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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73007926fa184342830a1dbd65d16aa0 | COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CC(=O)O)cc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CC(=O)OC)N(C1=O)C.[OH-].[Na+].C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CC(=O)O)N(C1=O)C | C[O:27][C:25]([CH2:24][c:23]1[cH:22][cH:21][c:20]([NH:19][c:18]2[n:17][cH:16][c:15]3[cH:14][c:5](-[c:6]4[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]4[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:31]3[n:30]2)[cH:29][cH:28]1)=[O:26]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2... | COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CC(=O)O)cc3)nc21 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A quantity of 0.065 g (0.14 mmol) of {4-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]phenyl}-acetic acid, methyl ester of Example 84 was dissolved in 25 mL of hot methanol with stirring. At the boiling point, 1 mL of 2N sodium hydroxide was added. After 1 hour reflux, the solution... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | CO | null | null | COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1>CO>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CC(=O)O)cc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9fd5cd2b22e5454fb149f6f3ed738293 | CCOC(=O)c1cccc(N)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.NC=1C=C(C(=O)OCC)C=CC1.C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC=2C=C(C(=O)OCC)C=CC2)N(C1=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:32]1.CS(=O)(=O)[c:12]1[n:13][cH:14][c:15]2[cH:16][c:17](-[c:18]3[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]3[Cl:25])[c:26](=[O:27])[n:28]([CH3:29])[c:30]2[n:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13... | CCOC(=O)c1cccc(N)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 100 | CELSIUS | 6 | MINUTE | A mixture of 0.226 g (0.58 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.40 g (2.42 mmol) of 3-aminobenzoic acid, ethyl ester was fused in a 170° C. oil bath to give a clear melt. After 6 minutes, the melt was cooled to ca. 100° C. Glacial acetic acid (1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | 100 | 0.1 | CCOC(=O)c1cccc(N)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>O>CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b1496d4ad5040759352f2bc285c5252 | CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(C(=O)O)c3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC=2C=C(C(=O)OCC)C=CC2)N(C1=O)C.[OH-].[Na+].C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC=2C=C(C(=O)O)C=CC2)N(C1=O)C | CC[O:27][C:25]([c:24]1[cH:23][cH:22][cH:21][c:20]([NH:19][c:18]2[n:17][cH:16][c:15]3[cH:14][c:5](-[c:6]4[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]4[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:30]3[n:29]2)[cH:28]1)=[O:26]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16]... | CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(C(=O)O)c3)nc21 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-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 | null | null | A quantity of 0.065 g (0.139 mmol) of 3-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-benzoic acid, ethyl ester of Example 89 was dissolved in 75 mL of boiling methanol. 2N Sodium hydroxide (2 mL) was added, and the clear solution was maintained at reflux for 2 hours. The solution... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | CO | null | null | CCOC(=O)c1cccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)c1>CO>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(C(=O)O)c3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a983572781e049c5930f6eb5910fc562 | CCOC(=O)CCCc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CCCC(=O)O)cc3)nc21 | [OH-].[Na+].ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CCCC(=O)OCC)N(C1=O)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CCCC(=O)O)N(C1=O)C | CC[O:29][C:27]([CH2:26][CH2:25][CH2:24][c:23]1[cH:22][cH:21][c:20]([NH:19][c:18]2[n:17][cH:16][c:15]3[cH:14][c:5](-[c:6]4[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]4[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:33]3[n:32]2)[cH:31][cH:30]1)=[O:28]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:1... | CCOC(=O)CCCc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CCCC(=O)O)cc3)nc21 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 34.5 | [{"value": 34.5, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CCCC(=O)O)N(C1=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A volume of 5 mL of 2N sodium hydroxide was added to a hot stirred solution of 0.170 g (0.33 mmol) of 4-[4-{6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-phenyl}-butyric acid, ethyl ester of Example 91. The solution was maintained at reflux for 1 hour. Glacial acetic acid (1 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | C(C)(=O)O | null | null | CCOC(=O)CCCc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1>C(C)(=O)O>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(CCCC(=O)O)cc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40e5a488e6884a15aae82381ce1c1729 | CCN.CCOC(=O)c1cnc(SC)nc1Cl>>CCNc1nc(SC)ncc1C(=O)OCC | C(C)N.C(C)OC(=O)C=1C(=NC(=NC1)SC)Cl.C(C)N(CC)CC>>C(C)OC(=O)C=1C(=NC(=NC1)SC)NCC | [CH3:1][CH2:2][NH2:3].Cl[c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[C:12](=[O:13])[O:14][CH2:15][CH3:16] | CCN.CCOC(=O)c1cnc(SC)nc1Cl | CCNc1nc(SC)ncc1C(=O)OCC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[C;D1;H3:11]-[C:12]-[NH2;D1;+0:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C;D1;H3:11] | 90 | [{"value": 90.0, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a room temperature solution of 4-chloro-2-methylthio-5-pyrimidinecarboxylate ethyl ester (10.00 g, 43.10 mmol) in 150 mL of tetrahydrofuran was added triethylamine (18.5 mL, 133 mmol) followed by 9 mL of a 70% aqueous solution of ethylamine. The solution was stirred for 30 minutes, then concentrated in vacuo and par... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCCC1 | null | 0.5 | CCN.CCOC(=O)c1cnc(SC)nc1Cl>O1CCCC1>CCNc1nc(SC)ncc1C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f2375584c8354f2a9aff7eb95f5d470f | CCNc1nc(SC)ncc1C(=O)OCC>>CCNc1nc(SC)ncc1CO | C(C)OC(=O)C=1C(=NC(=NC1)SC)NCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)NC1=NC(=NC=C1CO)SC | CCO[C:12]([c:11]1[c:4]([NH:3][CH2:2][CH3:1])[n:5][c:6]([S:7][CH3:8])[n:9][cH:10]1)=[O:13]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH2:12][OH:13] | CCNc1nc(SC)ncc1C(=O)OCC | CCNc1nc(SC)ncc1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cncnc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9]>>[#7:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 92 | [{"value": 92.0, "product": "C(C)NC1=NC(=NC=C1CO)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "C(C)NC1=NC(=NC=C1CO)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 4-ethylamino-2-methylthio-5-pyrimidinecarboxylate ethyl ester (8.93 g, 37.1 mmol) in 100 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (2.30 g, 60.5 mmol) in 100 mL of tetrahydrofuran. After 10 minutes, the reaction was carefully quenched with 4.5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cncnc1 | HO- | O1CCCC1 | null | 0.166667 | CCNc1nc(SC)ncc1C(=O)OCC>O1CCCC1>CCNc1nc(SC)ncc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f80dab124bd4936956f14f0363292fa | CCNc1nc(SC)ncc1CO>>CCNc1nc(SC)ncc1C=O | C(C)NC1=NC(=NC=C1CO)SC>>C(C)NC1=NC(=NC=C1C=O)SC | [CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH2:12][OH:13]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH:12]=[O:13] | CCNc1nc(SC)ncc1CO | CCNc1nc(SC)ncc1C=O | null | [O-2].[Mn+2].[O-2].[Mn+2] | C(Cl)(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cncnc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[OH;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[O;H0;D1;+0:9] | 97.8 | [{"value": 97.0, "product": "C(C)NC1=NC(=NC=C1C=O)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "C(C)NC1=NC(=NC=C1C=O)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 4-ethylamino-2-methylthio-5-pyrimidinemethanol (6.44 g, 32.4 mmol) in 600 mL of chloroform was added manganese oxide (21.0 g, 241 mmol) over 3 minutes. The suspension was stirred at room temperature for 2 hours, and an additional 5.5 g of manganese oxide was added. Stirring was continued for 4.5 hours. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1 | null | [O-2].[Mn+2].[O-2].[Mn+2].C(Cl)(Cl)Cl | null | 2 | CCNc1nc(SC)ncc1CO>[O-2].[Mn+2].[O-2].[Mn+2].C(Cl)(Cl)Cl>CCNc1nc(SC)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d3784f90e3f54ca8a6dd0f00da8e8fa4 | CCNc1nc(Nc2ccccc2)ncc1C(=O)OCC>>CCNc1nc(Nc2ccccc2)ncc1CO | C(C)OC(=O)C=1C(=NC(=NC1)NC1=CC=CC=C1)NCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)NC1=NC(=NC=C1CO)NC1=CC=CC=C1 | CCO[C:17]([c:16]1[c:4]([NH:3][CH2:2][CH3:1])[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][cH:15]1)=[O:18]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][cH:15][c:16]1[CH2:17][OH:18] | CCNc1nc(Nc2ccccc2)ncc1C(=O)OCC | CCNc1nc(Nc2ccccc2)ncc1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9]>>[#7:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 39 | [{"value": 39.0, "product": "C(C)NC1=NC(=NC=C1CO)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.8, "product": "C(C)NC1=NC(=NC=C1CO)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 25 | MINUTE | A solution of 4-ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl ester (109 mg, 0.38 mmol) in 6 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (35 mg, 0.92 mmol) in 5 mL of tetrahydrofuran. After 25 minutes, an additional 30 mg of lithium aluminum hydrid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cncnc1.c1ccccc1 | HO- | O1CCCC1 | null | 0.416667 | CCNc1nc(Nc2ccccc2)ncc1C(=O)OCC>O1CCCC1>CCNc1nc(Nc2ccccc2)ncc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01090b6109b34cf4ad06377fa270ba3b | CCNc1nc(Nc2ccccc2)ncc1CO>>CCNc1nc(Nc2ccccc2)ncc1C=O | C(C)NC1=NC(=NC=C1CO)NC1=CC=CC=C1>>C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1 | [CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][cH:15][c:16]1[CH2:17][OH:18]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][cH:15][c:16]1[CH:17]=[O:18] | CCNc1nc(Nc2ccccc2)ncc1CO | CCNc1nc(Nc2ccccc2)ncc1C=O | null | [O-2].[Mn+2] | C(Cl)(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(Nc2ncccn2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[OH;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[O;H0;D1;+0:9] | 99 | [{"value": 99.0, "product": "C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (4-ethylamino-2-phenylamino-pyrimidin-5-yl)methanol (173 mg, 0.71 mmol) in 15 mL of chloroform was added manganese oxide (600 mg, 6.89 mmol). After stirring at room temperature overnight, the mixture was filtered through a pad of Celite, washing with chloroform. The filtrate was concentrated in vacuo t... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1.c1ccccc1 | null | [O-2].[Mn+2].C(Cl)(Cl)Cl | null | 8 | CCNc1nc(Nc2ccccc2)ncc1CO>[O-2].[Mn+2].C(Cl)(Cl)Cl>CCNc1nc(Nc2ccccc2)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ac9e9c1c2b44b098f10a1ddc3f11428 | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccsc1>>CCn1c(=N)c(-c2ccsc2)cc2cnc(Nc3ccccc3)nc21 | O.S1C=C(C=C1)CC#N.[H-].[Na+].C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1>>C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CSC=C2)=N | O=[CH:12][c:13]1[cH:14][n:15][c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1[NH:3][CH2:2][CH3:1].[C:4](#[N:5])[CH2:6][c:7]1[cH:8][cH:9][s:10][cH:11]1>>[CH3:1][CH2:2][n:3]1[c:4](=[NH:5])[c:6](-[c:7]2[cH:8][cH:9][s:10][cH:11]2)[cH:12][c:13]2[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][c... | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccsc1 | CCn1c(=N)c(-c2ccsc2)cc2cnc(Nc3ccccc3)nc21 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 0563001d31884c03e15e9f4307d31ffde7ef37fabfd8267db28237eb39076249 | 869483589005a5aba7d1617b2e2f826aa2ded09152e8d61d0607fd18c3c9c8b9 | N=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccsc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10].[N;H0;D1;+0:11]#[C;H0;D2;+0:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:14]1:[c:15]:[#16;a:16]:[c:17]:[c:18]:1>>[C;D1;H3:10]-[C:9]-[n;H0;D3;+0:8]1:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:13](-[c;H0;D3;+0:14]2:[c... | 78.9 | [{"value": 78.0, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CSC=C2)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CSC=C2)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 3-thiopheneacetonitrile (168 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added, and the reaction heated at 120° C. for 2 hours, resul... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Secondary amine | null | c1cncnc1 | c1cnc2ncncc2c1 | c1ccsc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | 0.083333 | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccsc1>C(C)OCCO>CCn1c(=N)c(-c2ccsc2)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-231cd6e88b2340b49783a8530c5952cf | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1cccs1>>CCn1c(=N)c(-c2cccs2)cc2cnc(Nc3ccccc3)nc21 | O.S1C(=CC=C1)CC#N.[H-].[Na+].C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1>>C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C=2SC=CC2)=N | O=[CH:12][c:13]1[cH:14][n:15][c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1[NH:3][CH2:2][CH3:1].[C:4](#[N:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1>>[CH3:1][CH2:2][n:3]1[c:4](=[NH:5])[c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12][c:13]2[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][c... | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1cccs1 | CCn1c(=N)c(-c2cccs2)cc2cnc(Nc3ccccc3)nc21 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 0563001d31884c03e15e9f4307d31ffde7ef37fabfd8267db28237eb39076249 | 869483589005a5aba7d1617b2e2f826aa2ded09152e8d61d0607fd18c3c9c8b9 | N=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1cccs1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10].[N;H0;D1;+0:11]#[C;H0;D2;+0:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[C;D1;H3:10]-[C:9]-[n;H0;D3;+0:8]1:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:13](-[c;H0;D3;+0:14]2:[#... | 85.9 | [{"value": 85.0, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C=2SC=CC2)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C=2SC=CC2)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 2-thiopheneacetonitrile (168 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added, and the reaction heated at 120° C. for 2 hours, resul... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Secondary amine | null | c1cncnc1 | c1cnc2ncncc2c1 | c1ccsc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | 0.083333 | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1cccs1>C(C)OCCO>CCn1c(=N)c(-c2cccs2)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8101dbefc33b4ad5952d74a7f2f862b6 | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21>>CCn1c(=O)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21 | BrC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=N)CC.C(C)(=O)OC(C)=O.Cl>>BrC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)CC | CC(=O)OC(C)=[O:5].N=[c:4]1[n:3]([CH2:2][CH3:1])[c:28]2[c:16]([cH:15][c:6]1-[c:7]1[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]1[Br:14])[cH:17][n:18][c:19]([NH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[n:27]2>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Br:14])[cH:15][c:16]2[... | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21 | CCn1c(=O)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21 | null | null | O | Miscellaneous | OtherReaction | dd6199f82f5f25315dda3b0cdb80b809165964de59b82b4515ab2b9ff97290b0 | 41e7ec317aa33bd872bc25f64db351112544c3e9bc552c10a46e7a1666c9e76a | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-C(=O)-O-C(-C)=[O;H0;D1;+0:1].N=[c;H0;D3;+0:2](:[#7;a:3](-[C:4]):[c:5]:[#7;a:6]):[c:7](-[c:8]):[c:9]>>[#7;a:6]:[c:5]:[#7;a:3](-[C:4]):[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[c:7](-[c:8]):[c:9] | null | [] | null | null | null | null | (6-(2-Bromo-6-chlorophenyl)-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine (150 mg) was added to 1 mL of acetic anhydride and heated at reflux for 5 minutes. The reaction was cooled and concentrated resulting in an oil which was heated at reflux with 10 mL of 6N HCl for 10 minutes. The reaction wa... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | null | null | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21>O>CCn1c(=O)c(-c2c(Cl)cccc2Br)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abec610d41fa4460bcec11b0f48f849d | CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CC(=O)O)c2n1 | C(C)OCC.C(C)(C)(C)OC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O.FC(C(=O)O)(F)F>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(=O)O | CC(C)(C)[O:22][C:20]([CH2:19][n:18]1[c:16](=[O:17])[c:7](-[c:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[Cl:15])[cH:6][c:5]2[cH:4][n:3][c:2]([NH2:1])[n:24][c:23]21)=[O:21]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[n:18]([CH2:19][C:20](=[O:21])[... | CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CC(=O)O)c2n1 | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 52.5 | [{"value": 52.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.5, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid tert-butyl ester (157 mg, 0.37 mmol) from Example 36 in 4 mL of methylene chloride was added 2 mL of trifluoroacetic acid. The solution was stirred at room temperature for 5 hours, then concentrated in vacuo. The resultan... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | C(Cl)Cl | null | 5 | CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>C(Cl)Cl>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CC(=O)O)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d37a984a916b40a38246819bac9f0f12 | BrCc1cccc(Br)c1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3cccc(Br)c3)c2n1 | NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.[H-].[Na+].BrC=1C=C(CBr)C=CC1>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=CC(=CC=C2)Br | Br[CH2:19][c:20]1[cH:21][cH:22][cH:23][c:24]([Br:25])[cH:26]1.[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[nH:18][c:27]2[n:28]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[n:18](... | BrCc1cccc(Br)c1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3cccc(Br)c3)c2n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:5]=[c:6](:[c:7]):[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 58 | [{"value": 58.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=CC(=CC=C2)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=CC(=CC=C2)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 10 | MINUTE | To a suspension of NaH (60% in mineral oil, 38 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (200 mg, 0.65 mmol). The mixture was heated at 50° C. for 20 minutes resulting in a clear solution. The heating mantle was removed, and 3-bromobenzyl bromide (240 μL,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | 50 | 0.166667 | BrCc1cccc(Br)c1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3cccc(Br)c3)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-145f75e858214880a64bbd4992e3190e | COC(=O)c1ccc(CBr)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>COC(=O)c1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 | [H-].[Na+].C(C)(=O)OCC.NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.COC(=O)C1=CC=C(C=C1)CBr>>COC(C1=CC=C(C=C1)CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:31][cH:30]1.[nH:10]1[c:11](=[O:12])[c:13](-[c:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]2[Cl:21])[cH:22][c:23]2[cH:24][n:25][c:26]([NH2:27])[n:28][c:29]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[c:11](=[O:12])[c:13](-[c:14]3[c:1... | COC(=O)c1ccc(CBr)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | COC(=O)c1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:5]=[c:6](:[c:7]):[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 70 | [{"value": 70.0, "product": "COC(C1=CC=C(C=C1)CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of NaH (60% in mineral oil, 36 mg) in 7 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (195 mg, 0.64 mmol). The mixture was heated at 40° C. to 50° C. for 20 minutes, resulting in a clear solution. Methyl 4-(bromomethyl) benzoate (206 mg, 0.90 mmol) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1ccccc1.c1cnc2ncncc2c1 | HBr | CN(C=O)C | null | null | COC(=O)c1ccc(CBr)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>COC(=O)c1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eccbafead2a446cdb38d33e16b8e1e3f | Clc1cccc(Cl)c1CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3c(Cl)cccc3Cl)c2n1 | [H-].[Na+].NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.BrCC1=C(C=CC=C1Cl)Cl>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=C(C=CC=C2Cl)Cl | Br[CH2:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]1[Cl:27].[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[nH:18][c:28]2[n:29]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[... | Clc1cccc(Cl)c1CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3c(Cl)cccc3Cl)c2n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:5]=[c:6](:[c:7]):[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 35.3 | [{"value": 35.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=C(C=CC=C2Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.3, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=C(C=CC=C2Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | To a suspension of NaH (60% in mineral oil, 36 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (208 mg, 0.68 mmol). The mixture was heated at 70° C. for 10 minutes and then at 50° C. for 30 minutes, resulting in a clear solution. α-Bromo-2,6-dichlorotoluene (21... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | 70 | 0.5 | Clc1cccc(Cl)c1CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3c(Cl)cccc3Cl)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-afbdbf0f072e4583b666e79f728d3640 | COc1ccc(CCl)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>COc1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 | COC1=CC=C(CCl)C=C1.[H-].[Na+].NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=CC=C(C=C2)OC | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][cH:28]1.[nH:8]1[c:9](=[O:10])[c:11](-[c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]2[Cl:19])[cH:20][c:21]2[cH:22][n:23][c:24]([NH2:25])[n:26][c:27]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[c:9](=[O:10])[c:11](-[c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:1... | COc1ccc(CCl)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | COc1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:5]=[c:6](:[c:7]):[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 38 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (208 mg, 0.68 mmol). The mixture was heated at 50° C. for 1 hour, resulting in a clear solution. 4-Methoxybenzyl chloride (130 μL, 0.95 mmol) was added, and the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1ccccc1.c1cnc2ncncc2c1 | HCl | CN(C=O)C | 50 | null | COc1ccc(CCl)cc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>COc1ccc(Cn2c(=O)c(-c3c(Cl)cccc3Cl)cc3cnc(N)nc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d68719fd07424782a508df3f799b02af | ClCc1ccncc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3ccncc3)c2n1 | Cl.N1=CC=C(C=C1)CCl.[Na].NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.C(C)N(CC)CC.[H-].[Na+]>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC2=CC=NC=C2 | Cl[CH2:19][c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1.[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[nH:18][c:26]2[n:27]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[n:18]([CH2:19][... | ClCc1ccncc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3ccncc3)c2n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1Cc1ccncc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[c:9](:[c:10]):[nH;D2;+0:11]:[c:12]1:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1>>[O;D1;H0:8]=[c:9](:[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1):[c:12]1:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1 | null | [] | 70 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 32 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (200 mg, 0.65 mmol) and the mixture heated to 70° C. In a second flask containing triethyl amine (220 μL, 1.59 mmol) in 4 mL of dimethylformamide was added 4-picolyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1.c1ccncc1 | HCl | CN(C=O)C | 70 | null | ClCc1ccncc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(Cc3ccncc3)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce2698e35bd94905bfdf55ec0d5c3c0a | ClCCCc1ccccc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CCCc3ccccc3)c2n1 | [H-].[Na+].NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.ClCCCC1=CC=CC=C1>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC2=CC=CC=C2 | Cl[CH2:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17])[nH:18][c:28]2[n:29]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16](=[O:17]... | ClCCCc1ccccc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CCCc3ccccc3)c2n1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c(-c2ccccc2)cc2cncnc2n1CCCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7](:[c:5](=[O;D1;H0:4]):[c:6]):[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 57.2 | [{"value": 57.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.2, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 58 mg) in 10 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (320 mg, 1.04 mmol). The mixture was heated to 60° C. resulting in a clear solution. 1-Chloro-3-phenylpropane (260 μL, 1.81 mmol) was added, and the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | 60 | null | ClCCCc1ccccc1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C.C(C)(=O)OCC>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(CCCc3ccccc3)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5004f689fe8441b7b8fb304853ccbbc3 | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccc2ccccc2c1>>CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 | O.C1=C(C=CC2=CC=CC=C12)CC#N.[H-].[Na+].C(C)NC1=NC(=NC=C1C=O)NC1=CC=CC=C1>>C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC1=CC=CC=C1C=C2)=N | O=[CH:17][c:18]1[cH:19][n:20][c:21]([NH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:29][c:30]1[NH:3][CH2:2][CH3:1].[C:4](#[N:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1>>[CH3:1][CH2:2][n:3]1[c:4](=[NH:5])[c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[cH:16]2... | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccc2ccccc2c1 | CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 0563001d31884c03e15e9f4307d31ffde7ef37fabfd8267db28237eb39076249 | 869483589005a5aba7d1617b2e2f826aa2ded09152e8d61d0607fd18c3c9c8b9 | N=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccc2ccccc2c1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10].[N;H0;D1;+0:11]#[C;H0;D2;+0:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C;D1;H3:10]-[C:9]-[n;H0;D3;+0:8]1:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:13](-[c;H0;D3;+0:14](:[c:15]:... | 82.4 | [{"value": 82.0, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC1=CC=CC=C1C=C2)=N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC1=CC=CC=C1C=C2)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 2-naphthyl-acetonitrile (227 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added and the reaction heated at 110° C. for 1 hour, resulti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Secondary amine | null | c1cncnc1 | c1cnc2ncncc2c1 | c1ccc2ccccc2c1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | 0.083333 | CCNc1nc(Nc2ccccc2)ncc1C=O.N#CCc1ccc2ccccc2c1>C(C)OCCO>CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbffcf2db8554d41a139114578bcbcd5 | CC(=O)OC(C)=O.CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21>>CCn1c(=O)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 | C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC1=CC=CC=C1C=C2)=N.C(C)(=O)OC(C)=O.Cl>>C(C)N1C(C(=CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC1=CC=CC=C1C=C2)=O | CC(=O)OC(C)=[O:5].N=[c:4]1[n:3]([CH2:2][CH3:1])[c:30]2[c:18]([cH:17][c:6]1-[c:7]1[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[cH:16]1)[cH:19][n:20][c:21]([NH:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[n:29]2>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:... | CC(=O)OC(C)=O.CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 | CCn1c(=O)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 | null | null | O | Miscellaneous | OtherReaction | dd6199f82f5f25315dda3b0cdb80b809165964de59b82b4515ab2b9ff97290b0 | 41e7ec317aa33bd872bc25f64db351112544c3e9bc552c10a46e7a1666c9e76a | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccc2ccccc2c1 | C-C(=O)-O-C(-C)=[O;H0;D1;+0:1].N=[c;H0;D3;+0:2](:[#7;a:3](-[C:4]):[c:5]:[#7;a:6]):[c:7](-[c:8]):[c:9]>>[#7;a:6]:[c:5]:[#7;a:3](-[C:4]):[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[c:7](-[c:8]):[c:9] | null | [] | null | null | null | null | (8-Ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine (150 mg) was added to 1 mL of acetic anhydride and heated at reflux for 2 minutes. The reaction was cooled and concentrated, resulting in an oil which was heated at reflux with 10 mL of 6N HCl for 10 minutes. The reaction was cooled... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2ccccc2c1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | null | null | CC(=O)OC(C)=O.CCn1c(=N)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21>O>CCn1c(=O)c(-c2ccc3ccccc3c2)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee329cf9c57341ee87f8398d0e4b9f66 | ClCc1ccccn1.O=C1CNC(=S)N1>>O=C1CNC(SCc2ccccn2)=N1 | N1C(=S)NC(=O)C1.C[O-].[Na+].Cl.ClCC1=NC=CC=C1>>N1=C(C=CC=C1)CSC=1NCC(N1)=O | Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.[O:1]=[C:2]1[CH2:3][NH:4][C:5](=[S:6])[NH:14]1>>[O:1]=[C:2]1[CH2:3][NH:4][C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)=[N:14]1 | ClCc1ccccn1.O=C1CNC(=S)N1 | O=C1CNC(SCc2ccccn2)=N1 | null | null | CO | Protection | OtherReaction | 46cef1e48600fcd6705529550ccb17b294e17c854f6cacd0473e52ed0910cca7 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | O=C1CNC(SCc2ccccn2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C;H0;D3;+0:10](=[S;H0;D1;+0:11])-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C;H0;D3;+0:10](-[S;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])=[N;H0;D2;+0:12]-1 | null | [] | null | null | null | null | Initially, 1 g of 2-thiohydantoin and 2.5 g of sodium methylate were dissolved in 50 mL of methanol (MeoH), and 1.5 g of 2-chloromethylpyridine hydrochloride was added to the solution. The reaction mixture was stirred under reflux for one and a half hour and concentrated in vacuo. To the residue, there was added 50 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNCN1 | C1=NCCN1 | C1=NCCN1.c1ccncc1 | HCl | CO | null | null | ClCc1ccccn1.O=C1CNC(=S)N1>CO>O=C1CNC(SCc2ccccn2)=N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f1dc421f62bb4c91b491d7738aa0887d | CC1(C)NC(=S)NC1=O.CN(C)c1ccccc1CCl>>CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1 | [OH-].[Na+].Cl.CN(C1=C(CCl)C=CC=C1)C.CC1(C(NC(N1)=S)=O)C.O>>CN(C1=C(CSC=2NC(C(N2)=O)(C)C)C=CC=C1)C | [S:11]=[C:12]1[NH:13][C:14](=[O:15])[C:16]([CH3:17])([CH3:18])[NH:19]1.Cl[CH2:10][c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14](=[O:15])[C:16]([CH3:17])([CH3:18])[NH:19]1 | CC1(C)NC(=S)NC1=O.CN(C)c1ccccc1CCl | CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1 | null | null | CS(=O)C | Protection | OtherReaction | 46cef1e48600fcd6705529550ccb17b294e17c854f6cacd0473e52ed0910cca7 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | O=C1CNC(SCc2ccccc2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[NH;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])=[N;H0;D2;+0:11]-1 | null | [] | null | null | 1 | HOUR | Initially, 1 g of 5,5-dimethyl-2-thiohydantoin was dissolved in 20 mL of dimethylsulfoxide, and 1.7 g of 2-dimethylaminobenzylchloride hydrochloride was added to the solution. The reaction mixture was stirred at the room temperature for one hour, and poured into 50 mL of water. The pH value of the solution was adjusted... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNCN1 | C1=NCCN1 | c1ccccc1.C1=NCCN1 | HCl | CS(=O)C | null | 1 | CC1(C)NC(=S)NC1=O.CN(C)c1ccccc1CCl>CS(=O)C>CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e2a38ef21493407faefa7a6e38761e24 | CC(=O)N1C(=S)NC(=O)C1(C)C.CN(C)c1ccccc1CCl>>CC(=O)N1C(SCc2ccccc2N(C)C)=NC(=O)C1(C)C | Cl.CN(C1=C(CCl)C=CC=C1)C.C(C)(=O)N1C(=S)NC(=O)C1(C)C.[OH-].[Na+]>>C(C)(=O)N1C(=NC(C1(C)C)=O)SCC1=C(C=CC=C1)N(C)C | [CH3:1][C:2](=[O:3])[N:4]1[C:5](=[S:6])[NH:17][C:18](=[O:19])[C:20]1([CH3:21])[CH3:22].Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]([CH3:15])[CH3:16]>>[CH3:1][C:2](=[O:3])[N:4]1[C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[N:14]([CH3:15])[CH3:16])=[N:17][C:18](=[O:19])[C:20]1([CH3:21])[CH3:22] | CC(=O)N1C(=S)NC(=O)C1(C)C.CN(C)c1ccccc1CCl | CC(=O)N1C(SCc2ccccc2N(C)C)=NC(=O)C1(C)C | null | null | O | Protection | OtherReaction | 06d9f5797382049cde551f4363f7a6db1ae0ad2d934c141a8c10a407d5578211 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | O=C1CNC(SCc2ccccc2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13]-1=[S;H0;D1;+0:14]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[O;D1;H0:11])-[N;H0;D2;+0:12]=[C;H0;D3;+0:13]-1-[S;H0;D2;+0:14]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | Initially, 4.18g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 3.43 g of 1-N-acetyl-5,5-dimethyl-2-thiohydantoin in 50 mL of N,N-dimethylsulfoxide. The reaction mixture was stirred for one hour at the room temperature and poured into 100 mL of water. The pH of the solution was adjusted to 7-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1C[NH]CN1 | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1 | HCl | O | null | 1 | CC(=O)N1C(=S)NC(=O)C1(C)C.CN(C)c1ccccc1CCl>O>CC(=O)N1C(SCc2ccccc2N(C)C)=NC(=O)C1(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6678ac22aa94fabbc9a581571db8c5e | CCC1(C)C(=O)NC(=S)N1C(C)=O.CN(C)c1ccccc1CCl>>CCC1(C)C(=O)N=C(SCc2ccccc2N(C)C)N1C(C)=O | Cl.CN(C1=C(CCl)C=CC=C1)C.C(C)(=O)N1C(=S)NC(=O)C1(C)CC>>C(C)(=O)N1C(=NC(C1(C)CC)=O)SCC1=C(C=CC=C1)N(C)C | [CH3:1][CH2:2][C:3]1([CH3:4])[C:5](=[O:6])[NH:7][C:8](=[S:9])[N:20]1[C:21]([CH3:22])=[O:23].Cl[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N:17]([CH3:18])[CH3:19]>>[CH3:1][CH2:2][C:3]1([CH3:4])[C:5](=[O:6])[N:7]=[C:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N:17]([CH3:18])[CH3:19])[N:20]1[C:21]([C... | CCC1(C)C(=O)NC(=S)N1C(C)=O.CN(C)c1ccccc1CCl | CCC1(C)C(=O)N=C(SCc2ccccc2N(C)C)N1C(C)=O | null | null | null | Protection | OtherReaction | c436e84a346efd362c8a87a765b28845692c52ac6abb03e951ff1b63a6e85de9 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | O=C1CNC(SCc2ccccc2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13]-1=[S;H0;D1;+0:14]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](=[O;D1;H0:11])-[N;H0;D2;+0:12]=[C;H0;D3;+0:13]-1-[S;H0;D2;+0:14]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In the present Example, 2.27 g of 2-dimethylaminobenzylchloride hydrochloride and 2.0 g of 1-N-acetyl-5-ethyl-5-methyl-2-thiohydantoin were reacted following the procedure of Example 33. The desired compound was obtained in the form of needle-like crystal. The yield of this compound was 1.37 g with a yield ratio of 41.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNC[NH]1 | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1 | HCl | null | null | null | CCC1(C)C(=O)NC(=S)N1C(C)=O.CN(C)c1ccccc1CCl>>CCC1(C)C(=O)N=C(SCc2ccccc2N(C)C)N1C(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a413f39439cd436fae92766aebf207f9 | CI.CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1>>CN1C(=O)C(C)(C)N=C1SCc1ccccc1N(C)C | CI.C(C)(=O)OCC.CN(C1=C(CSC=2NC(C(N2)=O)(C)C)C=CC=C1)C.[H-].[Na+]>>CN1C(=NC(C1=O)(C)C)SCC1=C(C=CC=C1)N(C)C | I[CH3:1].[N:2]1=[C:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[N:18]([CH3:19])[CH3:20])[NH:8][C:5]([CH3:6])([CH3:7])[C:3]1=[O:4]>>[CH3:1][N:2]1[C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[N:8]=[C:9]1[S:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N:18]([CH3:19])[CH3:20] | CI.CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1 | CN1C(=O)C(C)(C)N=C1SCc1ccccc1N(C)C | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 0be3157781bde9164f230f39a40e60ca4b3fb1f0c76158e8c5f3dfbca33c830f | 4ba71d6749f69ee61012b6d9409145f900f668ab403cb291b681d5aeae64f724 | O=C1CN=C(SCc2ccccc2)N1 | I-[CH3;D1;+0:1].[C:2]-[#16:3]-[C;H0;D3;+0:4]1=[N;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH;D2;+0:11]-1>>[C:2]-[#16:3]-[C;H0;D3;+0:4]1=[N;H0;D2;+0:11]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:5]-1-[CH3;D1;+0:1] | null | [] | null | null | 15 | MINUTE | To a solution of 0.5 g of 2-(2-dimethylaminobenzylthio)-5,5-dimethylimidazolin-4-one in 20 mL of N,N-dimethylformamide, there was added 60% sodium hydride in 0.09 g of mineral oil at -10° C. After the mixture was stirred for 15 minutes, 1 mL of methyl iodide was added to the mixture, and the stirring was continued for ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amide.Monosulfide | C1=NCCN1 | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1 | HI | CN(C=O)C.O | null | 0.25 | CI.CN(C)c1ccccc1CSC1=NC(=O)C(C)(C)N1>CN(C=O)C.O>CN1C(=O)C(C)(C)N=C1SCc1ccccc1N(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-673e7e0da0374e52b0efea0bb7e74951 | CC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl>>CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C | Cl.CN(C1=C(CCl)C=CC=C1)C.CC1(C(NC(N1)=O)=S)C>>CN(C1=C(CSC2=NC(NC2(C)C)=O)C=CC=C1)C | [S:11]=[C:12]1[NH:13][C:14](=[O:15])[NH:16][C:17]1([CH3:18])[CH3:19].Cl[CH2:10][c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14](=[O:15])[NH:16][C:17]1([CH3:18])[CH3:19] | CC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl | CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C | null | null | CO | Protection | OtherReaction | 9b3fffcd549d2c61072b189884f428b95bb57a9cdd6f96fd60fb385384688724 | a0306b442dafb3274f3ed52a8c28cb63392109c07f21b1295aafb9782efd645c | O=C1N=C(SCc2ccccc2)CN1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6]1(-[C;D1;H3:7])-[#7:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12]-1=[S;H0;D1;+0:13]>>[C;D1;H3:5]-[C:6]1(-[C;D1;H3:7])-[#7:8]-[C:9](=[O;D1;H0:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12]-1-[S;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | Initially, 2.5 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 1.5 g of 5,5-dimethyl-4-thiohydantoin in 50 mL of methanol (MeQH). The reaction mixture was stirred for two hours at the room temperature and concentrated in vacuo. To the residue, there was added 100 mL of CHCl3. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea.Thioamide | Monosulfide | C1CNCN1 | C1=NCNC1 | c1ccccc1.C1=NCNC1 | HCl | CO | null | 2 | CC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl>CO>CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-963943015c7a4df68483236ac94750d2 | CI.CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C>>CN(C)c1ccccc1CSC1=NC(=O)N(C)C1(C)C | CN(C1=C(CSC2=NC(NC2(C)C)=O)C=CC=C1)C.CI>>CN1C(N=C(C1(C)C)SCC1=C(C=CC=C1)N(C)C)=O | I[CH3:17].[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14](=[O:15])[NH:16][C:18]1([CH3:19])[CH3:20]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14](=[O:15])[N:16]([CH3:17])[C:18]1([CH3:19])[CH3:20] | CI.CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C | CN(C)c1ccccc1CSC1=NC(=O)N(C)C1(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d5e3d23d7d875f5fef574aa8ac112f262bc116b9d0f20a791bb9059d51b12b58 | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1N=C(SCc2ccccc2)CN1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]=[#7:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-1>>[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]=[#7:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9]-1-[CH3;D1;+0:1] | null | [] | null | null | null | null | Initially, 0.5 g of 4-(2-dimethylaminobenzylthio)-5,5-dimethyl-3-imidazolin-2-one was reacted with 1 mL of methyl iodide following the procedure used in Example 35. The desired compound was obtained in the form of a syrup. The yield of this compound was 0.43 g with a yield ratio of 81.9%. A result of a 1 H-NMR analysis... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | C1=NCNC1 | C1=NC[NH]C1 | c1ccccc1.C1=NC[NH]C1 | HI | null | null | null | CI.CN(C)c1ccccc1CSC1=NC(=O)NC1(C)C>>CN(C)c1ccccc1CSC1=NC(=O)N(C)C1(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7b3987398bb64abd9f359af3d6a7e88d | CCC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl>>CCC1(C)NC(=O)N=C1SCc1ccccc1N(C)C | Cl.CN(C1=C(CCl)C=CC=C1)C.C(C)C1(C(NC(N1)=O)=S)C>>CN(C1=C(CSC2=NC(NC2(C)CC)=O)C=CC=C1)C | [CH3:1][CH2:2][C:3]1([CH3:4])[NH:5][C:6](=[O:7])[NH:8][C:9]1=[S:10].Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N:18]([CH3:19])[CH3:20]>>[CH3:1][CH2:2][C:3]1([CH3:4])[NH:5][C:6](=[O:7])[N:8]=[C:9]1[S:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N:18]([CH3:19])[CH3:20] | CCC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl | CCC1(C)NC(=O)N=C1SCc1ccccc1N(C)C | null | null | null | Protection | OtherReaction | 9b3fffcd549d2c61072b189884f428b95bb57a9cdd6f96fd60fb385384688724 | a0306b442dafb3274f3ed52a8c28cb63392109c07f21b1295aafb9782efd645c | O=C1N=C(SCc2ccccc2)CN1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]1(-[C;D1;H3:7])-[#7:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12]-1=[S;H0;D1;+0:13]>>[C:5]-[C:6]1(-[C;D1;H3:7])-[#7:8]-[C:9](=[O;D1;H0:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12]-1-[S;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In the present Example, 2.3 g of 2-dimethylaminobenzylchloride hydrochloride and 1.5 g of 5-ethyl-5-methyl-4-thiohydantoin were reacted following the procedure used in Example 36. Crystallization from diethyl ether-n-hexane gave the desired compound in the form of a needle-like crystal. The yield of this compound was 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea.Thioamide | Monosulfide | C1CNCN1 | C1=NCNC1 | C1=NCNC1.c1ccccc1 | HCl | null | null | null | CCC1(C)NC(=O)NC1=S.CN(C)c1ccccc1CCl>>CCC1(C)NC(=O)N=C1SCc1ccccc1N(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4c2572338d149fc9b4505fc6cb945cf | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl>>CN(C)c1ccccc1CSC1=NC(C)(C)C(SCc2ccccc2N(C)C)=N1 | Cl.CN(C1=C(CCl)C=CC=C1)C.CC1(C(NC(N1)=S)=S)C>>CN(C1=C(CSC2=NC(C(=N2)SCC2=C(C=CC=C2)N(C)C)(C)C)C=CC=C1)C | [NH:2]1[C:12](=[S:11])[NH:13][C:14]([CH3:15])([CH3:16])[C:17]1=[S:18].Cl[CH2:10][c:9]1[cH:8][cH:7][cH:23][cH:24][c:25]1[N:26]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14]([CH3:15])([CH3:16])[C:17]([S:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[N:... | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl | CN(C)c1ccccc1CSC1=NC(C)(C)C(SCc2ccccc2N(C)C)=N1 | null | null | C(C)O.CCO | Aromatic Heterocycle Formation | OtherReaction | e9e0dcb8157350c39f7294759583be48483c609eab6bad3b352b3679b60ba21a | e14cd4806f58873333c499a92a4f5dd98ee7ba7de93b394b5f309b7d3984cce3 | c1ccc(CSC2=NC(SCc3ccccc3)=NC2)cc1 | Cl-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c;H0;D3;+0:7]:1-[N;H0;D3;+0:8](-[CH3;D1;+0:9])-[CH3;D1;+0:10].[C;D1;H3:11]-[C:12]1(-[C;D1;H3:13])-[NH;D2;+0:14]-[C;H0;D3;+0:15](=[S;H0;D1;+0:16])-[NH;D2;+0:17]-[C;H0;D3;+0:18]-1=[S;H0;D1;+0:19]>>[C;D1;H3:11]-[C:12]1(-[C;D1;H3:13])-[N;H0;D2;+0:14]=[... | null | [] | null | null | 1.5 | HOUR | Initially, a solution of 9.1 g of 2-dimethylaminobenzylchloride hydrochloride in 50 mL of EtOH was added to a solution of 7 g of 5,5-dimethyl-2,4-dithiohydantoin in 100 mL of ethanol (EtOH). The reaction mixture was stirred for 1.5 hour at the room temperature and concentrated in vacuo. To the residue, there was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea.Thioamide.Tertiary amine | Tertiary amine.Tertiary amine.Monosulfide.Monosulfide | C1CNCN1.c1ccccc1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | null | C(C)O.CCO | null | 1.5 | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl>C(C)O.CCO>CN(C)c1ccccc1CSC1=NC(C)(C)C(SCc2ccccc2N(C)C)=N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5666a9282ea5444b92b3aab759b61587 | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl>>CN(C)c1ccccc1CSC1=NC(=S)C(C)(C)N1 | Cl.CN(C1=C(CCl)C=CC=C1)C.CC1(C(NC(N1)=S)=S)C>>CN(C1=C(CSC=2NC(C(N2)=S)(C)C)C=CC=C1)C | [S:11]=[C:12]1[NH:13][C:14](=[S:15])[C:16]([CH3:17])([CH3:18])[NH:19]1.Cl[CH2:10][c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14](=[S:15])[C:16]([CH3:17])([CH3:18])[NH:19]1 | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl | CN(C)c1ccccc1CSC1=NC(=S)C(C)(C)N1 | null | null | C(Cl)(Cl)Cl | Protection | OtherReaction | 46cef1e48600fcd6705529550ccb17b294e17c854f6cacd0473e52ed0910cca7 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | S=C1CNC(SCc2ccccc2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[NH;D2;+0:11]-1>>[S;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])=[N;H0;D2;+0:11]-1 | null | [] | null | null | 30 | MINUTE | Initially, 11 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 8 g of 5,5-dimethyl-2,4-dithiohydantoin in 200 mL of chloroform (CHCl3) at about 60° C. The reaction mixture was stirred for 30 minutes and washed with an aqueous solution of NaHCO3, dried over MgSO4, and concentrated in vacuo. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNCN1 | C1=NCCN1 | c1ccccc1.C1=NCCN1 | HCl | C(Cl)(Cl)Cl | null | 0.5 | CC1(C)NC(=S)NC1=S.CN(C)c1ccccc1CCl>C(Cl)(Cl)Cl>CN(C)c1ccccc1CSC1=NC(=S)C(C)(C)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc25bdb7c4ad482f819d561626b78d70 | CC1(C)NC(=S)NC1=S.ClCc1ccccn1>>CC1(C)NC(SCc2ccccn2)=NC1=S | Cl.ClCC1=NC=CC=C1.CC1(C(NC(N1)=S)=S)C.[OH-].[Na+]>>N1=C(C=CC=C1)CSC=1NC(C(N1)=S)(C)C | [CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[S:6])[NH:14][C:15]1=[S:16].Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)=[N:14][C:15]1=[S:16] | CC1(C)NC(=S)NC1=S.ClCc1ccccn1 | CC1(C)NC(SCc2ccccn2)=NC1=S | null | null | null | Protection | OtherReaction | 46cef1e48600fcd6705529550ccb17b294e17c854f6cacd0473e52ed0910cca7 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | S=C1CNC(SCc2ccccn2)=N1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[S;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C;H0;D3;+0:10](=[S;H0;D1;+0:11])-[NH;D2;+0:12]-1>>[S;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C;H0;D3;+0:10](-[S;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])=[N;H0;D2;+0:12]-1 | null | [] | null | null | 1 | HOUR | Initially, 2.7 g of 2-chloromethylpyridine hydrochloride was added to a solution of 2.4g of 5,5-dimethyl-2,4-dithiohydantoin in 17 mL of 2N aqueous solution of NaOH. The reaction mixture was stirred for one hour at the room temperature, and extracted with 100 mL of chloroform (CHCl3). The CHCl3 layer was dried over MgS... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNCN1 | C1=NCCN1 | C1=NCCN1.c1ccncc1 | HCl | null | null | 1 | CC1(C)NC(=S)NC1=S.ClCc1ccccn1>>CC1(C)NC(SCc2ccccn2)=NC1=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-483dd6c046dd4bfda158d9c42f0f2afc | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1>>CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 | Cl.CN(C=1C=C(CCl)C=CC1)C.CC1(C(NC(N1)=S)=S)C.C[O-].[Na+]>>CN(C=1C=C(CSC2=NC(C(=N2)SCC2=CC(=CC=C2)N(C)C)(C)C)C=CC1)C | [NH:2]1[C:11](=[S:10])[NH:28][C:16](=[S:17])[C:13]1([CH3:14])[CH3:15].Cl[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]([N:24]([CH3:1])[CH3:3])[cH:27]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][S:10][C:11]2=[N:12][C:13]([CH3:14])([CH3:15])[C:16]([S:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][c:23]([N:24]([CH3:... | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1 | CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 0a28fd05626e226c3e61952969504b1e7c751e2809b3309b230576220ee1b0a7 | e14cd4806f58873333c499a92a4f5dd98ee7ba7de93b394b5f309b7d3984cce3 | c1ccc(CSC2=NC(SCc3ccccc3)=NC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[N;H0;D3;+0:6](-[CH3;D1;+0:7])-[CH3;D1;+0:8]):[c:9].[C;D1;H3:10]-[C;H0;D4;+0:11]1(-[C;D1;H3:12])-[NH;D2;+0:13]-[C;H0;D3;+0:14](=[S;H0;D1;+0:15])-[NH;D2;+0:16]-[C;H0;D3;+0:17]-1=[S;H0;D1;+0:18]>>[C;D1;H3:10]-[C;H0;D4;+0:11]1(-[C;D1;H3:12])-[#7:19]=[C;H0;D3;+0:14](-[S;H0;D2;+0:... | null | [] | null | null | 1 | HOUR | Initially, 2.94 g of 3-dimethylaminobenzylchloride hydrochloride was added to a mixture of 1.6 g of 5,5-dimethyl-2,4-dithiohydantoin and 1.3 g of sodium methoxide in 50 mL of methanol (MeOH). The reaction mixture was stirred at the room temperature for one hour, and concentrated in vacuo. The residue was treated follow... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea.Thioamide.Tertiary amine | Tertiary amine.Tertiary amine.Monosulfide.Monosulfide | C1CNCN1 | c1ccccc1.C1=NC=NC1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | null | CO | null | 1 | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1>CO>CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4efbc932fc544199dcb61e6467fceea | BrCc1cccc2cccnc12.CC1(C)NC(=S)NC1=S>>CC1(C)N=C(SCc2cccc3cccnc23)N=C1SCc1cccc2cccnc12 | BrCC=1C=CC=C2C=CC=NC12.CC1(C(NC(N1)=S)=S)C>>N1=CC=CC2=CC=CC(=C12)CSC1=NC(C(=N1)SCC=1C=CC=C2C=CC=NC12)(C)C | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]12.[CH3:1][C:2]1([CH3:27])[NH:4][C:5](=[S:6])[NH:18][C:19]1=[S:20]>>[CH3:1][C:2]1([CH3:3])[N:4]=[C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][n:16][c:17]23)[N:18]=[C:19]1[S:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][c:26]... | BrCc1cccc2cccnc12.CC1(C)NC(=S)NC1=S | CC1(C)N=C(SCc2cccc3cccnc23)N=C1SCc1cccc2cccnc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 02d24859d5480827ffc30869aaf0794e217b6a931fcfe10e3ee2647b9a0cbcbf | 99e12b03eade0fe69501b6a285a6b4a4c50012c54f35269925bc496acff18eb3 | c1cnc2c(CSC3=NC(SCc4cccc5cccnc45)=NC3)cccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[C;D1;H3:8]-[C;H0;D4;+0:9]1(-[CH3;D1;+0:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[S;H0;D1;+0:13])-[NH;D2;+0:14]-[C;H0;D3;+0:15]-1=[S;H0;D1;+0:16]>>[C;D1;H3:8]-[C;H0;D4;+0:9]1(-[C;D1;H3:17])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12](-[S;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:2](:[c:3]... | null | [] | null | null | 1.5 | HOUR | Initially, 3 g of 8-bromomethylquinoline was added to a solution of 1 g of 5,5-dimethyl-2,4-dithiohydantoin in 50 mL of ethanol (EtOH). The reaction mixture was stirred at the room temperature for 1.5 hour, and concentrated in vacuo. To the residue, 100 mL of CHCl3 was added. The mixture was washed with an aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea.Thioamide | Monosulfide.Monosulfide | C1CNCN1 | C1=NC=NC1.c1ccc2ncccc2c1 | C1=NC=NC1.c1ccc2ncccc2c1.c1ccc2ncccc2c1 | Br- | C(C)O | null | 1.5 | BrCc1cccc2cccnc12.CC1(C)NC(=S)NC1=S>C(C)O>CC1(C)N=C(SCc2cccc3cccnc23)N=C1SCc1cccc2cccnc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ddb24d2ec1c4eb5b7c0603a217b4d61 | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1>>CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 | Cl.CN(C=1C=C(CCl)C=CC1)C.CC1(C(NC(N1)=S)=S)C.C[O-].[Na+]>>CN(C=1C=C(CSC2=NC(C(=N2)SCC2=CC(=CC=C2)N(C)C)(C)C)C=CC1)C | [NH:2]1[C:11](=[S:10])[NH:28][C:16](=[S:17])[C:13]1([CH3:14])[CH3:15].Cl[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]([N:24]([CH3:1])[CH3:3])[cH:27]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][S:10][C:11]2=[N:12][C:13]([CH3:14])([CH3:15])[C:16]([S:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][c:23]([N:24]([CH3:... | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1 | CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 0a28fd05626e226c3e61952969504b1e7c751e2809b3309b230576220ee1b0a7 | e14cd4806f58873333c499a92a4f5dd98ee7ba7de93b394b5f309b7d3984cce3 | c1ccc(CSC2=NC(SCc3ccccc3)=NC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[N;H0;D3;+0:6](-[CH3;D1;+0:7])-[CH3;D1;+0:8]):[c:9].[C;D1;H3:10]-[C;H0;D4;+0:11]1(-[C;D1;H3:12])-[NH;D2;+0:13]-[C;H0;D3;+0:14](=[S;H0;D1;+0:15])-[NH;D2;+0:16]-[C;H0;D3;+0:17]-1=[S;H0;D1;+0:18]>>[C;D1;H3:10]-[C;H0;D4;+0:11]1(-[C;D1;H3:12])-[#7:19]=[C;H0;D3;+0:14](-[S;H0;D2;+0:... | null | [] | null | null | null | null | Initially, 3.1 g of 3-dimethylaminobenzylchloride hydrochloride was added to a mixture of 0.8 g of 5,5-dimethyl-2,4-dithiohydantoin and 1.34 g of sodium methoxide in 50 mL of methanol (MeOH). The reaction mixture was treated following the procedure used in Example 56, and purified by column chromatograph (CHCl3) to giv... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea.Thioamide.Tertiary amine | Tertiary amine.Tertiary amine.Monosulfide.Monosulfide | C1CNCN1 | c1ccccc1.C1=NC=NC1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | null | CO | null | null | CC1(C)NC(=S)NC1=S.CN(C)c1cccc(CCl)c1>CO>CN(C)c1cccc(CSC2=NC(C)(C)C(SCc3cccc(N(C)C)c3)=N2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f30ba70e6f749ca9b50c7fefb87d362 | CC1(C)NC(=S)NC1=S.CN(C)c1ccc(CCl)cc1>>CN(C)c1ccc(CSC2=NC(C)(C)C(SCc3ccc(N(C)C)cc3)=N2)cc1 | Cl.CN(C1=CC=C(CCl)C=C1)C.CC1(C(NC(N1)=S)=S)C>>CN(C1=CC=C(CSC2=NC(C(=N2)SCC2=CC=C(C=C2)N(C)C)(C)C)C=C1)C | [NH:2]1[C:10](=[S:9])[NH:27][C:15](=[S:16])[C:12]1([CH3:13])[CH3:18].Cl[CH2:8][c:7]1[cH:6][cH:25][c:21]([N:22]([CH3:1])[CH3:3])[cH:29][cH:28]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][S:9][C:10]2=[N:11][C:12]([CH3:13])([CH3:14])[C:15]([S:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([N:22]([CH3:23])[CH3:24])[cH:2... | CC1(C)NC(=S)NC1=S.CN(C)c1ccc(CCl)cc1 | CN(C)c1ccc(CSC2=NC(C)(C)C(SCc3ccc(N(C)C)cc3)=N2)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e9e0dcb8157350c39f7294759583be48483c609eab6bad3b352b3679b60ba21a | e14cd4806f58873333c499a92a4f5dd98ee7ba7de93b394b5f309b7d3984cce3 | c1ccc(CSC2=NC(SCc3ccccc3)=NC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[N;H0;D3;+0:6](-[CH3;D1;+0:7])-[CH3;D1;+0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H3:11]-[C;H0;D4;+0:12]1(-[CH3;D1;+0:13])-[NH;D2;+0:14]-[C;H0;D3;+0:15](=[S;H0;D1;+0:16])-[NH;D2;+0:17]-[C;H0;D3;+0:18]-1=[S;H0;D1;+0:19]>>[C;D1;H3:11]-[C;H0;D4;+0:12]1(-[C;D1;H3:20... | null | [] | null | null | null | null | Initially, 3.2 g of 4-dimethylaminobenzylchloride hydrochloride was added to a solution of 1 g of 5,5-dimethyl-2,4-dithiohydantoin in 50 mL of ethanol (EtOH). The reaction mixture was treated following the procedure used in Example 62, and purified by column chromatography (CHCl3). Recrystallization form diethyl ether-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea.Thioamide.Tertiary amine | Tertiary amine.Tertiary amine.Monosulfide.Monosulfide | C1CNCN1.c1ccccc1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | null | C(C)O | null | null | CC1(C)NC(=S)NC1=S.CN(C)c1ccc(CCl)cc1>C(C)O>CN(C)c1ccc(CSC2=NC(C)(C)C(SCc3ccc(N(C)C)cc3)=N2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f49fa4e191649188ac77496c1af416a | BrCc1ccccc1.CC1(C)NC(=S)NC1=S>>CC1(C)NC(SCc2ccccc2)=NC1=S | C(C1=CC=CC=C1)Br.CC1(C(NC(N1)=S)=S)C>>C(C1=CC=CC=C1)SC=1NC(C(N1)=S)(C)C | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[S:6])[NH:14][C:15]1=[S:16]>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)=[N:14][C:15]1=[S:16] | BrCc1ccccc1.CC1(C)NC(=S)NC1=S | CC1(C)NC(SCc2ccccc2)=NC1=S | null | null | C(C)O | Protection | OtherReaction | 46cef1e48600fcd6705529550ccb17b294e17c854f6cacd0473e52ed0910cca7 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | S=C1CNC(SCc2ccccc2)=N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[NH;D2;+0:11]-1>>[S;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C;H0;D3;+0:9](-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])=[N;H0;D2;+0:11]-1 | null | [] | null | null | 1 | HOUR | Initially, 1.91 mL of benzylbromide was added to a solution of 1.6 g of 5,5-dimethyl-2,4-dithiohydantoin in 50 mL of ethanol (EtOH). The reaction mixture was stirred at the room temperature for one hour, and concentrated in vacuo. The residue was treated following the procedure used in Example 62, and purified by colum... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | C1CNCN1 | C1=NCCN1 | C1=NCCN1.c1ccccc1 | HBr | C(C)O | null | 1 | BrCc1ccccc1.CC1(C)NC(=S)NC1=S>C(C)O>CC1(C)NC(SCc2ccccc2)=NC1=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a24f90cc7884da083a28d124bc01ed8 | CC1(C)NC(SCc2ccccc2)=NC1=S.CN(C)c1ccccc1CCl>>CN(C)c1ccccc1CSC1=NC(SCc2ccccc2)=NC1(C)C | Cl.CN(C1=C(CCl)C=CC=C1)C.C(C1=CC=CC=C1)SC=1NC(C(N1)=S)(C)C>>C(C1=CC=CC=C1)SC1=NC(C(=N1)SCC1=C(C=CC=C1)N(C)C)(C)C | [S:11]=[C:12]1[N:13]=[C:14]([S:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[NH:23][C:24]1([CH3:25])[CH3:26].Cl[CH2:10][c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][S:11][C:12]1=[N:13][C:14]([S:15][CH2:16][c:17]2[cH:18][cH:19][cH... | CC1(C)NC(SCc2ccccc2)=NC1=S.CN(C)c1ccccc1CCl | CN(C)c1ccccc1CSC1=NC(SCc2ccccc2)=NC1(C)C | null | null | C(C)O | Protection | OtherReaction | 2cae177f6d4ae1a04201a67501987621d8d2eea3bcb1c5c3e45f226cf8eb2595 | 73c8878a4ec89c98dabc6fa1f37724ccebee7c1f418fd0d5ec558cb2e2ee1385 | c1ccc(CSC2=NC(SCc3ccccc3)=NC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#16:6]-[C;H0;D3;+0:7]1=[N;H0;D2;+0:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[NH;D2;+0:14]-1>>[C:5]-[#16:6]-[C;H0;D3;+0:7]1=[N;H0;D2;+0:14]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;H0;D3;+0:9](-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])=[... | null | [] | null | null | 1 | HOUR | Initially, 0.65 g of 2-dimethylaminobenzylchloride hydrochloride was added to a solution of 0.7 g of 2-benzylthio-5,5-dimethylimidazolin-4-thione in 20 mL of ethanol (EtOH). The reaction mixture was stirred at the room temperature for one hour, and concentrated in vacuo. The residue was treated following the procedure ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Monosulfide | Monosulfide.Monosulfide | C1=NCCN1 | C1=NC=NC1 | c1ccccc1.C1=NC=NC1.c1ccccc1 | HCl | C(C)O | null | 1 | CC1(C)NC(SCc2ccccc2)=NC1=S.CN(C)c1ccccc1CCl>C(C)O>CN(C)c1ccccc1CSC1=NC(SCc2ccccc2)=NC1(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8004c340bcb48f79c38943b43d382ec | COc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>>COc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 | C1(=CC=CC=C1)C.C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=C(C=C1)OC)SSC1=C(C=CC(=C1)OC)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)OC)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)OC | CC(C)(C)[O:17][C:15]([CH:10]([NH:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][c:18]1[S:19][S:20][c:21]1[cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27][c:28]1[C:29](=[O:30])[NH:31][CH:32]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:37](=[O:38])[O:39]C(C)(C)C)=[O:8])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:16]>>[CH3:1][O:2][c:... | COc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1 | COc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 | null | null | ClCCl | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 69.5 | [{"value": 69.5, "product": "C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=C(C=C1)OC)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of [S-(R*,R*)-2[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-methoxyphenyldisulfanyl]-4-methoxybenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (1.2 g, 1.7 mmol) and anisole (1 mL) in 10 mL dichloromethane, cooled to about 0° C., was treated dropwise with 10 mL of trifluoroacetic acid. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | 4 | COc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>ClCCl>COc1ccc(C(=O)NC(CC(C)C)C(=O)O)c(SSc2cc(OC)ccc2C(=O)NC(CC(C)C)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-119962b494b84a6c9cbee5d7dffaf002 | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | C(C)(C)(C)OC(C(CC(C)C)N(C(C1=CC=CC(=C1)F)=O)SSC1=C(C=C(C=C1)F)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O.FC(C(=O)O)(F)F>>C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)F)SSC1=C(C(=O)NC(C(=O)O)CC(C)C)C=C(C=C1)F | CC(C)(C)[O:35][C:33]([CH:28]([N:27]([S:17][S:16][c:15]1[c:9]([C:7]([NH:6][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:36](=[O:37])[O:38]C(C)(C)C)=[O:8])[cH:10][c:11]([F:12])[cH:13][cH:14]1)[C:25]([c:24]1[cH:18][cH:19][cH:20][c:21]([F:22])[cH:23]1)=[O:26])[CH2:29][CH:30]([CH3:31])[CH3:32])=[O:34]>>[CH3:1][CH:2]([CH3:3])[CH2:... | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | null | null | ClCCl.C1(=CC=CC=C1)OC | Miscellaneous | OtherReaction | 09c4d392b48c016291b6d1ce537fb29e14ce0694d0a924f483700fcd8f1e3231 | 6001f211511fe6682852bbd6a1d306f30447f74f772ed9de084e37d61a5abdd7 | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8](-[C:9])-[N;H0;D3;+0:10](-[S;H0;D2;+0:11]-[#16:12]-[c:13])-[C:14](=[O;D1;H0:15])-[c:16](:[c:17]):[cH;D2;+0:18]:[c:19]:[c:20]>>[C:9]-[C:8](-[NH;D2;+0:10]-[C:14](=[O;D1;H0:15])-[c:16](:[c:17]):[c;H0;D3;+0:18](-[S;H0;D... | null | [] | null | null | null | null | The general method of Preparation 20 was followed using [S-(R*,R*)]-2-[2-[[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino]-4-methyl pentanoic acid tert-butyl ester (1.8 g, 2.6 mmol) in 20 mL dichloromethane, anisole (2 mL), and 20 mL trifluoroacetic acid. The crude prod... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Tertiary amide.Disulfide.Boc.Boc | Carboxylic acid.Carboxylic acid.Secondary amide.Disulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | ClCCl.C1(=CC=CC=C1)OC | null | null | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl.C1(=CC=CC=C1)OC>CC(C)CC(NC(=O)c1cc(F)ccc1SSc1ccc(F)cc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30c9c4c43e504a87b22ef5a3d62b32e8 | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>>Cc1cccc([SH](Sc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(CC(C)C)C(=O)O)c1 | C(C)(C)(C)OC(C(CC(C)C)NC(C1=C(C=C(C=C1)C)SSC1=C(C=CC(=C1)C)C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O)=O.FC(C(=O)O)(F)F>>C(=O)(O)C(CC(C)C)NC(=O)S(SC1=C(C(=O)NC(C(=O)O)CC(C)C)C=CC(=C1)C)C1=CC=CC(=C1)C | CC(C)(C)[O:26][C:24]([CH:19]([NH:18][C:16]([c:15]1[c:9]([S:8][S:7][c:6]2[c:5]([C:27](=[O:28])[NH:29][CH:30]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:35](=[O:36])[O:37]C(C)(C)C)[cH:4][cH:3][c:2]([CH3:1])[cH:38]2)[cH:10][c:11]([CH3:12])[cH:13][cH:14]1)=[O:17])[CH2:20][CH:21]([CH3:22])[CH3:23])=[O:25]>>[CH3:1][c:2]1[cH:3][cH:... | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1 | Cc1cccc([SH](Sc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(CC(C)C)C(=O)O)c1 | null | null | ClCCl.C1(=CC=CC=C1)OC | Miscellaneous | OtherReaction | 97cc7ca54c3504cdddd49cbb6f307a3515c6323edeca45fe75deed785c490c73 | d55bea45c3105c0907c3b9459dc25f38e24a2cb4199f6499f0844204a38592ad | c1ccc(SSc2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[S;H0;D2;+0:16]-[#16:17]-[c:18]):[c:19]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:11]=[C;H0;D3;+0:10](-[#7:9]-[C:8]-[C:6](=[O;D1;... | null | [] | null | null | null | null | The general method of Preparation 20 was followed using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-methyl-phenyldisulfanyl]-4-methyl-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester (1.9 g, 2.8 mmol) in 20 mL dichloromethane, anisole (2.0 mL), and 10 mL trifluoroacetic acid. The crude p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary amide.Disulfide.Boc.Boc | Carboxylic acid.Carboxylic acid.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | ClCCl.C1(=CC=CC=C1)OC | null | null | Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1>ClCCl.C1(=CC=CC=C1)OC>Cc1cccc([SH](Sc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(CC(C)C)C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e43db34740c4500b323da3d86603bf8 | CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | C(C)(C)(C)OC(C(CC(C)C)NC(=O)C=1C(=NC=CC1)SSC1=NC=CC=C1C(NC(CC(C)C)C(=O)OC(C)(C)C)=O)=O.FC(C(=O)O)(F)F>>C(=O)(O)C(CC(C)C)NC(=O)C=1C(=NC=CC1)SSC1=NC=CC=C1C(=O)NC(C(=O)O)CC(C)C | CC(C)(C)[O:33][C:31]([CH:26]([NH:25][C:23]([c:22]1[c:17]([S:16][S:15][c:14]2[c:9]([C:7]([NH:6][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:34](=[O:35])[O:36]C(C)(C)C)=[O:8])[cH:10][cH:11][cH:12][n:13]2)[n:18][cH:19][cH:20][cH:21]1)=[O:24])[CH2:27][CH:28]([CH3:29])[CH3:30])=[O:32]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([NH:6][... | CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O | null | null | ClCCl.C1(=CC=CC=C1)OC | Deprotection | OtherReaction | ca505900a12db9f5b5e9f03319157f3a1866191dca0d7b3ac3055953edad48a1 | 6963b6f47a0b0b5cff914a710e9b301204a20bd63f6727c47e40cb3bb5699806 | c1ccc(SSc2ccccn2)nc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C(-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5] | 77.4 | [{"value": 77.4, "product": "C(=O)(O)C(CC(C)C)NC(=O)C=1C(=NC=CC1)SSC1=NC=CC=C1C(=O)NC(C(=O)O)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The general method of Preparation 20 was followed using [S-(R*,R*)]-2-([2-[3-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-pyridin-2-yldisulfanyl]pyridine-3-carbonyl]-amino)-4-methyl-pentanoic acid tert-butyl ester (1.9 g, 2.9 mmol) in 20 mL dichloromethane, anisole (1.5 mL), and 10 mL trifluoroacetic acid. The crude... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid.Carboxylic acid | null | null | c1ccncc1.c1ccncc1 | Other | ClCCl.C1(=CC=CC=C1)OC | null | null | CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl.C1(=CC=CC=C1)OC>CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-669072172d11414b8d8b946fb369fa91 | O=C(O)c1cc([N+](=O)[O-])ccc1Cl>>NC(=O)c1cc([N+](=O)[O-])ccc1Cl | CN(C=O)C.ClC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].ClCCl.C(C(=O)Cl)(=O)Cl>>ClC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-] | O[C:2](=[O:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[Cl:13]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[Cl:13] | O=C(O)c1cc([N+](=O)[O-])ccc1Cl | NC(=O)c1cc([N+](=O)[O-])ccc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 25 | CELSIUS | 3 | HOUR | A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) and 200 mL of dichloromethane was reacted with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. The mixture was stirred at 25° C. for 3 hours. The solvent was removed in vacuo, and the residue was redissolved in 200 mL of di... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1 | null | null | 25 | 3 | O=C(O)c1cc([N+](=O)[O-])ccc1Cl>>NC(=O)c1cc([N+](=O)[O-])ccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-31a8839874394a4985cf9f31ccc798f0 | NC(=O)c1cc([N+](=O)[O-])ccc1SSc1ccc([N+](=O)[O-])cc1C(N)=O>>NC(=O)c1cc(N)ccc1SSc1ccc(N)cc1C(N)=O | [OH-].[Na+].[N+](=O)([O-])C=1C=CC(=C(C(=O)N)C1)SSC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-].C(C)(=O)O>>NC=1C=CC(=C(C(=O)N)C1)SSC1=C(C(=O)N)C=C(C=C1)N | O=[N+:7]([O-])[c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:10]([S:11][S:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=O)[O-])[cH:18][c:19]2[C:20]([NH2:21])=[O:22])[cH:9][cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:8][cH:9][c:10]1[S:11][S:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:18][c:19]1[C:20]([NH2:21])=[O:22] | NC(=O)c1cc([N+](=O)[O-])ccc1SSc1ccc([N+](=O)[O-])cc1C(N)=O | NC(=O)c1cc(N)ccc1SSc1ccc(N)cc1C(N)=O | null | null | O | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc(SSc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2,2'-Dithiobis(5-nitrobenzamide) (2.6 g, 7.0 mmol) was added portion-wise to a refluxing slurry of reduced iron (8.7 g) in 65 mL of water containing 0.1 mL of acetic acid. The resulting slurry was heated at reflux for 2.0 hours, then cooled to room temperature. The slurry was made strongly basic (pH 11) by the addition... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | O | null | null | NC(=O)c1cc([N+](=O)[O-])ccc1SSc1ccc([N+](=O)[O-])cc1C(N)=O>O>NC(=O)c1cc(N)ccc1SSc1ccc(N)cc1C(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2c072d6e317473092782f2fc460da4e | CC(=O)NS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CC(=O)NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(=O)(=O)NC(C)=O)cc2)cc1 | C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl.C(C)(=O)NS(=O)(=O)C1=CC=C(N)C=C1>>C(C)(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC(C)=O)C=CC=C1)=O | [CH3:1][C:2](=[O:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:45][cH:46]1.Cl[C:29]([c:28]1[c:23]([S:22][S:21][c:20]2[cH:15][cH:13][cH:17][cH:16][c:41]2[C:40](Cl)=[O:42])[cH:24][cH:25][cH:26][cH:27]1)=[O:30]>>[CH3:1][C:2](=[O:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=... | CC(=O)NS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CC(=O)NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(=O)(=O)NC(C)=O)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 22cd1dc72a4041b0ef5b7db292b4184290c99b70de74a0aed5aa6007b828688f | 01a9fdf9dcb9d81e0891ccaaf29dcc22bb434a60fd36ce79777612cbb6766e1f | O=C(Nc1ccccc1)c1ccccc1SSc1ccccc1C(=O)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[#16:6]-[#16:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[C;H0;D3;+0:14](-Cl)=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[#16:20]-[#7:21]-[C;H0;D3;+0:14](-[CH3;D1;+0:13])=[O;D1;H0:15].[O;D1;H0:22]=[C;H0;D3;+0:10... | 8.9 | [{"value": 8.9, "product": "C(C)(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SSC1=C(C(=O)NC2=CC=C(C=C2)S(=O)(=O)NC(C)=O)C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound was prepared according to the general method of Preparation 9 using 2,2'-dithiobisbenzoyl chloride (3.0 g, 8.0 mmol) in 30 mL of dichloromethane and 4-[(acetylamino) sulfonyl]aniline (5.6 g, 26.0 mmol) in 100 mL of pyridine. The crude product was purified on a silica gel column using chloroform/methanol (1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Sulfonamide.Secondary amide.Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl.N1=CC=CC=C1 | null | null | CC(=O)NS(=O)(=O)c1ccc(N)cc1.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>ClCCl.N1=CC=CC=C1>CC(=O)NS(=O)(=O)c1ccc(NC(=O)c2ccccc2SSc2ccccc2C(=O)Nc2ccc(S(=O)(=O)NC(C)=O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93e8df1342c5499d9b84345b5640a0a8 | CC(C)[C@H](N)C(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CC(C)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O | N[C@@H](C(C)C)C(=O)O.C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl>>C(=O)(O)C(C(C)C)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NC(C(=O)O)C(C)C)C=CC=C1 | [CH3:1][CH:2]([C@H:4]([NH2:5])[C:32](=[O:33])[OH:34])[CH3:22].Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14][S:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:25]1[C:26](Cl)=[O:23]>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14][S:15][c:16]1[cH:17][cH:18][cH:19][c... | CC(C)[C@H](N)C(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | CC(C)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O | null | null | null | Acylation | OtherReaction | 96aec30bc29f8a10c5a9c59dd38293a9e70242b09892d1cb15e88bd21ee48682 | 562f98a770adee9ece495a4b94774feb5cfb15c943140651fe293450590314a5 | c1ccc(SSc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[#16:9]-[#16:10]-[c:11]:[c:12](-[C;H0;D3;+0:13](-Cl)=[O;D1;H0:14]):[c:15].[C;D1;H3:16]-[CH;D3;+0:17](-[CH3;D1;+0:18])-[C@H;D3;+0:19](-[NH2;D1;+0:20])-[C:21](=[O;D1;H0:22])-[O;D1;H1:23]>>[C;D1;H3:16]-[CH;D3;+0:17](-[C;D1;H... | null | [] | null | null | null | null | Using the method employed in Preparation 30, 17.8 g (0.15 mol) of D,L valine was reacted with 17.2 g (0.05 mol) of 2,2'-dithiobisbenzoyl chloride to produce 11.4 g of the title compound after recrystallization from acetic acid, mp 226.5°-227.5° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Carboxylic acid.Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)[C@H](N)C(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>CC(C)C(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-22175d52cf8d4bbdad038a1e70ab65ca | NCCCC(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O | NCCCC(=O)O.C(C1=C(C=CC=C1)SSC1=C(C(=O)Cl)C=CC=C1)(=O)Cl>>C(=O)(O)CCCNC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NCCCC(=O)O)C=CC=C1 | [C:2](=[O:3])([CH2:4][CH2:5][CH2:6][NH2:7])[OH:32].Cl[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:29][cH:28][cH:27][c:23]1[C:24](Cl)=[O:1]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][S:17][c:18]1[cH:19][cH:20][cH:21... | NCCCC(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl | O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O | null | null | null | C-C Coupling | OtherReaction | d181252499baa49109ed23d54d62027be0aa3b7f5e994ef4d92e4bdf0a015f68 | a985834843373a464595eec57cb32af1587b5397fe48448982dd54839413def7 | c1ccc(SSc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:1-[#16:14].[NH2;D1;+0:15]-[C:16]-[C:17]-[C:18]-[C;H0;D3;+0:19](=[O;H0;D1;+0:20])-[OH;D1;+0:21]>>[#16:14]-[c:13]1:[cH;D2;+0:12]:[c:22]:[c:23]:[c:24]:[c;H0;D... | 49.9 | [{"value": 49.9, "product": "C(=O)(O)CCCNC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NCCCC(=O)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure in Preparation 30, 16 g (0.15 mol) of 4-amino-butanoic acid was reacted with 10.8 g (0.03 mol) of 2,2'-dithiobisbenzoyl chloride to afford 7.14 g of the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | NCCCC(=O)O.O=C(Cl)c1ccccc1SSc1ccccc1C(=O)Cl>>O=C(O)CCCNC(=O)c1ccccc1SSc1ccccc1C(=O)NCCCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a1716f3e5114ac89523fbe7390dee6c | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1Cl.S>>CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S | C(C)N(CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)Cl)CC.S.[Na]>>C(C)N(CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S)CC | Cl[c:22]1[c:11]([C:9]([NH:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:10])[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1.[SH2:23]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21][c:2... | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1Cl.S | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 070c5e407a5456f15b44a24a4a55d2593c0b85e22043fab594367ab9ef8d8c3e | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccc(-c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#7:10]-[C:11].[SH2;D0;+0:12]>>[C:11]-[#7:10]-[C:8](=[O;D1;H0:9])-[c:7]1:[c:6]:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[SH;D1;+0:12] | 63.6 | [{"value": 63.6, "product": "C(C)N(CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure in Preparation 34, 6.4 g (0.02 mol) of 4-chloro-2-phenyl-pyrimidine-5-carboxylic acid (2-diethylamino-ethyl)-amide was reacted with 4.8 g (0.066 mol) of sodium hydrogen sulfide to afford 4.2 g of the title compound, mp 178°-180° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1Cl.S>>CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1bfad829bc4246f8aaa002d4fbd32d86 | CN(C)c1ncc(C(=O)NCc2ccccc2)c(Cl)n1.S>>CN(C)c1ncc(C(=O)NCc2ccccc2)c(S)n1 | C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)N(C)C)Cl.S.[Na]>>C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)N(C)C)S | Cl[c:18]1[c:7]([C:8](=[O:9])[NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:6][n:5][c:4]([N:2]([CH3:1])[CH3:3])[n:20]1.[SH2:19]>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]([C:8](=[O:9])[NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([SH:19])[n:20]1 | CN(C)c1ncc(C(=O)NCc2ccccc2)c(Cl)n1.S | CN(C)c1ncc(C(=O)NCc2ccccc2)c(S)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 070c5e407a5456f15b44a24a4a55d2593c0b85e22043fab594367ab9ef8d8c3e | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | O=C(NCc1ccccc1)c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#7:10]-[C:11].[SH2;D0;+0:12]>>[#7:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[SH;D1;+0:12]):[c:7](-[C:8](=[O;D1;H0:9])-[#7:10]-[C:11]):[c:6]:[#7;a:5]:1 | 43.9 | [{"value": 43.9, "product": "C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)N(C)C)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Preparation 34, 14.3 g (0.045 mol) of 4-chloro-2-dimethylamino-pyrimidine-5-carboxylic acid benzylamide and 12 g (0.21 mol) of sodium hydrogen sulfide were reacted to give 5.7 g of the title compound, mp 175°-178° C.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | CN(C)c1ncc(C(=O)NCc2ccccc2)c(Cl)n1.S>>CN(C)c1ncc(C(=O)NCc2ccccc2)c(S)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73bd32edf0dc4454ae0af2e0d20af183 | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1Cl.S>>O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S | C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)Cl.S.[Na]>>C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S | Cl[c:22]1[c:11]([C:2](=[O:1])[NH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1.[SH2:23]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21][c:22]1[SH:23] | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1Cl.S | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 070c5e407a5456f15b44a24a4a55d2593c0b85e22043fab594367ab9ef8d8c3e | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#7:10]-[C:11].[SH2;D0;+0:12]>>[C:11]-[#7:10]-[C:8](=[O;D1;H0:9])-[c:7]1:[c:6]:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[SH;D1;+0:12] | 65.2 | [{"value": 65.2, "product": "C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure from Preparation 34, 5.8 g (17.9 mmol) of 4-chloro-2-phenyl-pyrimidine-5-carboxylic acid benzylamide was reacted with 5.1 g (72 mmol) of sodium hydrogen sulfide to give 3.75 g of the title compound, mp 189°-193° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1Cl.S>>O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4067666dc2a34bd280d72f658a8ab4f7 | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O>>CCC(C)C(C(=O)O)n1sc2ccccc2c1=O | C(=O)(O)C(C(CC)C)NC(=O)C1=C(C(=O)N(C(C(=O)O)C(CC)C)SSC2=CC=CC=C2)C=CC=C1.BrBr>>CC(C(C(=O)O)N1SC2=C(C1=O)C=CC=C2)CC | CCC(C)C(NC(=O)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([N:9]([CH:5]([CH:3]([CH2:2][CH3:1])[CH3:4])[C:6](=[O:7])[OH:8])[S:10]Sc1ccccc1)=[O:18])C(=O)O>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]([C:6](=[O:7])[OH:8])[n:9]1[s:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[c:17]1=[O:18] | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O | CCC(C)C(C(=O)O)n1sc2ccccc2c1=O | null | null | ClCCl | Miscellaneous | OtherReaction | e2926d905a02e34c58aa119038113df327a8b0c9b951a9c6c07d2367edb1d58e | 95efc4ecf4ace74c5432ec55a35221782e607c11c8e2bcb5f206d10c974b4c9d | O=c1[nH]sc2ccccc12 | C-C-C(-C)-C(-N-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[S;H0;D2;+0:8]-S-c1:c:c:c:c:c:1)-[C:9](-[C:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c:14])-C(-O)=O>>[C:10]-[C:9](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[n;H0;D3;+0:7]1:[s;H0;D2;+0:8]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:... | null | [] | null | null | 2 | HOUR | To a stirred suspension of 5.3 g (10.0 mmol) of [S-(R*,R*)]-2-[2-[2-(1-carboxy-2-methylbutylcarbamoyl) phenyldisulfanylbenzoylamino]-3-methylpentanoic acid (from Preparation 19) in 200 mL of dichloromethane was added dropwise 2.4 g (15.0 mmol) of liquid bromine. The reaction mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Tertiary amide.Disulfide | null | c1ccccc1.c1ccccc1 | c1ccc2sncc2c1 | c1ccc2sncc2c1 | Other | ClCCl | null | 2 | CCC(C)C(NC(=O)c1ccccc1C(=O)N(SSc1ccccc1)C(C(=O)O)C(C)CC)C(=O)O>ClCCl>CCC(C)C(C(=O)O)n1sc2ccccc2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0793e59e7ec647808746d733896f2b78 | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)O)C(=O)O>>CC(C)C[C@@H](C(=O)O)n1sc2ccc(F)cc2c1=O | C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)F)SSN(C(C(=O)O)CC(C)C)C(C1=CC=CC(=C1)F)=O.BrBr>>CC(C[C@@H](C(=O)O)N1SC2=C(C1=O)C=C(C=C2)F)C | CC(C)CC(C(=O)O)N(S[S:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[C:18]([NH:9][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[OH:8])=[O:19])C(=O)c1cccc(F)c1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@@H:5]([C:6](=[O:7])[OH:8])[n:9]1[s:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[c:18]1=[O:19] | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)O)C(=O)O | CC(C)C[C@@H](C(=O)O)n1sc2ccc(F)cc2c1=O | null | null | C(C)#N.ClCCl | Functional Group Interconversion | OtherReaction | 76bf87ae358ee0e4e582cc211ac6dce89f9be7272cf4d3f440d8e6109870eedb | 4b1cb94b9bd3f930196129229de6ede3f354bb1dc0c097c3268db81c49624c65 | O=c1[nH]sc2ccccc12 | C-C(-C)-C-C(-C(-O)=O)-N(-S-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[CH;D3;+0:8](-[C:9]-[C:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c:14])-C(=O)-c1:c:c:c:c(-F):c:1>>[C:10]-[C:9]-[C@@H;D3;+0:8](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[n;H0;D3;+0:7]1:[s;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:... | 137.3 | [{"value": 137.3, "product": "CC(C[C@@H](C(=O)O)N1SC2=C(C1=O)C=C(C=C2)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general method of Example 3, a slurry of {s-(R*,R*)]-2-{-[2-(1-carboxy-3-methylbutylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino}-4-methyl-pentanoic acid (2.1 g, 3.6 mmol) (from Preparation 21) in 8 mL acetonitrile and 25 mL dichloromethane was treated with bromine (0.7 g, 4.4 mmol) in 15 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Secondary amide.Tertiary amide.Disulfide | null | c1ccccc1.c1ccccc1 | c1ccc2sncc2c1 | c1ccc2sncc2c1 | HF | C(C)#N.ClCCl | null | null | CC(C)CC(NC(=O)c1cc(F)ccc1SSN(C(=O)c1cccc(F)c1)C(CC(C)C)C(=O)O)C(=O)O>C(C)#N.ClCCl>CC(C)C[C@@H](C(=O)O)n1sc2ccc(F)cc2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ee8845e6af847a2859d929ed8e2b575 | Cc1cccc(C(=O)N(SSc2ccc(C)cc2C(=O)NC(CC(C)C)C(=O)O)C(CC(C)C)C(=O)O)c1>>Cc1ccc2c(=O)n([C@@H](CC(C)C)C(=O)O)sc2c1 | C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC(=C1)C)SSN(C(C(=O)O)CC(C)C)C(C1=CC=CC(=C1)C)=O.BrBr.C(C)#N>>CC(C[C@@H](C(=O)O)N1SC2=C(C1=O)C=CC(=C2)C)C | Cc1cccc(C(=O)N(S[S:17][c:18]2[cH:4][cH:3][c:2]([CH3:1])[cH:19][c:5]2[C:6](=[O:7])[NH:8][CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14](=[O:15])[OH:16])C(CC(C)C)C(=O)O)c1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](=[O:7])[n:8]([C@@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14](=[O:15])[OH:16])[s:17][c:18]2[cH:19]1 | Cc1cccc(C(=O)N(SSc2ccc(C)cc2C(=O)NC(CC(C)C)C(=O)O)C(CC(C)C)C(=O)O)c1 | Cc1ccc2c(=O)n([C@@H](CC(C)C)C(=O)O)sc2c1 | null | null | ClCCl | Miscellaneous | OtherReaction | e2926d905a02e34c58aa119038113df327a8b0c9b951a9c6c07d2367edb1d58e | 95efc4ecf4ace74c5432ec55a35221782e607c11c8e2bcb5f206d10c974b4c9d | O=c1[nH]sc2ccccc12 | C-C(-C)-C-C(-C(-O)=O)-N(-S-[S;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4]:[c:5](-[C;D1;H3:6]):[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[CH;D3;+0:12](-[C:13]-[C:14])-[C:15](=[O;D1;H0:16])-[O;D1;H1:17])-C(=O)-c1:c:c:c:c(-C):c:1>>[C:14]-[C:13]-[C@@H;D3;+0:12](-[C:15](=[O;D1;H0:16])-[O;D... | null | [] | null | null | null | null | Following the general method of Example 3, a slurry of [s-(R*,R*)]-2-[-[2-(1-carboxy-3-methylbutylcarbamoyl)-4-methylphenyldisulfanyl]-5-methylbenzoylamino]-4-methyl-pentanoic acid (1.8 g, 3.2 mmol) (from Preparation 22) in 5 mL acetonitrile and 20 mL dichloromethane was reacted with bromine (0.6 g, 3.7 mmol) in 10 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Tertiary amide.Disulfide | null | c1ccccc1.c1ccccc1 | c1ccc2sncc2c1 | c1ccc2sncc2c1 | Other | ClCCl | null | null | Cc1cccc(C(=O)N(SSc2ccc(C)cc2C(=O)NC(CC(C)C)C(=O)O)C(CC(C)C)C(=O)O)c1>ClCCl>Cc1ccc2c(=O)n([C@@H](CC(C)C)C(=O)O)sc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c22db2c5c35e41f08e3017072fa1182e | CC(C)CC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O>>CC(C)C(C(=O)O)n1sc2ccccc2c1=O | C(=O)(O)C(CC(C)C)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)NC(C(=O)O)C(C)C)C=CC=C1.BrBr>>CC(C(C(=O)O)N1SC2=C(C1=O)C=CC=C2)C | CC(C)CC(NC(=O)c1ccccc1S[S:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]([NH:8][CH:4]([CH:2]([CH3:1])[CH3:3])[C:5](=[O:6])[OH:7])=[O:17])C(=O)O>>[CH3:1][CH:2]([CH3:3])[CH:4]([C:5](=[O:6])[OH:7])[n:8]1[s:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1=[O:17] | CC(C)CC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O | CC(C)C(C(=O)O)n1sc2ccccc2c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 0da1c302bf8994aa4fa64122a299c748e0825162a15b81dbc8c678803311ec95 | 9dd1e9ea00940727b8b4f2806b324bac3e6ef39570802956483a80b59e367fa2 | O=c1[nH]sc2ccccc12 | C-C(-C)-C-C(-N-C(=O)-c1:c:c:c:c:c:1-S-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8](-[C:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13])-C(-O)=O>>[C:9]-[C:8](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[n;H0;D3;+0:7]1:[s;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:13]):[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 0.1 | [{"value": 0.1, "product": "CC(C(C(=O)O)N1SC2=C(C1=O)C=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 13, 6.0 g (13.6 mol) of 2-[2-[2-(1-carboxy-3-methylbutyl carbamoyl)phenyldisulfanyl]benzoylamino]-3-methylbutanoic acid was reacted with bromine to provide 2.25 g of the title compound, mp 166°-168° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Secondary amide.Disulfide | null | c1ccccc1.c1ccccc1 | c1ccc2sncc2c1 | c1ccc2sncc2c1 | Other | null | null | null | CC(C)CC(NC(=O)c1ccccc1SSc1ccccc1C(=O)NC(C(=O)O)C(C)C)C(=O)O>>CC(C)C(C(=O)O)n1sc2ccccc2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a3df734465742dfad570b95ad696165 | Cc1ccnc(N)c1.O=C(Cl)c1ccccc1SCl>>Cc1ccnc(-n2sc3ccccc3c2=O)c1 | NC1=NC=CC(=C1)C.ClSC1=C(C(=O)Cl)C=CC=C1>>CC1=CC(=NC=C1)N1SC2=C(C1=O)C=CC=C2 | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[cH:17]1.Cl[S:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](Cl)=[O:16]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6](-[n:7]2[s:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2=[O:16])[cH:17]1 | Cc1ccnc(N)c1.O=C(Cl)c1ccccc1SCl | Cc1ccnc(-n2sc3ccccc3c2=O)c1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | c34db5504b6723593932211c018846dbbfd64df4cc5099d5a4650ff0dff0cc55 | 0fba682bfb017234b2a9a0cddcd0a6c1cf200968add3d32ec4b8be184522b775 | O=c1c2ccccc2sn1-c1ccccn1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6]):[c:7].[NH2;D1;+0:8]-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:6]=[c;H0;D3;+0:5]1:[c:4](:[c:7]):[c:2](:[c:3]):[s;H0;D2;+0:1]:[n;H0;D3;+0:8]:1-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12]:[c:13] | 37.1 | [{"value": 37.1, "product": "CC1=CC(=NC=C1)N1SC2=C(C1=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Using the method of Fischer and Hurni (Arzneimittel Forsch., 1964;14:1301) 5.4 g (0.05 mol) of 2-amino-4-methylpyridine in 50 mL of pyridine at 10° C. was reacted with 10.3 g (0.05 mol) of 2-chlorosulfenylbenzoyl chloride. The mixture was heated to 50° C. and maintained at that temperature for 2 hours. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Monosulfide | null | c1ccccc1 | c1ccc2sncc2c1 | c1ccncc1.c1ccc2sncc2c1 | HCl | N1=CC=CC=C1 | 50 | null | Cc1ccnc(N)c1.O=C(Cl)c1ccccc1SCl>N1=CC=CC=C1>Cc1ccnc(-n2sc3ccccc3c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b393218356b401fbefc98b26c343968 | Nc1ccc(CC(=O)O)cc1.O=C(Cl)c1ccccc1SCl>>O=C(O)Cc1ccc(-n2sc3ccccc3c2=O)cc1 | NC1=CC=C(C=C1)CC(=O)O.C(C)N(CC)CC.ClSC1=C(C(=O)Cl)C=CC=C1>>O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)CC(=O)O | [O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:19][cH:20]1.Cl[S:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](Cl)=[O:18]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:8](-[n:9]2[s:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2=[O:18])[cH:19][cH:20]1 | Nc1ccc(CC(=O)O)cc1.O=C(Cl)c1ccccc1SCl | O=C(O)Cc1ccc(-n2sc3ccccc3c2=O)cc1 | null | null | CCOCCO | Aromatic Heterocycle Formation | OtherReaction | c34db5504b6723593932211c018846dbbfd64df4cc5099d5a4650ff0dff0cc55 | 0fba682bfb017234b2a9a0cddcd0a6c1cf200968add3d32ec4b8be184522b775 | O=c1c2ccccc2sn1-c1ccccc1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6]):[c:7].[NH2;D1;+0:8]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:6]=[c;H0;D3;+0:5]1:[c:4](:[c:7]):[c:2](:[c:3]):[s;H0;D2;+0:1]:[n;H0;D3;+0:8]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 69.4 | [{"value": 69.4, "product": "O=C1N(SC2=C1C=CC=C2)C2=CC=C(C=C2)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a mixture of 7.55 g (0.05 mol) of 4-aminophenylacetic acid and 15.15 g (0.15 mol) of triethylamine in 25 mL of ethyl cellosolve was added 10.3 g (0.05 mol) of 2-chlorosulfenylbenzoyl chloride (Arzneimittel Forsch., 1964;14:1301). The mixture was stirred at room temperature for 3 hours, concentrated in vacuo, and wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Monosulfide | null | c1ccccc1 | c1ccc2sncc2c1 | c1ccccc1.c1ccc2sncc2c1 | HCl | CCOCCO | null | 3 | Nc1ccc(CC(=O)O)cc1.O=C(Cl)c1ccccc1SCl>CCOCCO>O=C(O)Cc1ccc(-n2sc3ccccc3c2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-612c475449ba4056a49ab5f66bcc7953 | O=C(NCCc1ccccn1)c1cnc2cc3c(cc2c1S)OCO3>>O=c1c2cnc3cc4c(cc3c2sn1CCc1ccccn1)OCO4 | N1=C(C=CC=C1)CCNC(=O)C=1C=NC=2C=C3C(=CC2C1S)OCO3.C(C)N(CC)CC.II>>N1=C(C=CC=C1)CCN1SC2=C(C=NC=3C=C4C(=CC23)OCO4)C1=O | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6]2[cH:7][c:8]3[c:9]([cH:10][c:11]2[c:12]1[SH:13])[O:23][CH2:24][O:25]3)[NH:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6]3[cH:7][c:8]4[c:9]([cH:10][c:11]3[c:12]2[s:13][n:14]1[CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1)[O:... | O=C(NCCc1ccccn1)c1cnc2cc3c(cc2c1S)OCO3 | O=c1c2cnc3cc4c(cc3c2sn1CCc1ccccn1)OCO4 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 1e253101091a8f64f2a51d3c4b1ecc40da62f3180df666e96348f00c187cd3e0 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc3cc4c(cc3c2sn1CCc1ccccn1)OCO4 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[c:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 83 | [{"value": 83.0, "product": "N1=C(C=CC=C1)CCN1SC2=C(C=NC=3C=C4C(=CC23)OCO4)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 4.1 g (0.012 mol) of 8-mercapto-[1,3]dioxolo [4,5-g]quinoline-7-carboxylic acid (2-pyridin-2-yl-ethyl)-amide (from Preparation 34) and 5 mL (0.035 mol) of triethylamine in 750 mL of methanol was added 2.95 g (0.012 mol) of iodine in 100 mL of methanol. The mixture was heated at reflux for 2 hours, cooled, and then c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cnc2cc3c(cc2c1)OCO3 | c1nsc2c1cnc1cc3c(cc12)OCO3 | c1ccncc1.c1nsc2c1cnc1cc3c(cc12)OCO3 | null | CO | null | null | O=C(NCCc1ccccn1)c1cnc2cc3c(cc2c1S)OCO3>CO>O=c1c2cnc3cc4c(cc3c2sn1CCc1ccccn1)OCO4 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-930c4b70242b44ebba4db43c1eff2ea3 | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S>>CCN(CC)CCn1sc2nc(-c3ccccc3)ncc2c1=O | C(C)N(CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S)CC.II>>C(C)N(CCN1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:22]([c:21]1[c:10]([SH:9])[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][cH:20]1)=[O:23]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][n:8]1[s:9][c:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][c:21]2[c:22]1=[O... | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S | CCN(CC)CCn1sc2nc(-c3ccccc3)ncc2c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1[nH]sc2nc(-c3ccccc3)ncc12 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 68.5 | [{"value": 68.5, "product": "C(C)N(CCN1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 3.3 g (0.01 mol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid (2-diethylamino-ethyl)-amide (from Preparation 36) and 2.54 g (0.01 mol) of iodine were reacted to give 2.25 g of the title compound after recrystallization from isopropanol, mp 106°-107° C.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1 | null | null | null | null | CCN(CC)CCNC(=O)c1cnc(-c2ccccc2)nc1S>>CCN(CC)CCn1sc2nc(-c3ccccc3)ncc2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2baa31474e604438bd652d473531a78e | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccc1 | C(C1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S.II>>C(C1=CC=CC=C1)N1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S | O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccc1 | [O;D1;H0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[C:4]-[c:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2:[s;H0;D2;+0:12]:[n;H0;D3;+0:3]:1-[C:4]-[c:5] | 87.6 | [{"value": 87.6, "product": "C(C1=CC=CC=C1)N1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 2.0 g (6.22 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid benzylamide (from Preparation 42) was reacted with 1.74 g (6.8 mmol) of iodine to give 1.74 g of the title compound after crystallization from isopropanol, mp 166°-167° C.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1.c1ccccc1 | null | null | null | null | O=C(NCc1ccccc1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa0ff816dc704f9d9450baa6edce85dc | O=C(NCCN1CCOCC1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCN1CCOCC1 | N1(CCOCC1)CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S.II>>N1(CCOCC1)CCN1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][O:22][CH... | O=C(NCCN1CCOCC1)c1cnc(-c2ccccc2)nc1S | O=c1c2cnc(-c3ccccc3)nc2sn1CCN1CCOCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(-c3ccccc3)nc2sn1CCN1CCOCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 60.8 | [{"value": 60.8, "product": "N1(CCOCC1)CCN1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 2.0 g (5.81 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid (2-morpholin-4-yl-ethyl)-amide were treated with 1.47 g (5.81 mmol) of iodine to give 1.21 g of the title compound after recrystallization from isopropanol, mp 163°-165° C.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1.C1COCC[NH]1 | null | null | null | null | O=C(NCCN1CCOCC1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCN1CCOCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-156358fb63ab4966938ac93b299a8521 | O=C(NCCc1ccccc1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccc1 | C(CC1=CC=CC=C1)NC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S.II>>C(CC1=CC=CC=C1)N1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23]... | O=C(NCCc1ccccc1)c1cnc(-c2ccccc2)nc1S | O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 71.5 | [{"value": 71.5, "product": "C(CC1=CC=CC=C1)N1SC2=NC(=NC=C2C1=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 2.0 g (5.96 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid phenethyl-amide were treated with 1.66 g (6.56 mmol) of iodine to give 1.42 g of the title compound after recrystallization from isopropanol, mp 144°-147° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1.c1ccccc1 | null | null | null | null | O=C(NCCc1ccccc1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9ccc055e75654930ad54bd09e669b039 | O=C(NCc1ccccn1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccn1 | N1=C(C=CC=C1)CNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S.II>>C1(=CC=CC=C1)C1=NC=C2C(=N1)SN(C2=O)CC2=NC=CC=C2 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1 | O=C(NCc1ccccn1)c1cnc(-c2ccccc2)nc1S | O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccn1 | [#7;a:1]:[c:2]-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[SH;D1;+0:13]>>[#7;a:1]:[c:2]-[C:3]-[n;H0;D3;+0:4]1:[s;H0;D2;+0:13]:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c:7]:2:[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 81.6 | [{"value": 81.6, "product": "C1(=CC=CC=C1)C1=NC=C2C(=N1)SN(C2=O)CC2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 2.0 g (6.20 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid (pyridin-2-ylmethyl)-amide were treated with 1.73 g (6.82 mmol) of iodine to give 1.62 g of the title compound after recrystallization from isopropanol, mp 154°-156° C.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1.c1ccncc1 | null | null | null | null | O=C(NCc1ccccn1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1Cc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e975da98711c4fb78288d40e04fa9597 | O=C(NCCc1ccccn1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccn1 | N1=C(C=CC=C1)CCNC(=O)C=1C(=NC(=NC1)C1=CC=CC=C1)S.II>>C1(=CC=CC=C1)C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][... | O=C(NCCc1ccccn1)c1cnc(-c2ccccc2)nc1S | O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccn1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 91.3 | [{"value": 91.3, "product": "C1(=CC=CC=C1)C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 14.0 g (41.6 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid (2-pyridin-2-yl-ethyl)-amide were treated with 10.6 g (41.7 mmol) of iodine to give 12.7 g of the title compound after recrystallization from ethanol, mp 132°-133° C.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1.c1ccncc1 | null | null | null | null | O=C(NCCc1ccccn1)c1cnc(-c2ccccc2)nc1S>>O=c1c2cnc(-c3ccccc3)nc2sn1CCc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5f6858b110b847e7ba5291b91729d48c | O=C(NCCc1ccccn1)c1cnc(N2CCCCC2)nc1S>>O=c1c2cnc(N3CCCCC3)nc2sn1CCc1ccccn1 | N1=C(C=CC=C1)CCNC(=O)C=1C(=NC(=NC1)N1CCCCC1)S.II>>N1(CCCCC1)C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6]([N:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22]... | O=C(NCCc1ccccn1)c1cnc(N2CCCCC2)nc1S | O=c1c2cnc(N3CCCCC3)nc2sn1CCc1ccccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(N3CCCCC3)nc2sn1CCc1ccccn1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 65.2 | [{"value": 65.2, "product": "N1(CCCCC1)C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 33.0 g (96.2 mmol) of 4-mercapto-2-piperidin-1-yl-pyrimidine-5-carboxylic acid (2-pyridin-2-yl-ethyl)-amide were treated with 24.4 g (96.1 mmol) of iodine to give 21.4 g of the title compound after recrystallization from aqueous ethanol, mp 109°-110° C.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.C1CC[NH]CC1.c1ccncc1 | null | null | null | null | O=C(NCCc1ccccn1)c1cnc(N2CCCCC2)nc1S>>O=c1c2cnc(N3CCCCC3)nc2sn1CCc1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a80f1938cee54d1f95b65dadd5c69df2 | NC(=O)c1cnc(N2CCCCC2)nc1S>>O=c1[nH]sc2nc(N3CCCCC3)ncc12 | SC1=NC(=NC=C1C(=O)N)N1CCCCC1.II>>N1(CCCCC1)C1=NC=C2C(=N1)SNC2=O | [O:1]=[C:2]([NH2:3])[c:16]1[c:5]([SH:4])[n:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[n:14][cH:15]1>>[O:1]=[c:2]1[nH:3][s:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[n:14][cH:15][c:16]12 | NC(=O)c1cnc(N2CCCCC2)nc1S | O=c1[nH]sc2nc(N3CCCCC3)ncc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2b243efd5a58cc7d731ba0d6fa9ecf63de0734418474b3dbffe96158346ff9ac | 6b0db660e0291978d674b73a7c89887755b1df41fe1fdc91387cf4ba3ba27df4 | O=c1[nH]sc2nc(N3CCCCC3)ncc12 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[SH;D1;+0:10]>>[O;D1;H0:3]=[c;H0;D3;+0:2]1:[nH;D2;+0:1]:[s;H0;D2;+0:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:[c:4]:2:1 | 69.6 | [{"value": 69.6, "product": "N1(CCCCC1)C1=NC=C2C(=N1)SNC2=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 20.8 g (87.4 mmol) of 4-mercapto-2-piperidin-1-yl-pyrimidine-5-carboxylic acid amide were treated with 22.2 g (87.4 mmol) of iodine to give 14.37 g of the title compound after recrystallization from dimethylformamide, mp 268°-269° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.C1CC[NH]CC1 | null | null | null | null | NC(=O)c1cnc(N2CCCCC2)nc1S>>O=c1[nH]sc2nc(N3CCCCC3)ncc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94a6104e52474749a6d636e419fc633b | O=C(NCCN1CCCCC1)c1cnc(N2CCOCC2)nc1S>>O=c1c2cnc(N3CCOCC3)nc2sn1CCN1CCCCC1 | N1(CCCCC1)CCNC(=O)C=1C(=NC(=NC1)N1CCOCC1)S.II>>N1(CCOCC1)C1=NC=C2C(=N1)SN(C2=O)CCN2CCCCC2 | [O:1]=[C:2]([c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[n:13][c:14]1[SH:15])[NH:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1>>[O:1]=[c:2]1[c:3]2[cH:4][n:5][c:6]([N:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[n:13][c:14]2[s:15][n:16]1[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH... | O=C(NCCN1CCCCC1)c1cnc(N2CCOCC2)nc1S | O=c1c2cnc(N3CCOCC3)nc2sn1CCN1CCCCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cnc(N3CCOCC3)nc2sn1CCN1CCCCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 50.3 | [{"value": 50.3, "product": "N1(CCOCC1)C1=NC=C2C(=N1)SN(C2=O)CCN2CCCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 5.2 g (14.8 mmol) of 4-mercapto-2-morpholin-4-yl-pyrimidine-5-carboxylic acid (2-piperidin-1-yl-ethyl)-amide were treated with 3.81 g (15.0 mmol) of iodine to give 2.6 g of the title compound after recrystallization from aqueous isopropanol, mp 98°-100° C.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.C1COCC[NH]1.C1CC[NH]CC1 | null | null | null | null | O=C(NCCN1CCCCC1)c1cnc(N2CCOCC2)nc1S>>O=c1c2cnc(N3CCOCC3)nc2sn1CCN1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69d151f088ba4ac0ba3a99cb32f5d727 | CN(C)c1ncc(C(=O)NCCc2ccccn2)c(S)n1>>CN(C)c1ncc2c(=O)n(CCc3ccccn3)sc2n1 | N1=C(C=CC=C1)CCNC(=O)C=1C(=NC(=NC1)N(C)C)S.II>>CN(C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2)C | [CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]([C:8](=[O:9])[NH:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[c:20]([SH:19])[n:21]1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]2[c:8](=[O:9])[n:10]([CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][n:18]3)[s:19][c:20]2[n:21]1 | CN(C)c1ncc(C(=O)NCCc2ccccn2)c(S)n1 | CN(C)c1ncc2c(=O)n(CCc3ccccn3)sc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cncnc2sn1CCc1ccccn1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 56.3 | [{"value": 56.3, "product": "CN(C1=NC=C2C(=N1)SN(C2=O)CCC2=NC=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 7.5 g (24.8 mmol) of 2-dimethylamino-4-mercapto-pyrimidine-5-carboxylic acid (2-pyridin-2-yl-ethyl)-amide were treated with 6.4 g (25.2 mmol) of iodine to give 4.21 g of the title compound after recrystallization from isopropanol, mp 134°-136° C.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccncc1 | null | null | null | null | CN(C)c1ncc(C(=O)NCCc2ccccn2)c(S)n1>>CN(C)c1ncc2c(=O)n(CCc3ccccn3)sc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02fbceb3836e48fcbd825773c2f9dfe9 | CN(C)c1ncc(C(=O)NCCN2CCCCC2)c(S)n1>>CN(C)c1ncc2c(=O)n(CCN3CCCCC3)sc2n1 | N1(CCCCC1)CCNC(=O)C=1C(=NC(=NC1)N(C)C)S.II>>CN(C1=NC=C2C(=N1)SN(C2=O)CCN2CCCCC2)C | [CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]([C:8](=[O:9])[NH:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[c:20]([SH:19])[n:21]1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]2[c:8](=[O:9])[n:10]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[s:19][c:20]2[n:21]1 | CN(C)c1ncc(C(=O)NCCN2CCCCC2)c(S)n1 | CN(C)c1ncc2c(=O)n(CCN3CCCCC3)sc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 84d493baceb442fb301ce0e11443d8e4936de615e1a03601e93a225a211a6c68 | 8f50334308725dd70cedd05b954818305340e80580bc2a806e37bb42f552bc62 | O=c1c2cncnc2sn1CCN1CCCCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[SH;D1;+0:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[s;H0;D2;+0:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:2:[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 85.9 | [{"value": 85.9, "product": "CN(C1=NC=C2C(=N1)SN(C2=O)CCN2CCCCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example 20, 6.2 g (20.1 mmol) of 2-dimethylamino-4-mercapto-pyrimidine-5-carboxylic acid (2-piperidin-1-yl-ethyl)-amide were treated with 5.08 g (20.0 mmol) of iodine to give 5.31 g of the title compound after recrystallization from ethyl acetate, mp 128°-129° C.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic thiol | null | c1cncnc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.C1CC[NH]CC1 | null | null | null | null | CN(C)c1ncc(C(=O)NCCN2CCCCC2)c(S)n1>>CN(C)c1ncc2c(=O)n(CCN3CCCCC3)sc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a13f316069a49f782b0a73c4007b4d6 | CC(C)=NO.COC(=O)C12CCCN1CCC2>>Cc1cc(C23CCCN2CCC3)on1 | COC(=O)C12CCCN2CCC1.CC(C)=NO.C(CCC)[Li]>>CC1=NOC(=C1)C12CCCN2CCC1 | [CH3:1][C:2]([CH3:3])=[N:14][OH:13].CO[C:4](=O)[C:5]12[CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH2:12]2>>[CH3:1][c:2]1[cH:3][c:4]([C:5]23[CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12]3)[o:13][n:14]1 | CC(C)=NO.COC(=O)C12CCCN1CCC2 | Cc1cc(C23CCCN2CCC3)on1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 165c42ecc4e9a86073de2acc4f780dc1e165e79d7d4cbb91db7ccb9ad870fea7 | b8f4c4009b37b1a89bb4a410e1a9199087d89cbf0a469ca338bf9434c4096abc | c1cc(C23CCCN2CCC3)on1 | C-O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])(-[C:4])-[#7:5](-[C:6])-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[CH3;D1;+0:10])=[N;H0;D2;+0:11]-[OH;D1;+0:12]>>[C:6]-[#7:5](-[C:7])-[C:2](-[c;H0;D3;+0:1]1:[cH;D2;+0:10]:[c;H0;D3;+0:9](-[C;D1;H3:8]):[n;H0;D2;+0:11]:[o;H0;D2;+0:12]:1)(-[C:3])-[C:4] | 11.2 | [{"value": 11.0, "product": "CC1=NOC(=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.2, "product": "CC1=NOC(=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-(Methoxycarbonyl)-hexahydro-1H-pyrrolizine (from step 1d, 1.56 g, 9.22 mmol), acetone oxime (1.45 g, 19.8 mmol) and n-butyllithium (2.5M in hexane, 16 mL, 39.6 mmol) were combined in a similar fashion as that outlined by J. Saunders et at., J. Med. Chem. 1990, 33: 1128. The crude material was chromatographed (silica ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Oxime | null | null | c1cnoc1 | c1cnoc1.C1CC2CCCN2C1 | HO- | null | null | null | CC(C)=NO.COC(=O)C12CCCN1CCC2>>Cc1cc(C23CCCN2CCC3)on1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8ec9bcee30b4b59a1991ab13c706c61 | Cl>>Cl | Cl.CC1=NOC(=C1)C12CCCN2CCC1>>Cl.CC1=NOC(=C1)C12CCCN2CCC1 | [ClH:15]>>[ClH:15] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 0 | CELSIUS | null | null | 7a-(3-methyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine (from step 1e, 189 mg, 0.98 mmol) was immersed in Et2O (7 mL) and cooled to 0° C. A solution of Et2O saturated with HCl (g) was added to the reaction vessel dropwise with stirring. The solvent was carefully removed and the remaining white solid triturated with Et2O (2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | 0 | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a0b85df694b48eb9e5baebab0e7dade | c1cncc(C23CCCN2CCC3)c1>>c1cncc(C23CCCN2CCC3)c1 | N1=CC(=CC=C1)C12CCCN2CCC1.CCOCC.Cl>>Cl.N1=CC(=CC=C1)C12CCCN2CCC1 | [cH:2]1[cH:3][n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15]1>>[cH:2]1[cH:3][n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15]1 | c1cncc(C23CCCN2CCC3)c1 | c1cncc(C23CCCN2CCC3)c1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 81 | [{"value": 81.0, "product": "Cl.N1=CC(=CC=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 3a, 125 mg, 0.66 mmol) was dissolved in CH2Cl2 (15 mL) and Et2O saturated with HCl (g) was added dropwise. The solvent was removed, and the remaining solid was triturated with CH2Cl2 (2×) to afford a hygroscopic yellow solid (140 mg, 81%). MS (CI/NH3) m/e: 189 (M+H)+... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | C(Cl)Cl | null | null | c1cncc(C23CCCN2CCC3)c1>C(Cl)Cl>c1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-56ddd89618f84964b94d7784a2774ae5 | Brc1cnc2ccccc2c1.C1CC2=[N+](C1)CCC2>>c1ccc2ncc(C34CCCN3CCC4)cc2c1 | Cl.[Li]CCCC.BrC=1C=NC2=CC=CC=C2C1.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>N1=CC(=CC2=CC=CC=C12)C12CCCN2CCC1 | Br[c:7]1[cH:6][n:5][c:4]2[cH:3][cH:2][cH:1][cH:18][c:17]2[cH:16]1.[C:8]12=[N+:12]([CH2:11][CH2:10][CH2:9]1)[CH2:13][CH2:14][CH2:15]2>>[cH:1]1[cH:2][cH:3][c:4]2[n:5][cH:6][c:7]([C:8]34[CH2:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH2:15]4)[cH:16][c:17]2[cH:18]1 | Brc1cnc2ccccc2c1.C1CC2=[N+](C1)CCC2 | c1ccc2ncc(C34CCCN3CCC4)cc2c1 | null | null | C1CCOC1.CCOC(=O)C | Functional Group Interconversion | OtherReaction | d081eb00c0c32ed930f1ba0aa9086d7aa7ea50889798160c9d43b81f9c26861b | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1ccc2ncc(C34CCCN3CCC4)cc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]1-[C:8]-[N+;H0;D3:9]2=[C;H0;D3;+0:10](-[C:11]-[C:12]-[C:13]-2)-[C:14]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:9]-2-[C:8]-[C:7]-[C:14]-3):[c:6]:1 | 48.5 | [{"value": 46.0, "product": "N1=CC(=CC2=CC=CC=C12)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "N1=CC(=CC2=CC=CC=C12)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -100 | CELSIUS | 2 | HOUR | A solution of 2.5M nBuLi (1.2 mL, 2.8 mmol) in hexanes was added to 3-bromoquinoline (386 μL, 2.8 mmol) in THF (10 mL) at -100° C. followed immediately by 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (200 mg, 0.9 mmol). The reaction mixture was allowed to stir for 2 hours at -100° C. and then 2N HCl was added at 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | c1ccc2ncccc2c1.C1CC2=[N+](C1)CCC2 | c1ccc2ncccc2c1.C1CC2CCCN2C1 | c1ccc2ncccc2c1.C1CC2CCCN2C1 | Br- | C1CCOC1.CCOC(=O)C | -100 | 2 | Brc1cnc2ccccc2c1.C1CC2=[N+](C1)CCC2>C1CCOC1.CCOC(=O)C>c1ccc2ncc(C34CCCN3CCC4)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a738c3035f24486b85c6366c76778e5e | Clc1ccc(C23CCCN2CCC3)cn1>>Clc1ccc(C23CCCN2CCC3)cn1 | Cl.ClC1=CC=C(C=N1)C12CCCN2CCC1>>Cl.ClC1=CC=C(C=N1)C12CCCN2CCC1 | [Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][n:16]1>>[Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][n:16]1 | Clc1ccc(C23CCCN2CCC3)cn1 | Clc1ccc(C23CCCN2CCC3)cn1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 155.2 | [{"value": 78.0, "product": "Cl.ClC1=CC=C(C=N1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 155.2, "product": "Cl.ClC1=CC=C(C=N1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(6-Chloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 5a, 210 mg, 0.94 mmol) was dissolved in Et2O (8 mL), and Et2O saturated with HCl (g) was added at ambient temperature. Solvent was then removed, and the remaining solid was recrystallized from MeOH/Et2O to afford short white needles (189 mg, 78%). mp 141°-14... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Clc1ccc(C23CCCN2CCC3)cn1>CCOCC>Clc1ccc(C23CCCN2CCC3)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d856ea1f5d4426aaad2bca65084aa0a | Fc1ncccc1C12CCCN1CCC2>>Fc1ncccc1C12CCCN1CCC2 | Cl.FC1=NC=CC=C1C12CCCN2CCC1>>Cl.FC1=NC=CC=C1C12CCCN2CCC1 | [F:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9]12[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]2>>[F:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9]12[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]2 | Fc1ncccc1C12CCCN1CCC2 | Fc1ncccc1C12CCCN1CCC2 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 77 | [{"value": 77.0, "product": "Cl.FC1=NC=CC=C1C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(2-fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 6a, 59 mg, 0.3 mmol) was dissolved in Et2O (8 mL), and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was recrystallized from MeOH/Et2O to afford a white solid (54 mg, 77%). mp 185°-186° C. MS (CI/NH3) m/e: 207 (M+H)+. 1H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Fc1ncccc1C12CCCN1CCC2>CCOCC>Fc1ncccc1C12CCCN1CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-092e97d5277f41ea9797e8d42117af0e | Clc1ncccc1C12CCCN1CCC2>>Clc1ncccc1C12CCCN1CCC2 | ClC1=NC=CC=C1C12CCCN2CCC1.Cl>>Cl.ClC1=NC=CC=C1C12CCCN2CCC1 | [Cl:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9]12[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]2>>[Cl:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9]12[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]2 | Clc1ncccc1C12CCCN1CCC2 | Clc1ncccc1C12CCCN1CCC2 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | null | [] | null | null | null | null | 7a-(2-Chloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (21 mg, 0.1 mmol) was dissolved in Et2O (6 mL), and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was triturated (3×) with Et2O to afford a yellow solid (26 mg, quant). mp 186°-188° C. MS (CI/NH3) m/e: 223 (M+H)+. 1H NMR D2O, 300 M... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Clc1ncccc1C12CCCN1CCC2>CCOCC>Clc1ncccc1C12CCCN1CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e0688aadb234b04b09dab3cc2fb6604 | C1CC2=[N+](C1)CCC2.Clc1cc(I)cnc1Cl>>Clc1cc(C23CCCN2CCC3)cnc1Cl | Cl.[Li]C(C)(C)C.ClC1=NC=C(C=C1Cl)I.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>ClC=1C=C(C=NC1Cl)C12CCCN2CCC1 | [C:5]12=[N+:9]([CH2:8][CH2:7][CH2:6]1)[CH2:10][CH2:11][CH2:12]2.I[c:4]1[cH:3][c:2]([Cl:1])[c:15]([Cl:16])[n:14][cH:13]1>>[Cl:1][c:2]1[cH:3][c:4]([C:5]23[CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12]3)[cH:13][n:14][c:15]1[Cl:16] | C1CC2=[N+](C1)CCC2.Clc1cc(I)cnc1Cl | Clc1cc(C23CCCN2CCC3)cnc1Cl | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:9]-[C:8]-[C:7]-[N;H0;D3;+0:11]-2-[C:12]-[C:13]-[C:14]-3):[c:6]:[c:5]:[c:4]:1 | 54.3 | [{"value": 54.0, "product": "ClC=1C=C(C=NC1Cl)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "ClC=1C=C(C=NC1Cl)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2 | MINUTE | A solution of 1.7M tBuLi (4.7 mL, 8.0 mmol) in pentane was added to 2,3-dichloro-5-iodopyridine (from step 8a, 1.0 g, 3.65 mmol) in Et2O (15 mL) precooled to -100° C. After stirring for 2 minutes, 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (1.5 g, 7.3 mmol) was added, and the reaction mixture was allowed to stir fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | I- | CCCCC.CCOCC | -20 | 0.033333 | C1CC2=[N+](C1)CCC2.Clc1cc(I)cnc1Cl>CCCCC.CCOCC>Clc1cc(C23CCCN2CCC3)cnc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ea4bec3ef5714df3ac618bb631d33e9f | Clc1cc(C23CCCN2CCC3)cnc1Cl>>Clc1cc(C23CCCN2CCC3)cnc1Cl | Cl.ClC=1C=C(C=NC1Cl)C12CCCN2CCC1>>Cl.ClC=1C=C(C=NC1Cl)C12CCCN2CCC1 | [Cl:2][c:3]1[cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][n:15][c:16]1[Cl:17]>>[Cl:2][c:3]1[cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][n:15][c:16]1[Cl:17] | Clc1cc(C23CCCN2CCC3)cnc1Cl | Clc1cc(C23CCCN2CCC3)cnc1Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 151.2 | [{"value": 75.0, "product": "Cl.ClC=1C=C(C=NC1Cl)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 151.2, "product": "Cl.ClC=1C=C(C=NC1Cl)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(5,6-dichloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 8b, 128 mg, 0.50 mmol) was slurried in Et2O (8 mL), and Et2O saturated with HCl (g) added. The solvent was removed, and the solid was recrystallized from MeOH/Et2O to afford a white solid (111 mg, 75%). mp 215°-217° C. MS (CI/NH3) m/e: 257 (M+H)+. 1H NMR... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Clc1cc(C23CCCN2CCC3)cnc1Cl>CCOCC>Clc1cc(C23CCCN2CCC3)cnc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-00d6327228e6450289cc61943cc4bea5 | Brc1cncnc1.C1CC2=[N+](C1)CCC2>>c1ncc(C23CCCN2CCC3)cn1 | Cl.[Li]C(C)(C)C.BrC=1C=NC=NC1.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>N1=CN=CC(=C1)C12CCCN2CCC1 | Br[c:4]1[cH:3][n:2][cH:1][n:14][cH:13]1.[C:5]12=[N+:9]([CH2:8][CH2:7][CH2:6]1)[CH2:10][CH2:11][CH2:12]2>>[cH:1]1[n:2][cH:3][c:4]([C:5]23[CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12]3)[cH:13][n:14]1 | Brc1cncnc1.C1CC2=[N+](C1)CCC2 | c1ncc(C23CCCN2CCC3)cn1 | null | null | CCCCC.CCOCC.C1CCOC1.CCOCC | Functional Group Interconversion | OtherReaction | c0d44c5278a39501c3cd78edf0b0d4543f902aa8d82206524b4ad2ed2c40732b | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1ncc(C23CCCN2CCC3)cn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:9]-[C:8]-[C:7]-[N;H0;D3;+0:11]-2-[C:12]-[C:13]-[C:14]-3):[c:6]:[#7;a:5]:[c:4]:1 | 18 | [{"value": 18.0, "product": "N1=CN=CC(=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.6, "product": "N1=CN=CC(=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | A solution of 1.7M tBuLi (1.6 mL, 2.6 mmol) in pentane was added to 5-bromopyrimidine (190 mg, 1.2 mmol) in Et2O:THF (1:1, 12 mL) at -100° C. After stirring for 10 minutes, 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (500 mg, 2.4 mmol) was added to the reaction slurry, and stirring was continued for 30 minutes. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | c1cncnc1.C1CC2=[N+](C1)CCC2 | c1cncnc1.C1CC2CCCN2C1 | c1cncnc1.C1CC2CCCN2C1 | Br- | CCCCC.CCOCC.C1CCOC1.CCOCC | 0 | 0.166667 | Brc1cncnc1.C1CC2=[N+](C1)CCC2>CCCCC.CCOCC.C1CCOC1.CCOCC>c1ncc(C23CCCN2CCC3)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d55b4270d2e84321a49a35cd7ef17438 | C1CC2=[N+](C1)CCC2.Fc1cccc(F)n1>>Fc1ccc(C23CCCN2CCC3)c(F)n1 | Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12.[Li]CCCC.C(C)(C)NC(C)C.FC1=NC(=CC=C1)F>>FC1=NC(=CC=C1C12CCCN2CCC1)F | [C:6]12=[N+:10]([CH2:9][CH2:8][CH2:7]1)[CH2:11][CH2:12][CH2:13]2.[F:1][c:2]1[cH:3][cH:4][cH:5][c:14]([F:15])[n:16]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[c:14]([F:15])[n:16]1 | C1CC2=[N+](C1)CCC2.Fc1cccc(F)n1 | Fc1ccc(C23CCCN2CCC3)c(F)n1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2744e2374166f7e3b0005d81a2c1df8d47ee0788b4fc7944419feeb27a3619ea | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1cncc(C23CCCN2CCC3)c1 | [C:1]1-[C:2]-[C:3]-[C;H0;D3;+0:4]2=[N+;H0;D3:5]-1-[C:6]-[C:7]-[C:8]-2.[F;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[F;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:15]:1-[C;H0;D4;+0:4]12-[C:3]-[C:2]-[C:1]-[N;H0;D3;+0:5]-1-[C:6]-[C:7]-[C:8]-2 | 50.2 | [{"value": 50.0, "product": "FC1=NC(=CC=C1C12CCCN2CCC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "FC1=NC(=CC=C1C12CCCN2CCC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | A solution of 2.5M nBuLi (675 μL, 1.7 mmol) in hexanes was added to diisopropylamine (220 μL, 1.6 mmol) in THF (4.5 mL) at ambient temperature. After 10 minutes of stirring, the reaction mixture was cooled to -78° C., 2,6-difluoropyridine (145 μL, 1.6 mmol) was introduced, and stirring was continued for 1 hour at -78° ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | null | C1CCOC1 | -78 | 0.166667 | C1CC2=[N+](C1)CCC2.Fc1cccc(F)n1>C1CCOC1>Fc1ccc(C23CCCN2CCC3)c(F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c055acb214344a499e3a8c789597d987 | Fc1ccc(C23CCCN2CCC3)c(F)n1>>Fc1ccc(C23CCCN2CCC3)c(F)n1 | Cl.FC1=NC(=CC=C1C12CCCN2CCC1)F>>Cl.FC1=NC(=CC=C1C12CCCN2CCC1)F | [F:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[c:15]([F:16])[n:17]1>>[F:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[c:15]([F:16])[n:17]1 | Fc1ccc(C23CCCN2CCC3)c(F)n1 | Fc1ccc(C23CCCN2CCC3)c(F)n1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 68 | [{"value": 68.0, "product": "Cl.FC1=NC(=CC=C1C12CCCN2CCC1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of Et2O saturated with HCl (g) was added to 7a-(2,6-difluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 10a, 174 mg, 0.8 mmol) in Et2O (10 mL). The slurry was filtered, and the filter cake was washed with Et2O to afford a white solid (138 mg, 68%). mp 205°-206° C. MS (CI/NH3) m/e: 225 (M+H)+. 1H NMR D2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Fc1ccc(C23CCCN2CCC3)c(F)n1>CCOCC>Fc1ccc(C23CCCN2CCC3)c(F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c171067de28743cf9e9bdee6ad6c9574 | C1CC2=[N+](C1)CCC2.Clc1cccc(Cl)n1>>Clc1ccc(C23CCCN2CCC3)c(Cl)n1 | Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12.[Li]CCCC.C(C)(C)NC(C)C.Cl.ClC1=NC(=CC=C1)Cl>>ClC1=NC(=CC=C1C12CCCN2CCC1)Cl | [C:6]12=[N+:10]([CH2:9][CH2:8][CH2:7]1)[CH2:11][CH2:12][CH2:13]2.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:14]([Cl:15])[n:16]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[c:14]([Cl:15])[n:16]1 | C1CC2=[N+](C1)CCC2.Clc1cccc(Cl)n1 | Clc1ccc(C23CCCN2CCC3)c(Cl)n1 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | OtherReaction | 2744e2374166f7e3b0005d81a2c1df8d47ee0788b4fc7944419feeb27a3619ea | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1cncc(C23CCCN2CCC3)c1 | [C:1]1-[C:2]-[C:3]-[C;H0;D3;+0:4]2=[N+;H0;D3:5]-1-[C:6]-[C:7]-[C:8]-2.[Cl;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[Cl;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:15]:1-[C;H0;D4;+0:4]12-[C:3]-[C:2]-[C:1]-[N;H0;D3;+0:5]-1-[C:6]-[C:7]-[C:8]-2 | 17.2 | [{"value": 17.0, "product": "ClC1=NC(=CC=C1C12CCCN2CCC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.2, "product": "ClC1=NC(=CC=C1C12CCCN2CCC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | A solution of 2.5M nBuLi (675 μL, 1.7 mmol) in hexanes was added to diisopropylamine (220 μL, 1.7 mmol) in THF (4.5 mL) at ambient temperature. After 10 minutes of stirring, the reaction mixture was cooled to -78° C., 2,6-dichloropyridine (237 μL, 1.60 mmol) was added neat, and stirring was continued for 1 hour at -78°... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | null | C1CCOC1.CCOC(=O)C | -78 | 0.166667 | C1CC2=[N+](C1)CCC2.Clc1cccc(Cl)n1>C1CCOC1.CCOC(=O)C>Clc1ccc(C23CCCN2CCC3)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6a4ede5955b04d74b49bc94baae656f9 | Clc1ccc(C23CCCN2CCC3)c(Cl)n1>>Clc1ccc(C23CCCN2CCC3)c(Cl)n1 | Cl.ClC1=NC(=CC=C1C12CCCN2CCC1)Cl>>Cl.ClC1=NC(=CC=C1C12CCCN2CCC1)Cl | [Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[c:15]([Cl:16])[n:17]1>>[Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[c:15]([Cl:16])[n:17]1 | Clc1ccc(C23CCCN2CCC3)c(Cl)n1 | Clc1ccc(C23CCCN2CCC3)c(Cl)n1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 101 | [{"value": 101.0, "product": "Cl.ClC1=NC(=CC=C1C12CCCN2CCC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(2,6-dichloro-3-pyridinyl)-hexahydro-1H-pyrrolizine (from step 11a, 62 mg, 0.24 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was triturated with Et2O to give a white solid (35.6 mg). mp 212°-214° C. 1H NMR D2O, 300 MHz) δ2.02-2.18 (m, 2H), 2.28-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Clc1ccc(C23CCCN2CCC3)c(Cl)n1>CCOCC>Clc1ccc(C23CCCN2CCC3)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c3b0e2987bf6463288457f21739f34ea | O=[N+]([O-])c1ccc(Cl)nc1.[F-]>>O=[N+]([O-])c1ccc(F)nc1 | ClC1=NC=C(C=C1)[N+](=O)[O-].[F-].[K+].C(C)#N>>FC1=NC=C(C=C1)[N+](=O)[O-] | Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:10][n:9]1.[F-:8]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[n:9][cH:10]1 | O=[N+]([O-])c1ccc(Cl)nc1.[F-] | O=[N+]([O-])c1ccc(F)nc1 | null | [P+](C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Br-] | CCOCC | Functional Group Interconversion | OtherReaction | c5ee9801df82c43b4536f3b3bcf4d5fc4f4f88678c4231db54140fcd8ba626c5 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[F-;H0;D0:6]>>[F;H0;D1;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 2-Chloro-5-nitropyridine (100 g, 0.656 mol, Aldrich), KF (84.1 g, 1.448 mol), Ph4PBr (95.3 g, 0.227 mol) and acetonitrile (1.5 L) were combined and heated at reflux until no starting material remained. The volume was reduced to 750 mL, and the mixture was diluted with 2 L of ether, filtered and concentrated. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | [P+](C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Br-].CCOCC | null | null | O=[N+]([O-])c1ccc(Cl)nc1.[F-]>[P+](C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Br-].CCOCC>O=[N+]([O-])c1ccc(F)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d3051c784ee74eefb4384c960765bcf2 | C1CC2=[N+](C1)CCC2.Fc1ccc(I)cn1>>Fc1ccc(C23CCCN2CCC3)cn1 | FC1=NC=C(C=C1)I.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>FC1=CC=C(C=N1)C12CCCN2CCC1 | [C:6]12=[N+:10]([CH2:9][CH2:8][CH2:7]1)[CH2:11][CH2:12][CH2:13]2.I[c:5]1[cH:4][cH:3][c:2]([F:1])[n:15][cH:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][n:15]1 | C1CC2=[N+](C1)CCC2.Fc1ccc(I)cn1 | Fc1ccc(C23CCCN2CCC3)cn1 | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:9]-[C:8]-[C:7]-[N;H0;D3;+0:11]-2-[C:12]-[C:13]-[C:14]-3):[c:6]:[c:5]:[c:4]:1 | 40.4 | [{"value": 40.0, "product": "FC1=CC=C(C=N1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.4, "product": "FC1=CC=C(C=N1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | MINUTE | 2-Fluoro-5-iodopyridine (200 μL, 0.90 mmol) was dissolved in Et2O and cooled to -78° C. A solution of 2.5M t-BuLi (1.2 mL, 1.98 mmol) in pentane was added, and the reaction was stirred for 2 minutes. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (375 mg, 1.80 mmol) was added, and the reaction mixture was allowed to st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | I- | CCCCC.CCOCC | -78 | 0.033333 | C1CC2=[N+](C1)CCC2.Fc1ccc(I)cn1>CCCCC.CCOCC>Fc1ccc(C23CCCN2CCC3)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9f158cd252c4dcaaab2ab046391e1e9 | Fc1cncc(C23CCCN2CCC3)c1>>Fc1cncc(C23CCCN2CCC3)c1 | Cl.FC=1C=C(C=NC1)C12CCCN2CCC1>>Cl.FC=1C=C(C=NC1)C12CCCN2CCC1 | [F:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]23[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15]3)[cH:16]1>>[F:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]23[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15]3)[cH:16]1 | Fc1cncc(C23CCCN2CCC3)c1 | Fc1cncc(C23CCCN2CCC3)c1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 69 | [{"value": 69.0, "product": "Cl.FC=1C=C(C=NC1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(5-fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine (62 mg, 0.24 mmol, from step 12d) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was triturated with to give a white solid (57.1 mg, 69%). mp 168°-169° C. 1H NMR D2O, 300 MHz) 67 2.13-2.50 (m, 6H), 2.58-2.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Fc1cncc(C23CCCN2CCC3)c1>CCOCC>Fc1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eafa3d7b107148f580724adaf23e414c | [CH+]1CCN2CCCC12>>C#CC12CCCN1CCC2 | Cl(=O)(=O)(=O)[O-].[CH+]1CCN2CCCC12.C(#C)[Mg]Br.[OH-].[Na+]>>C(#C)C12CCCN2CCC1 | [CH:3]12[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH+:10]2>>[CH:1]#[C:2][C:3]12[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10]2 | [CH+]1CCN2CCCC12 | C#CC12CCCN1CCC2 | null | null | [Cl-].[Na+].O.O.C1CCOC1 | Functional Group Interconversion | OtherReaction | b404c07d8cc44b859c403c8f07b0facb1ff137e72068444aa4bfd36e8160f6a7 | c4460923656748296c1ad8c3927d77d5a4d016526df2201ea5f91f81ef0c2060 | C1CC2CCCN2C1 | [C:1]1-[C:2]-[C:3]-[#7:4]2-[C:5]-[C:6]-[CH+;D2:7]-[CH;D3;+0:8]-1-2>>[C;D1;H1:9]#[C:10]-[C;H0;D4;+0:8]12-[C:1]-[C:2]-[C:3]-[#7:4]-1-[C:5]-[C:6]-[CH2;D2;+0:7]-2 | 71.3 | [{"value": 71.0, "product": "C(#C)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "C(#C)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | 1,2,3,5,6,7-Hexahydropyrrolizinylium perchlorate (1.0 g, 4.8 mmol) was added to a solution of 0.5M ethynylmagnesium bromide (29 mL, 14.3 mmol) in THF at room temperature. The reaction mixture was allowed to stir for 45 minutes, and 15% NaOH solution was added. The slurry was diluted with brine:water (1:1) and extracted... | 10.6084/m9.figshare.5104873.v1 | null | null | Alkyne | [CH+]1CCN2CCCC12 | C1CC2CCCN2C1 | C1CC2CCCN2C1 | null | [Cl-].[Na+].O.O.C1CCOC1 | null | 0.75 | [CH+]1CCN2CCCC12>[Cl-].[Na+].O.O.C1CCOC1>C#CC12CCCN1CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8757226fe4fa4085a41ed03eefc15d62 | C#CC12CCCN1CCC2.CCC[N+](=O)[O-]>>CCc1cc(C23CCCN2CCC3)on1 | [N+](=O)([O-])CCC.C1(=CC=CC=C1)N=C=O.C(#C)C12CCCN2CCC1>>C(C)C1=NOC(=C1)C12CCCN2CCC1 | [CH:4]#[C:5][C:6]12[CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH2:13]2.O=[N+:15]([CH2:3][CH2:2][CH3:1])[O-:14]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[o:14][n:15]1 | C#CC12CCCN1CCC2.CCC[N+](=O)[O-] | CCc1cc(C23CCCN2CCC3)on1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 85ed1de7d01eb5a1475dc4727791ddb53417125ab3beeb28225b6652ffdb9c73 | 7108617e87a7921f39c453b93eea7dbd08d46222031ed4533f4e27c039907e0d | c1cc(C23CCCN2CCC3)on1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[CH2;D2;+0:3]-[C:4]-[C;D1;H3:5].[C:6]-[#7:7](-[C:8])-[C:9](-[C;H0;D2;+0:10]#[CH;D1;+0:11])(-[C:12])-[C:13]>>[C:6]-[#7:7](-[C:8])-[C:9](-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[n;H0;D2;+0:1]:[o;H0;D2;+0:2]:1)(-[C:12])-[C:13] | 50.1 | [{"value": 50.0, "product": "C(C)C1=NOC(=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "C(C)C1=NOC(=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Nitropropane (0.475 mL, 5.29 mmol) and phenylisocyanate (1.0 mL, 9.5 mmol) were dissolved in benzene (10 mL) and added to a flask containing 7a-ethynyl-hexahydro-1H-pyrrolizine (358 mg, 2.65 mmol, from step 13a). The solution was stirred at ambient temperature for 1 hour and at reflux for 5 hours. The mixture was coole... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Alkyne | null | null | c1cnoc1 | c1cnoc1.C1CC2CCCN2C1 | HO- | C1=CC=CC=C1 | null | 1 | C#CC12CCCN1CCC2.CCC[N+](=O)[O-]>C1=CC=CC=C1>CCc1cc(C23CCCN2CCC3)on1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6a17fe06ca0a4559821af5872f757c00 | Cl>>Cl | Cl.C(C)C1=NOC(=C1)C12CCCN2CCC1>>Cl.C(C)C1=NOC(=C1)C12CCCN2CCC1 | [ClH:16]>>[ClH:16] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 7a-(3-ethyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine (265 mg, 1.30 mmol, from step 13b) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was recrystallized from methanol/ethanol to afford the title compound as a white solid: mp 139°-140° C.; 1H NMR D2O, 300 MH... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbc0aabc6c144848bb5aa35cb5124c07 | C#CC12CCCN1CCC2.CCCC[N+](=O)[O-]>>CCCc1cc(C23CCCN2CCC3)on1 | [N+](=O)([O-])CCCC.C1(=CC=CC=C1)N=C=O.C(#C)C12CCCN2CCC1>>C(CC)C1=NOC(=C1)C12CCCN2CCC1 | [CH:5]#[C:6][C:7]12[CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14]2.O=[N+:16]([CH2:4][CH2:3][CH2:2][CH3:1])[O-:15]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[o:15][n:16]1 | C#CC12CCCN1CCC2.CCCC[N+](=O)[O-] | CCCc1cc(C23CCCN2CCC3)on1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 85ed1de7d01eb5a1475dc4727791ddb53417125ab3beeb28225b6652ffdb9c73 | 7108617e87a7921f39c453b93eea7dbd08d46222031ed4533f4e27c039907e0d | c1cc(C23CCCN2CCC3)on1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[CH2;D2;+0:3]-[C:4]-[C:5].[C:6]-[#7:7](-[C:8])-[C:9](-[C;H0;D2;+0:10]#[CH;D1;+0:11])(-[C:12])-[C:13]>>[C:6]-[#7:7](-[C:8])-[C:9](-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c;H0;D3;+0:3](-[C:4]-[C:5]):[n;H0;D2;+0:1]:[o;H0;D2;+0:2]:1)(-[C:12])-[C:13] | 53.4 | [{"value": 53.0, "product": "C(CC)C1=NOC(=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "C(CC)C1=NOC(=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Nitrobutane (0.705 mL, 6.66 mmol) and phenylisocyanate (1.50 mL, 13.3 mmol) were dissolved in benzene (13.5 mL) and added to a flask containing 7a-ethynyl-hexahydro-1H-pyrrolizine (450 mg, 3.33 mmol, from step 13a). The solution was stirred at ambient temperature for 1 hour and at reflux for 5 hours. The mixture was co... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Alkyne | null | null | c1cnoc1 | c1cnoc1.C1CC2CCCN2C1 | HO- | C1=CC=CC=C1 | null | 1 | C#CC12CCCN1CCC2.CCCC[N+](=O)[O-]>C1=CC=CC=C1>CCCc1cc(C23CCCN2CCC3)on1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-402839b675474c22a8bd5c354e9adae4 | Cl>>Cl | Cl.C(CC)C1=NOC(=C1)C12CCCN2CCC1>>Cl.C(CC)C1=NOC(=C1)C12CCCN2CCC1 | [ClH:17]>>[ClH:17] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 7a-(3-propyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine (265 mg, 1.30 mmol, from step 14a) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was triturated with Et2O and dried to afford the title compound as a free flowing white powder. mp 97°-98° C. MS (NH3 /CI)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e4c5a915e9a24293aae0af7d3e5b3bcb | C[N+](=O)[O-].O=Cc1ccccc1>>O=[N+]([O-])C=Cc1ccccc1 | Cl.C(C1=CC=CC=C1)=O.[N+](=O)([O-])C.[OH-].[Na+]>>C1(=CC=CC=C1)C=C[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH3:4].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C[N+](=O)[O-].O=Cc1ccccc1 | O=[N+]([O-])C=Cc1ccccc1 | null | null | CO | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 37 | [{"value": 37.0, "product": "C1(=CC=CC=C1)C=C[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "C1(=CC=CC=C1)C=C[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -18 | CELSIUS | 2 | HOUR | Benzaldehyde (10.0 g, 94.2 mmol) and nitromethane (5.1 mL, 94.2 mmol) were dissolved in MeOH, the solution was cooled to -18° C., and NaOH (3.9 g, 98.9 mmol) in aqueous solution (80 mL) was added while maintaining the temperature below -10° C. The mixture was stirred at 0° C. for 2 hours, then stored at 5° C. overnight... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | CO | -18 | 2 | C[N+](=O)[O-].O=Cc1ccccc1>CO>O=[N+]([O-])C=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d656571e780d4bccad9fd6471b2c4bc3 | O=[N+]([O-])C=Cc1ccccc1>>O=[N+]([O-])CCc1ccccc1 | Cl.C1(=CC=CC=C1)C=C[N+](=O)[O-].[BH4-].[Na+]>>C1(=CC=CC=C1)CC[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[N+:2]([O-:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | O=[N+]([O-])C=Cc1ccccc1 | O=[N+]([O-])CCc1ccccc1 | null | null | C(Cl)(Cl)Cl.CC(C)O | Reduction | Hydrogenation (double to single) | 1897ddb5557a7164dfa80083adb557accafa4233396f9576d5bfde28d2818919 | 92f8c31381fee05ef128b294b51ee13ebdada3b3789c3c4a7dc0a1d2ea4408c2 | c1ccccc1 | [O;-;D1;H0:1]-[#7;+:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;-;D1;H0:1]-[#7;+:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 75 | [{"value": 75.0, "product": "C1(=CC=CC=C1)CC[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "C1(=CC=CC=C1)CC[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | 2-Phenylnitroethene (5.12 g, 34.3 mmol, from step 15a) was dissolved in CHCl3 /i-PrOH (410:85 mL) and SiO2 (51.4 g) was added. NaBH4 (5.2 g, 137 mmol) was added in portions, and the mixture was stirred for 90 minutes at room temperature. HCl (0.5N, 100, mL) was added, and the mixture was stirred for 30 minutes. The lay... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | C(Cl)(Cl)Cl.CC(C)O | null | 1.5 | O=[N+]([O-])C=Cc1ccccc1>C(Cl)(Cl)Cl.CC(C)O>O=[N+]([O-])CCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58fe89ee31bc421fa1afea328a51d6a8 | C#CC12CCCN1CCC2.O=[N+]([O-])CCc1ccccc1>>c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | C1(=CC=CC=C1)CC[N+](=O)[O-].C1(=CC=CC=C1)N=C=O.C(#C)C12CCCN2CCC1>>C(C1=CC=CC=C1)C1=NOC(=C1)C12CCCN2CCC1 | [CH:7]#[C:8][C:9]12[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]2.O=[N+:18]([CH2:6][CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:20][cH:19]1)[O-:17]>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][c:6]2[cH:7][c:8]([C:9]34[CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16]4)[o:17][n:18]2)[cH:19][cH:20]1 | C#CC12CCCN1CCC2.O=[N+]([O-])CCc1ccccc1 | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 85ed1de7d01eb5a1475dc4727791ddb53417125ab3beeb28225b6652ffdb9c73 | 7108617e87a7921f39c453b93eea7dbd08d46222031ed4533f4e27c039907e0d | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[CH2;D2;+0:3]-[C:4]-[c:5].[C:6]-[C:7](-[C;H0;D2;+0:8]#[CH;D1;+0:9])(-[C:10])-[#7:11](-[C:12])-[C:13]>>[C:6]-[C:7](-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c;H0;D3;+0:3](-[C:4]-[c:5]):[n;H0;D2;+0:1]:[o;H0;D2;+0:2]:1)(-[C:10])-[#7:11](-[C:12])-[C:13] | 52.2 | [{"value": 52.0, "product": "C(C1=CC=CC=C1)C1=NOC(=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "C(C1=CC=CC=C1)C1=NOC(=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Phenylnitroethane (895 mg, 5.92 mmol, from step 15b) and phenylisocyanate (1.3 mL, 11.8 mmol) were dissolved in benzene (12 mL) and added to a flask containing 7a-ethynyl-hexahydro-1H-pyrrolizine (400 mg, 2.96 mmol, from step 13a). The solution was stirred at reflux for 5 hours, cooled and stirred for 48 hours at roo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Alkyne | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.C1CC2CCCN2C1 | HO- | C1=CC=CC=C1 | null | null | C#CC12CCCN1CCC2.O=[N+]([O-])CCc1ccccc1>C1=CC=CC=C1>c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72dde4f2823b4e96864c3d6a03b9a1bd | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1>>c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | Cl.C(C1=CC=CC=C1)C1=NOC(=C1)C12CCCN2CCC1>>Cl.C(C1=CC=CC=C1)C1=NOC(=C1)C12CCCN2CCC1 | [cH:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][c:9]([C:10]34[CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17]4)[o:18][n:19]2)[cH:20][cH:21]1>>[cH:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][c:9]([C:10]34[CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17]4)[o:18][n:19]2)[cH:20][cH:21]1 | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 | null | null | [] | null | null | null | null | 7a-(3-Benzyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine (407 mg, 1.52 mmol, from step 15c) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the precipitate was recrystallized from MeOH and dried to afford the title compound as white needles: mp 126°-127° C.; 1H NMR D2O, 300 MHz... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cnoc1.C1CC2CCCN2C1 | null | CCOCC | null | null | c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1>CCOCC>c1ccc(Cc2cc(C34CCCN3CCC4)on2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4279b67233d44b409a5090ce4f747f2e | Brc1cncc(Br)c1.OCc1ccccc1>>Brc1cncc(OCc2ccccc2)c1 | [NH4+].[Cl-].C(C1=CC=CC=C1)O.[H-].[Na+].BrC=1C=NC=C(C1)Br>>C(C1=CC=CC=C1)OC=1C=NC=C(C1)Br | Br[c:6]1[cH:5][n:4][cH:3][c:2]([Br:1])[cH:15]1.[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1 | Brc1cncc(Br)c1.OCc1ccccc1 | Brc1cncc(OCc2ccccc2)c1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[OH;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 72.1 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (60% in mineral oil, 40.9 g, 1.0 mol) in DMF (800 mL) was cooled to 0° C., and benzyl alcohol (105 mL, 1.0 mol) was slowly added. After stirring for 1 hour at ambient temperature, 3,5-dibromopyridine (200.4 g, 846 mmol) was added and the mixture allowed to stir for 16 hours. Saturated NH4Cl solution (500... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O.O | null | 1 | Brc1cncc(Br)c1.OCc1ccccc1>CN(C)C=O.O>Brc1cncc(OCc2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-227b359fc5e7487cb58b11323a1b2724 | Brc1cncc(OCc2ccccc2)c1.C1CC2=[N+](C1)CCC2>>c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1 | C(C1=CC=CC=C1)OC=1C=NC=C(C1)Br.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>C(C1=CC=CC=C1)OC=1C=NC=C(C1)C12CCCN2CCC1 | Br[c:11]1[cH:10][n:9][cH:8][c:7]([O:6][CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:22][cH:21]2)[cH:20]1.[C:12]12=[N+:16]([CH2:15][CH2:14][CH2:13]1)[CH2:17][CH2:18][CH2:19]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][n:9][cH:10][c:11]([C:12]34[CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19]4)[cH:20]2)[cH:21][cH:22]... | Brc1cncc(OCc2ccccc2)c1.C1CC2=[N+](C1)CCC2 | c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1 | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[N+;H0;D3:10]2=[C;H0;D3;+0:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:11]23-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-2-[C:14]-[C:13]-[C:12]-3):[c:6]:[c:5]:[c:4]:1 | 22 | [{"value": 22.0, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.7, "product": "C(C1=CC=CC=C1)OC=1C=NC=C(C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | 3-Benzyloxy-5-bromopyridine (1.18 g, 4.47 mmol) was dissolved in Et2O and cooled to -78° C. A solution of 2.5M t-BuLi (5.8 mL, 9.83 mmol) in pentane was added, and the reaction was stirred for 10 minutes. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (1.4 g, 6.70 mmol) was added, and the reaction mixture was allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | c1ccncc1.C1CC2=[N+](C1)CCC2 | c1ccncc1.C1CC2CCCN2C1 | c1ccccc1.c1ccncc1.C1CC2CCCN2C1 | Br- | CCCCC.CCOCC | -78 | 0.166667 | Brc1cncc(OCc2ccccc2)c1.C1CC2=[N+](C1)CCC2>CCCCC.CCOCC>c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94eabea82a724e06b470656c1d0fc4ec | c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1>>Oc1cncc(C23CCCN2CCC3)c1 | C(C1=CC=CC=C1)OC=1C=NC=C(C1)C12CCCN2CCC1>>OC=1C=NC=C(C1)C12CCCN2CCC1 | c1ccc(C[O:1][c:2]2[cH:3][n:4][cH:5][c:6]([C:7]34[CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14]4)[cH:15]2)cc1>>[OH:1][c:2]1[cH:3][n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15]1 | c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1 | Oc1cncc(C23CCCN2CCC3)c1 | null | [Pt] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1cncc(C23CCCN2CCC3)c1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]:[#7;a:5]:[c:6]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4]:[#7;a:5]:[c:6] | 63.4 | [{"value": 63.0, "product": "OC=1C=NC=C(C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "OC=1C=NC=C(C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 7a-(3-Benzyloxy-5-pyridinyl)-hexahydro-1H-pyrrolizine (260 mg, 0.88 mmol, from step 16b) was dissolved in methanol (9 mL), 10% Pt/C (35 mg) was added, and the mixture stirred under 1 arm of H2 for 16 hours. The catalyst was removed, the filtrate was concentrated, and the residue was chromatographed (silica gel; CHCl3 /... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccncc1.C1CC2CCCN2C1 | Other | [Pt].CO | null | 16 | c1ccc(COc2cncc(C34CCCN3CCC4)c2)cc1>[Pt].CO>Oc1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-024cc166a8ad4750aa817d400f40ba7a | Oc1cncc(C23CCCN2CCC3)c1>>Oc1cncc(C23CCCN2CCC3)c1 | OC=1C=NC=C(C1)C12CCCN2CCC1.CCOCC.Cl>>Cl.OC=1C=NC=C(C1)C12CCCN2CCC1 | [OH:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]23[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15]3)[cH:16]1>>[OH:2][c:3]1[cH:4][n:5][cH:6][c:7]([C:8]23[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15]3)[cH:16]1 | Oc1cncc(C23CCCN2CCC3)c1 | Oc1cncc(C23CCCN2CCC3)c1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 91 | [{"value": 91.0, "product": "Cl.OC=1C=NC=C(C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(3-Hydroxy-5-pyridinyl)-hexahydro-1H-pyrrolizine (150 mg, 0.56 mmol, from step 16c) was dissolved in methylene chloride, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was dried to afford the title compound as a white powder (114 mg, 91%): mp 175°-180° C. (dec.); 1H NMR D2O, 300 MH... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | C(Cl)Cl | null | null | Oc1cncc(C23CCCN2CCC3)c1>C(Cl)Cl>Oc1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8f9af624c254aa681fb4cd3472eb869 | Brc1cncc(Br)c1.C1CC2=[N+](C1)CCC2>>Brc1cncc(C23CCCN2CCC3)c1 | BrC=1C=NC=C(C1)Br.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>BrC=1C=C(C=NC1)C12CCCN2CCC1 | Br[c:6]1[cH:5][n:4][cH:3][c:2]([Br:1])[cH:15]1.[C:7]12=[N+:11]([CH2:10][CH2:9][CH2:8]1)[CH2:12][CH2:13][CH2:14]2>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15]1 | Brc1cncc(Br)c1.C1CC2=[N+](C1)CCC2 | Brc1cncc(C23CCCN2CCC3)c1 | null | null | CCCCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:14]-[C:13]-[C:12]-[N;H0;D3;+0:11]-2-[C:7]-[C:8]-[C:9]-3):[c:6]:1 | 28.4 | [{"value": 28.0, "product": "BrC=1C=C(C=NC1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.4, "product": "BrC=1C=C(C=NC1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -95 | CELSIUS | null | null | 3,5-dibromopyridine (500 mg, 2.11 mmol, Aldrich) was dissolved in Et2 O and cooled to -95° C. A solution of 2.5M t-BuLi (1.7M in pentane, 2.7 mL, 4.64 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (663 mg, 3.2 mmol) was added, and the reaction mixture was allowed to stir and warm t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | c1ccncc1.C1CC2=[N+](C1)CCC2 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | Br- | CCCCC | -95 | null | Brc1cncc(Br)c1.C1CC2=[N+](C1)CCC2>CCCCC>Brc1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1d18582f0384a23a908dc1e462f1ea7 | Cl>>Cl | BrC=1C=C(C=NC1)C12CCCN2CCC1.CCOCC.Cl>>Cl.BrC=1C=C(C=NC1)C12CCCN2CCC1 | [ClH:16]>>[ClH:16] | Cl | Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 7a-(5-bromo-3-pyridinyl)-hexahydro-1H-pyrrolizine (107 mg, 0.52 mmol, from step 16c) was dissolved in methylene chloride, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was crystallized from MeOH/Et2O and dried to afford the title compound as an off-white powder (118 mg). mp 192°-194°... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)Cl | null | null | Cl>C(Cl)Cl>Cl |
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