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-07e13572c7374292938c79bf24b4e98d | N#Cc1c(N)cc(N)nc1Br>>N#Cc1cnc(N)cc1N | [H][H].[H][H].BrC1=C(C(=CC(=N1)N)N)C#N.C(C)(=O)[O-].[K+].CO>>NC1=NC=C(C(=C1)N)C#N | Br[c:4]1[c:3]([C:2]#[N:1])[c:9]([NH2:10])[cH:8][c:6]([NH2:7])[n:5]1>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH2:7])[cH:8][c:9]1[NH2:10] | N#Cc1c(N)cc(N)nc1Br | N#Cc1cnc(N)cc1N | null | [Pd] | O1CCCC1 | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | null | [] | null | null | 2 | HOUR | A suspension of 21.3 g of 6-bromo-2,4-diamino-5-cyanopyridine (JACS, 80:2838-2840 (1958)) and 1 g of 20% palladium on charcoal in 250 mL of tetrahydrofuran was shaken in a Parr apparatus under an atmosphere hydrogen. After 2 hours, the reaction was stopped and 10 g of potassium acetate and 50 mL of methanol added. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | [Pd].O1CCCC1 | null | 2 | N#Cc1c(N)cc(N)nc1Br>[Pd].O1CCCC1>N#Cc1cnc(N)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-66fceab868444128830a463ef7b06941 | N#Cc1cnc(N)cc1N.O=CO>>Nc1ccnc(N)c1C=O | NC1=NC=C(C(=C1)N)C#N.C(=O)O.[H][H]>>NC1=C(C=O)C(=CC=N1)N | N#C[c:3]1[c:2]([NH2:1])[cH:8][c:6]([NH2:7])[n:5][cH:4]1.O[CH:9]=[O:10]>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[c:8]1[CH:9]=[O:10] | N#Cc1cnc(N)cc1N.O=CO | Nc1ccnc(N)c1C=O | null | [Ni] | O | C-C Coupling | OtherReaction | 9c897deafa93b8c294aa9a7254d1bc614a85c0561ff3175ebcfb7515ac22f5f6 | ff28b2f4178de41cb9fadf57eb34b930a975d9e7cd5557702e6d4fcb75002b86 | c1ccncc1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[N;D1;H2:5]):[cH;D2;+0:6]:[c:7]:1-[N;D1;H2:8].O-[CH;D2;+0:9]=[O;D1;H0:10]>>[N;D1;H2:8]-[c:7]1:[cH;D2;+0:1]:[c:2]:[#7;a:3]:[c:4](-[N;D1;H2:5]):[c;H0;D3;+0:6]:1-[CH;D2;+0:9]=[O;D1;H0:10] | null | [] | null | null | null | null | A suspension of 13.4 g of 2,4-diamino-5-cyanopyridine from Example 14, 2 g of Raney nickel catalyst, 40 mL of 97-100% formic acid, and 80 mL of water were shaken in a Parr apparatus under an atmosphere of nitrogen until the requisite amount of hydrogen was consumed. The solvents were removed under reduced pressure and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | [Ni].O | null | null | N#Cc1cnc(N)cc1N.O=CO>[Ni].O>Nc1ccnc(N)c1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-133c343446384739816db3dc834ba58e | CC(C)(C)N=C=O.CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | C.C(C)(C)(C)N=C=O.NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl.[H-].[Na+]>>C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl | [C:26](=[O:27])=[N:28][C:29]([CH3:30])([CH3:31])[CH3:32].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]([NH2:25])[n:33][c:34]2[n:35]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][... | CC(C)(C)N=C=O.CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | null | null | CN(C)C=O.O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | 27.9 | [{"value": 27.9, "product": "C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 7-amino-6-(2,6-dichlorophenyl)-2-(3-diethylamino-propylamino)-pyrido[2,3-d]pyrimidine (0.48 g) from Example 20 in DMF (5 mL) was added 60% sodium hydride suspension (46 mg), and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added t-butyl isocyanate (0.113 g), and t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | CN(C)C=O.O | null | 1 | CC(C)(C)N=C=O.CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>CN(C)C=O.O>CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-364ed88f220643f79ef9dda9075acba3 | CCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCNC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.C(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)NC(=O)NCC | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][c:15]2[cH:16][c:17]1-[c:18]1[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]1[Cl:25]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][c:15]2[cH:16][c:17]1-[c:18]1[c:19]([Cl:20])[cH:21][cH:22... | CCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCNC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7]):[c:6] | null | [] | null | null | null | null | 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine was reacted with ethyl isocyanate according to the general procedure of Example 2. The crude product was purified by radial chromatography eluting with a gradient of 70% ethyl acetate/30% chloroform to 100% chloroform to give the title compound, 1-[2-amino-6-(2... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCNC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53faf84c535e451092b026fc23418be8 | CCCCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCCCNC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NCCCC)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.C(CCC)N=C=O>>C(CCC)NC(=O)NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)NC(=O)NCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[Cl:22])[c:23]([NH2:24])[n:32][c:33]2[n:34]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19]... | CCCCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCCCNC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NCCCC)nc2n1 | null | null | null | Acylation | OtherReaction | 4cd4a24ba08f7bf502b3150ee8b2fb0c67292b0872d42e763884f695ebc3e7df | 0ec38b10255bbfaa941365846c10b48228a0d7b15bea6d4efd05967a51aa7d5f | c1ccc(-c2cnc3ncncc3c2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]:[#7;a:11]:[c:12](-[NH2;D1;+0:13]):[#7;a:14]:[c:15]>>[#7:16]-[C:17](=[O;D1;H0:18])-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]:[#7;a:11]:[c:12](-[NH;D2;+0:13]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C:1]):[#7;a:14]:... | null | [] | null | null | null | null | A mixture of 0.5 g 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 and 15 mL of n-butyl isocyanate is refluxed for 2 hours. The reaction mixture is allowed to cool to room temperature and the insoluble material filtered. The solid is recrystallized several times from ethanol to give the title ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine.Primary amine | Urea.Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CCCCN=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCCCNC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NCCCC)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa8c49ae8b804ac38747f04987a4248a | CN(C)CCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.CN(CCCN)C>>NC=1C(=CC2=C(N=C(N=C2)NCCCN(C)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7].N[c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22]([NH2:23])[n:24][c:25]2[n:26]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c... | CN(C)CCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3ncncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[#7;a:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[#7;a:8]:1 | null | [] | null | null | null | null | The title compound was prepared as in Example 20 by reacting 3.0 g of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 and 60 mL of 3-(dimethylamino)propylamine to give the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: The title compound was prepared as in Example 20 | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CN(C)CCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8a7cc3b2c0c44c8b531e7c79d2b25ab | CC(C)(C)N=C=O.CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | NC=1C(=CC2=C(N=C(N=C2)NCCCN(C)C)N1)C1=C(C=CC=C1Cl)Cl.C(C)(C)(C)N=C=O>>C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN(C)C)N1)C1=C(C=CC=C1Cl)Cl | [C:24](=[O:25])=[N:26][C:27]([CH3:28])([CH3:29])[CH3:30].[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22]([NH2:23])[n:31][c:32]2[n:33]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][cH:10][c:11]2[cH:12... | CC(C)(C)N=C=O.CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | Following the procedure of Example 21, 1.62 g of 7-amino-6-(2,6-dichlorophenyl)-2-(3-dimethylamino-propylamino)-pyrido[2,3-d]pyrimidine from Example 27 was reacted with 0.48 g of t-butyl isocyanate to give the title compound; mp gradually dec above 130° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e213f658a414f92bb126f7532f74911 | CN(C)CC(C)(C)CN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.CN(CC(CN)(C)C)C>>NC=1C(=CC2=C(N=C(N=C2)NCC(CN(C)C)(C)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH2:9].N[c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]([NH2:25])[n:26][c:27]2[n:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH:9][c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c... | CN(C)CC(C)(C)CN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3ncncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1 | null | [] | null | null | null | null | The title compound was prepared as described above in Example 20 by reacting 2.0 g of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 and 15 mL of N,N,2,2-tetramethyl-1,3-propanediamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CN(C)CC(C)(C)CN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-326fafa628c647c289831bc3d9609957 | CC(C)(C)N=C=O.CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | NC=1C(=CC2=C(N=C(N=C2)NCC(CN(C)C)(C)C)N1)C1=C(C=CC=C1Cl)Cl.C(C)(C)(C)N=C=O>>C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCC(CN(C)C)(C)C)N1)C1=C(C=CC=C1Cl)Cl | [C:26](=[O:27])=[N:28][C:29]([CH3:30])([CH3:31])[CH3:32].[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH:9][c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]([NH2:25])[n:33][c:34]2[n:35]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH... | CC(C)(C)N=C=O.CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | Following the procedure of Example 21, 1.0 g of 7-amino-6-(2,6-dichlorophenyl)-2-(3-dimethylamino-2,2-dimethyl-propylamino)-pyrido[2,3-d]pyrimidine from Example 29 was reacted with 0.26 g of t-butyl isocyanate to give the title compound; mp 161°-170° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)CC(C)(C)CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-028f0867c6414e2baa7beafce58df965 | CN1CCN(CCCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.NCCCCN1CCN(CC1)C>>NC=1C(=CC2=C(N=C(N=C2)NCCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH2:30][CH2:31]1.N[c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]([NH2:26])[n:27][c:28]2[n:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]2[n:12][cH:13][c:14... | CN1CCN(CCCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3nc(NCCCCN4CCNCC4)ncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1 | null | [] | null | null | null | null | Following the procedure of Example 20, 2.0 g of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 was reacted with 15 mL of 1-(4-aminobutyl)-4-methyl-piperazine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CN1CCN(CCCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9674881c08004af9ba181216cc7781b2 | CN1CCN(CCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | C([O-])(O)=O.[Na+].NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.S(N)(O)(=O)=O.NCCCN1CCN(CC1)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH2:9])[CH2:29][CH2:30]1.N[c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]([NH2:25])[n:26][c:27]2[n:28]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](... | CN1CCN(CCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3nc(NCCCN4CCNCC4)ncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1 | null | [] | 150 | CELSIUS | null | null | A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (3.0 g) from Example 1, sulfamic acid (1.9 g), and 1-(3-aminopropyl)-4-methylpiperazine (15 mL) was heated to approximately 150° C. for 24 hours. After cooling, the residue was dissolved in water. The aqueous solution was made alkaline with a solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1 | Other | O | 150 | null | CN1CCN(CCCN)CC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>O>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50520c4996e84d08a9b75967501e0b2b | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=NCc1ccccc1>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)NCc4ccccc4)nc3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]4[Cl:23])[c:24]([NH2:25])[n:36][c:37]3[n:38]2)[CH2:39][CH2:40]1.[C:26](=[O:27])=[N:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=NCc1ccccc1 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)NCc4ccccc4)nc3n2)CC1 | null | null | CO.CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:6] | 63.4 | [{"value": 63.4, "product": "C(C1=CC=CC=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.08 g) from Example 36 was reacted with 0.298 g of benzyl isocyanate according to the general procedure of Example 37 to give 0.822 g of 1-benzyl-3-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-py... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CO.CC#N | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=NCc1ccccc1>CO.CC#N>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)NCc4ccccc4)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d255ebcb23144a4b195e3bc10791314 | C=CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>>C=CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C(C=C)N=C=O>>C(C=C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl | [CH2:1]=[CH:2][CH2:3][N:4]=[C:5]=[O:6].[NH2:7][c:8]1[n:9][c:10]2[n:11][c:12]([NH:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]3)[n:24][cH:25][c:26]2[cH:27][c:28]1-[c:29]1[c:30]([Cl:31])[cH:32][cH:33][cH:34][c:35]1[Cl:36]>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][c:8]1[n:9][c:1... | C=CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | C=CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3nc(NCCCN4CCNCC4)ncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H2:7]=[C:8]-[C:9]-[N;H0;D2;+0:10]=[C;H0;D2;+0:11]=[O;D1;H0:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[NH;D2;+0:10]-[C:9]-[C:8]=[C;D1;H2:7]):[c:6] | 26.2 | [{"value": 26.2, "product": "C(C=C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.186 g of allyl isocyanate according to the general procedure of Example 37. The product was purified by chromatography and crystallized from ethyl acetate to give 0.31 g of 1-al... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | null | null | null | C=CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>>C=CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-002722963a3747c394ad244025da8c2d | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccc(N=C=O)cc1>>COc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 | CO.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.COC1=CC=C(C=C1)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=C(C=C1)OC | [NH2:10][c:11]1[n:12][c:13]2[n:14][c:15]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH3:24])[CH2:25][CH2:26]3)[n:27][cH:28][c:29]2[cH:30][c:31]1-[c:32]1[c:33]([Cl:34])[cH:35][cH:36][cH:37][c:38]1[Cl:39].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:40][cH:41]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccc(N=C=O)cc1 | COc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 | null | null | CC(=O)O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 87 | [{"value": 87.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 4-methoxyphenyl isocyanate (0.334 g) according to the general procedure of Example 37 to give 1.16 g of 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrid... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | CC(=O)O | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccc(N=C=O)cc1>CC(=O)O>COc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-28a36116f8ad42a28acebdd668b243cb | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1cccc(N=C=O)c1>>COc1cccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)c1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.COC=1C=C(C=CC1)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC(=CC=C1)OC | [NH2:11][c:12]1[n:13][c:14]2[n:15][c:16]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]3)[n:28][cH:29][c:30]2[cH:31][c:32]1-[c:33]1[c:34]([Cl:35])[cH:36][cH:37][cH:38][c:39]1[Cl:40].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]=[C:9]=[O:10])[cH:41]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1cccc(N=C=O)c1 | COc1cccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)c1 | null | null | CO.CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 69 | [{"value": 69.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.334 g of 3-methoxyphenyl isocyanate according to the general procedure of Example 37 to give 0.920 g of 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | CO.CC#N | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1cccc(N=C=O)c1>CO.CC#N>COc1cccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f0ff9f57d10448aaa6472d0ca16d530 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccccc1N=C=O>>COc1ccccc1NC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.COC1=C(C=CC=C1)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=C(C=CC=C1)OC | [NH2:12][c:13]1[n:14][c:15]2[n:16][c:17]([NH:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]3)[n:29][cH:30][c:31]2[cH:32][c:33]1-[c:34]1[c:35]([Cl:36])[cH:37][cH:38][cH:39][c:40]1[Cl:41].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]=[C:10]=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccccc1N=C=O | COc1ccccc1NC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | CO.CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 69.2 | [{"value": 69.2, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.334 g of 2-methoxyphenyl isocyanate according to the general procedure of Example 37 to give 0.9232 g of 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-py... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | CO.CC#N | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.COc1ccccc1N=C=O>CO.CC#N>COc1ccccc1NC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0155f9bda79c45a19ebf7c83b24671e6 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Br)cc1>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Br)cc4)nc3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.BrC1=CC=C(C=C1)N=C=O>>BrC1=CC=C(C=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]4[Cl:23])[c:24]([NH2:25])[n:36][c:37]3[n:38]2)[CH2:39][CH2:40]1.[C:26](=[O:27])=[N:28][c:29]1[cH:30][cH:31][c:32]([Br:33])[cH:34][cH:35]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Br)cc1 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Br)cc4)nc3n2)CC1 | null | null | CC(=O)O.CS(=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 67.7 | [{"value": 67.7, "product": "BrC1=CC=C(C=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.44 g of 4-bromophenyl isocyanate according to the general procedure of Example 37 to give 0.97 g of 1-(4-Bromo-phenyl)-3-{6-(2,6-dichlorophenyl)-2-[3-(4-methylpiperazin-1-yl)-pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CC(=O)O.CS(=O)C | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Br)cc1>CC(=O)O.CS(=O)C>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Br)cc4)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b05d5c213f2423e91bc370c032c23bf | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Cl)cc1>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Cl)cc4)nc3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.ClC1=CC=C(C=C1)N=C=O>>ClC1=CC=C(C=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]4[Cl:23])[c:24]([NH2:25])[n:36][c:37]3[n:38]2)[CH2:39][CH2:40]1.[C:26](=[O:27])=[N:28][c:29]1[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Cl)cc1 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Cl)cc4)nc3n2)CC1 | null | null | CO.CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 62.7 | [{"value": 62.7, "product": "ClC1=CC=C(C=C1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.344 g of 4-chlorophenyl isocyanate according to the general procedure of Example 37 to give 0.8424 g of 1-(4-Chloro-phenyl)-3-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CO.CC#N | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccc(Cl)cc1>CO.CC#N>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccc(Cl)cc4)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a2ff7c5beaf44d2db01256a375ab8682 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.Cc1ccc(N=C=O)cc1>>Cc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C1(=CC=C(C=C1)N=C=O)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=C(C=C1)C | [NH2:9][c:10]1[n:11][c:12]2[n:13][c:14]([NH:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]3)[n:26][cH:27][c:28]2[cH:29][c:30]1-[c:31]1[c:32]([Cl:33])[cH:34][cH:35][cH:36][c:37]1[Cl:38].[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:39][cH:40]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.Cc1ccc(N=C=O)cc1 | Cc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | null | [] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 36 was reacted with 0.29 g of 4-tolyl isocyanate according to the general procedure of Example 37 to give 0.9492 g of the title compound. ESMS (20/80 MeOH/CH3CN+0.1% AcOH): M+ +H=579;
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | null | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.Cc1ccc(N=C=O)cc1>>Cc1ccc(NC(=O)Nc2nc3nc(NCCCN4CCN(C)CC4)ncc3cc2-c2c(Cl)cccc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-edc6efc454f94549afcbc19e46c92c40 | CCCCCCCCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>>CCCCCCCCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C(CCCCCCC)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11].[NH2:12][c:13]1[n:14][c:15]2[n:16][c:17]([NH:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]3)[n:29][cH:30][c:31]2[cH:32][c:33]1-[c:34]1[c:35]([Cl:36])[cH:37][cH:38][cH:39][c:40]1[Cl:41]>>[CH3:1][CH2:2][CH2:3]... | CCCCCCCCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | CCCCCCCCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3nc(NCCCN4CCNCC4)ncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:8]-[C:7]):[c:6] | 75 | [{"value": 75.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.348 g of octyl isocyanate according to the general procedure of Example 21. Chromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (90:10:1) then switchin... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | null | null | null | CCCCCCCCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>>CCCCCCCCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-779eaaeec17943afacf419b93f07f9f2 | CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>>CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C(C)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NCC | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]3)[n:23][cH:24][c:25]2[cH:26][c:27]1-[c:28]1[c:29]([Cl:30])[cH:31][cH:32][cH:33][c:34]1[Cl:35]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[n:10][c:11](... | CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1 | CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | CO.CC#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3nc(NCCCN4CCNCC4)ncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7]):[c:6] | 74.3 | [{"value": 74.3, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.159 g of ethyl isocyanate according to the general procedure of Example 37 to give 0.86 g of 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrido-[2,3-d]... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | CO.CC#N | null | null | CCN=C=O.CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1>CO.CC#N>CCNC(=O)Nc1nc2nc(NCCCN3CCN(C)CC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90223fc6a1a9418ca6f3dde54ad1b634 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1cccc2ccccc12>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4cccc5ccccc45)nc3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.C1(=CC=CC2=CC=CC=C12)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=CC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]4[Cl:23])[c:24]([NH2:25])[n:39][c:40]3[n:41]2)[CH2:42][CH2:43]1.[C:26](=[O:27])=[N:28][c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12>>[CH3:1][N:... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1cccc2ccccc12 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4cccc5ccccc45)nc3n2)CC1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1)Nc1cccc2ccccc12 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 70.5 | [{"value": 70.5, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.378 g of 1-naphthyl isocyanate according to the general procedure of Example 37. Chromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (90:10:1) then swi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1.c1ccc2ccccc2c1 | null | null | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1cccc2ccccc12>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4cccc5ccccc45)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0c89e86bbe14f759fdce4cd0dfbf012 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccccc1>>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccccc4)nc3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1N.[H-].[Na+].C1(=CC=CC=C1)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=CC=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][c:10]2[n:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]4[Cl:23])[c:24]([NH2:25])[n:35][c:36]3[n:37]2)[CH2:38][CH2:39]1.[C:26](=[O:27])=[N:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:... | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccccc1 | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccccc4)nc3n2)CC1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2nc(NCCCN3CCNCC3)ncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 65.5 | [{"value": 65.5, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N=C1NC(=O)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (13.0 g) from Example 36 in DMF (160 mL) was reacted with 60% sodium hydride suspension (1.16 g) and phenyl isocyanate (3.47 g) according to the general procedure of Example 37. Recrystallization of the chromatographed p... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | null | CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(N)nc3n2)CC1.O=C=Nc1ccccc1>CN(C)C=O>CN1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(NC(=O)Nc4ccccc4)nc3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0e5a6c6eb1740d4b28e4ccae931db8f | CCN(CC)CCCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.S(N)(O)(=O)=O.C(C)N(CC)CCCCN>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1N | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].N[c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]([NH2:26])[n:27][c:28]2[n:29]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][cH:13][c:14]2[cH:15][c:16... | CCN(CC)CCCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3ncncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:1 | null | [] | 150 | CELSIUS | null | null | A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (40 g) from Example 1, sulfamic acid (25.4 g) and diethylaminobutylamine (205 mL) was heated to approximately 150° C. for 28 hours. The reaction temperature was lowered to 50° C., and excess diethylaminobutylamine was removed in vacuo. After coolin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | 150 | null | CCN(CC)CCCCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e67c6fe74c75494e9570b2bde6a06c78 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=Nc1ccccc1>>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)Nc3ccccc3)nc2n1 | C1(=CC=CC=C1)N=C=O.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1N.[H-].[Na+]>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NC1=CC=CC=C1 | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]([NH2:26])[n:36][c:37]2[n:38]1.[C:27](=[O:28])=[N:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2... | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=Nc1ccccc1 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)Nc3ccccc3)nc2n1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1nc2ncncc2cc1-c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6] | 66.4 | [{"value": 66.4, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 53 in DMF (15 mL) was added one equivalent of 60% sodium hydride suspension (0.93 g). After stirring for approximately 1 hour at room temperature, one equivalent of phenyl isocyanate (0.275 g) was... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | 1 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=Nc1ccccc1>CN(C)C=O>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)Nc3ccccc3)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-62852d9a12b3459797e4f780f0a64cab | CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl>>CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl.CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NCC.Cl>>Cl.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NCC.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NCC | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:43]2[n:44][c:45]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][N:51]([CH2:16][CH3:9])[CH2:54][CH3:55])[n:56][cH:57][c:58]2[cH:59][c:26]1-[c:27]1[c:62]([Cl:29])[cH:64][cH:65][cH:66][c:67]1[Cl:68]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH:12][... | CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl.CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 244f7a11c55fb1df7bfe156291fbafe8023d129bc9b41b77bc74f79a07137d34 | 44e2a7dc6cb4e607002e0c0700015f0ec63db22af21fd0fcaa2166b71da299ad | c1ccc(-c2cnc3ncncc3c2)cc1.c1ccc(-c2cnc3ncncc3c2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[cH;D2;+0:13]:[c;H0;D3;+0:14]:1-[c;H0;D3;+0:15]1:[c;H0;D3;+0:16](-[Cl;H0;D1;+0:17]):[c:18]:[c:19]:[c:20]:[c;H0;D3;+0:21]:1-[Cl;D1;H0:22].[C:23]-[C:24]-[N;H0;D3;+0:25](-[C:26]-[C;D1;H3:27])-[CH2;D2;+0:28]-[CH... | null | [] | null | null | null | null | To a solution of 1-[6-(2,6-dichlorophenyl)-2-(4-diethylamino-butylamino)-pyrido[2,3-d]pyrimidin-7-yl]-3-ethyl-urea (3.253 g) from Example 55 in water (250 mL) was added one equivalent of 1N hydrochloric acid (6.44 mL). The solution was stirred at room temperature until the solid was dissolved, filtered, and frozen. Lyo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Urea.Secondary amine.Tertiary amine.Tertiary amine | c1cnc2ncncc2c1.c1ccccc1 | c1cnc2ncncc2c1.c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | c1cnc2ncncc2c1.c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | O | null | null | CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl>O>CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl.CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a49379abcf2e4a209bfcea21a184af43 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=NC1CCCCC1>>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC3CCCCC3)nc2n1 | CO.CC#N.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1N.[H-].[Na+].C1(CCCCC1)N=C=O>>C1(CCCCC1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]([NH2:26])[n:36][c:37]2[n:38]1.[C:27](=[O:28])=[N:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:... | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=NC1CCCCC1 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC3CCCCC3)nc2n1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1nc2ncncc2cc1-c1ccccc1)NC1CCCCC1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C:7]-[C:8](-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11])-[C:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:8](-[C:7])-[C:12]):[c:6] | 71.9 | [{"value": 71.9, "product": "C1(CCCCC1)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2,6-Dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 53 in DMF (15 mL) was reacted with 60% sodium hydride suspension (0.092 g) and cyclohexyl isocyanate (0.289 g) according to the general procedure of Example 54 to give 0.927 g of the title compound, ESMS (20/80 Me... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1.C1CCCCC1 | null | CN(C)C=O | null | null | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.O=C=NC1CCCCC1>CN(C)C=O>CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC3CCCCC3)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f61888cd7d804b09a5851ce22ce962d0 | NCCCN1CCOCC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.S(N)(O)(=O)=O.NCCCN1CCOCC1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCOCC2)N=C1N | [NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.N[c:6]1[n:5][c:4]2[n:3][c:2]([NH2:1])[c:21](-[c:22]3[c:23]([Cl:24])[cH:25][cH:26][cH:27][c:28]3[Cl:29])[cH:20][c:19]2[cH:18][n:17]1>>[NH2:1][c:2]1[n:3][c:4]2[n:5][c:6]([NH:7][CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[... | NCCCN1CCOCC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3nc(NCCCN4CCOCC4)ncc3c2)cc1 | N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]:[#7;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:6]:[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (4.00 g) from Example 1, sulfamic acid (2.53 g) and aminopropylmorpholine (30 mL) was reacted as in Example 53. In this instance, the crude residue was washed with hot ethyl acetate followed by diethyl ether to afford 3.95 g of the title compound 6... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.C1COCC[NH]1.c1ccccc1 | Other | null | null | null | NCCCN1CCOCC1.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ede167eccc134bd3a388eacac4ece473 | CC(C)(C)N=C=O.Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl>>CC(C)(C)NC(=O)Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl | C(C)(C)(C)N=C=O.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCOCC2)N=C1N.[H-].[Na+]>>C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCOCC2)N1)C1=C(C=CC=C1Cl)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[n:24][cH:25][c:26]2[cH:27][c:28]1-[c:29]1[c:30]([Cl:31])[cH:32][cH:33][cH:34][c:35]1[Cl:36]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1... | CC(C)(C)N=C=O.Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl | CC(C)(C)NC(=O)Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3nc(NCCCN4CCOCC4)ncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | 79.8 | [{"value": 79.8, "product": "C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NCCCN2CCOCC2)N1)C1=C(C=CC=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6-(2,6-dichlorophenyl)-N2 -(3-morpholin-4-yl-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 58 in DMF (15 mL) was added one equivalent of 60% sodium hydride suspension (0.92 g). After stirring for approximately 1 hour at room temperature, one equivalent of tert-butyl isocyanate (0.230... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.C1COCC[NH]1.c1ccccc1 | null | CN(C)C=O | null | 1 | CC(C)(C)N=C=O.Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl>CN(C)C=O>CC(C)(C)NC(=O)Nc1nc2nc(NCCCN3CCOCC3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c9858bf611994d008d92d1a95facaa9c | N#CCc1c(Br)cccc1Br.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1 | [H-].[Na+].BrC1=C(C(=CC=C1)Br)CC#N.NC1=NC=C(C(=N1)N)C=O>>BrC1=C(C(=CC=C1)Br)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[c:9]([Br:10])[cH:11][cH:12][cH:13][c:14]1[Br:15])[C:16]#[N:17].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:20][c:19]1[NH2:18]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Br:10])[cH:11][cH:12][cH:13][c:14]3[Br:15])[c:16]([NH2:17])[n:18][c:19]2[n:20]1 | N#CCc1c(Br)cccc1Br.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Br;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Br;D1;H0:17]):[c:18]>>[Br;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | 63.3 | [{"value": 63.3, "product": "BrC1=C(C(=CC=C1)Br)C1=CC2=C(N=C(N=C2)N)N=C1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.23 g 60% sodium hydride suspension in 11.0 mL of 2-ethoxyethanol was added 4.18 g of 2,6-dibromophenylacetonitrile and 2.00 g of 2,4-diaminopyrimidine-5-carboxaldehyde. The reaction was refluxed for 4 hours, cooled, and poured into ice water. The residue was washed well with acetonitrile then diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | null | N#CCc1c(Br)cccc1Br.Nc1ncc(C=O)c(N)n1>C(C)OCCO>Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6a90e5dbf8d9440f860586cc73a69716 | CCN(CC)CCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCN(CC)CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.N | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.S(N)(O)(=O)=O.C(C)N(CC)CCN>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCN(CC)CC)N=C1N.N | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].[c:9]1([NH2:28])[n:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[Cl:22])[c:23]([NH2:24])[n:25][c:26]2[n:27]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][c:9]1[n:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17... | CCN(CC)CCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCN(CC)CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.N | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 45222f4b8b91934634a3f382489f0bc07c8c1cc91e45799dc8ede1bc82f31bf2 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccc(-c2cnc3ncncc3c2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:1.[NH3;D0;+0:4] | 1 | [{"value": 1.0, "product": "N", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (4.0 g) from Example 1, sulfamic acid (2.53 g), and diethylaminoethylamine (40 mL) was heated to approximately 150° C. for 20 hours. The excess diethylaminoethylamine was removed in vacuo. The resulting oil was dissolved in diethyl ether, diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | null | null | 150 | null | CCN(CC)CCN.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCN(CC)CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-748a2d0593d44481a5c135fdf239e33d | N#Cc1cnc(Nc2ccccc2)nc1N.O=CO>>Nc1nc(Nc2ccccc2)ncc1C=O | NC1=NC(=NC=C1C#N)NC1=CC=CC=C1.C(=O)O>>NC1=NC(=NC=C1C=O)NC1=CC=CC=C1 | N#[C:15][c:14]1[c:2]([NH2:1])[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][cH:13]1.OC=[O:16]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][cH:13][c:14]1[CH:15]=[O:16] | N#Cc1cnc(Nc2ccccc2)nc1N.O=CO | Nc1nc(Nc2ccccc2)ncc1C=O | null | [Ni] | O | Miscellaneous | OtherReaction | dd48b99193436fbe7b6cc0a1621b6770f60b9def12aae5a3798f5538fe569c97 | 0897ec40f28c09937bcdbb0203ea69433f1817427a4cf5fff67c67ea215ea2af | c1ccc(Nc2ncccn2)cc1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8].O-C=[O;H0;D1;+0:9]>>[N;D1;H2:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[O;H0;D1;+0:9] | null | [] | null | null | 20 | MINUTE | 4-Amino-2-phenylamino-pyrimidine-5-carbonitrile (2.00 g) obtained from Example 71 was combined with wet Raney nickel (2.00 g), 98% formic acid (60 mL) and water (40 mL) in a Parr shaker. The reaction was placed under hydrogen (42 psi) and shaken for 20 minutes. The reaction was filtered, and the filtrate was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Aldehyde | null | null | c1cncnc1.c1ccccc1 | HO- | [Ni].O | null | 0.333333 | N#Cc1cnc(Nc2ccccc2)nc1N.O=CO>[Ni].O>Nc1nc(Nc2ccccc2)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32214df9473647ba998abcb895c010fa | N#CCc1c(Cl)cccc1Cl.Nc1nc(Nc2ccccc2)ncc1C=O>>Nc1nc2nc(Nc3ccccc3)ncc2cc1-c1c(Cl)cccc1Cl | O.[H-].[Na+].ClC1=C(C(=CC=C1)Cl)CC#N.NC1=NC(=NC=C1C=O)NC1=CC=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N=C1N | [N:1]#[C:2][CH2:18][c:19]1[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]1[Cl:26].O=[CH:17][c:16]1[c:4]([NH2:3])[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>>[NH2:1][c:2]1[n:3][c:4]2[n:5][c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14][cH:15][c:16]2[cH:17][c:18]1-[c:19]1[c:20]([Cl:21... | N#CCc1c(Cl)cccc1Cl.Nc1nc(Nc2ccccc2)ncc1C=O | Nc1nc2nc(Nc3ccccc3)ncc2cc1-c1c(Cl)cccc1Cl | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(Nc2ncc3cc(-c4ccccc4)cnc3n2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | 68.4 | [{"value": 68.4, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N=C1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.022 g 60% sodium hydride suspension in 2.00 mL of 2-ethoxyethanol was added 0.46 g of 2,6-dichlorophenylacetonitrile and 0.50 g of 4-amino-2-phenylamino-pyrimidine-5-carboxaldehyde from Example 72. The reaction was refluxed for 4 hours, cooled, poured into water, and extracted several times with dich... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | C(C)OCCO | null | null | N#CCc1c(Cl)cccc1Cl.Nc1nc(Nc2ccccc2)ncc1C=O>C(C)OCCO>Nc1nc2nc(Nc3ccccc3)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f60b9d4041c0469591d62275b8e1d8d7 | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+]>>CCOC(=O)c1cnc(SC)nc1N | ClC1=NC(=NC=C1C(=O)OCC)SC.[OH-].[NH4+]>>C(C)OC(=O)C=1C(=NC(=NC1)SC)N | Cl[c:13]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([S:10][CH3:11])[n:12]1.[NH4+:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([S:10][CH3:11])[n:12][c:13]1[NH2:14] | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+] | CCOC(=O)c1cnc(SC)nc1N | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 1b077d7db1392b159d0fd0777de714d1fad7ef0bbe69adc404d2d103f4416610 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH4+;D0:12]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:12]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | null | [] | null | null | 5 | HOUR | To a suspension of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (25 g) in ethanol (200 mL) was added 30% ammonium hydroxide (38 mL). After stirring 5 hours at room temperature, the reaction was concentrated in vacuo. The residue was suspended in water and filtered. The filter pad, washed with water then diethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | C(C)O | null | 5 | CCOC(=O)c1cnc(SC)nc1Cl.[NH4+]>C(C)O>CCOC(=O)c1cnc(SC)nc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e715d98ba3a64d67bf7124f153c54da7 | CSc1ncc(C=O)c(N)n1.N#CCc1c(Cl)cccc1Cl>>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | NC1=NC(=NC=C1C=O)SC.ClC1=C(C(=CC=C1)Cl)CC#N.[H-].[Na+]>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N=C1N | O=[CH:7][c:6]1[cH:5][n:4][c:3]([S:2][CH3:1])[n:21][c:20]1[NH2:19].[CH2:8]([c:9]1[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]1[Cl:16])[C:17]#[N:18]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17]([NH2:18])[n:19][c:20]2[n:21]1 | CSc1ncc(C=O)c(N)n1.N#CCc1c(Cl)cccc1Cl | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | 32.1 | [{"value": 32.1, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N=C1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Into a solution of 2,6-dichlorophenylacetonitrile (0.55 g) in dimethylformamide (5 mL) was added one equivalent of 60% sodium hydride suspension (0.12 g). After 10 minutes, 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (0.50 g) obtained from Example 76 was added. After stirring overnight at room temperature, the r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | CN(C=O)C | null | 0.166667 | CSc1ncc(C=O)c(N)n1.N#CCc1c(Cl)cccc1Cl>CN(C=O)C>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b18944e08c244489c0c882a36845a09 | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.COC(OC)N(C)C>>CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 | NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl.CN(C)C(OC)OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN(CC)CC)N=C1N=CN(C)C | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]([NH2:25])[n:30][c:31]2[n:32]1.CO[CH:26](OC)[N:27]([CH3:28])[CH3:29]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[n:11][cH:12]... | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.COC(OC)N(C)C | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1ccc(-c2cnc3ncncc3c2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:10] | 68 | [{"value": 68.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN(CC)CC)N=C1N=CN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5.5 | HOUR | To a suspension of 210 mg (1 mmol) of 7-amino-6-(2,6-dichlorophenyl)-2-[3-(diethylamino) propylamino]-pyrido[2,3-d]pyrimidine from Example 20 in 0.8 mL of DMF was added 0.8 mL of DMF dimethyl acetal. The mixture was stirred at room temperature for 5.5 hours, then concentrated in vacuo. The residual oil was distributed ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | CN(C)C=O | null | 5.5 | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.COC(OC)N(C)C>CN(C)C=O>CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72ff6e6fed6a469e82049eb403a60197 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl.COC(OC)N(C)C>>CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)NC(=O)NC(C)(C)C.CN(C)C(OC)OC>>C(C)(C)(C)NC(NC=1C(=CC2=C(N=C(N=C2)N=CN(C)C)N1)C1=C(C=CC=C1Cl)Cl)=O | [NH2:5][c:6]1[n:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[Cl:19])[c:20]([NH:21][C:22](=[O:23])[NH:24][C:25]([CH3:26])([CH3:27])[CH3:28])[n:29][c:30]2[n:31]1.CO[CH:4](OC)[N:2]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH:4]=[N:5][c:6]1[n:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[c:13]([Cl:1... | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl.COC(OC)N(C)C | CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1ccc(-c2cnc3ncncc3c2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[NH2;D1;+0:9]):[#7;a:10]:[c:11]>>[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4]):[#7;a:10]:[c:11] | null | [] | null | null | null | null | 1-[2-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea from Example 3 was reacted with DMF dimethyl acetal for 13.5 hours as described in Example 78. Workup as described above, followed by purification on flash silica gel chromatography eluting sequentially with 100:0, 3:1, 1:1, and 0:100 dichl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl.COC(OC)N(C)C>>CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(NC(=O)NC(C)(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a307a99b72164a51b19fd145458a144d | COC(OC)N(C)C.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.CN(C)C(OC)OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)N=CN(C)C)N=C1N=CN(C)C | O([CH3:1])[CH:22](O[CH3:24])[N:2]([CH3:3])[CH3:4].[NH2:5][c:6]1[n:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[Cl:19])[c:20]([NH2:21])[n:26][c:27]2[n:28]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[N:5][c:6]1[n:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[Cl:19])... | COC(OC)N(C)C.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6baa63c8b4d9961e0f6bda8591341abc659a8cefc6b5cf264925a8aad45b2265 | 6b77b78b381a809bbd9ce9b668f84f1964e16ba55dd802e95251ba5b52e9eefc | c1ccc(-c2cnc3ncncc3c2)cc1 | [C;D1;H3:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:3])-[CH;D3;+0:4](-O-[CH3;D1;+0:5])-O-[CH3;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]:[#7;a:12]:[c:13](-[NH2;D1;+0:14]):[#7;a:15]:[c:16]>>[C;D1;H3:17]-[#7:18](-[CH3;D1;+0:6])-[CH;D2;+0:4]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]:[#7;a:12]:[c:13](-[N;H0;D2;+0:14]=[CH... | null | [] | null | null | null | null | 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 was reacted with DMF dimethyl acetal for 23 hours as described in Example 78. Workup as described above followed by purification on flash silica gel chromatography eluting sequentially with 100:0, 9:1, 4:1, and 7:3 ethyl acetate:methanol gave an ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Primary amine.Tertiary amine | Tertiary amine.Tertiary amine | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | COC(OC)N(C)C.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CN(C)C=Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N=CN(C)C)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8da630abf3734058b3c2ab512c708bab | N#CCc1ccccc1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3ccccc3)c(N)nc2n1 | C1(=CC=CC=C1)CC#N.NC1=NC=C(C(=N1)N)C=O>>C1(=CC=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14]#[N:15].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:18][c:17]1[NH2:16]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:14]([NH2:15])[n:16][c:17]2[n:18]1 | N#CCc1ccccc1.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3ccccc3)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12](:[c:13]:[c:14])... | null | [] | null | null | null | null | Following the procedure of Example 1, phenylacetonitrile was reacted with 2,4-diamino-5-pyrimidinecarboxaldehyde to give the title compound; mp 317°-318° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | N#CCc1ccccc1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3ccccc3)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb55381982674218abb1b1e6f7a008fd | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccccc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccccc1 | C1(=CC=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=CC=C2)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccccc3)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccccc1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | Following the procedure of Example 2, 0.246 g of 6-phenyl-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 81 was reacted with 0.128 mL of tert-butyl isocyanate. The product is purified by medium pressure chromatography using silica gel and eluting with a gradient of 1:1 CHCl3 :EtOAc to EtOAc to afford the title compou... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccccc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8c13763cc914441818511d7ea59651a | N#CCc1cccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1 | ClC1=C(C=CC=C1Cl)CC#N.NC1=NC=C(C(=N1)N)C=O>>ClC1=C(C=CC=C1Cl)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[c:14]1[Cl:15])[C:16]#[N:17].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:20][c:19]1[NH2:18]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([Cl:13])[c:14]3[Cl:15])[c:16]([NH2:17])[n:18][c:19]2[n:20]1 | N#CCc1cccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16]:[c:17]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[n;H0;D2;+0:8]:[... | null | [] | null | null | null | null | Following the procedure of Example 1, 2,3-dichlorophenylacetonitrile was reacted with 2,4-diamino-5-pyrimidinecarboxaldehyde to give the title compound; mp 366°-369° C. (dec).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | N#CCc1cccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9b59e62182af43278d1cf7bf128220cd | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccc(Cl)c1Cl | ClC1=C(C=CC=C1Cl)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C(=CC=C2)Cl)Cl)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21][cH:22][cH:23][c:24]([Cl:25])[c:26]1[Cl:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccc(Cl)c1Cl | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | Following the general procedure of Example 2, 0.502 g of 6-(2,3-dichlorophenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 83 was reacted with 0.206 mL of tert-butyl isocyanate. The product is purified by silica gel chromatography eluting with a gradient of CHCl3 :EtOAc (98:2) to CHCl3 :EtOAc (1:2) to afford the ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccc(Cl)c3Cl)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccc(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf51f18e6d724e79a90be7ff7f0aee82 | N#CCc1c(Cl)ccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1 | ClC1=C(C(=CC=C1Cl)Cl)CC#N.NC1=NC=C(C(=N1)N)C=O>>ClC1=C(C(=CC=C1Cl)Cl)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[c:9]([Cl:10])[cH:11][cH:12][c:13]([Cl:14])[c:15]1[Cl:16])[C:17]#[N:18].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:21][c:20]1[NH2:19]>>[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][c:13]([Cl:14])[c:15]3[Cl:16])[c:17]([NH2:18])[n:19][c:20]2[n:21]1 | N#CCc1c(Cl)ccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 1.0 g of (2,3,6-trichloro)-phenyl-acetonitrile and 0.6 g of 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 320°-322° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | N#CCc1c(Cl)ccc(Cl)c1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5063b3f8c14448a99f32b694931ab7f1 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)ccc(Cl)c1Cl | ClC1=C(C(=CC=C1Cl)Cl)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C(=CC=C2Cl)Cl)Cl)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([Cl:26])[c:27]1[Cl:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)ccc(Cl)c1Cl | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The procedure of Example 2 was followed to react 0.30 g of 6-(2,3,6-trichloro-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 85 with tert-butyl isocyanate (0.108 mL). The product is purified by medium pressure chromatography (MPLC) using silica gel and eluting with 1:1 CHCl3 :EtOAc to afford the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)ccc(Cl)c3Cl)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)ccc(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f181ec7fa91846eca2529e969dd97cf0 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(F)cccc3F)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(F)cccc1F | FC1=C(C(=CC=C1)F)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O.N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2F)F)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[c:21]([F:22])[cH:23][cH:24][cH:25][c:26]1[F:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(F)cccc3F)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(F)cccc1F | null | null | C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.25 g of 6-(2,6-difluoro-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 63 and 0.112 mL of tert-butyl isocyanate according to Example 2. The product was purified by MPLC eluting with a gradient of CHCl3 :EtOAc (1:1) to EtOAc to afford the pure product; mp >300° C., CIMS (... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | C | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(F)cccc3F)c(N)nc2n1>C>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(F)cccc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ab63274be3c343d394a72d185205b8f1 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Br)cccc1Br | BrC1=C(C(=CC=C1)Br)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Br)Br)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[c:21]([Br:22])[cH:23][cH:24][cH:25][c:26]1[Br:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Br)cccc1Br | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.25 g of 6-(2,6-dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 60 and 0.077 mL of tert-butyl isocyanate according to Example 2. The product was purified by MPLC eluting with a gradient of CHCl3 :EtOAc (1:1) to EtOAc to afford the pure product; mp >300° C. (dec).
C... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Br)cccc3Br)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Br)cccc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-98fd6ea357a243d78e0bdcc503d56dcd | CC(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CC(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.C(C)(C)N=C=O.N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)NC(=O)NC(C)C | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH2:7][c:8]1[n:9][c:10]2[n:11][c:12]([NH2:13])[n:14][cH:15][c:16]2[cH:17][c:18]1-[c:19]1[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]1[Cl:26]>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[NH:7][c:8]1[n:9][c:10]2[n:11][c:12]([NH2:13])[n:14][cH:15][c:16]2[cH:17][c:18]1-[c:19]1[c:20]([Cl... | CC(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CC(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | null | null | C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[N;H0;D2;+0:10]=[C;H0;D2;+0:11]=[O;D1;H0:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[NH;D2;+0:10]-[C:8](-[C;D1;H3:7])-[C;D1;H3:9]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.5 g of 6-(2,6-dichlorophenyl)-pyrido{2,3-d]pyrimidine-2,7-diamine from Example 1 and 0.172 mL of isopropyl isocyanate according to Example 2. The product was purified by MPLC eluting with a gradient of CHCl3 :EtOAc (1:1) to afford the pure product; mp 184°-188° C., CIMS (1% ammoni... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | C | null | null | CC(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>C>CC(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1548a866caff46c6ae756f22bc4ec8be | Cc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1>>Cc1ccccc1-c1cc2cnc(N)nc2nc1N | CC1=C(CC#N)C=CC=C1.NC1=NC=C(C(=N1)N)C=O>>C1(=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][C:18]#[N:19].O=[CH:9][c:10]1[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]1[NH2:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]2[n:17][c:18]1[NH2:19] | Cc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1 | Cc1ccccc1-c1cc2cnc(N)nc2nc1N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16]:[c:17]>>[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[n;H0;D2;+0:8]:[c;... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 2-methylbenzyl cyanide and 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 300°-302° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | Cc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1>>Cc1ccccc1-c1cc2cnc(N)nc2nc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-402f050ecfe844a4a9c4948e241fc170 | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N>>Cc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C | C1(=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N)C.C(C)(C)(C)N=C=O.N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2)C)NC(=O)NC(C)(C)C | [C:20](=[O:21])=[N:22][C:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]2[n:17][c:18]1[NH2:19]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]2[n:17][c:18]1[NH:19][C:20](=[O... | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N | Cc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C | null | null | C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 6-o-tolyl-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 90 and tert-butyl isocyanate according to Example 2. The product was purified by MPLC eluting with CHCl3 :EtOAc (1:1) afford the pure product; mp 195°-197° C., CIMS (1% ammonia in methane): m/z (relative intensity) 351 (MH+ ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | C | null | null | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N>C>Cc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91ea30b3e47b401fb2ab322e9d64acea | Cc1cccc(CC#N)c1C.Nc1ncc(C=O)c(N)n1>>Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C | CC1=C(C=CC=C1C)CC#N.NC1=NC=C(C(=N1)N)C=O>>CC1=C(C=CC=C1C)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][C:17]#[N:18])[c:19]1[CH3:20].O=[CH:8][c:9]1[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[NH2:18])[c:19]1[CH3:20] | Cc1cccc(CC#N)c1C.Nc1ncc(C=O)c(N)n1 | Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16]:[c:17]>>[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[n;H0;D2;+0:8]:[c;... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 2,3-dimethylphenylacetonitrile and 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 330°-333° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | Cc1cccc(CC#N)c1C.Nc1ncc(C=O)c(N)n1>>Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05b4c1e1bd144a7cb6cd10e428c21328 | CC(C)(C)N=C=O.Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C>>Cc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C | CC1=C(C=CC=C1C)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C(=CC=C2)C)C)NC(=O)NC(C)(C)C | [C:19](=[O:20])=[N:21][C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[NH2:18])[c:26]1[CH3:27]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[NH:18][C:19](=... | CC(C)(C)N=C=O.Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C | Cc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.5007 g of 6-(2,3-dimethyl-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 92 and 0.23 mL tert-butyl isocyanate according to Example 2. The product was purified by MPLC eluting with a gradient of CHCl3 :EtOAc (2:1) to CHCl3 :EtOAc (1:1); mp 326°-330° C., MS(CI).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.Cc1cccc(-c2cc3cnc(N)nc3nc2N)c1C>>Cc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-779916ef9f6645fd852eee00cd88177c | Cc1cc(C)cc(CC#N)c1.Nc1ncc(C=O)c(N)n1>>Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1 | CC=1C=C(C=C(C1)C)CC#N.NC1=NC=C(C(=N1)N)C=O>>CC=1C=C(C=C(C1)C)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][C:18]#[N:19])[cH:20]1.O=[CH:9][c:10]1[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]1[NH2:17]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH2:19])[cH:20]1 | Cc1cc(C)cc(CC#N)c1.Nc1ncc(C=O)c(N)n1 | Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12](:[c:13]:[c:14])... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 2.0 g of 3,5-dimethylphenyl-acetonitrile and 1.81 g of 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 298°-302° C., MS(CI).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | Cc1cc(C)cc(CC#N)c1.Nc1ncc(C=O)c(N)n1>>Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f03d647d1d394659beb1e6de74a454ce | CC(C)(C)N=C=O.Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1>>Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 | CC=1C=C(C=C(C1)C)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC(=CC(=C2)C)C)NC(=O)NC(C)(C)C | [C:20](=[O:21])=[N:22][C:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH2:19])[cH:27]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH:... | CC(C)(C)N=C=O.Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1 | Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.3 g of 6-(3,5-dimethyl-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 94 and 0.14 mL of tert-butyl isocyanate according to Example 2. The product is purified by MPLC eluting with 1:1 CHCl3 :EtOAc; mp 180°-182° C., CIMS (1% ammonia in methane): m/z (relative intensity) 36... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2N)c1>>Cc1cc(C)cc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eedfd839ca854dbab9b143c699ca72ca | Cc1cc(C)c(CC#N)c(C)c1.Nc1ncc(C=O)c(N)n1>>Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1 | CC1=C(CC#N)C(=CC(=C1)C)C.NC1=NC=C(C(=N1)N)C=O.N>>CC1=C(C(=CC(=C1)C)C)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][C:17]#[N:18])[c:19]([CH3:20])[cH:21]1.O=[CH:8][c:9]1[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]1[NH2:16]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[NH2:18])[c:19]([CH3:20])[cH:21]1 | Cc1cc(C)c(CC#N)c(C)c1.Nc1ncc(C=O)c(N)n1 | Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1 | null | null | C | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[C;D1;H3:17]):[c:18]>>[C;D1;H3:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[n;... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 0.915 g of 2,4,6-trimethyl-benzyl cyanide and 0.76 g of 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 276°-282° C.; CIMS (1% ammonia in methane): m/z (relative intensity) 279 (MH+, 54), 280 (MH+ +1, 100).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | C | null | null | Cc1cc(C)c(CC#N)c(C)c1.Nc1ncc(C=O)c(N)n1>C>Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48bb0cbfb35c4f2d93ffd1055607d342 | CC(C)(C)N=C=O.Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1>>Cc1cc(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c(C)c1 | CC1=C(C(=CC(=C1)C)C)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=C(C=C2C)C)C)NC(=O)NC(C)(C)C | [C:19](=[O:20])=[N:21][C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[NH2:18])[c:26]([CH3:27])[cH:28]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[N... | CC(C)(C)N=C=O.Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1 | Cc1cc(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c(C)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.25 g of 6-(2,4,6-trimethyl-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 96 and 0.109 mL of tert-butyl isocyanate according to Example 2. The product was purified by medium pressure liquid chromatography eluting with 1:1 CHCl3 :EtOAc; mp 281°-297° C.; CIMS (1% ammonia i... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.Cc1cc(C)c(-c2cc3cnc(N)nc3nc2N)c(C)c1>>Cc1cc(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c69ff002447f448f808b08dbb0ba58fb | CC(C)(C)N=C=O.Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2N)c1C>>Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C | CC1=C(C(=C(C=C1C)C)C)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C(=CC(=C2C)C)C)C)NC(=O)NC(C)(C)C | [C:21](=[O:22])=[N:23][C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]3[n:18][c:19]2[NH2:20])[c:28]1[CH3:29]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[n:16... | CC(C)(C)N=C=O.Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2N)c1C | Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.3 g of 6-(2,3,5,6-tetramethyl-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 98 and 0.125 mL of tert-butyl isocyanate according to Example 2. The product was purified by medium pressure liquid chromatography eluting with 1:1CHCl3 :EtOAc; mp >300° C.; CIMS (1% ammonia in ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2N)c1C>>Cc1cc(C)c(C)c(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-74d6fcc0722a4bd7bcda26708f3e9dee | COc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1>>COc1ccccc1-c1cc2cnc(N)nc2nc1N | COC1=C(CC#N)C=CC=C1.NC1=NC=C(C(=N1)N)C=O>>COC1=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:19]#[N:20].O=[CH:10][c:11]1[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]1[NH2:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[n:18][c:19]1[NH2:20] | COc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1 | COc1ccccc1-c1cc2cnc(N)nc2nc1N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[#8:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16]:[c:17]>>[#8:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[n;H0;D2;+0:8]:[c;H0;D3;+0:1... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 2-methoxybenzyl cyanide and 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 304°-306° C. (dec).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | COc1ccccc1CC#N.Nc1ncc(C=O)c(N)n1>>COc1ccccc1-c1cc2cnc(N)nc2nc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-79172b828eed4860b302bd1140b5d8e1 | CC(C)(C)N=C=O.COc1ccccc1-c1cc2cnc(N)nc2nc1N>>COc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C | COC1=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2)OC)NC(=O)NC(C)(C)C | [C:21](=[O:22])=[N:23][C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[n:18][c:19]1[NH2:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[n:18][c:19]1[NH:2... | CC(C)(C)N=C=O.COc1ccccc1-c1cc2cnc(N)nc2nc1N | COc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.203 g of 6-(2-methoxy-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 100 and 0.093 mL of tert-butyl isocyanate according to Example 2. The product was purified by medium pressure liquid chromatography eluting with 1:1CHCl3 :EtOAc; mp 300°-301° C.; CIMS (1% ammonia in met... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.COc1ccccc1-c1cc2cnc(N)nc2nc1N>>COc1ccccc1-c1cc2cnc(N)nc2nc1NC(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa8564de9b1f4376bd8bb985447ab6eb | COc1cccc(CC#N)c1.Nc1ncc(C=O)c(N)n1>>COc1cccc(-c2cc3cnc(N)nc3nc2N)c1 | COC=1C=C(CC#N)C=CC1.NC1=NC=C(C(=N1)N)C=O>>COC=1C=C(C=CC1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][C:18]#[N:19])[cH:20]1.O=[CH:9][c:10]1[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]1[NH2:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH2:19])[cH:20]1 | COc1cccc(CC#N)c1.Nc1ncc(C=O)c(N)n1 | COc1cccc(-c2cc3cnc(N)nc3nc2N)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12](:[c:13]:[c:14])... | null | [] | null | null | null | null | The title compound was prepared according to Example 1, starting from 3-methoxybenzyl cyanide and 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 284°-286 ° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | COc1cccc(CC#N)c1.Nc1ncc(C=O)c(N)n1>>COc1cccc(-c2cc3cnc(N)nc3nc2N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2cf9bbec5bb141e9ab82db85d13180a8 | CC(C)(C)N=C=O.COc1cccc(-c2cc3cnc(N)nc3nc2N)c1>>COc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 | COC=1C=C(C=CC1)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC(=CC=C2)OC)NC(=O)NC(C)(C)C | [C:20](=[O:21])=[N:22][C:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH2:19])[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]3[n:17][c:18]2[NH:19][C:... | CC(C)(C)N=C=O.COc1cccc(-c2cc3cnc(N)nc3nc2N)c1 | COc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from 0.50 g of 6-(3-methoxy-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 102 and 0.23 mL tert-butyl isocyanate according to Example 2. The product was purified by medium pressure liquid chromatography eluting with a gradient of CHCl3 :EtOAc (2:1) to CHCl3 :EtOAc (1:1) to EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | null | null | null | CC(C)(C)N=C=O.COc1cccc(-c2cc3cnc(N)nc3nc2N)c1>>COc1cccc(-c2cc3cnc(N)nc3nc2NC(=O)NC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2dc98d8590054382bf5219d4a3442d75 | N#CCc1c(Cl)cccc1Br.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1 | BrC1=C(C(=CC=C1)Cl)CC#N.NC1=NC=C(C(=N1)N)C=O>>BrC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]1[Br:15])[C:16]#[N:17].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:20][c:19]1[NH2:18]>>[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[Br:15])[c:16]([NH2:17])[n:18][c:19]2[n:20]1 | N#CCc1c(Cl)cccc1Br.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Br;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Br;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | null | [] | null | null | null | null | Prepared as described in Example 1, starting from 1.0 g of 2-bromo-6-chlorophenylacetonitrile and 0.57 g of 2,4-diamino-5-pyrimidine-carboxaldehyde, mp 264°-280° C.; MS(CI).
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | N#CCc1c(Cl)cccc1Br.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e93aa3e0e454f9b818344212ecfd465 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Br | BrC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Br)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]1[Br:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Br | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | The title compound was prepared using 0.30 g of 6-(2-bromo-6-chloro-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 104 and 0.105 mL of tert-butyl isocyanate according to Example 2. The product was purified by MPLC eluting with 1:1CHCl3 :EtOAc; mp 314° C. (dec); MS(CI).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3c(Cl)cccc3Br)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-587171f404ec4562b7f202a047a9a693 | CCCS(=O)(=O)Cl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>>CCCS(=O)(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | C(CC)S(=O)(=O)Cl.NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N.[H-].[Na+]>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)NS(=O)(=O)CCC | Cl[S:4]([CH2:3][CH2:2][CH3:1])(=[O:5])=[O:6].[NH2:7][c:8]1[n:9][c:10]2[n:11][c:12]([NH2:13])[n:14][cH:15][c:16]2[cH:17][c:18]1-[c:19]1[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]1[Cl:26]>>[CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[NH:7][c:8]1[n:9][c:10]2[n:11][c:12]([NH2:13])[n:14][cH:15][c:16]2[cH:17][c:18]1-[c:19]1[c:2... | CCCS(=O)(=O)Cl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | CCCS(=O)(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl | null | null | CN(C)C=O | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(-c2cnc3ncncc3c2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[NH;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]):[c:11] | null | [] | null | null | 1 | HOUR | To a slurry of 1.00 g of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 in 15 mL of DMF was added 0.15 g sodium hydride (60% in mineral oil) portionwise and the mixture stirred for 1 hour. Propanesulfonyl chloride (0.39 mL) is added dropwise, and the reaction mixture stirred at ambient temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cnc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | null | 1 | CCCS(=O)(=O)Cl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1>CN(C)C=O>CCCS(=O)(=O)Nc1nc2nc(N)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a76dcd362764370a4ab0d70f23633f8 | N#CCc1cccnc1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3cccnc3)c(N)nc2n1 | N1=CC(=CC=C1)CC#N.NC1=NC=C(C(=N1)N)C=O>>N1=CC(=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1)[C:14]#[N:15].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:18][c:17]1[NH2:16]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][n:12][cH:13]3)[c:14]([NH2:15])[n:16][c:17]2[n:18]1 | N#CCc1cccnc1.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3cccnc3)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1cncc(-c2cnc3ncncc3c2)c1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]:[c:16]:[c:17]:1>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12]1:[c:... | null | [] | null | null | null | null | The procedure of Example 1 was followed to react 3-pyridylacetonitrile and 2,4-diamino-5-pyrimidine-carboxaldehyde to afford the title compound; mp 317°-319° C. (dec).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccncc1 | HO- | null | null | null | N#CCc1cccnc1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3cccnc3)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc8c8ca81e37430d86a55fa62768c787 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccnc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccnc1 | N1=CC(=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C=2C=NC=CC2)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21]... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccnc3)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccnc1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1cncc(-c2cnc3ncncc3c2)c1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | By following the procedure of Example 2, 0.30 g of 2,7-diamino-6-(3-pyridyl)-pyrido[2,3-d]pyrimidine from Example 107 was reacted with 0.16 mL of tert-butyl isocyanate. The product was purified by medium pressure chromatography using silica gel and eluting with 90:10:1EtOAc:MeOH:TEA to afford the title compound; mp >30... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccncc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3cccnc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bdd2ed9a9fea4fb5aa31a3576cfe1141 | N#CCc1ccncc1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3ccncc3)c(N)nc2n1 | [H-].[Na+].Cl.N1=CC=C(C=C1)CC#N.N1=CC=C(C=C1)CC#N.C(C)OCC[O-].[Na+].NC1=NC=C(C(=N1)N)C=O>>N1=CC=C(C=C1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[C:14]#[N:15].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:18][c:17]1[NH2:16]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[c:14]([NH2:15])[n:16][c:17]2[n:18]1 | N#CCc1ccncc1.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3ccncc3)c(N)nc2n1 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1cc(-c2cnc3ncncc3c2)ccn1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12]1:[c:... | null | [] | null | null | 10 | MINUTE | To cooled (0° C.) 2-ethoxyethanol (13 mL) was added portionwise 0.30 g of sodium hydride (60% in mineral oil), and the suspension was stirred for 10 minutes. To this suspension was added 1.06 g of 4-pyridylaceto-nitrile hydrochloride, and the mixture was stirred at room temperature for 30 minutes. The neutralized solut... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccncc1 | HO- | C(C)OCCO | null | 0.166667 | N#CCc1ccncc1.Nc1ncc(C=O)c(N)n1>C(C)OCCO>Nc1ncc2cc(-c3ccncc3)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-538f0bbbc6f24db58b5cc24a0e7e9419 | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccncc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccncc1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=NC=C2)N.C(C)(C)(C)N=C=O>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=NC=C2)NC(=O)NC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH2:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[NH:8][c:9]1[n:10][c:11]2[n:12][c:13]([NH2:14])[n:15][cH:16][c:17]2[cH:18][c:19]1-[c:20]1[cH:21]... | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccncc3)c(N)nc2n1 | CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccncc1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1cc(-c2cnc3ncncc3c2)ccn1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:6] | null | [] | null | null | null | null | Following the procedure of Example 2, 0.30 g of 2,7-diamino-6-(4-pyridyl)-pyrido[2,3-d]pyrimidine from Example 109 was reacted with 0.154 mL of tert-butyl isocyanate. The product was purified by medium pressure chromatography using silica gel and eluting with 90:10:1 EtOAc:MeOH:TEA, to afford the title compound, mp >35... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccncc1 | null | null | null | null | CC(C)(C)N=C=O.Nc1ncc2cc(-c3ccncc3)c(N)nc2n1>>CC(C)(C)NC(=O)Nc1nc2nc(N)ncc2cc1-c1ccncc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1d437903b7d7465cbd657fadc7a517dd | N#CCc1ccccn1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3ccccn3)c(N)nc2n1 | N1=C(C=CC=C1)CC#N.NC1=NC=C(C(=N1)N)C=O>>N1=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N=C1N | [CH2:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1)[C:14]#[N:15].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:18][c:17]1[NH2:16]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14]([NH2:15])[n:16][c:17]2[n:18]1 | N#CCc1ccccn1.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3ccccn3)c(N)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)nc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[NH2;D1;+0:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:11]:1-[c;H0;D3;+0:12](:[#7;a:13]:[... | null | [] | null | null | null | null | The procedure of Example 1 was followed to react 0.84 mL of 2-pyridylacetonitrile and 1.0 g of 2,4-diamino-5-pyrimidinecarboxaldehyde to afford the title compound, mp 312°-321° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccncc1 | HO- | null | null | null | N#CCc1ccccn1.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3ccccn3)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dab042d9b57c40d48f4e99770ca752dd | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCN=C=O>>CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | Cl.C[Si](N[Si](C)(C)C)(C)C.[K].ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1N.C(C)N=C=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN(CC)CC)N=C1NC(=O)NCC | [NH2:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[n:22][cH:23][c:24]2[cH:25][c:26]1-[c:27]1[c:28]([Cl:29])[cH:30][cH:31][cH:32][c:33]1[Cl:34].[CH3:1][CH2:2][N:3]=[C:4]=[O:5]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH:12][... | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCN=C=O | CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(-c2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7]):[c:6] | null | [] | null | null | 30 | MINUTE | To a cooled (5° C.) solution of 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (0.61 g) from Example 53 in THF (6 mL) was added potassium hexamethyldisilazane (0.308 g) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for 30 minutes. Then et... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cnc2ncncc2c1.c1ccccc1 | null | C1CCOC1 | null | 0.5 | CCN(CC)CCCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCN=C=O>C1CCOC1>CCNC(=O)Nc1nc2nc(NCCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c27caf508a841fda99b0fa1d4d3b784 | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCSC(=NC(=O)OC(C)(C)C)N(CC)C(=O)OC(C)(C)C>>CCN=C(N)Nc1nc2nc(NCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl.[H-].[Na+].NC=1C(=CC2=C(N=C(N=C2)NCCCN(CC)CC)N1)C1=C(C=CC=C1Cl)Cl.CC(C)(C)OC(N)=O.C(C)(C)(C)OC(=O)N(C(SCC)=NC(=O)OC(C)(C)C)CC.N1=C(C=CC=C1C)C.FC(S(=O)(=O)O[Si](C)(C)C)(F)F.C([O-])(O)=O.[Na+]>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN(CC)CC)N=C1NC(=NCC)N | [NH2:6][c:7]1[n:8][c:9]2[n:10][c:11]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[n:21][cH:22][c:23]2[cH:24][c:25]1-[c:26]1[c:27]([Cl:28])[cH:29][cH:30][cH:31][c:32]1[Cl:33].CCS[C:4]([N:3](C(=O)OC(C)(C)C)[CH2:2][CH3:1])=[N:5]C(=O)OC(C)(C)C>>[CH3:1][CH2:2][N:3]=[C:4]([NH2:5])[NH:6][c:7]1[n:8]... | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCSC(=NC(=O)OC(C)(C)C)N(CC)C(=O)OC(C)(C)C | CCN=C(N)Nc1nc2nc(NCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl | null | null | ClCCl.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 700feb28a74e6c460c615b00fab7d5a7d0cf355bbef6492277ff27578a3af127 | a696dc8158c7e216b5b37327aa457956784ed7f1b0c386ee665b6ceb07f07277 | c1ccc(-c2cnc3ncncc3c2)cc1 | C-C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-C(=O)-O-C(-C)(-C)-C)-[N;H0;D3;+0:3](-[C:4]-[C;D1;H3:5])-C(=O)-O-C(-C)(-C)-C.[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[N;H0;D2;+0:3]-[C:4]-[C;D1;H3:5]):[c:11] | 14.3 | [{"value": 14.3, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN(CC)CC)N=C1NC(=NCC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 7-amino-6-(2,6-dichlorophenyl)-2-(3-diethylamino-propylamino)-pyrido[2,3-d]pyrimidine (42 mg) from Example 20 in DMF (1 mL) was added 60% sodium hydride suspension (5 mg), and the mixture was stirred at room temperature for 0.5 hour. To the reaction mixture was added N,N'-Bis(tert-butoxycarbonyl)-N-(et... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Primary amine.Monosulfide.Boc.Boc | Primary amine.Secondary amine | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | ClCCl.CN(C)C=O | null | 0.5 | CCN(CC)CCCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1.CCSC(=NC(=O)OC(C)(C)C)N(CC)C(=O)OC(C)(C)C>ClCCl.CN(C)C=O>CCN=C(N)Nc1nc2nc(NCCCN(CC)CC)ncc2cc1-c1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d120900bcd1d4b5b9cba3cd8953676b0 | O=C1Nc2sccc2Cn2cccc21>>c1cc2n(c1)Cc1ccsc1NC2 | O=C1C=2N(CC3=C(N1)SC=C3)C=CC2.[B].CSC>>S1C=CC2=C1NCC=1N(C2)C=CC1 | O=[C:13]1[c:3]2[cH:2][cH:1][cH:5][n:4]2[CH2:6][c:7]2[cH:8][cH:9][s:10][c:11]2[NH:12]1>>[cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[cH:8][cH:9][s:10][c:11]1[NH:12][CH2:13]2 | O=C1Nc2sccc2Cn2cccc21 | c1cc2n(c1)Cc1ccsc1NC2 | null | null | null | Reduction | Reduction of secondary amides to amines | 9e91eacb74cbbf4130abb8d9752cfa9ba051e175e09dfd15ba3bdc56e16af65a | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1cc2n(c1)Cc1ccsc1NC2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[#16;a:4])-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9]>>[#16;a:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9] | null | [] | null | null | null | null | The synthesis of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepin-9-one ##STR143## is reported by F. Povazunec, B. Decroix and J. Morel, J. Het. Chem. 29, 1507(1992) and is reduced to give the tricyclic heterocycle 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine. ##STR144## The tricyclic 5,10-dihydro-4H-p... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cc2n(c1)Cc1ccsc1NC2 | c1cc2n(c1)Cc1ccsc1NC2 | c1cc2n(c1)Cc1ccsc1NC2 | Other | null | null | null | O=C1Nc2sccc2Cn2cccc21>>c1cc2n(c1)Cc1ccsc1NC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95eb3d169e474576a6d1ab68db567bf1 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cccc(F)c1F>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cccc(F)c1F | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.FC1=C(C(=O)Cl)C=CC=C1F.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC=C1)F)F)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][cH:29][c:30]([F:31])[c:32]1[F:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][c... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cccc(F)c1F | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cccc(F)c1F | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 13.7 | [{"value": 13.7, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC=C1)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.350 g of 2,3-difluorobenzoyl chloride in 5 ml of methylene chloride is added 0.346 ml of triethylamine. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours. The reaction mixture is filtere... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl | null | 0.05 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cccc(F)c1F>C(Cl)Cl>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cccc(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-356e4250fa99402a9ddf384789be3f77 | COc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>COc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.COC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)OC)=O | Cl[C:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13]... | COc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | COc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 59.6 | [{"value": 59.6, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.362 g of 2-methoxybenzoyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 18 hours at room temperature. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | COc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>COc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c90afcddae0140da8c78ba26df0ff270 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C=1C=CN2C1CNC1=C(C2)C=CC=C1.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC>>CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC=C1 | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:32][cH:31]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23]2[CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 131.1 | [{"value": 131.1, "product": "CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | MINUTE | To a mixture of 1.93 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.13 ml of triethylamine. After stirring for 3 minutes, a mixture of 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 5 ml of methylene chloride is added. The cooling bath is remov... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | 0 | 0.05 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e47f1ffed9849499b9c294ce8e76732 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)ccc1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)ccc1Cl | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.ClC1=C(C(=O)Cl)C=C(C=C1)Cl.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC(=C1)Cl)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][c:28]([Cl:29])[cH:30][cH:31][c:32]1[Cl:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13]... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)ccc1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)ccc1Cl | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 35 | [{"value": 35.0, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC(=C1)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 414.5 mg of 2,5-dichlorobenzoyl chloride in 5 ml of methylene chloride is added 276 μl of triethylamine. After stirring at 0° C. for 3 minutes 400 mg of the 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 3 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)ccc1Cl>C(Cl)Cl.C(C)(=O)OCC>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)ccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-27e8f2b8906a42fb97a235b7a925cc8e | Cc1ccsc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1ccsc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.CC1=C(SC=C1)C(=O)Cl.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C=1SC=CC1C | Cl[C:7]([c:6]1[c:2]([CH3:1])[cH:3][cH:4][s:5]1)=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[CH2:17][c:18]3[cH:19][cH:20][cH:21][n:22]3[CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15]... | Cc1ccsc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1ccsc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 113.5 | [{"value": 113.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C=1SC=CC1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a solution of 318 mg of 3-methyl-2-thiophenecarbonyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of the 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | Cc1ccsc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1ccsc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35f83a206245410e867603ca398e5466 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.ClC1=C(C(=O)Cl)C=CC(=C1)Cl.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][c:32]1[Cl:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13]... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 53.5 | [{"value": 53.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a solution of 415 mg of 2,4-dichlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 0.05 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>C(Cl)Cl.C(C)(=O)OCC>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30afe811bcc64b1893cb0de1def7b791 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1Cl | ClC1=C(C(=O)Cl)C=CC=C1.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1Cl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 72.1 | [{"value": 72.1, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a solution of 347 mg of 2-chlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamineo After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl | null | 0.05 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1Cl>C(Cl)Cl>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91c60168886c4ed1b4061e458c59eaf4 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1F>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1F | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.FC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)F)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[F:32]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][c... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1F | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1F | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 88.4 | [{"value": 88.4, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a solution of 314 mg of 2-fluorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl | null | 0.05 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1ccccc1F>C(Cl)Cl>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55fec56560e9482e9d9c7fdf722ba15c | CN(C)C=O.O=[N+]([O-])c1ccccc1-n1cccc1>>O=Cc1cccn1-c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)N1C=CC=C1.CN(C=O)C.P(=O)(Cl)(Cl)Cl.[OH-].[Na+]>>[N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)C=O | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16] | CN(C)C=O.O=[N+]([O-])c1ccccc1-n1cccc1 | O=Cc1cccn1-c1ccccc1[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 99620052917c00b5f629c60fcbc4d83feed5453722b70d63562a363e88f8a562 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-n2cccc2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[c:3]-[#7;a:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[#7;a:4]:1-[c:3] | null | [] | 90 | CELSIUS | 30 | MINUTE | To a solution of 3.76 g of 1-(2-nitrophenyl)pyrrole in 20 ml of N,N-dimethylformamide at 0° C. is added dropwise with stirring 3 ml of phosphorus oxychloride. Stirring is continued for 30 minutes and the reaction mixture is heated at 90° C. for 1 hour. After cooling to room temperature the mixture is treated with crush... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccccc1 | Other | null | 90 | 0.5 | CN(C)C=O.O=[N+]([O-])c1ccccc1-n1cccc1>>O=Cc1cccn1-c1ccccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f2ec50dbf2f74eb09d479fedd495864b | O=Cc1cccn1-c1ccccc1[N+](=O)[O-]>>c1ccc2c(c1)NCc1cccn1-2 | [N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)C=O>>C1=CC=C2N1C1=CC=CC=C1NC2 | O=[N+:7]([O-])[c:5]1[c:4](-[n:13]2[c:9]([CH:8]=O)[cH:10][cH:11][cH:12]2)[cH:3][cH:2][cH:1][cH:6]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][n:13]1-2 | O=Cc1cccn1-c1ccccc1[N+](=O)[O-] | c1ccc2c(c1)NCc1cccn1-2 | null | [Pd] | C(C)O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 6ef220715e5f189ef4aedc3f4ef437b65ff6691fc0e464447391897dde763e9e | 8d376a33ce625efea21a727d4a046134c1d759eb13efe5fa1e2683895e99352c | c1ccc2c(c1)NCc1cccn1-2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4](-[c:5]:[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]):[c:9]>>[c:3]:[c:2]1:[#7;a:4](:[c:9])-[c:5]:[c:6](:[c:8])-[NH;D2;+0:7]-[CH2;D2;+0:1]-1 | 44.5 | [{"value": 44.5, "product": "C1=CC=C2N1C1=CC=CC=C1NC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1.0 g of 1-(2-nitrophenyl)-1H-pyrrole-2-carboxaldehyde in 40 ml of ethyl alcohol and 40 ml of ethyl acetate, under argon, is added 40 mg of 10% Pd/C. The mixture is hydrogenated at 40 psi for 2 hours and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is di... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Secondary amine | null | c1ccc2c(c1)NCc1cccn12 | c1ccc2c(c1)NCc1cccn12 | Other | [Pd].C(C)O.C(C)(=O)OCC | null | 2 | O=Cc1cccn1-c1ccccc1[N+](=O)[O-]>[Pd].C(C)O.C(C)(=O)OCC>c1ccc2c(c1)NCc1cccn1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-487ac92980e343ec8d41d66e51566ec1 | CCOC(=O)c1ccc(N)cc1.Cc1ccccc1C(=O)Cl>>CCOC(=O)c1ccc(NC(=O)c2ccccc2C)cc1 | O.NC1=CC=C(C(=O)OCC)C=C1.CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>CC1=C(C(=O)NC2=CC=C(C(=O)OCC)C=C2)C=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:20][cH:21]1.Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[cH:20][cH:21]1 | CCOC(=O)c1ccc(N)cc1.Cc1ccccc1C(=O)Cl | CCOC(=O)c1ccc(NC(=O)c2ccccc2C)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 76.5 | [{"value": 76.5, "product": "CC1=C(C(=O)NC2=CC=C(C(=O)OCC)C=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 43.42 g of ethyl 4-aminobenzoate and 40.8 g of 2-methylbenzoyl chloride in 150 ml of dichloromethane is cooled in an ice bath and 26.56 g of triethylamine the solution is stirrer the addition, the solution is stirred at room temperature overnight. The mixture is poured into water and the organic layer sepa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 8 | CCOC(=O)c1ccc(N)cc1.Cc1ccccc1C(=O)Cl>ClCCl>CCOC(=O)c1ccc(NC(=O)c2ccccc2C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6a9d24539574639bdbc2294d2722940 | Cc1ccccc1C(=O)Nc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1 | CC1=C(C(=O)NC2=CC=C(C(=O)O)C=C2)C=CC=C1.S(=O)(Cl)Cl>>CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1 | O[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:19][cH:18]1)=[O:16].O=S(Cl)[Cl:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[Cl:17])[cH:18][cH:19]1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)O)cc1.O=S(Cl)Cl | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(Nc1ccccc1)c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 10.3 g of 4-[(2-methylbenzoyl)amino]benzoic acid and 32 ml of thionyl chloride is refluxed for 1.5 hours. The solution is concentrated in vacuo. Toluene is added and the solvent removed in vacuo. Toluene is added and the mixture chilled and filtered to give the desired product as a yellow solid, 135°-141° ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | Cc1ccccc1C(=O)Nc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f8be2da1ade4ec08c800b2739b8b3df | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCc1cccn1-2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.C1=CC=C2N1C1=CC=CC=C1NC2>>CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=CC=C1 | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:31][cH:30]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23]2-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCc1cccn1-2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | null | null | O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | ec52d278830efdaee8ac897d4cca585d04ae9529b1822869284bce5446c8c555 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[c:7]1:[c:8]-[#7;a:9]:[c:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[c:10]:[#7;a:9]-[c:8]:[c:7]-1:[c:6])-[c:3](:[c:4]):[c:5] | 34.4 | [{"value": 34.4, "product": "CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 0.51 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 0.36 g of 1,1'-carbonyldiimidazole in 6 ml of tetrahydrofuran is stirred at room temperature for 1 hour. To the reaction mixture is added 0.17 g of 4,5-dihydropyrrolo-[1,2-a]-quinoxaline followed by heating at reflux for 60 hours. The volatiles are c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCc1cccn12 | c1ccc2c(c1)[NH]Cc1cccn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | HCl | O1CCCC1 | null | 1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCc1cccn1-2>O1CCCC1>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3085189734d041b78484ffa27fd0825c | O=Cc1cccn1C(=O)c1ccccc1[N+](=O)[O-]>>O=C1c2ccccc2NCc2cccn21 | [N+](=O)([O-])C1=C(C(=O)N2C(=CC=C2)C=O)C=CC=C1>>C=1C=CN2C1CNC1=C(C2=O)C=CC=C1 | O=[N+:9]([O-])[c:8]1[c:3]([C:2](=[O:1])[n:15]2[c:11]([CH:10]=O)[cH:12][cH:13][cH:14]2)[cH:4][cH:5][cH:6][cH:7]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][n:15]21 | O=Cc1cccn1C(=O)c1ccccc1[N+](=O)[O-] | O=C1c2ccccc2NCc2cccn21 | null | Cl.[Pd] | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | c1a0903850e5ee790d4c072add317d49699fb5d2a58f13379b43d3709958c227 | 8d376a33ce625efea21a727d4a046134c1d759eb13efe5fa1e2683895e99352c | O=C1c2ccccc2NCc2cccn21 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4](-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[N+;H0;D3:9](=O)-[O-]):[c:10]):[c:11]>>[O;D1;H0:6]=[C:5]1-[c:7]:[c:8](:[c:10])-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]-1:[c:11] | 82.1 | [{"value": 82.1, "product": "C=1C=CN2C1CNC1=C(C2=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.75 | HOUR | A mixture of 1.5 g of N-(2-nitrobenzoyl)pyrrole-2-carboxaldehyde in 50 ml of ethyl acetate, 2 drops of concentrated HCl and 0.3 g of 10% Pd/C is shaken in a Parr apparatus under hydrogen pressure for 1.75 hours. The mixture is filtered, 0.4 g of 10% Pd/C added and the mixture shaken in a Parr apparatus under hydrogen p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Secondary amine | null | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1CN2 | Other | Cl.[Pd].C(C)(=O)OCC | null | 1.75 | O=Cc1cccn1C(=O)c1ccccc1[N+](=O)[O-]>Cl.[Pd].C(C)(=O)OCC>O=C1c2ccccc2NCc2cccn21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7175f44ac6d749ba89cb1056b6480d11 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.O=C1c2ccccc2NCc2cccn21>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3C(=O)c3ccccc32)cc1 | C=1C=CN2C1CNC1=C(C2=O)C=CC=C1.C(C)N(CC)CC.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1>>CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(C(C4=C2C=CC=C4)=O)C=CC3)C=CC=C1 | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:33][cH:32]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23]2[C:24](=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:1... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.O=C1c2ccccc2NCc2cccn21 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3C(=O)c3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3C(=O)c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7]1-[#7;a:8]:[c:9]-[C:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[c:9]:[#7;a:8]-[C:7](=[O;D1;H0:6])-[c:14]:[c:12]-1:[c:13])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 6 | HOUR | To a stirred solution of 107 mg of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one in 3 ml of methylene chloride containing 0.084 ml of triethylamine is added 165 mg of 4-[(2-methylbenzoyl)amino]benzoyl chloride and stirring continued for 6 hours. The volatiles are removed in vacuo to a residue which is purifie... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 6 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.O=C1c2ccccc2NCc2cccn21>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3C(=O)c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-541e4ed91a3e4fd299ddfcb9db583d18 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C1CCC(=O)N1Cl>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC=C1.ClN1C(CCC1=O)=O>>ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1.O=C1CCC(=O)N1[Cl:23]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:... | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C1CCC(=O)N1Cl | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Chlorination | da6523409e08baaf4e598b0486fe8fa0aaa502a3453aa872a1e66fb4f69d7901 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[C:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-[Cl;H0;D1;+0:1] | 68.8 | [{"value": 68.8, "product": "ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To an ice-water cooled suspension of 211 mg of 2-methyl-N-[4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)-phenyl]benzamide in 5 ml of tetrahydrofuran is added 67 mg of N-chlorosuccinimide followed by continued stirring in the cold for 10 minutes. The bath is removed and stirring continued for 2.25 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)Cn1cccc1C[NH]2.C1CCNC1 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HO- | O1CCCC1 | null | 0.166667 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C1CCC(=O)N1Cl>O1CCCC1>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cd1f0dfdfdae4d4a90baca0886e63208 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C1CCC(=O)N1Cl>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3-c3ccccc32)cc1 | CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=CC=C1.ClN1C(CCC1=O)=O>>CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CC=3N(C4=CC=CC=C24)C(=CC3)Cl)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:24]3-[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1.O=C1CCC(=O)N1[Cl:23]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:... | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C1CCC(=O)N1Cl | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3-c3ccccc32)cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Chlorination | 22f32870a37b98eae1f49bd00f4d9d712ddcc6449754f25e7754c82edd15c879 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[c:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[#7;a:3]:1-[c:2] | null | [] | null | null | 10 | MINUTE | To an ice-water cooled suspension of 5 mmol of 2-methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)-phenyl]benzamide in 5 ml of tetrahydrofuran is added 5.5 mmol of N-chlorosuccinimide followed by continued stirring in the cold for 10 minutes. The bath is removed and stirring continued for 2.25 hours. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)[NH]Cc1cccn12.C1CCNC1 | c1ccc2c(c1)[NH]Cc1cccn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | HO- | O1CCCC1 | null | 0.166667 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C1CCC(=O)N1Cl>O1CCCC1>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9414b7fc6c2b4a35b0deb6bc71152998 | O=C(c1ccc(N[N+](=O)[O-])cc1)N1Cc2ccc(Cl)n2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(C3=CC=C(C=C3)N[N+](=O)[O-])=O.NN>>ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(C3=CC=C(C=C3)N)=O | O=[N+]([O-])[NH:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[n:15]3[CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]32)[cH:23][cH:24]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[n:15]3[CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:... | O=C(c1ccc(N[N+](=O)[O-])cc1)N1Cc2ccc(Cl)n2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | OtherReaction | fe527b85581211cb9016f52ce5075fcd19e925137ae670ee815f49930c328a7b | c34a0864b4cde9df22def8e26ec6eb2dcc481cc1077d7e69366e5df89d0fa8b0 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | O=[N+](-[O-])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 1 mmol of 3-chloro-10,11-dihydro-10-(4-nitroaminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 2.5 mmol of anhydrous hydrazine, 50 mg of palladium on carbon and 10 ml of ethyl alcohol is refluxed for 1.5 hours. The mixture is filtered through diatomaceous earth and the filtrate concentrated to dryness to ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc(N[N+](=O)[O-])cc1)N1Cc2ccc(Cl)n2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0324d1ccc345444c9eb2d3d9fc2f1123 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(C3=CC=C(C=C3)N)=O.C(C)N(CC)CC.CC1=C(C(=O)Cl)C=CC=C1>>ClC1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][c:22]([Cl:23])[n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | A mixture of 1 mmol of 3-chloro-10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 2 mmol of triethylamine, and 1.1 mmol of 2-methylbenzoylchloride in 8 ml of dichloromethane is stirred at room temperature overnight. The mixture is washed with water, and 1M NaHCO3 and dried(Na2 SO4). The solvent is... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | ClCCl | null | 8 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1>ClCCl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccc(Cl)n3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6cf1c224c2e047dda0712160d1f7fd19 | O=Cc1cccn1Cc1ccccc1[N+](=O)[O-]>>c1ccc2c(c1)Cn1cccc1CN2 | [N+](=O)([O-])C1=C(CN2C(=CC=C2)C=O)C=CC=C1>>C=1C=CN2C1CNC1=C(C2)C=CC=C1 | O=[CH:13][c:12]1[n:8]([CH2:7][c:5]2[c:4]([N+:14](=O)[O-])[cH:3][cH:2][cH:1][cH:6]2)[cH:9][cH:10][cH:11]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][n:8]1[cH:9][cH:10][cH:11][c:12]1[CH2:13][NH:14]2 | O=Cc1cccn1Cc1ccccc1[N+](=O)[O-] | c1ccc2c(c1)Cn1cccc1CN2 | null | [Pd] | C(C)O.C(Cl)Cl.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | c1a0903850e5ee790d4c072add317d49699fb5d2a58f13379b43d3709958c227 | 8d376a33ce625efea21a727d4a046134c1d759eb13efe5fa1e2683895e99352c | c1ccc2c(c1)Cn1cccc1CN2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4](-[C:5]-[c:6]:[c:7](-[N+;H0;D3:8](=O)-[O-]):[c:9]):[c:10]>>[c:3]:[c:2]1:[#7;a:4](:[c:10])-[C:5]-[c:6]:[c:7](:[c:9])-[NH;D2;+0:8]-[CH2;D2;+0:1]-1 | 66.6 | [{"value": 66.6, "product": "C=1C=CN2C1CNC1=C(C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 30.6 g of 1-(2-nitrobenzyl)-2-pyrrolecarboxaldehyde and 3.06 g of 10% Pd/C in 400 ml of ethyl acetate and 400 ml of ethyl alcohol is hydrogenated over 18 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate is treated with activated carbon and filtered through diatomaceous ea... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Secondary amine | null | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1CN2 | Other | [Pd].C(C)O.C(Cl)Cl.C(C)(=O)OCC | null | 18 | O=Cc1cccn1Cc1ccccc1[N+](=O)[O-]>[Pd].C(C)O.C(Cl)Cl.C(C)(=O)OCC>c1ccc2c(c1)Cn1cccc1CN2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c3b42b17a5748819721657743389fb5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][... | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.8 | [{"value": 97.8, "product": "NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 21.58 g of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 325 ml of ethyl alcohol is added 2.15 g of 10% Pd/C and 5.16 g of hydrazine followed by stirring and heating under reflux for 15 hours. The room temperature reaction mixture is filtered through diatomaceous earth. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-26852837714a48d0acc9eda7e9ce55f7 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1sc2ccccc2c1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1sc2ccccc2c1Cl | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.ClC=1C2=C(SC1C(=O)Cl)C=CC=C2.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C1=C(C2=C(S1)C=CC=C2)Cl | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[s:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[c:34]1[Cl:35]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1sc2ccccc2c1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1sc2ccccc2c1Cl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc2ccccc2s1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 61.5 | [{"value": 61.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C1=C(C2=C(S1)C=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution of 0.440 g of 3-chlorobenzo[b]thiophen-2-carbonyl chloride in 10 ml of methylene chloride is added 0.33 ml of triethylamine. After stirring for 15 minutes, 0.485 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 18 hours. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccc2sccc2c1 | HCl | C(Cl)Cl | null | 0.25 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1sc2ccccc2c1Cl>C(Cl)Cl>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1sc2ccccc2c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-11110d9b69ed424a9d0f85c1479cb24e | Cc1cccc(C(=O)Cl)c1C.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1cccc(C(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.CC1=C(C(=O)Cl)C=CC=C1C.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC=C1)C)C)=O | Cl[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:32]1[CH3:33])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[CH2:17][c:18]3[cH:19][cH:20][cH:21][n:22]3[CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13... | Cc1cccc(C(=O)Cl)c1C.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1cccc(C(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 56 | [{"value": 56.0, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC=C1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution of 0.320 g of 2,3-dimethylbenzoyl chloride in 10 ml of methylene chloride is added 0.33 ml of triethylamine. After stirring for 15 minutes, 0.485 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 5 hours. The reaction mixture is washed ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.25 | Cc1cccc(C(=O)Cl)c1C.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1cccc(C(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9bacf453371f41c29a68bca6e3de295d | CCOc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>CCOc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)OC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)OCC)=O | Cl[C:10]([c:9]1[c:4]([O:3][CH2:2][CH3:1])[cH:5][cH:6][cH:7][cH:8]1)=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][c:21]3[cH:22][cH:23][cH:24][n:25]3[CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]32)[cH:33][cH:34]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:1... | CCOc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | CCOc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 100.5 | [{"value": 100.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.362 g of 2-ethoxybenzoyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0,500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | CCOc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>CCOc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-153a87d527a043ec894c6247133c8150 | CSc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>CSc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.CSC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SC)=O | Cl[C:9]([c:8]1[c:3]([S:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13]... | CSc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | CSc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 64.2 | [{"value": 64.2, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0,364 g of 2-(methylthio)benzoyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | CSc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>CSc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ef06148d7704fcfb2cdb77a0af43bea | Cc1c(CC(=O)O)sc2ccccc12.O=S(Cl)Cl>>Cc1c(CC(=O)Cl)sc2ccccc12 | CC=1C2=C(SC1CC(=O)O)C=CC=C2.S(=O)(Cl)Cl>>CC1=C(SC2=CC=CC=C12)CC(=O)Cl | O[C:5]([CH2:4][c:3]1[c:2]([CH3:1])[c:14]2[c:9]([s:8]1)[cH:10][cH:11][cH:12][cH:13]2)=[O:6].O=S(Cl)[Cl:7]>>[CH3:1][c:2]1[c:3]([CH2:4][C:5](=[O:6])[Cl:7])[s:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | Cc1c(CC(=O)O)sc2ccccc12.O=S(Cl)Cl | Cc1c(CC(=O)Cl)sc2ccccc12 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2sccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | A mixture of 2.0 g of 3-methylbenzo[b]thiophene-2-acetic acid and 19.4 ml of thionyl chloride is heated at reflux for 1 hour. The volatiles are evaporated in vacuo to give a residue which is concentrated from toluene three times and dried under vacuum to give 2.25 g of the desired product as a residue.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2sccc2c1 | HCl | null | null | null | Cc1c(CC(=O)O)sc2ccccc12.O=S(Cl)Cl>>Cc1c(CC(=O)Cl)sc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf44478c214d45669a98c1e50f33d79f | Cc1c(CC(=O)Cl)sc2ccccc12.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1c(CC(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)sc2ccccc12 | CC1=C(SC2=CC=CC=C12)CC(=O)Cl.C(C)N(CC)CC.CN(C)C1=NC=CC=C1.CC1=C(SC2=CC=CC=C12)CC(=O)Cl.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CC1=C(C2=C(S1)C=CC=C2)C)=O | Cl[C:5]([CH2:4][c:3]1[c:2]([CH3:1])[c:36]2[c:31]([s:30]1)[cH:32][cH:33][cH:34][cH:35]2)=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][c:16]3[cH:17][cH:18][cH:19][n:20]3[CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]32)[cH:28][cH:29]1>>[CH3:1][c:2]1[c:3]([CH2:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][c... | Cc1c(CC(=O)Cl)sc2ccccc12.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1c(CC(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)sc2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1cc2ccccc2s1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#16;a:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[#16;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 39.5 | [{"value": 39.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CC1=C(C2=C(S1)C=CC=C2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride in 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room te... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccc2sccc2c1 | HCl | C(Cl)Cl | null | 0.05 | Cc1c(CC(=O)Cl)sc2ccccc12.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1c(CC(=O)Nc2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)sc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33ac9464e5e1486c8765991c4ac756d8 | COc1cc(Cl)ccc1C(=O)O.O=S(Cl)Cl>>COc1cc(Cl)ccc1C(=O)Cl | ClC=1C=C(C(C(=O)O)=CC1)OC.S(=O)(Cl)Cl>>ClC1=CC(=C(C(=O)Cl)C=C1)OC | O[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([Cl:6])[cH:7][cH:8]1)=[O:11].O=S(Cl)[Cl:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[Cl:12] | COc1cc(Cl)ccc1C(=O)O.O=S(Cl)Cl | COc1cc(Cl)ccc1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 2.0 g of 4-chloro-o-anisic acid in 22 ml of thionyl chloride is heated at reflux for 1 hour. The volatiles are evaporated in vacuo to give a residue which is concentrated from toluene three times and dried under vacuum to give 2.0 g of the desired product as a residue.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | COc1cc(Cl)ccc1C(=O)O.O=S(Cl)Cl>>COc1cc(Cl)ccc1C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c50d1d1a27e41ddbdd4c578fbb9d72a | COc1cc(Cl)ccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>COc1cc(Cl)ccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | ClC1=CC(=C(C(=O)Cl)C=C1)OC.C(C)N(CC)CC.ClC1=CC(=C(C(=O)Cl)C=C1)OC.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)OC)=O | Cl[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([Cl:6])[cH:7][cH:8]1)=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][c:21]3[cH:22][cH:23][cH:24][n:25]3[CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]32)[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:1... | COc1cc(Cl)ccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | COc1cc(Cl)ccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 41.1 | [{"value": 41.1, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.406 g of 4-chloro-2-methoxybenzoyl chloride in 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 18 hours at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | COc1cc(Cl)ccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>COc1cc(Cl)ccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
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