, 4.7 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary amide | c1ccccc1.C1CC[NH]C1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | 100 | 24 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1.CN1CCCC1=O>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f962debf297146cf800bf33d073b19e4 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1>>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 | O.[OH-].[Na+].NC(=O)C=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.Cl>>NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC | C[O:20][C:18]([c:17]1[cH:16][c:12]([C:13]([NH2:14])=[O:15])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:21]1)=[O:19]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 22.5 | CELSIUS | 24 | HOUR | To a mixture of methyl 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoate (XXII, PREPARATION 5, 0.197 g, 0.64 mmol) in methanol (5.0 mL) is added sodium hydroxide (1N, 3.0 mL). The mixture is stirred at 20-25 degrees C. for 24 hours. The mixture is acidified to about pH 5 with hydrochloric acid (10%). Water (50 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | 22.5 | 24 | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)OC)c1>CO>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-494fa8b7d0714b6aac6de3a0fdac6d91 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1>>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1 | BrC=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.CN1C(CCC1)=O>>C(#N)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC | Br[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:20][c:16]([C:17](=[O:18])[OH:19])[cH:15]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20]1 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1 | null | null | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:12]#[N;D1;H0:13]):[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | 175 | CELSIUS | 2.5 | HOUR | A mixture of 3-bromo-5-[(dipropylamino)carbonyl]benzoic acid (PREPARATION 4, 0.596 9, 1.82 mmol) and copper nitrile (0.325 g, 3.63 mmol) in N-methylpyrrolidinone (1.5 mL) is stirred at 175 degrees C. for 2.5 hour, at which time the mixture is cooled and partitioned between ethyl acetate and hydrochloric acid (3N). The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | null | 175 | 2.5 | CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)O)c1>>CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-621e11d13b4e4ae9a66d214890fcf000 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.NC(N)=O>>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 | NC(=O)N.OO.C(#N)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC.C([O-])([O-])=O.[K+].[K+].CC(=O)C.NC(=O)N.OO.NC(=O)N.OO>>NC(=O)C=1C=C(C(=O)O)C=C(C1)C(=O)N(CCC)CCC | [CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13]#[N:14])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]1.NC(N)=[O:15]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]1 | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.NC(N)=O | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 | null | null | O | Miscellaneous | OtherReaction | c996d5ba5bc39df12c82584dc1cdf2f89ff026637849db6379a667b6e060cf08 | 169ed421a83f9db2e7fbded644f3f5bbb9f7fbdf41a5d23752f3a3088d8b4660 | c1ccccc1 | N-C(-N)=[O;H0;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | 22.5 | CELSIUS | null | null | A mixture of 3-cyano-5-[(dipropylamino)carbonyl]benzoic acid (IX/XXXII, PREPARATION 7, 0.602 g, 2.19 mmol), potassium carbonate (0.212 g, 1.53 mmol), and acetone (2.5 mL) is stirred at 20-25 degrees C. Water (2.5 mL) and urea-hydrogen peroxide adduct (0.825 g, 8.78 mmol) are added and the mixture is stirred for 15 hour... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Nitrile | Primary amide | null | null | c1ccccc1 | Other | O | 22.5 | null | CCCN(CCC)C(=O)c1cc(C#N)cc(C(=O)O)c1.NC(N)=O>O>CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37a4bd4f0f694aebac122f2c3f589643 | CCCNCCC.COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1>>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1 | C(=O)(C=1NC=CN1)C=1NC=CN1.[N+](=O)([O-])C=1C=C(C=C(C(=O)OC)C1)C(=O)[O-].C(CC)NCCC>>C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)[N+](=O)[O-])CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH3:7].[O-][C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:... | CCCNCCC.COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1 | null | null | C1CCOC1 | Acylation | OtherReaction | 4cfceec1aea84a79816c41fae0c81172c18248078f31ae4437446c5821f56e86 | abe2f9e72dd5fcaae131e2f313c58ce84793c9db4899e2929efc0f663f613b41 | c1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[O-]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C:4]-[C:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 0.5 | HOUR | Carbonyl diimidazole (3.90 g, 24.0 mmol) is added to a mixture of mono-methyl 5-nitro-isophthalate (XXVIII, 4.50 g, 20.0 mmol) in dry THF (50 mL). The mixture is stirred for 0.5 hours. Dipropylamine (3.28 mL, 24.0 mmol) is added slowly to the mixture. The reaction mixture is then stirred for 4 hours. The solvent is rem... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 0.5 | CCCNCCC.COC(=O)c1cc(C(=O)[O-])cc([N+](=O)[O-])c1>C1CCOC1>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ad4aa36b19048e5bdc7ad490731e929 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1>>CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1 | C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)[N+](=O)[O-])CCC>>NC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC | O=[N+:13]([O-])[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:20][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:14]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([NH2:13])[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20]1 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1 | CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1 | 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 | 3 | HOUR | A suspension of methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate (XXX, PREPARATION 9, 6.00g, 20.0 mmol) and palladium on carbon (5%, 0.600 g) in methanol (40 mL) is shaken in a hydrogenation apparatus under hydrogen (45 psi) for 3 hours. The mixture is then filtered through diatomaceous earth and concentrated to give... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 3 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1>[Pd].CO>CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a60583637294df3891878bc2624c23b | CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1.Cl.O=S=O>>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1 | NC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.Cl.S(=O)=O.N(=O)[O-].[Na+]>>ClS(=O)(=O)C=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC | N[c:18]1[cH:17][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:23]1.[ClH:22].[S:19](=[O:20])=[O:21]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17][c:18]([S:19](=[O:20])(=[O:21... | CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1.Cl.O=S=O | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1 | null | null | O.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | f504dd8e212a2c0fafdf34fbf25a73c5d5727688de19bdf5f114d4b2423e5951 | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#7:10])=[O;D1;H0:11].[ClH;D0;+0:12].[O;D1;H0:13]=[S;H0;D2;+0:14]=[O;D1;H0:15]>>[#7:10]-[C:9](=[O;D1;H0:11])-[c:8]:[c:7]:[c;H0;D3;+0:1](-[S;H0;D4;+0:14](-[Cl;H0;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:15]):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | null | [] | null | null | 0.5 | HOUR | Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate (XXXI, PREPARATION 10, 1.11 g, 4 mmol) is added to a mixture of water (5 mL) and concentrated hydrochloric acid (1 mL). Sodium nitrite (0.276 g, 4 mmol) is added to the mixture slowly at 0 degrees C. The mixture is then added to an acetic acid solution (5 mL) of CuCl2.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O.C(C)(=O)O | null | 0.5 | CCCN(CCC)C(=O)c1cc(N)cc(C(=O)OC)c1.Cl.O=S=O>O.C(C)(=O)O>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23bb6ff3ad984fab9cbc4bd47236c996 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1.N>>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(N)(=O)=O)c1 | ClS(=O)(=O)C=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC.N>>NS(=O)(=O)C=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC | Cl[S:19]([c:18]1[cH:17][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:23]1)(=[O:21])=[O:22].[NH3:20]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17][c:18]([S:19]([NH2:20])(=[O... | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1.N | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(N)(=O)=O)c1 | null | null | C1CCOC1 | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 18 | HOUR | To a solution of methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]benzoate (XXXVII, PREPARATION 11, 0.100 g, 0.300 mmol) in dry THF (3 mL) is added ammonia (7 N solution in methanol, 0.214 mL, 1.50 mmol). The mixture is stirred for 18 hours and solvent is then removed. The residue is partitioned between ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C1CCOC1 | null | 18 | CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(=O)(=O)Cl)c1.N>C1CCOC1>CCCN(CCC)C(=O)c1cc(C(=O)OC)cc(S(N)(=O)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7bf219a4d7644408dbd74ef03fe29c7 | CCB(O)O.CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1 | C(C)B(O)O.C([O-])([O-])=O.[K+].[K+].[Cl-].[Li+].BrC=1C=C(C(=O)OC)C=C(C1)C(=O)N(CCC)CCC>>C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)CC)CCC | OB(O)[CH2:13][CH3:14].Br[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:21][c:16]([C:17](=[O:18])[O:19][CH3:20])[cH:15]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][CH3:14])[cH:15][c:16]([C:17](=[O:18])[O:19][CH3:20])[cH:21]1 | CCB(O)O.CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Suzuki coupling with boronic acids | 39f7c0774f1dd85658d7924179547f5320f630d82338595500ea075e526c2566 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11].O-B(-O)-[CH2;D2;+0:12]-[C;D1;H3:13]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:12]-[C;D1;H3:13]):[c:7]:[c:8]-[C:9](-[#8:10])=[O;D1;H0:11] | null | [] | 100 | CELSIUS | 18 | HOUR | Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 9, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | 100 | 18 | CCB(O)O.CCCN(CCC)C(=O)c1cc(Br)cc(C(=O)OC)c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f149a2ad67a4bcfabe09922fc8d9ce0 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1>>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1 | O.[OH-].[Li+].C(CC)N(C(=O)C=1C=C(C(=O)OC)C=C(C1)CC)CCC>>C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC | C[O:19][C:17]([c:16]1[cH:15][c:12]([CH2:13][CH3:14])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:20]1)=[O:18]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH2:13][CH3:14])[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20]1 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1 | null | null | Cl.O.C1CCOC1.CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 22.5 | CELSIUS | 3 | HOUR | Lithium hydroxide monohydrate (0.0680 g, 1.6 mmol) is added to a mixture of methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate (PREPARATION 20, 0.450 g, 1.6 mmol) in a mixture of THF/methanol/water (2/1/1, 8 mL). The mixture is stirred at 20-25 degrees C. for 3 hours. The mixture is then diluted with water (20 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | Cl.O.C1CCOC1.CO.O | 22.5 | 3 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)OC)c1>Cl.O.C1CCOC1.CO.O>CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb684f35d1024cdfb4817d3c7b9e6d8d | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr>>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr | [BH4-].[Na+].BrCC([C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)=O>>BrC[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[C:19](=[O:20])[CH2:21][Br:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[C@H:19]([OH:20])[CH2:21][Br:2... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [Br;D1;H0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5](-[C:6])-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[Br;D1;H0:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[C:5](-[C:6])-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14] | null | [] | null | null | 0.5 | HOUR | Sodium borohydride (1.32 g, 34.9 mmole, 1.1 eq.) is added to tert-Butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate (III, EXAMPLE 1, 12 g, 31.75 mmole) dissolved in absolute alcohol (500 mL) at −78 degrees C. The reaction mixture is stirred for 0.5 hour and monitored by TLC (ethyl acetate/hexane, 20/80; Rf... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | C(C)(=O)OCC.CCCCCC | null | 0.5 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)CBr>C(C)(=O)OCC.CCCCCC>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-873ccf4c46ea4fa28e13d81098c6543f | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr>>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1 | C(C)(=O)OCC.[OH-].[K+].BrC[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)O>>FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O | Br[CH2:20][C@H:19]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[OH:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[C@H:19]1[CH2:20][O:21]1 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis (intra to epoxy) | ebf120e9288f48b61f87dafb00b4bacd480e273fa54208a20ed1d8b8a8581b3e | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(CC[C@H]2CO2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[OH;D1;+0:4]>>[C:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1 | null | [] | null | null | 0.5 | HOUR | tert-Butyl (1S, 2S)-3-bromo-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate (IV, EXAMPLE 2) is dissolved in absolute alcohol (150 mL) and ethyl acetate (100 mL) and potassium hydroxide (2.3 g, 34.9 mmole, 1.1 eq.) in ethyl alcohol (85%, 5 mL) is added at −20 degrees C. The cold bath is then removed and the mixture stir... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | C1CO1 | c1ccccc1.C1CO1 | HBr | C(C)O | null | 0.5 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CBr>C(C)O>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-988810b99aa04e93adb20d694dcc0a82 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.COc1cccc(CN)c1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.COC=1C=C(CN)C=CC1>>FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(OC(C)(C)C)=O)C=C(C1)F | [CH2:10]1[C@H:11]([C@H:13]([CH2:14][c:15]2[cH:16][c:17]([F:18])[cH:19][c:20]([F:21])[cH:22]2)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[O:12]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]([OH:12])[C@H:13]... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.COc1cccc(CN)c1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCCCNCc2ccccc2)cc1 | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C@H;D3;+0:11]1-[CH2;D2;+0:12]-[O;H0;D2;+0:13]-1.[NH2;D1;+0:14]-[C:15]-[c:16]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C@H;D3;+0:11](-[OH;D1;+0:13])-[CH2;D2;+0:12]-[NH;D... | null | [] | 22.5 | CELSIUS | null | null | tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3, 245 mg, 0.82 mmol) is suspended in isopropyl alcohol (6 mL) and 3-methoxybenzylamine (160 microL, 1.22 mmol) is added with stirring at 20-25 degrees C. This mixture is heated to gentle reflux (bath temp 85 degrees C.) under nitrogen f... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.c1ccccc1 | null | C(C)(C)O | 22.5 | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.COc1cccc(CN)c1>C(C)(C)O>COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa60b7869d174ce692ae91006104b899 | COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1>>COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(OC(C)(C)C)=O)C=C(C1)F.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F | CC(C)(C)OC(=O)[NH:14][C@H:13]([C@@H:11]([CH2:10][NH:9][CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24]1)[OH:12])[CH2:15][c:16]1[cH:17][c:18]([F:19])[cH:20][c:21]([F:22])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][C@@H:11]([OH:12])[C@@H:13]([NH2:14])[CH2:15][c:16]2[cH:17][c:18]([F:... | COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1 | COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CCCCNCc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | tert-Butyl (1S, 2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, EXAMPLE 4, 258 mg, 0.59 mmol) is dissolved in methylene chloride (1 mL) at 20-25 degrees C., and trifluoroacetic acid (1 mL) is added with stirring under nitrogen. The reaction mixture is stirred at 20-25 degrees C. for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)OC(C)(C)C)c1>C(Cl)Cl>COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76bb768dedac418d869ba9fd52472074 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 | Cl.CN(CCCN=C=NCC)C.C(C)N(CC)CC.CC=1C=C(C=C(C(=O)O)C1)C(=O)N(CCC)CCC.ON1N=NC2=C1C=CC=C2.FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F>>FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | O[C:16]([c:15]1[cH:14][c:12]([CH3:13])[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:42]1)=[O:17].[NH2:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@H:29]([OH:30])[CH2:31][NH:32][CH2:33][c:34]1[cH:35][cH:36][cH:37][c:38]([O:39][CH3:40])[cH:41]1>>[CH3... | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 5 | MINUTE | (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol trifluoroacetate salt (VIII, EXAMPLE 5) is dissolved in anhydrous DMF (3 mL) and cooled to 0 degrees C. Triethylamine (500 microliter, 3.6 mmol) and 5-methyl-N,N-dipropylisophthalamic acid (156 mg, 0.59 mmol) are added with stirring. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 0 | 0.083333 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>CN(C)C=O>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-089365d5f4f843d58963dd0afea1e9e7 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.[N-]=[N+]=[N-]>>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN=[N+]=[N-] | [N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O>>C(C)(C)(C)OC(N[C@H]([C@@H](CN=[N+]=[N-])O)CC1=CC(=CC(=C1)F)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[C@@H:19]1[O:20][CH2:21]1.[N-:22]=[N+:23]=[N-:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]([F:14])[cH:15][c:16]([F:17])[cH:18]1)[C@H:19]([O... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.[N-]=[N+]=[N-] | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN=[N+]=[N-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8b95d1be17197eb0a426d15b96ad1ee2792062f84ac5ead23197000584509030 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | c1ccccc1 | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C@H;D3;+0:11]1-[CH2;D2;+0:12]-[O;H0;D2;+0:13]-1.[N-;H0;D1:14]=[#7;+:15]=[N;-;D1;H0:16]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C@H;D3;+0:11](-[OH;D1;+0:13])-[CH2;D2;+0... | null | [] | 77.5 | CELSIUS | 16 | HOUR | Sodium azide (0.22 g, 4 mmole) and ammonium chloride (2 eq) are added to tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3, 0.6 g, 2 mmole). The reaction is heated to 75-80 degrees C. and stirred for 16 hours. The reaction is monitored by TLC to insure completion. The solvent is remov... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1CO1 | null | c1ccccc1 | null | null | 77.5 | 16 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.[N-]=[N+]=[N-]>>CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN=[N+]=[N-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d15c470fb8b4e158fbe021b237720dc | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.[N-]=[N+]=NC[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1 | N[C@H]([C@@H](CN=[N+]=[N-])O)CC1=CC(=CC(=C1)F)F.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.C(C)(C)(C)O.C(C)N(CC)CC.C(C)N=C=NCCCN(C)C>>N(=[N+]=[N-])C[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)O | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:35][c:15]([C:16](O)=[O:17])[cH:14]1.[NH2:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@H:29]([OH:30])[CH2:31][N:32]=[N+:33]=[N-:34]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8]... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.[N-]=[N+]=NC[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1 | null | null | C(C)(=O)OCC.CCCCCC.CO.ClCCl.ClCCl | Acylation | OtherReaction | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8].[C:9]-[C:10](-[C:11])-[NH2;D1;+0:12]>>[C:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:5](:[c:8]):[c:4]:[c:2](-[CH3;D1;+0:1]):[c:3] | null | [] | 22.5 | CELSIUS | 16 | HOUR | To (2R, 3S)-3-amino-1-azido-4-(3,5-difluorophenyl)-2-buta (XIV, EXAMPLE 166, 0.34 g, 1.4 mmole) in dichloromethane (20 ml) is added N,N-dipropylamidoisophthalic acid (IX, 0.53 g, 2 mmole), t-butyl alcohol (0.27 g, 2 mmole) and triethylamine (0.84 ml, 6 mmole) and ethyl-1-(3-dimethylaminopropyl)carbodiimide (0.58 g, 3 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC.CO.ClCCl.ClCCl | 22.5 | 16 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.[N-]=[N+]=NC[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1>C(C)(=O)OCC.CCCCCC.CO.ClCCl.ClCCl>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1428e371c4e4b2ba18d67318db642aa | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1.CCOC(C)=O>>CC(=O)O.CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1 | N(=[N+]=[N-])C[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)O.C(C)(=O)OCC>>C(C)(=O)O.NC[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)O | [N-]=[N+]=[N:36][CH2:35][C@H:33]([C@@H:23]([NH:22][C:20]([c:19]1[cH:18][c:16]([CH3:17])[cH:15][c:14]([C:12]([N:8]([CH2:7][CH2:6][CH3:5])[CH2:9][CH2:10][CH3:11])=[O:13])[cH:37]1)=[O:21])[CH2:24][c:25]1[cH:26][c:27]([F:28])[cH:29][c:30]([F:31])[cH:32]1)[OH:34].CC[O:4][C:2]([CH3:1])=[O:3]>>[CH3:1][C:2](=[O:3])[OH:4].[CH3:... | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1.CCOC(C)=O | CC(=O)O.CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1 | null | [Pd] | C(C)(=O)O | Miscellaneous | OtherReaction | fe7918cbb9f8bcab28fdc5619cd3481539a7cf80710801933ec824d72c77ce1f | e3d244ee829ca90588cf72183525e2ba7b3f2c53e89a9052d43bdcba18acd789 | O=C(NCCc1ccccc1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[C:5]-[C:6]-[N;H0;D2;+0:7]=[N+]=[N-]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:5]-[C:6]-[NH2;D1;+0:7] | null | [] | null | null | 2 | HOUR | N1-[(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropyl]5-methyl -N3,N3-dipropylisophthalamide (XV, EXAMPLE 167, 0.3 9, 0.62 mmole) in ethyl acetate (20 ml) and acetic acid (5ml) is placed in a Parr pressure bottle. Palladium on carbon (10%, 5 g) is added and the mixture shaken under hydrogen at 50 psi for 2 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Azide | Carboxylic acid.Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)O | null | 2 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN=[N+]=[N-])c1.CCOC(C)=O>[Pd].C(C)(=O)O>CC(=O)O.CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b81deedf452447e8891a1cb795db847b | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1.O=Cc1ccoc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccco2)c1 | C(C)(=O)O.NC[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)O.O1C=C(C=C1)C=O.C(C)N(CC)CC>>FC=1C=C(C[C@@H]([C@@H](CNCC=2OC=CC2)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | [CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12]([CH3:13])[cH:14][c:15]([C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]2[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]2)[C@H:29]([OH:30])[CH2:31][NH2:32])[cH:39]1.O=[CH:33][c:34]1[cH:35][cH:36][o:38][cH:37]1>>[CH3:1][CH2:2][CH2:3][N:4](... | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1.O=Cc1ccoc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccco2)c1 | null | [Pd] | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 6450b3e23174bbcf0dd79f9efcaeaeac903e55395f8392c094134b4d274b1f72 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(N[C@H](CCNCc1ccco1)Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[o;H0;D2;+0:5]:[cH;D2;+0:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:6]:[o;H0;D2;+0:5]:1 | null | [] | 22.5 | CELSIUS | 10 | MINUTE | N1-[(1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-5-methyl-N3,N3-dipropylisophthalamide acetic acid salt (XVI, EXAMPLE 168, 76 mg, 0.146 mmol) is dissolved in absolute ethanol (2 mL). 3-Furaldehyde (20 microL, 0.231 mmol) and triethylamine (30 microL, 0.215 mmol) are added via syringe, with stirring at 20-25 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | c1ccoc1 | c1ccoc1 | c1ccccc1.c1ccccc1.c1ccoc1 | Other | [Pd].C(C)O | 22.5 | 0.166667 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CN)c1.O=Cc1ccoc1>[Pd].C(C)O>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccco2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb83c7a951fa4e2b99ae626c954d9ec0 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCNC(=O)[C@H](C)N>>CCNC(=O)[C@H](C)NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.N[C@H](C(=O)NCC)C>>FC=1C=C(C[C@@H]([C@@H](CN[C@H](C(=O)NCC)C)O)NC(OC(C)(C)C)=O)C=C(C1)F | [CH2:9]1[C@H:10]([C@H:12]([CH2:13][c:14]2[cH:15][c:16]([F:17])[cH:18][c:19]([F:20])[cH:21]2)[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[O:11]1.[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]([CH3:7])[NH2:8]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]([CH3:7])[NH:8][CH2:9][C@@H:10]([OH:11])[C@H:12]([CH2:13][c... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCNC(=O)[C@H](C)N | CCNC(=O)[C@H](C)NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C;D1;H3:6])-[NH2;D1;+0:7].[C:8]-[C:9](-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])-[C@H;D3;+0:18]1-[CH2;D2;+0:19]-[O;H0;D2;+0:20]-1>>[C:8]-[C:9](-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4 and 14-164 and making non-critical variations and reacting tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3) with (2S)-2-amino-N-ethylpropanamide (VI), the title compound is obtained.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1 | null | null | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCNC(=O)[C@H](C)N>>CCNC(=O)[C@H](C)NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58c617337dde4983b00cc67a19472259 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)CCCC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CNCc1cccc(OC)c1 | FC(C(=O)O)(F)F.N[C@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)CC1=CC(=CC(=C1)F)F.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC>>FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OC)O)NC(CCCC(=O)N(CCC)CCC)=O)C=C(C1)F | CCc1c[c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:11][c:12]([C:13](O)=[O:14])c1.[NH2:15][C@@H:16]([CH2:17][c:18]1[cH:19][c:20]([F:21])[cH:22][c:23]([F:24])[cH:25]1)[C@H:26]([OH:27])[CH2:28][NH:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][c:35]([O:36][CH3:37])[cH:38]1>>[CH3:1][CH2:2][CH2:3][N:4](... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCN(CCC)C(=O)CCCC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CNCc1cccc(OC)c1 | null | null | null | Acylation | OtherReaction | 8ec1c1e5e7430f1d6f8fc1cd47268cc5dab63ed7beaad658ca69f15ca5276629 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(CCCCNCc2ccccc2)cc1 | C-C-c1:c:[c;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6]):[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:9](-O)=[O;D1;H0:10]):c:1.[C:11]-[C:12](-[C:13])-[NH2;D1;+0:14]>>[C:11]-[C:12](-[C:13])-[NH;D2;+0:14]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 6 and making non-critical variations and using (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol (VIII, EXAMPLE 5) with 5-(dipropylamino)-5-oxopentanoic acid (IX), the title compound is obtained, MH+=534.2.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1>>CCCN(CCC)C(=O)CCCC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CNCc1cccc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d80d320358b34e2787f75677ac3ae9f2 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCCOc2ccccc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.C1(CCCC2=CC=CC=C12)N>>FC=1C=C(C[C@@H]([C@@H](CNCCOC2=CC=CC=C2)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:42][c:15](C(=O)O)[cH:14]1.c1ccc2c(c1)CCC[CH:33]2[NH2:32].[C:16](=[O:17])([NH:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@@H:29]1[O:30][CH2:31]1)[O:35][CH2:34][c:36]1[cH:37][cH:38][cH:39... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCCOc2ccccc2)c1 | null | null | null | C-C Coupling | OtherReaction | c42db6eb3f368be389b6601c4f852b2fade8e5b35786330659e6bdd29731bafe | dd7e3ecc652307d8e90e467b7fbd71c75a79b8294c159d15908537cdcf39b29d | O=C(N[C@H](CCNCCOc1ccccc1)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[O;H0;D2;+0:16]-[CH2;D2;+0:17]-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22])-[C@H;D3;+0:23]1-[CH2;D2;+0:24]-[O;H0;D2;+0:25]-1.[NH2;D1;+0:26]-[CH;D3;+0:27]1-C-C-C... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), H2N—CH2—CH2—O-phenyl (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=582.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Ether.Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.C1CO1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCCOc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0513e3bdf4b4036a27a41877ea30055 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OCC(C)C)c2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.C1(CCCC2=CC=CC=C12)N>>FC=1C=C(C[C@@H]([C@@H](CNCC2=CC(=CC=C2)OCC(C)C)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:45][c:15](C(=O)O)[cH:14]1.C1C[CH:33]([NH2:32])[c:34]2[cH:35][cH:36][cH:37][cH:44][c:38]2C1.c1c[cH:42][c:41]([CH2:40][O:39][C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]2[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]2)[C@... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OCC(C)C)c2)c1 | null | null | null | C-C Coupling | OtherReaction | c42db6eb3f368be389b6601c4f852b2fade8e5b35786330659e6bdd29731bafe | dd7e3ecc652307d8e90e467b7fbd71c75a79b8294c159d15908537cdcf39b29d | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[O;H0;D2;+0:16]-[C:17]-[c;H0;D3;+0:18]1:[cH;D2;+0:19]:c:c:c:[cH;D2;+0:20]:1)-[C@H;D3;+0:21]1-[CH2;D2;+0:22]-[O;H0;D2;+0:23]-1.[NH2;D1;+0:24]-[CH;D3;+0:25]1-C-C-C-... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), H2N—CH2-phenyl-O-i-butyl (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=624.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Ether.Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1.C1CO1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(OCC(C)C)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ce8802a0bd64889a6be2265b91227b6 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1ccc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccccc2)o1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.C1(CCCC2=CC=CC=C12)N.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC>>C(C1=CC=CC=C1)NC[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(=O)C=1OC(=CC1)C(=O)N(CCC)CCC)O | CC[c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])cc(C(=O)[OH:38])[cH:13]1.c1ccc2c(c1)CCCC2[NH2:30].O([C:14](=[O:15])[NH:16][C@@H:17]([CH2:18][c:19]1[cH:20][c:21]([F:22])[cH:23][c:24]([F:25])[cH:26]1)[C@@H:27]1[O:28][CH2:29]1)[CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1>>[CH3:... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1ccc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccccc2)o1 | null | null | null | C-C Coupling | OtherReaction | 7dc5096045eb3fb57b0c60d2eb210bfae56569f1d29b8a496fa87a3605627575 | da0b085b8ba37603d3f6e9c5274df1ce23f2e8cf9bc9dbd5a0baf66136930e3b | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccco1 | C-C-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]):c:c(-C(=O)-[OH;D1;+0:9]):[cH;D2;+0:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-[CH2;D2;+0:16]-[c:17](:[c:18]):[c:19])-[C@H;D3;+0:20]1-[CH2;D2;+0:21]-[O;H0;D2;+0:22]-1.[NH2;D1;+0:23]-C1-C-C-C-c2:c:c:c:c:c:2-1>>[C:11]-[C... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), H2N—CH2-phenyl (VI) and (CH3—CH2—CH2—)2N—CO-(2,5-furanyl)-CO— (IX), the title compound is obtained, MH+=528.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.C1CO1 | c1ccoc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1ccc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccccc2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a237d6258019441b9f36f22bb1133ee0 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC(Cc2ccccc2)c2ccccc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.C1(CCCC2=CC=CC=C12)N>>FC=1C=C(C[C@@H]([C@@H](CNC(CC2=CC=CC=C2)C2=CC=CC=C2)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:47][c:15](C(=O)O)[cH:14]1.C1C[CH:33]([NH2:32])[c:41]2[cH:45][cH:44][cH:43][cH:42][c:46]2C1.O([C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@@H:29]1[O:30][CH2:31]1)[CH2:3... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC(Cc2ccccc2)c2ccccc2)c1 | null | null | null | C-C Coupling | OtherReaction | 48f59043422306903835d10148bfc3ecb03172612d94b6d30d1e50fbfff7b12c | da0b085b8ba37603d3f6e9c5274df1ce23f2e8cf9bc9dbd5a0baf66136930e3b | O=C(N[C@H](CCNC(Cc1ccccc1)c1ccccc1)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-[CH2;D2;+0:16]-[c:17](:[c:18]):[c:19])-[C@H;D3;+0:20]1-[CH2;D2;+0:21]-[O;H0;D2;+0:22]-1.[NH2;D1;+0:23]-[CH;D3;+0:24]1-C-C-C-[c;H0;D3;+0:25]2:[cH;D2;+0:26]:[c:27... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), NH2—CH( )—CH2-phenyl (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=642.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.C1CO1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.NC1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC(Cc2ccccc2)c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efcb36ee38284cd8adee45818e4134b7 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.COC1=CC=C2CCCC(C2=C1)N>>FC=1C=C(C[C@@H]([C@@H](CNC2CCCC3=CC=C(C=C23)OC)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:45][c:15](C(=O)O)[cH:14]1.[NH2:32][CH:33]1[CH2:34][CH2:35][CH2:36][c:37]2[cH:38][cH:39][c:40]([O:41][CH3:42])[cH:43][c:44]21.c1ccc(CO[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]2[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 | null | null | null | C-C Coupling | OtherReaction | 2854b742cb51c939453389efd08e442b156ed0763156ae8bc54989e828761176 | da0b085b8ba37603d3f6e9c5274df1ce23f2e8cf9bc9dbd5a0baf66136930e3b | O=C(N[C@H](CCNC1CCCc2ccccc21)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-C-c1:c:c:c:c:c:1)-[C@H;D3;+0:16]1-[CH2;D2;+0:17]-[O;H0;D2;+0:18]-1.[C:19]-[C:20](-[NH2;D1;+0:21])-[c:22]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[c:2](-[CH3;D1... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), 7-methoxy-1,2,3,4-tetrahydro-1-naphthalenylamine (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=622.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccccc1.C1CO1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6db85f8cbdad4ceb99435bdbff9f5e76 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.COC1=CC=C2CCCC(C2=C1)N>>FC=1C=C(C[C@@H]([C@@H](CNC2CCCC3=CC=C(C=C23)OC)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:45][c:15](C(=O)O)[cH:14]1.[NH2:32][CH:33]1[CH2:34][CH2:35][CH2:36][c:37]2[cH:38][cH:39][c:40]([O:41][CH3:42])[cH:43][c:44]21.c1ccc(CO[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]2[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 | null | null | null | C-C Coupling | OtherReaction | 2854b742cb51c939453389efd08e442b156ed0763156ae8bc54989e828761176 | da0b085b8ba37603d3f6e9c5274df1ce23f2e8cf9bc9dbd5a0baf66136930e3b | O=C(N[C@H](CCNC1CCCc2ccccc21)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-C-c1:c:c:c:c:c:1)-[C@H;D3;+0:16]1-[CH2;D2;+0:17]-[O;H0;D2;+0:18]-1.[C:19]-[C:20](-[NH2;D1;+0:21])-[c:22]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[c:2](-[CH3;D1... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), 7-methoxy-1,2,3,4-tetrahydro-1-naphthalenylamine (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=622.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccccc1.C1CO1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNC2CCCc3ccc(OC)cc32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-010ea26158b441409d08b14c87d3ca58 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(C#N)c2)c1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.COC1=CC=C2CCCC(C2=C1)N.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(=CC=C1)C#N)=O | CCC[N:9](CCC)C(=O)[c:24]1[cH:25][c:26](CC)[cH:27][c:28]([C:29](=O)O)[cH:31]1.C1C[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:7]2[CH:8]([NH2:30])C1.Fc1cc(F)c[c:15]([CH2:14][C@@H:13]([C@H:11]2[CH2:10][O:12]2)[NH:21][C:22](OCc2[cH:16][cH:17][cH:18][cH:19][cH:20]2)=[O:23])c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(C#N)c2)c1 | null | null | null | C-C Coupling | OtherReaction | 064105fa6cc372b507b4fc8f4129f14e1df5741723a3af26757b475e7d9cb4b7 | 4aa46988fcd991f01533e94b85021b09773c4319a16372ebd0f42aa44eed5fd7 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-C-C-[N;H0;D3;+0:1](-C-C-C)-C(=O)-[c;H0;D3;+0:2]1:[c:3]:[c;H0;D3;+0:4](-C-C):[c:5]:[c:6](-[C;H0;D3;+0:7](-O)=O):[c:8]:1.F-c1:c:[c;H0;D3;+0:9](-[C:10]-[C:11](-[#7:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-C-c2:[cH;D2;+0:15]:[c:16]:[c:17]:[c:18]:[cH;D2;+0:19]:2)-[C@H;D3;+0:20]2-[CH2;D2;+0:21]-[O;H0;D2;+0:22]-2):c:c(-F):c:1.[... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl 1-(2-oxiranyl)-2-phenylethylcarbamate (V), 3-methoxybenzylamine (VI) and 3-cyanobenzoic acid (IX), the title compound is obtained, MH+=430.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Carboxylic acid.Ether.Ether.Tertiary amide.Primary amine | Nitrile.Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1.C1CO1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(C#N)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7aac799fc054ee18236ae733e91f66e | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCCNc1ccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.COC1=CC=C2CCCC(C2=C1)N.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC=C(C=C1)NCCCC)=O | CC[CH2:4][N:5](C(=O)[c:8]1[cH:7][c:6](CC)[cH:35][c:34](C(=O)O)[cH:9]1)[CH2:3][CH2:2][CH3:1].C1C[CH:25]([NH2:24])[c:26]2[c:27]([cH:28][cH:29][c:30]([O:31][CH3:32])[cH:33]2)C1.Fc1cc(F)c[c:15]([CH2:14][C@H:13]([NH:12][C:10](OCc2[cH:16][cH:17][cH:18][cH:19][cH:20]2)=[O:11])[C@@H:21]2[O:22][CH2:23]2)c1>>[CH3:1][CH2:2][CH2:3... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCCNc1ccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc1 | null | null | null | C-C Coupling | OtherReaction | 49be9c10da129ba302eb6ad83751592b4730e788ac426351ebf64b6df7a89673 | ff2421de7ca377918a5b4cf48c098ed41bc7a479094008325f8603f1e00bd0e6 | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-C-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-[CH2;D2;+0:3]-[C:4]-[C;D1;H3:5])-C(=O)-[c;H0;D3;+0:6]1:[c:7]:[c;H0;D3;+0:8](-C-C):[c:9]:[c;H0;D3;+0:10](-C(-O)=O):[cH;D2;+0:11]:1.F-c1:c:[c;H0;D3;+0:12](-[C:13]-[C:14](-[#7:15]-[C;H0;D3;+0:16](=[O;D1;H0:17])-O-C-c2:[cH;D2;+0:18]:[c:19]:[c:20]:[c:21]:[cH;D2;+0:22]:2)-[C@H;D3;+0:23]2-[CH... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl 1-(2-oxiranyl)-2-phenylethylcarbamate (V), 3-methoxybenzylamine (VI) and 4-(butylamino)benzoic acid (IX), the title compound is obtained, MH+=476.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Carboxylic acid.Ether.Ether.Tertiary amide.Primary amine | Secondary amide.Secondary alcohol.Secondary amine.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1.c1ccccc1.C1CO1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCCNc1ccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbb59ec3a2884b44b9c0d2507b77058f | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(C)c2)c1 | FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.COC1=CC=C2CCCC(C2=C1)N.C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC>>C(C1=CC=CC=C1)[C@@H]([C@@H](CNCC1=CC(=CC=C1)OC)O)NC(C1=CC(=CC(=C1)C)C)=O | CCCN(CCC)C(=O)[c:24]1[cH:25][c:26]([CH2:27]C)[cH:28][c:29]([C:30](=O)O)[cH:31]1.C1C[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:7]2[CH:8]([NH2:9])C1.Fc1cc(F)c[c:15]([CH2:14][C@@H:13]([C@H:11]2[CH2:10][O:12]2)[NH:21][C:22](OCc2[cH:16][cH:17][cH:18][cH:19][cH:20]2)=[O:23])c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(C)c2)c1 | null | null | null | C-C Coupling | OtherReaction | acaa1a7a622bf4a256aaacbd72468366220b2f5bbd7e6a05c1251cb31610312a | 263fcd8e28ecc55014b77bbe8fc45377810af671741ac390058228b3cdb5c10b | O=C(N[C@H](CCNCc1ccccc1)Cc1ccccc1)c1ccccc1 | C-C-C-N(-C-C-C)-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[CH2;D2;+0:4]-C):[c:5]:[c:6](-[C;H0;D3;+0:7](-O)=O):[c:8]:1.F-c1:c:[c;H0;D3;+0:9](-[C:10]-[C:11](-[#7:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-C-c2:[cH;D2;+0:15]:[c:16]:[c:17]:[c:18]:[cH;D2;+0:19]:2)-[C@H;D3;+0:20]2-[CH2;D2;+0:21]-[O;H0;D2;+0:22]-2):c:c(-F):c:1.[NH2;D1;+0:... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl 1-(2-oxiranyl)-2-phenylethylcarbamate (V), 3-methoxybenzylamine (VI) and 3,5-dimethylbenzoic acid (IX), the title compound is obtained, MH+=433.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Carboxylic acid.Ether.Ether.Tertiary amide.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1.C1CO1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>COc1cccc(CNC[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cc(C)cc(C)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2d3c2a7faa443688651def880300bfc | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccoc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.COC1=CC=C2CCCC(C2=C1)N>>FC=1C=C(C[C@@H]([C@@H](CNCC2=COC=C2)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | CC(C)(C)O[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@@H:29]1[O:30][CH2:31]1.C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:39][c:15](C(=O)O)[cH:14]1.c1c2c(c[c:36]([O:37][CH3:38])[cH:35]1)[CH:33]([NH2:32])[CH2:34]C... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccoc2)c1 | null | null | null | C-C Coupling | OtherReaction | 6d2fe333158444f9a96faa4d5bf3a244aa86763a4781e2115e073861fe151523 | c34a80c34252db3a15d50c217762bbd2c5a6c4540ac320d0fed552301aaa523c | O=C(N[C@H](CCNCc1ccoc1)Cc1ccccc1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4](-[C:5])-[C@H;D3;+0:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1.C-[CH2;D2;+0:9]-[c:10]1:[c:11]:[c:12](-[C:13](-[#7:14])=[O;D1;H0:15]):[c:16]:[c;H0;D3;+0:17](-C(-O)=O):[c:18]:1.[CH3;D1;+0:19]-[O;H0;D2;+0:20]-[c;H0;D3;+0:21]1:[cH;D2;+0:22]:c:c2:c(:c:1)-[CH;D3;+0:23](-[NH2;D1;... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3), 3-furylmethylamine (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=542.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Ether.Primary amine.Boc | Secondary amide.Secondary alcohol.Secondary amine | C1CO1.c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2ccoc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6b573dce4a74696bbdf66a8bee6b0d0 | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCC2CCOC2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OC(C)(C)C)=O.COC1=CC=C2CCCC(C2=C1)N>>FC=1C=C(C[C@@H]([C@@H](CNCC2COCC2)O)NC(C2=CC(C(=O)N(CCC)CCC)=CC(=C2)C)=O)C=C(C1)F | C[C:36](C)(O[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@@H:29]1[O:30][CH2:31]1)[CH3:35].C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:39][c:15](C(=O)[OH:37])[cH:14]1.c1cc2c(cc1O[CH3:38])[CH:33]([NH2:32])[CH2:34]C... | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCC2CCOC2)c1 | null | null | null | C-C Coupling | OtherReaction | 929a239ce9a96e23b7a7ad6df2ce485ecbd11866b48c0f13a191721f4c22731e | 47d2035e40be1632377de10b5c997f78ae9b3a4a8f563eff1fd0115a19c104cf | O=C(N[C@H](CCNCC1CCOC1)Cc1ccccc1)c1ccccc1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:5]-[C:6](-[C:7])-[C@H;D3;+0:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1.C-[CH2;D2;+0:11]-[c:12]1:[c:13]:[c:14](-[C:15](-[#7:16])=[O;D1;H0:17]):[c:18]:[c;H0;D3;+0:19](-C(=O)-[OH;D1;+0:20]):[c:21]:1.[CH3;D1;+0:22]-O-c1:c:c:c2:c(:c:1)-[CH;D3;+0:23](-[NH2;D1;+... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3), (tetrahydro-3-furanylmethyl)amine (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=546.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Ether.Primary amine.Boc | Ether.Secondary amide.Secondary alcohol.Secondary amine | C1CO1.c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccccc1.C1CCOC1 | c1ccccc1.c1ccccc1.C1CCOC1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1.CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.COc1ccc2c(c1)C(N)CCC2>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCC2CCOC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3c6b0881eba41dbad393ebfae961605 | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNc2ccccc2)c1 | C(CC)N(C(=O)C=1C=C(C(=O)O)C=C(C1)CC)CCC.FC=1C=C(C=C(C1)F)C[C@@H]([C@@H]1OC1)NC(OCC1=CC=CC=C1)=O.[C@@H]1(CCCC2=CC=CC=C12)N>>N(C1=CC=CC=C1)C[C@H]([C@H](CC1=CC(=CC(=C1)F)F)NC(C1=CC(C(=O)N(CCC)CCC)=CC(=C1)C)=O)O | C[CH2:13][c:12]1[cH:11][c:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:39][c:15](C(=O)O)[cH:14]1.c1ccc2c(c1)CCC[C@@H]2[NH2:32].C(O[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][c:21]1[cH:22][c:23]([F:24])[cH:25][c:26]([F:27])[cH:28]1)[C@@H:29]1[O:30][CH2:31]1)[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:3... | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1 | CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNc2ccccc2)c1 | null | null | null | C-C Coupling | OtherReaction | e37a6eac3b148bbdae14f213fc9d458b8cdbfc618f6a2ab622e1c614f465d813 | da0b085b8ba37603d3f6e9c5274df1ce23f2e8cf9bc9dbd5a0baf66136930e3b | O=C(N[C@H](CCNc1ccccc1)Cc1ccccc1)c1ccccc1 | C-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9](-C(-O)=O):[c:10]:1.[C:11]-[C:12](-[#7:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-C-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20])-[C@H;D3;+0:21]1-[CH2;D2;+0:22]-[O;H0;D2;+0:23]-1.[NH2;D1;+0:24]-[C@H]1-C-C-C-c2:c:c:c:c:c:2-1>>[#7:6]-[C:5](=[O... | null | [] | null | null | null | null | Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), aniline (VI) and and “5-Me-PHTH” (IX), the title compound is obtained, MH+=538.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Primary amine | Secondary amide.Secondary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCCC2.C1CO1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCN(CCC)C(=O)c1cc(CC)cc(C(=O)O)c1.N[C@H]1CCCc2ccccc21.O=C(N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1)OCc1ccccc1>>CCCN(CCC)C(=O)c1cc(C)cc(C(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNc2ccccc2)c1 |
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