dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c1ae5b007ce40f89648f68658dddefe | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3ncccc23)c1>>Cl.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1 | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1>>Cl.ClC(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1 | O=C(C(=O)[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[n:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[n:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3ncccc23)c1 | Cl.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1cc(-n2cccc2)c2cccnc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.O=C(-[Cl;H0;D1;+0:9])-C(=O)-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[ClH;D0;+0:9] | 106.6 | [{"value": 106.6, "product": "Cl.ClC(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22 | CELSIUS | 15 | HOUR | 0.5 mL (5.73 mmol) of oxalyl chloride is added to a solution, cooled to a temperature in the region of 5° C., of 0.42 g (1.76 mmol) of 3-carboxy-1-(quinol-5-yl)-1H-pyrrole in 10 mL of dichloromethane under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 15 hours, concentrating the react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | ClCCl | 22 | 15 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3ncccc23)c1>ClCCl>Cl.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07442da8730b42eca62689c2a93e2166 | COC(=O)c1ccn(-c2cccc3ncccc23)c1>>O=C(O)c1ccn(-c2cccc3ncccc23)c1 | O.[OH-].[Li+].O.COC(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1>>C(=O)(O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[n:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[n:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | COC(=O)c1ccn(-c2cccc3ncccc23)c1 | O=C(O)c1ccn(-c2cccc3ncccc23)c1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(-n2cccc2)c2cccnc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(=O)(O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 0.36 g (8.58 mmol) of lithium hydroxide monohydrate and 20 mL of water are added to a solution at a temperature in the region of 22° C. of 0.5 g (1.98 mmol) of 3-methoxycarbonyl-1-(quinol-5-yl)-1H-pyrrole in 20 mL of tetrahydrofuran. After stirring at the reflux point of the solvent for 15 hours, the reaction mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | O1CCCC1 | null | 15 | COC(=O)c1ccn(-c2cccc3ncccc23)c1>O1CCCC1>O=C(O)c1ccn(-c2cccc3ncccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53e910dc6ecf4007b8f1e9f0503f1f12 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3cccnc23)c1>>O=C(Cl)c1ccn(-c2cccc3cccnc23)c1 | C(C(=O)Cl)(=O)Cl.C(C(=O)Cl)(=O)Cl.Cl.C(=O)(O)C1=CN(C=C1)C=1C=CC=C2C=CC=NC12>>Cl.ClC(=O)C1=CN(C=C1)C=1C=CC=C2C=CC=NC12 | O=C(Cl)C(=O)[Cl:4].O[C:3](=[O:2])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][n:17][c:18]23)[cH:19]1>>[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][n:17][c:18]23)[cH:19]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3cccnc23)c1 | O=C(Cl)c1ccn(-c2cccc3cccnc23)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1cnc2c(-n3cccc3)cccc2c1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6](-[c:7]:[c:8]:[#7;a:9]):[c:10]:[c:11]:1>>[#7;a:9]:[c:8]:[c:7]-[#7;a:6]1:[c:5]:[c:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3]):[c:11]:[c:10]:1 | 86.9 | [{"value": 86.9, "product": "Cl.ClC(=O)C1=CN(C=C1)C=1C=CC=C2C=CC=NC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22 | CELSIUS | 15 | HOUR | 0.45 mL (5.16 mmol) of oxalyl chloride is added to a solution, cooled to a temperature in the region of 5° C., of 0.45 g (1.64 mmol) of 3-carboxy-1-(quinol-8-yl)-1H-pyrrole hydrochloride in 20 mL of dichloromethane under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 15 hours, the reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | ClCCl | 22 | 15 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cccc3cccnc23)c1>ClCCl>O=C(Cl)c1ccn(-c2cccc3cccnc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5dc2a4c4c44e428ca878141a5f4b4e65 | Brc1cccc2cccnc12.COC(=O)c1cc[nH]c1>>COC(=O)c1ccn(-c2cccc3cccnc23)c1 | CCCCCCCCCCCC.BrC=1C=CC=C2C=CC=NC12.[C@@H]1([C@@H](CCCC1)N)N.COC(=O)C1=CNC=C1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>COC(=O)C1=CN(C=C1)C=1C=CC=C2C=CC=NC12 | Br[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]12.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][nH:8][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][n:17][c:18]23)[cH:19]1 | Brc1cccc2cccnc12.COC(=O)c1cc[nH]c1 | COC(=O)c1ccn(-c2cccc3cccnc23)c1 | null | [Cu](I)I | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnc2c(-n3cccc3)cccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14]:[c:15]:1>>[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:14]:[c:15]:1 | 124.1 | [{"value": 124.1, "product": "COC(=O)C1=CN(C=C1)C=1C=CC=C2C=CC=NC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | HOUR | 20 mL of 1,4-dioxane, 0.32 mL of n-dodecane, 1.5 g (7.21 mmol) of 8-bromoquinoline and 0.77 mL (6.41 mmol) of trans-1,2-cyclohexanediamine are added at a temperature in the region of 22° C. under an argon atmosphere to 0.8 g (6.39 mmol) of 3-methoxycarbonyl-1H-pyrrole, 3 g (14.13 mmol) of potassium orthophosphate and 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1.c1cc[nH]c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HBr | [Cu](I)I.O1CCOCC1 | 100 | 15 | Brc1cccc2cccnc12.COC(=O)c1cc[nH]c1>[Cu](I)I.O1CCOCC1>COC(=O)c1ccn(-c2cccc3cccnc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-711fc6486af344878cb5aa33070595c0 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cncc3ccccc23)c1>>Cl.O=C(Cl)c1ccn(-c2cncc3ccccc23)c1 | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=CN(C=C1)C1=CN=CC2=CC=CC=C12>>Cl.ClC(=O)C1=CN(C=C1)C1=CN=CC2=CC=CC=C12 | O=C(C(=O)[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][n:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][n:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cncc3ccccc23)c1 | Cl.O=C(Cl)c1ccn(-c2cncc3ccccc23)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2c(-n3cccc3)cncc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:1.O=C(-[Cl;H0;D1;+0:11])-C(=O)-[Cl;H0;D1;+0:12]>>[#7;a:8]:[c:7]:[c:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:12])=[O;D1;H0:2]):[c:10]:[c:9]:1.[ClH;D0;+0:11] | null | [] | 22 | CELSIUS | 15 | HOUR | 0.82 mL (9.4 mmol) of oxalyl chloride is added to a solution, cooled to a temperature in the region of 5° C., of 0.75 g (3.15 mmol) of 3-carboxy-1-(isoquinol-4-yl)-1H-pyrrole in 25 mL of dichloromethane under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 15 hours, the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | ClCCl | 22 | 15 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2cncc3ccccc23)c1>ClCCl>Cl.O=C(Cl)c1ccn(-c2cncc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a71ed9b08627498493d90473bab0af9f | COC(=O)c1ccn(-c2cncc3ccccc23)c1>>O=C(O)c1ccn(-c2cncc3ccccc23)c1 | [K+].[Br-].O.[OH-].[Li+].O.COC(=O)C1=CN(C=C1)C1=CN=CC2=CC=CC=C12>>C(=O)(O)C1=CN(C=C1)C1=CN=CC2=CC=CC=C12 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][n:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][n:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | COC(=O)c1ccn(-c2cncc3ccccc23)c1 | O=C(O)c1ccn(-c2cncc3ccccc23)c1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)cncc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 15 | HOUR | 0.63 g (15.02 mmol) of lithium hydroxide monohydrate and 20 mL of water are added to a solution, at a temperature in the region of 22° C., of 0.95 g (376 mmol) of 3-methoxycarbonyl-1-(isoquinol-4-yl)-1H-pyrrole in 20 mL of tetrahydrofuran. After stirring at the reflux point of the solvent for 15 hours, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | O1CCCC1 | null | 15 | COC(=O)c1ccn(-c2cncc3ccccc23)c1>O1CCCC1>O=C(O)c1ccn(-c2cncc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b5c08f7787d4c9ba741d3bb98e20248 | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl.N=C(N)N>>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)NC(=N)N | ClC(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12.C[O-].[Na+].CO.Cl.NC(=N)N>>N(C(=N)N)C(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12 | Cl[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].[NH2:19][C:20](=[NH:21])[NH2:22]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[NH:19][C:20](=[NH:21])[NH2:22] | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl.N=C(N)N | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)NC(=N)N | null | null | COCCOC.C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH2;D1;+0:12]>>[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 55 | [{"value": 55.0, "product": "N(C(=N)N)C(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 1.4 g (25.5 mmol) of sodium methoxide is added at a temperature in the region of 20° C. under an argon atmosphere to 25 mL of methanol. After complete dissolution, 2.5 g (26.2 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 1 hour, the reaction mixture is concentr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | COCCOC.C(Cl)(Cl)Cl | 20 | 1 | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl.N=C(N)N>COCCOC.C(Cl)(Cl)Cl>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3853d69d4f54b368c8fa00945753e65 | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O.O=S(Cl)Cl>>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl | S(=O)(Cl)Cl.C(=O)(O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12>>ClC(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12 | O[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[Cl:19] | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O.O=S(Cl)Cl | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6](-[c:7]):[c:8]:[c:9]:1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6](-[c:7]):[c:8]:[c:9]:1 | 100 | [{"value": 100.0, "product": "ClC(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 10 mL (137 mmol) of sulphinyl chloride are added at a temperature in the region of 20° C. under an argon atmosphere to 1 g (3.97 mmol) of 3-carboxy-4-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform. After stirring at the reflux point of the solvent for 1 hour, the reaction mixture is concentrated to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | C(Cl)(Cl)Cl | null | 1 | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O.O=S(Cl)Cl>C(Cl)(Cl)Cl>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2bee4fff69a42e4b9e7a6127aaa4781 | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C>>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O | O.[OH-].[Li+].COC(=O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12>>C(=O)(O)C1=CN(C=C1C)C1=CC=NC2=CC=CC=C12 | C[O:19][C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[OH:19] | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C | Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)ccnc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 0.63 g (15 mmol) of lithium hydroxide monohydrate is added at a temperature in the region of 20° C. to 1.21 g (4.54 mmol) of 3-methoxycarbonyl-4-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 22 hours, the reaction mixture is concentrated to dryn... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | O1CCCC1.O | null | null | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C>O1CCCC1.O>Cc1cn(-c2ccnc3ccccc23)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec81f6d9662f4a75babd0b2c6e4714da | Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl.N=C(N)N>>Cc1cn(-c2nccc3ccccc23)cc1C(=O)NC(=N)N | ClC(=O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12.Cl.NC(=N)N.C[O-].[Na+]>>Cl.N(C(=N)N)C(=O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12 | Cl[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].[NH2:19][C:20](=[NH:21])[NH2:22]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[NH:19][C:20](=[NH:21])[NH2:22] | Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl.N=C(N)N | Cc1cn(-c2nccc3ccccc23)cc1C(=O)NC(=N)N | null | null | COCCOC.C(Cl)(Cl)Cl.CO | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(-n3cccc3)nccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]:[#7;a:7]):[c:8]:[c:9]:1.[N;D1;H1:10]=[C:11](-[N;D1;H2:12])-[NH2;D1;+0:13]>>[#7;a:7]:[c:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:11](=[N;D1;H1:10])-[N;D1;H2:12]):[c:9]:[c:8]:1 | 43.1 | [{"value": 43.1, "product": "Cl.N(C(=N)N)C(=O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 1.37 g (25.37 mmol) of sodium methoxide are added at a temperature in the region of 20° C. under an argon atmosphere to 25 mL of methanol. After complete dissolution, 2.5 g (26.2 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 1 hour, the reaction mixture is conce... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | HCl | COCCOC.C(Cl)(Cl)Cl.CO | 20 | 1 | Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl.N=C(N)N>COCCOC.C(Cl)(Cl)Cl.CO>Cc1cn(-c2nccc3ccccc23)cc1C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a042881dff64ef283d4dabdea62cd6d | Cc1cn(-c2nccc3ccccc23)cc1C(=O)O.O=S(Cl)Cl>>Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl | S(=O)(Cl)Cl.C(=O)(O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12>>ClC(=O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12 | O[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[Cl:19] | Cc1cn(-c2nccc3ccccc23)cc1C(=O)O.O=S(Cl)Cl | Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(-n3cccc3)nccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:[c:10]:1>>[#7;a:8]:[c:7]-[#7;a:6]1:[c:5]:[c:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3]):[c:10]:[c:9]:1 | 100 | [{"value": 100.0, "product": "ClC(=O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 10 mL (137 mmol) of sulphinyl chloride are added at a temperature in the region of 20° C. under an argon atmosphere to 1.1 g (4.36 mmol) of 3-carboxy-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole dissolved in 20 mL of chloroform. After stirring at the reflux point of the solvent for 2 hours, the reaction mixture is concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | HCl | C(Cl)(Cl)Cl | null | 2 | Cc1cn(-c2nccc3ccccc23)cc1C(=O)O.O=S(Cl)Cl>C(Cl)(Cl)Cl>Cc1cn(-c2nccc3ccccc23)cc1C(=O)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4171eb3662dd4db3925a61d44be6d640 | COC(=O)c1cn(-c2nccc3ccccc23)cc1C>>Cc1cn(-c2nccc3ccccc23)cc1C(=O)O | O.[OH-].[Li+].C1(=NC=CC2=CC=CC=C12)N1C=C(C(=C1)C)C(=O)OC>>C(=O)(O)C1=CN(C=C1C)C1=NC=CC2=CC=CC=C12 | C[O:19][C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[OH:19] | COC(=O)c1cn(-c2nccc3ccccc23)cc1C | Cc1cn(-c2nccc3ccccc23)cc1C(=O)O | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)nccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 0.63 g (15 mmol) of lithium hydroxide monohydrate is added at a temperature in the region of 20° C. to 1.35 g (5 mmol) of 1-(isoquinol-1-yl)-3-methoxycarbonyl-4-methyl-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 25 hours, the reaction mixture is concentrated to dryn... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | O1CCCC1.O | null | null | COC(=O)c1cn(-c2nccc3ccccc23)cc1C>O1CCCC1.O>Cc1cn(-c2nccc3ccccc23)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0a24db0bb7c94ee295f37e6984effbc5 | COC(=O)c1c[nH]cc1C.Clc1nccc2ccccc12>>COC(=O)c1cn(-c2nccc3ccccc23)cc1C | ClC1=NC=CC2=CC=CC=C12.[H-].[Na+].COC(=O)C1=CNC=C1C.O>>C1(=NC=CC2=CC=CC=C12)N1C=C(C(=C1)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:18][c:19]1[CH3:20].Cl[c:8]1[n:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[CH3:20] | COC(=O)c1c[nH]cc1C.Clc1nccc2ccccc12 | COC(=O)c1cn(-c2nccc3ccccc23)cc1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 64941681a78379ce7a568f1d8a1309e87b488f1d656284455a26054be1853b83 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]):[c:14]:1 | null | [] | 40 | CELSIUS | 0.3 | HOUR | 0.208 g (6.5 mmol) of sodium hydride, at 75% by weight in liquid petroleum jelly, is added at a temperature in the region of 20° C. under an argon atmosphere to a solution of 0.903 g (6.5 mmol) of 3-methoxycarbonyl-4-methyl-1H-pyrrole in 20 mL of dimethylformamide. After stirring at a temperature in the region of 40° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | HCl | CN(C=O)C | 40 | 0.3 | COC(=O)c1c[nH]cc1C.Clc1nccc2ccccc12>CN(C=O)C>COC(=O)c1cn(-c2nccc3ccccc23)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0bdaf28d9484854bfe56b4706d69540 | Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C.Cl.N=C(N)N>>Cc1c(C(=O)NC(=N)N)cn(-c2ccnc3ccccc23)c1C.Cl | Cl.Cl.NC(=N)N.ClC(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12.C[O-].[Na+]>>Cl.Cl.N(C(=N)N)C(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12 | Cl[C:4]([c:3]1[c:2]([CH3:1])[c:22]([CH3:23])[n:11](-[c:12]2[cH:13][cH:14][n:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]23)[cH:10]1)=[O:5].[ClH:25].[NH2:6][C:7](=[NH:8])[NH2:9]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][C:7](=[NH:8])[NH2:9])[cH:10][n:11](-[c:12]2[cH:13][cH:14][n:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21... | Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C.Cl.N=C(N)N | Cc1c(C(=O)NC(=N)N)cn(-c2ccnc3ccccc23)c1C.Cl | null | null | O1CCOCC1.C(Cl)(Cl)Cl.CO.COCCOC.C(C)O | Acylation | OtherReaction | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH2;D1;+0:12]>>[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 61.6 | [{"value": 61.6, "product": "Cl.Cl.N(C(=N)N)C(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.5 | HOUR | 1.78 g (33 mmol) of sodium methoxide are added at a temperature in the region of 20° C. under an argon atmosphere to 20 mL of methanol. After complete dissolution, 3.34 g (35 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 0.5 hour, the reaction mixture is concent... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | O1CCOCC1.C(Cl)(Cl)Cl.CO.COCCOC.C(C)O | 20 | 0.5 | Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C.Cl.N=C(N)N>O1CCOCC1.C(Cl)(Cl)Cl.CO.COCCOC.C(C)O>Cc1c(C(=O)NC(=N)N)cn(-c2ccnc3ccccc23)c1C.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e005a6ec3d348a894d4a05f8676e56e | Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C.O=S(Cl)Cl>>Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C | S(=O)(Cl)Cl.C(=O)(O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12>>ClC(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12 | O[C:4]([c:3]1[c:2]([CH3:1])[c:19]([CH3:20])[n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:7]1)=[O:5].O=S(Cl)[Cl:6]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[Cl:6])[cH:7][n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[c:19]1[CH3:20] | Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C.O=S(Cl)Cl | Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[c:8]):[c:9]:1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[c:8]):[c:9]:1 | 100 | [{"value": 100.0, "product": "ClC(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 10 mL (137 mmol) of sulphinyl chloride are added at a temperature in the region of 20° C. under an argon atmosphere to 1.1 g (4.1 mmol) of 3-carboxy-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform. After stirring at the reflux point of the solvent for 1.5 hours, the reaction mixture is concentr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | C(Cl)(Cl)Cl | null | 1.5 | Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C.O=S(Cl)Cl>C(Cl)(Cl)Cl>Cc1c(C(=O)Cl)cn(-c2ccnc3ccccc23)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a5c448614724de781c0c90100dd80fc | CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C>>Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C | O.[OH-].[Li+].C(C)OC(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12>>C(=O)(O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12 | CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[c:19]([CH3:20])[n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:7]1)=[O:5]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[c:19]1[CH3:20] | CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C | Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C | null | null | Cl.O.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)ccnc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 1.89 g (45 mmol) of lithium hydroxide monohydrate are added at a temperature in the region of 20° C. to 1.3 g (4.42 mmol) of 3-ethoxycarbonyl-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 42 hours, the reaction mixture is concentrated virt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | Cl.O.O1CCCC1 | null | null | CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C>Cl.O.O1CCCC1>Cc1c(C(=O)O)cn(-c2ccnc3ccccc23)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e151ce452e1241aabb17de853cb0412b | CCOC(=O)c1c[nH]c(C)c1C.Clc1ccnc2ccccc12>>CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C | ClC1=CC=NC2=CC=CC=C12.[H-].[Na+].C(C)OC(=O)C1=CNC(=C1C)C.O>>C(C)OC(=O)C1=CN(C(=C1C)C)C1=CC=NC2=CC=CC=C12 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:19]([CH3:20])[c:21]1[CH3:22].Cl[c:9]1[cH:10][cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[c:19]([CH3:20])[c:21]1[CH3:22] | CCOC(=O)c1c[nH]c(C)c1C.Clc1ccnc2ccccc12 | CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[C;D1;H3:15]):[nH;D2;+0:16]:[c:17]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[C;D1;H3:15]):[n;H0;D3;+0:16](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[c:17]:1 | null | [] | 40 | CELSIUS | 0.3 | HOUR | 0.285 g (8.9 mmol) of sodium hydride, at 75% by weight in liquid petroleum jelly, is added at a temperature in the region of 20° C. under an argon atmosphere to a solution of 1.35 g (8.1 mmol) of 3-ethoxycarbonyl-4,5-dimethyl-1H-pyrrole in 8 mL of dimethylformamide. After stirring at a temperature in the region of 40° ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | CN(C=O)C | 40 | 0.3 | CCOC(=O)c1c[nH]c(C)c1C.Clc1ccnc2ccccc12>CN(C=O)C>CCOC(=O)c1cn(-c2ccnc3ccccc23)c(C)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-488f452e1c6146b4a870ed73f4b787fe | N=C(N)N.O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1>>N=C(N)NC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | ClC(=O)C1=CN(C=C1C1CC1)C1=CC=NC2=CC=CC=C12.Cl.NC(=N)N.C[O-].[Na+]>>C1(CC1)C=1C(=CN(C1)C1=CC=NC2=CC=CC=C12)C(=O)NC(=N)N | [NH:1]=[C:2]([NH2:3])[NH2:4].Cl[C:5](=[O:6])[c:7]1[cH:8][n:9](-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:20][c:21]1[CH:22]1[CH2:23][CH2:24]1>>[NH:1]=[C:2]([NH2:3])[NH:4][C:5](=[O:6])[c:7]1[cH:8][n:9](-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:20][c:21]1[... | N=C(N)N.O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | N=C(N)NC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | null | null | COCCOC.C(Cl)(Cl)Cl.CO | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(-n3ccc(C4CC4)c3)ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]):[c:8]:1.[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH2;D1;+0:12]>>[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]):[c:8]:1 | 63.8 | [{"value": 63.8, "product": "C1(CC1)C=1C(=CN(C1)C1=CC=NC2=CC=CC=C12)C(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.5 | HOUR | 1.19 g (22 mmol) of sodium methoxide are added to 25 mL of methanol at a temperature in the region of 20° C. under an argon atmosphere. After total dissolution, 2.2 g (23 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 0.5 hour, the reaction mixture is concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1.C1CC1 | HCl | COCCOC.C(Cl)(Cl)Cl.CO | 20 | 0.5 | N=C(N)N.O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1>COCCOC.C(Cl)(Cl)Cl.CO>N=C(N)NC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-705b602f839943f78bb12ba9d6253c13 | O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1.O=S(Cl)Cl>>O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | S(=O)(Cl)Cl.C(=O)(O)C1=CN(C=C1C1CC1)C1=CC=NC2=CC=CC=C12>>ClC(=O)C1=CN(C=C1C1CC1)C1=CC=NC2=CC=CC=C12 | O[C:2](=[O:1])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:17][c:18]1[CH:19]1[CH2:20][CH2:21]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:17][c:18]1[CH:19]1[CH2:20][CH2:21]1 | O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1.O=S(Cl)Cl | O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(-n3ccc(C4CC4)c3)ccnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[c:8]):[c:9]:1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7](-[c:8]):[c:9]:1 | 100 | [{"value": 100.0, "product": "ClC(=O)C1=CN(C=C1C1CC1)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 10 mL (137 mmol) of sulphinyl chloride are added to 1.05 g (3.78 mmol) of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform at a temperature in the region of 20° C. under an argon atmosphere. After stirring for one hour at the reflux temperature of the solvent, the reaction mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1.C1CC1 | HCl | C(Cl)(Cl)Cl | null | 1 | O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1.O=S(Cl)Cl>C(Cl)(Cl)Cl>O=C(Cl)c1cn(-c2ccnc3ccccc23)cc1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85bef526f5de461aa02d64133e4662c8 | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1>>O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | O.[OH-].[Li+].C1(CC1)C=1C(=CN(C1)C1=CC=NC2=CC=CC=C12)C(=O)OC>>C(=O)(O)C1=CN(C=C1C1CC1)C1=CC=NC2=CC=CC=C12 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:17][c:18]1[CH:19]1[CH2:20][CH2:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[cH:17][c:18]1[CH:19]1[CH2:20][CH2:21]1 | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3ccc(C4CC4)c3)ccnc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 26 | HOUR | 0.63 g (15 mmol) of lithium hydroxide monohydrate is added, at a temperature in the region of 20° C., to 1.3 g (4.4 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring for 26 hours at the reflux temperature of the solvent, the re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2ncccc2c1.C1CC1 | Other | O1CCCC1.O | null | 26 | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1>O1CCCC1.O>O=C(O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ef7b04f28b2421da6aa4ad91d5e166b | COC(=O)c1c[nH]cc1C1CC1.Clc1ccnc2ccccc12>>COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | ClC1=CC=NC2=CC=CC=C12.[H-].[Na+].C1(CC1)C=1C(=CNC1)C(=O)OC>>C1(CC1)C=1C(=CN(C1)C1=CC=NC2=CC=CC=C12)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:18][c:19]1[CH:20]1[CH2:21][CH2:22]1.Cl[c:8]1[cH:9][cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[cH:9][cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[CH:20]1[CH2:21][CH2:22]1 | COC(=O)c1c[nH]cc1C1CC1.Clc1ccnc2ccccc12 | COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 | null | null | [Cl-].[Na+].O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3ccc(C4CC4)c3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[n;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[c:16]:1 | null | [] | 40 | CELSIUS | 0.3 | HOUR | 0.208 g (6.5 mmol) of sodium hydride at 75% by weight in liquid petroleum jelly is added to a solution of 1.07 g (6.5 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1H-pyrrole in 20 mL of dimethylformamide at a temperature in the region of 20° C. under an argon atmosphere. After the reaction mixture has been stirred at a tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1.C1CC1 | HCl | [Cl-].[Na+].O.CN(C=O)C | 40 | 0.3 | COC(=O)c1c[nH]cc1C1CC1.Clc1ccnc2ccccc12>[Cl-].[Na+].O.CN(C=O)C>COC(=O)c1cn(-c2ccnc3ccccc23)cc1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af3ceb1fa390416d870629c341924f90 | COC(=O)C=CC1CC1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>COC(=O)c1c[nH]cc1C1CC1 | C1(=CC=C(C=C1)S(=O)(=O)C[N+]#[C-])C.C1(CC1)C=CC(=O)OC.[H-].[Na+]>>C1(CC1)C=1C(=CNC1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:9][CH:10]1[CH2:11][CH2:12]1.Cc1ccc(S(=O)(=O)[CH2:8][N+:7]#[C-:6])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:8][c:9]1[CH:10]1[CH2:11][CH2:12]1 | COC(=O)C=CC1CC1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | COC(=O)c1c[nH]cc1C1CC1 | null | null | CS(=O)C.[Cl-].[Na+].O.C(C)OCC | Functional Group Interconversion | OtherReaction | 222aa38425ebd527cae949f4f6a41b16a79f5bedc3b38d407b2efba1132a0002 | 2b254751295ab0c58d4be59c7dc1148a5e0af4419b8080ba37410673480117ee | c1cc(C2CC2)c[nH]1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:3]:[nH;D2;+0:2]:[cH;D2;+0:1]:[c;H0;D3;+0:9]:1-[C:10]1-[C:11]-[C:12]-1 | 86.1 | [{"value": 86.1, "product": "C1(CC1)C=1C(=CNC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.75 | HOUR | A solution of 8.77 g of p-toluenesulphonylmethyl isocyanide and 5.67 g of methyl 3-cyclopropylacrylate in 72 mL of dimethyl sulphoxide and 145 mL of diethyl ether is added dropwise over 1.5 hours and under an argon atmosphere to a suspension of 1.73 g (54 mmol) of sodium hydride (at 75% by weight in liquid petroleum je... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Isocyanide | Ester | c1ccccc1 | c1cc[nH]c1 | c1cc[nH]c1.C1CC1 | TsOH.HO- | CS(=O)C.[Cl-].[Na+].O.C(C)OCC | null | 2.75 | COC(=O)C=CC1CC1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>CS(=O)C.[Cl-].[Na+].O.C(C)OCC>COC(=O)c1c[nH]cc1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7dbe4b69649d42f4930f731530a40827 | Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.N=C(N)N>>Cc1cn(-c2cccc3ncccc23)cc1C(=O)NC(=N)N | Cl.NC(=N)N.C[O-].[Na+].Cl.ClC(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1>>Cl.N(C(=N)N)C(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1 | Cl[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].[NH2:19][C:20](=[NH:21])[NH2:22]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[NH:19][C:20](=[NH:21])[NH2:22] | Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.N=C(N)N | Cc1cn(-c2cccc3ncccc23)cc1C(=O)NC(=N)N | null | null | CO | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc(-n2cccc2)c2cccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH2;D1;+0:12]>>[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 40.8 | [{"value": 40.8, "product": "Cl.N(C(=N)N)C(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1.06 g (11.18 mmol) of guanidine hydrochloride is added to a solution of 0.604 g (11.18 mmol) of sodium methoxide in 50 mL of methanol at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 2 hours at this temperature, the mixture is concentrated to dryness under reduced pressure (2.7 kP... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | CO | null | 2 | Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.N=C(N)N>CO>Cc1cn(-c2cccc3ncccc23)cc1C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b00e031520ad46b79cebee264b8977d5 | Cc1cn(-c2cccc3ncccc23)cc1C(=O)O.O=S(Cl)Cl>>Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.Cl | S(=O)(Cl)Cl.C(=O)(O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1>>Cl.ClC(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1 | O[C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18].O=S([Cl:19])[Cl:20]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[Cl:19].[ClH:20] | Cc1cn(-c2cccc3ncccc23)cc1C(=O)O.O=S(Cl)Cl | Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1cc(-n2cccc2)c2cccnc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[ClH;D0;+0:10] | 100 | [{"value": 100.0, "product": "Cl.ClC(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 8 mL (110 mmol) of sulphinyl chloride are added to 0.47 g (1.86 mmol) of 3-carboxy-4-methyl-1-(quinolin-5-yl)-1H-pyrrole dissolved in 25 mL of chloroform at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 1.5 hours at the reflux temperature of the solvent, the reaction mixture is con... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | C(Cl)(Cl)Cl | null | 1.5 | Cc1cn(-c2cccc3ncccc23)cc1C(=O)O.O=S(Cl)Cl>C(Cl)(Cl)Cl>Cc1cn(-c2cccc3ncccc23)cc1C(=O)Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2213ef54f2049318553c7dac6821260 | COC(=O)c1cn(-c2cccc3ncccc23)cc1C>>Cc1cn(-c2cccc3ncccc23)cc1C(=O)O | O.[OH-].[Li+].COC(=O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1.O>>C(=O)(O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1 | C[O:19][C:17]([c:16]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15]1)=[O:18]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][c:16]1[C:17](=[O:18])[OH:19] | COC(=O)c1cn(-c2cccc3ncccc23)cc1C | Cc1cn(-c2cccc3ncccc23)cc1C(=O)O | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(-n2cccc2)c2cccnc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 65.2 | [{"value": 65.2, "product": "C(=O)(O)C1=CN(C=C1C)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | 0.504 g (12.2 mmol) of lithium hydroxide monohydrate is added to 0.8 g (3.04 mmol) of 3-methoxycarbonyl-4-methyl-1-(quinolin-5-yl)-1H-pyrrole dissolved in 25 mL of tetrahydrofuran and 25 mL of water at a temperature in the region of 20° C. After stirring for 30 hours at the reflux temperature of the solvent, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | Other | O1CCCC1 | null | 30 | COC(=O)c1cn(-c2cccc3ncccc23)cc1C>O1CCCC1>Cc1cn(-c2cccc3ncccc23)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b5bd54644864a379c57521b24b68dd2 | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1ccnc2ccccc12>>CCOC(=O)c1cn(-c2ccnc3ccccc23)cc1C(F)(F)F | O.C([O-])([O-])=O.[K+].[K+].C(C)OC(=O)C1=CNC=C1C(F)(F)F.ClC1=CC=NC2=CC=CC=C12>>C(C)OC(=O)C1=CN(C=C1C(F)(F)F)C1=CC=NC2=CC=CC=C12 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][cH:19][c:20]1[C:21]([F:22])([F:23])[F:24].Cl[c:9]1[cH:10][cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19][c:20]1[C:21]([F:22])([F:2... | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1ccnc2ccccc12 | CCOC(=O)c1cn(-c2ccnc3ccccc23)cc1C(F)(F)F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[n;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[c:16]:1 | 88.5 | [{"value": 88.5, "product": "C(C)OC(=O)C1=CN(C=C1C(F)(F)F)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 18 | HOUR | 1.73 g (12.5 mmol) of potassium carbonate are added to 1.036 g (5 mmol) of 3-ethoxycarbonyl-4-trifluoromethyl-1H-pyrrole and 0.82 g (5 mmol) of 4-chloroquinoline dissolved in 10 mL of dimethyl sulphoxide at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 18 hours at a temperature in ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | CS(=O)C | 110 | 18 | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1ccnc2ccccc12>CS(=O)C>CCOC(=O)c1cn(-c2ccnc3ccccc23)cc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd8cf941d89e4753913048bb8c4aed3f | O=C(Cl)C(=O)Cl.O=C(O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F>>Cl.O=C(Cl)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=CN(C=C1C(F)(F)F)C1=NC=CC2=CC=CC=C12>>Cl.ClC(=O)C1=CN(C=C1C(F)(F)F)C1=NC=CC2=CC=CC=C12 | O=C(C(=O)[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[C:20]([F:21])([F:22])[F:23]>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[C:20]([F:21])([F:22])... | O=C(Cl)C(=O)Cl.O=C(O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F | Cl.O=C(Cl)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2c(-n3cccc3)nccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:1.O=C(-[Cl;H0;D1;+0:10])-C(=O)-[Cl;H0;D1;+0:11]>>[#7;a:8]:[c:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:11])=[O;D1;H0:2]):[c:9]:1.[ClH;D0;+0:10] | 94.1 | [{"value": 94.1, "product": "Cl.ClC(=O)C1=CN(C=C1C(F)(F)F)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | 0.62 mL (7.18 mmol) of oxalyl chloride is added to 1.1 g (3.59 mmol) of 3-carboxy-4-trifluoromethyl-1-(isoquinolin-1-yl)-1H-pyrrole dissolved in 30 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 2 hours at a temperature in the region of 20° C., the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | ClCCl | 20 | 2 | O=C(Cl)C(=O)Cl.O=C(O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F>ClCCl>Cl.O=C(Cl)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8b8ad23069441068da762ab746c7678 | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1nccc2ccccc12>>CCOC(=O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F | C(C)OC(=O)C1=CNC=C1C(F)(F)F.ClC1=NC=CC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)C1=CN(C=C1C(F)(F)F)C1=NC=CC2=CC=CC=C12 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][cH:19][c:20]1[C:21]([F:22])([F:23])[F:24].Cl[c:9]1[n:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[n:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19][c:20]1[C:21]([F:22])([F:2... | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1nccc2ccccc12 | CCOC(=O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 64941681a78379ce7a568f1d8a1309e87b488f1d656284455a26054be1853b83 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]):[c:14]:1 | 87.3 | [{"value": 87.3, "product": "C(C)OC(=O)C1=CN(C=C1C(F)(F)F)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 17 | HOUR | 1.04 g (5 mmol) of 3-ethoxycarbonyl-4-trifluoromethyl-1H-pyrrole and 0.818 g (5 mmol) of 1-chloroisoquinoline are added to 1.73 g (12.5 mmol) of potassium carbonate suspended in 10 mL of dimethyl sulphoxide at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 17 hours at a temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | HCl | O.CS(=O)C | 110 | 17 | CCOC(=O)c1c[nH]cc1C(F)(F)F.Clc1nccc2ccccc12>O.CS(=O)C>CCOC(=O)c1cn(-c2nccc3ccccc23)cc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-99a153b06e49458686dfd8a4c0ec318a | COC(=O)c1c[nH]cc1C.Cc1cc(Cl)c2ccccc2n1>>COC(=O)c1cn(-c2cc(C)nc3ccccc23)cc1C | COC(=O)C1=CNC=C1C.ClC1=CC(=NC2=CC=CC=C12)C.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC(=O)C1=CN(C=C1C)C1=CC(=NC2=CC=CC=C12)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:19][c:20]1[CH3:21].Cl[c:8]1[cH:9][c:10]([CH3:11])[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[cH:9][c:10]([CH3:11])[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19][c:20]1[CH3:21] | COC(=O)c1c[nH]cc1C.Cc1cc(Cl)c2ccccc2n1 | COC(=O)c1cn(-c2cc(C)nc3ccccc23)cc1C | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[c:15]:[nH;D2;+0:16]:[c:17]:1>>[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[c:15]:[n;H0;D3;+0:16](-[c;H0;D3;+0:1]2:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:2:[c:9]):[c:17]:1 | null | [] | 80 | CELSIUS | 60 | HOUR | 1 mmol (139 mg) of 4-methylpyrrole-3-carboxylic acid methyl ester, 1.1 mmol (195 mg) 4-chloro-2-methyl-quinoline and 1.2 mmol (390 mg) of Cs2CO3 are suspended in 3 mL of dry DMF. The mixture is stirred for 60 h at 80° C. under Argon, allowed to cool to room temperature, and diluted with water (20 mL). Part of the produ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | O.CN(C)C=O | 80 | 60 | COC(=O)c1c[nH]cc1C.Cc1cc(Cl)c2ccccc2n1>O.CN(C)C=O>COC(=O)c1cn(-c2cc(C)nc3ccccc23)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12e788a19bb94873a9b8a0a69a0fa889 | COC(=O)c1cn(-c2ncccn2)cc1C.N=C(N)N>>Cc1cn(-c2ncccn2)cc1C(=O)NC(=N)N | COC(=O)C1=CN(C=C1C)C1=NC=CC=N1.NC(=N)N>>CC=1C(=CN(C1)C1=NC=CC=N1)C(=O)NC(=N)N | CO[C:13]([c:12]1[c:2]([CH3:1])[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][n:10]2)[cH:11]1)=[O:14].[NH2:15][C:16](=[NH:17])[NH2:18]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][cH:9][n:10]2)[cH:11][c:12]1[C:13](=[O:14])[NH:15][C:16](=[NH:17])[NH2:18] | COC(=O)c1cn(-c2ncccn2)cc1C.N=C(N)N | Cc1cn(-c2ncccn2)cc1C(=O)NC(=N)N | null | null | O.CN1CCCC1=O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cnc(-n2cccc2)nc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6](:[#7;a:7]):[#7;a:8]):[c:9]:[c:10]:1.[N;D1;H1:11]=[C:12](-[N;D1;H2:13])-[NH2;D1;+0:14]>>[#7;a:7]:[c:6](-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:12](=[N;D1;H1:11])-[N;D1;H2:13]):[c:10]:[c:9]:1):[#7;a:8] | 53.4 | [{"value": 53.4, "product": "CC=1C(=CN(C1)C1=NC=CC=N1)C(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 250 mg 4-methyl-1-pyrimidin-2-yl-1H-pyrrole-3-carboxylic acid methyl ester was dissolved in 0.3 mL of NMP. After addition of 1 g guanidine (preparation according to known literature) the mixture was heated under argon for 1 h to 90° C. Completion of the reaction was checked by LCMS. The mixture was cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1cncnc1 | HO- | O.CN1CCCC1=O | null | null | COC(=O)c1cn(-c2ncccn2)cc1C.N=C(N)N>O.CN1CCCC1=O>Cc1cn(-c2ncccn2)cc1C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c864c3cb49284f4dab9026da6cb4cf4e | Brc1ncccn1.COC(=O)c1c[nH]cc1C>>COC(=O)c1cn(-c2ncccn2)cc1C | COC(=O)C1=CNC=C1C.CCCCCCCCCCCC.NC1C(CCCC1)N.BrC1=NC=CC=N1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>COC(=O)C1=CN(C=C1C)C1=NC=CC=N1 | Br[c:8]1[n:9][cH:10][cH:11][cH:12][n:13]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:14][c:15]1[CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][c:15]1[CH3:16] | Brc1ncccn1.COC(=O)c1c[nH]cc1C | COC(=O)c1cn(-c2ncccn2)cc1C | null | [Cu]I | O1CCOCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 63bbfd98eb32b12003fd6c3367ae4b2d5032a668e503cabfa13b588e0290a766 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnc(-n2cccc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:13]:1 | 69.1 | [{"value": 69.1, "product": "COC(=O)C1=CN(C=C1C)C1=NC=CC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 333.9 mg (2.4 mmol) 4-methyl-1H-pyrrole-3-carboxylic acid methyl ester, 891.5 mg (4.2 mmol) tri-potassium phosphate, 4 mg (0.02 mmol) CuI, 22 mg (0.2 mmol) 1,2-diaminocyclohexane and 317.9 mg (2 mmol) of 2-bromopyrimidine was suspended in 3 mL of dioxane. After addition of 90 μl of dodecane the mixture was heated in a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1.c1cc[nH]c1 | c1cc[nH]c1.c1cncnc1 | c1cc[nH]c1.c1cncnc1 | HBr | [Cu]I.O1CCOCC1.O | 100 | null | Brc1ncccn1.COC(=O)c1c[nH]cc1C>[Cu]I.O1CCOCC1.O>COC(=O)c1cn(-c2ncccn2)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3dfb049cb4746e288a1f0696039d8f4 | NC(=O)[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1>>N#C[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1 | N1=CC=CC=C1.C1(=CC=CC=C1)CS(=O)(=O)N1[C@@H](CCC1)C(=O)N.CN(C)C=O.C(C(=O)Cl)(=O)Cl>>C1(=CC=CC=C1)CS(=O)(=O)N1[C@@H](CCC1)C#N | O=[C:2]([NH2:1])[C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1[S:8](=[O:9])(=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[N:1]#[C:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1[S:8](=[O:9])(=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | NC(=O)[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1 | N#C[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1 | null | null | O.C(C)#N | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=S(=O)(Cc1ccccc1)N1CCCC1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3](-[C:4])-[#7:5](-[#16:6])-[C:7]>>[#16:6]-[#7:5](-[C:7])-[C:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2])-[C:4] | 80 | [{"value": 80.0, "product": "C1(=CC=CC=C1)CS(=O)(=O)N1[C@@H](CCC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C1(=CC=CC=C1)CS(=O)(=O)N1[C@@H](CCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 0.67 ml DMF (8.7 mmol)in 10 ml acetonitrile at 0° C. was added 0.70 ml (8.0 mmol) oxalyl chloride. A white precipitate was formed immediately and was accompanied by gas evolution. When complete, a solution of 2.0 g (7.5 mmol) of (2S)-1-(phenylmethyl)sulfonyl-2-pyrrolidinecarboxamide in 5.0 ml acetonitr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | C1CC[NH]C1.c1ccccc1 | HO- | O.C(C)#N | null | 0.083333 | NC(=O)[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1>O.C(C)#N>N#C[C@@H]1CCCN1S(=O)(=O)Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e9a6a7c80639419f9d88502602309155 | CC(C)CBr.N#Cc1ccc(O)cc1>>CC(C)COc1ccc(C#N)cc1 | C(C(C)C)Br.C(#N)C1=CC=C(C=C1)O.C(C)N(CC)CC>>C(C(C)C)OC1=CC=C(C#N)C=C1 | Br[CH2:4][CH:2]([CH3:1])[CH3:3].[OH:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1 | CC(C)CBr.N#Cc1ccc(O)cc1 | CC(C)COc1ccc(C#N)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 85.6 | [{"value": 85.0, "product": "C(C(C)C)OC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "C(C(C)C)OC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 6 | HOUR | To a solution of 4-cyanophenol (1.2 g, 10 mmol) in dry DMF (20 mL) was added triethylamine (20 mmol) followed by i-butyl bromide (2.7 g, 20 mmol). The resulting reaction mixture was stirred at 100° C. for 6 h. After cooling to room temperature, the reaction mixture was diluted with water (100 mL) and extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 100 | 6 | CC(C)CBr.N#Cc1ccc(O)cc1>O.CN(C)C=O>CC(C)COc1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-677e608584e14eae9651397497b27789 | CCOC(=O)c1cc[nH]n1.OB(O)c1ccc(Oc2ccccc2)cc1.c1ccncc1>>CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.CCOC(=O)c1ccnn1-c1ccc(Oc2ccccc2)cc1 | N1=CC=CC=C1.O(C1=CC=CC=C1)C1=CC=C(C=C1)B(O)O.N1N=C(C=C1)C(=O)OCC>>C(C)OC(=O)C1=CC=NN1C1=CC=C(C=C1)OC1=CC=CC=C1.C(C)OC(=O)C1=NN(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:9][n:23]1.B([c:10]1[cH:11][cH:12][c:13]([O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1)([OH:26])[OH:28].[cH:24]1[n:32][cH:45][cH:46][cH:34][cH:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][n:9](-[c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3... | CCOC(=O)c1cc[nH]n1.OB(O)c1ccc(Oc2ccccc2)cc1.c1ccncc1 | CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.CCOC(=O)c1ccnn1-c1ccc(Oc2ccccc2)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | a85630168167151eeafbcbe0f4bebb6ba9bb7c40ddfe690cf48700330de56629 | c9a91b65b405014440f8dd316252f5fba458efc41eb66897e3c7221a91f12ced | c1ccc(Oc2ccc(-n3cccn3)cc2)cc1.c1ccc(Oc2ccc(-n3cccn3)cc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[nH;D2;+0:6]:[c:7]:[c:8]:1.[OH;D1;+0:9]-B(-[OH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[c:16]1:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:[n;H0;D2;+0:20]:[cH;D2;+0:21]:1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[n;H0;D3;+0:6](-[c;H0;D3;+0:11](:[c:12]:[c:13])... | 10.3 | [{"value": 4.6, "product": "C(C)OC(=O)C1=CC=NN1C1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.3, "product": "C(C)OC(=O)C1=NN(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 2 | DAY | To a suspension of 4-phenoxyphenylboronic acid (1.70 g, 7.85 mmol), ethyl 3-pyrazolecarboxylate (0.55 g, 3.92 mmol), copper(II)acetate (1.1 g, 5.89 mmol) and 4 Å molecular sieves (powdered and heated at 200° C. for 2 h prior to use) in 30 mL of anhydrous THF was added 0.6 mL of pyridine. The reaction was stirred open t... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | Ester.Ether | c1cn[nH]c1.c1ccccc1.c1ccncc1 | c1cc[nH]n1.c1ccccc1.c1cc[nH]n1.c1ccccc1.c1ccccc1 | c1cc[nH]n1.c1ccccc1.c1ccccc1.c1cc[nH]n1.c1ccccc1.c1ccccc1 | B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C1CCOC1 | 200 | 48 | CCOC(=O)c1cc[nH]n1.OB(O)c1ccc(Oc2ccccc2)cc1.c1ccncc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C1CCOC1>CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.CCOC(=O)c1ccnn1-c1ccc(Oc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47043342eedf41c39c183b9b9d91e68b | CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.N>>NC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1 | C(C)OC(=O)C1=NN(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1.N>>O(C1=CC=CC=C1)C1=CC=C(C=C1)N1N=C(C=C1)C(=O)N | CCO[C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[n:21]1.[NH3:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[n:21]1 | CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.N | NC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1 | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(Oc2ccc(-n3cccn3)cc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[NH3;D0;+0:9]>>[NH2;D1;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 52 | [{"value": 52.0, "product": "O(C1=CC=CC=C1)C1=CC=C(C=C1)N1N=C(C=C1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A solution of 3-ethoxycarbonyl-1-(4-phenoxyphenyl)-1H-pyrazole (120 mg, 0.39 mmol) in 5 mL of a 2N solution of ammonia in MeOH was stirred at rt for 4 d. TLC showed incomplete reaction and the solution was transferred to a sealed tube and heated at 70° C. overnight. The reaction was concentrated and purified by prepara... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1cc[nH]n1.c1ccccc1.c1ccccc1 | HO- | CO | 70 | null | CCOC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1.N>CO>NC(=O)c1ccn(-c2ccc(Oc3ccccc3)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-146028626a484ff4b6f99e630f21f98f | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(-n2cncn2)cc1>>O=[N+]([O-])c1ccc(Oc2ccc(-n3cncn3)cc2)cc1 | FC1=CC=C(C=C1)[N+](=O)[O-].N1(N=CN=C1)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>[N+](=O)([O-])C1=CC=C(OC2=CC=C(C=C2)N2N=CN=C2)C=C1 | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][cH:20]1.[OH:8][c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][n:15][cH:16][n:17]2)[cH:18][cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12](-[n:13]3[cH:14][n:15][cH:16][n:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(-n2cncn2)cc1 | O=[N+]([O-])c1ccc(Oc2ccc(-n3cncn3)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccc(-n3cncn3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 37 | [{"value": 37.0, "product": "[N+](=O)([O-])C1=CC=C(OC2=CC=C(C=C2)N2N=CN=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "[N+](=O)([O-])C1=CC=C(OC2=CC=C(C=C2)N2N=CN=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-fluoro-4-nitrobenzene (0.17 mL, 1.6 mmol), 4-{[1,2,4]triazol-1-yl}phenol (0.26 g, 1.58 mmol), and potassium carbonate (1.69 g, 12.2 mmol) in DMF was refluxed overnight. The reaction was cooled to room temperature, then partitioned between water and ethyl acetate. The aqueous layer was extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1nc[nH]n1 | HF | CN(C)C=O | null | null | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(-n2cncn2)cc1>CN(C)C=O>O=[N+]([O-])c1ccc(Oc2ccc(-n3cncn3)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea5003e1ea4245e69a25cbcadf491b4f | O=N[O-].O=[N+]([O-])Nc1ccccc1.Oc1ccccc1>>O=[N+]([O-])c1cccc(O)c1N=Nc1ccccc1O | C1(=CC=CC=C1)O.[OH-].[Na+].N(=O)[O-].[Na+].[N+](=O)([O-])NC1=CC=CC=C1.Cl.NC1=CC=CC=C1>>[N+](=O)([O-])C=1C(=C(C=CC1)O)N=NC1=C(C=CC=C1)O | O=[N:12][O-:9].[O:1]=[N+:2]([O-:3])[NH:11][c:10]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[cH:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[OH:19]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[c:10]1[N:11]=[N:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[OH:19] | O=N[O-].O=[N+]([O-])Nc1ccccc1.Oc1ccccc1 | O=[N+]([O-])c1cccc(O)c1N=Nc1ccccc1O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 7750ee4645b53126d634e4bc5688e84fdac9a5a48b07f7139ec6a9f4af77ecc3 | bf95fff5da4183d154466c3f1c3dd8ab7274e4ee078306c8c32913076deed1be | c1ccc(N=Nc2ccccc2)cc1 | O=[N;H0;D2;+0:1]-[O-;H0;D1:2].[O;-;D1;H0:3]-[N+;H0;D3:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1.[O;D1;H1:13]-[c:14](:[c:15]):[cH;D2;+0:16]:[c:17]:[c:18]>>[O;-;D1;H0:3]-[N+;H0;D3:4](=[O;D1;H0:5])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12](-[OH;D1;+0:2]):[c:7]:1-[N;H0;... | 51.5 | [{"value": 51.5, "product": "[N+](=O)([O-])C=1C(=C(C=CC1)O)N=NC1=C(C=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Nitro aniline (138.13 g) was mixed with 500 mL of concentrated HCl and stirred for several min. When all the aniline was dissolved, the solution was cooled down to room temperature and diluted with water (300 mL), and then a solution of NaNO2 (69 g) in 250 mL of water was dropwise added at 0° C. The solution became a c... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Nitroso | Diazene.Nitro group.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O | null | null | O=N[O-].O=[N+]([O-])Nc1ccccc1.Oc1ccccc1>O>O=[N+]([O-])c1cccc(O)c1N=Nc1ccccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bfe19503fdc247b9865afff196382cda | COc1c(Cl)cc(C)c(C)c1[N+](=O)[O-]>>COc1c(Cl)cc(C)c(C)c1N | ClC1=C(C(=C(C(=C1)C)C)[N+](=O)[O-])OC>>ClC=1C(=C(C(=C(C1)C)C)N)OC | O=[N+:12]([O-])[c:11]1[c:3]([O:2][CH3:1])[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]1[CH3:10]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[c:11]1[NH2:12] | COc1c(Cl)cc(C)c(C)c1[N+](=O)[O-] | COc1c(Cl)cc(C)c(C)c1N | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | HOUR | 1-Chloro-2-methoxy-4,5-dimethyl-3-nitro-benzene (10.0 g, 46.4 mmol; Stachel et. al., J. Org. Chem. 1997, 46, 4756) is dissolved in MeOH (200 mL) in a 500 mL round bottom flask. The flask is purged with N2 and 10% Pd on Carbon (0.7 g) is added and the reaction is again purged with N2. The reaction is purged with H2 and ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | 15 | COc1c(Cl)cc(C)c(C)c1[N+](=O)[O-]>CO>COc1c(Cl)cc(C)c(C)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9c0277dacc746b3a8d39d989cf54fd1 | CC(=O)OC(C)=O.COc1c(Cl)cc(C)c(C)c1N>>COc1c(Cl)cc(C)c(C)c1NC(C)=O | CO.N1=CC=CC=C1.ClC=1C(=C(C(=C(C1)C)C)N)OC.C(C)(=O)OC(C)=O>>ClC=1C(=C(C(=C(C1)C)C)NC(C)=O)OC | CC(=O)O[C:13]([CH3:14])=[O:15].[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[c:11]1[NH2:12]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[c:11]1[NH:12][C:13]([CH3:14])=[O:15] | CC(=O)OC(C)=O.COc1c(Cl)cc(C)c(C)c1N | COc1c(Cl)cc(C)c(C)c1NC(C)=O | null | CN(C)C=1C=CN=CC1 | ClCCl.CCOC(=O)C | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | 3-Chloro-2-methoxy-5,6-dimethyl-phenylamine (4.9 g, 26 mmol) is dissolved in dichloromethane (20 mL) and pyridine (8 mL) and cooled to 0° C. Acetic anhydride (3.7 mL, 39 mmol) and DMAP (85 mg, 0.7 mmol) are added and the reaction is allowed to warm to room temperature. After stirring 2 h, the reaction is diluted with E... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl.CCOC(=O)C | null | 2 | CC(=O)OC(C)=O.COc1c(Cl)cc(C)c(C)c1N>CN(C)C=1C=CN=CC1.ClCCl.CCOC(=O)C>COc1c(Cl)cc(C)c(C)c1NC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc3d07a142de43c993bd55af94fd01c6 | COc1c(Cl)cc(C)c(C)c1NC(C)=O>>COc1c(Cl)cc(C)c2cn[nH]c12 | Cl.ClC=1C(=C(C(=C(C1)C)C)NC(C)=O)OC.N(=O)[O-].[Na+]>>ClC1=CC(=C2C=NNC2=C1OC)C | CC(=O)[NH:12][c:13]1[c:3]([O:2][CH3:1])[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]1[CH3:10]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]2[cH:10][n:11][nH:12][c:13]12 | COc1c(Cl)cc(C)c(C)c1NC(C)=O | COc1c(Cl)cc(C)c2cn[nH]c12 | null | null | O.CC(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7c3f37568a0442a88eb873bc34c78039cddfa7e4dc5a6457eea74221a4843bd4 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | c1ccc2[nH]ncc2c1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH3;D1;+0:5]):[c:6]>>[c:3]:[c:2]1:[nH;D2;+0:1]:[#7;a:7]:[cH;D2;+0:5]:[c:4]:1:[c:6] | null | [] | 0 | CELSIUS | 45 | MINUTE | N-(3-Chloro-2-methoxy-5,6-dimethyl-phenyl)-acetamide (3.36 g, 17.4 mmol) is dissolved in HOAc (75 mL) and conc. HCl (30 mL) in a 1 L round bottom flask. The reaction is cooled to 0° C. with an ice/salt bath. Although some starting material crystallizes, a solution of NaNO2 (5.9 g, 86 mmol) in water (25 mL) is added por... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccccc1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | HO- | O.CC(=O)O | 0 | 0.75 | COc1c(Cl)cc(C)c(C)c1NC(C)=O>O.CC(=O)O>COc1c(Cl)cc(C)c2cn[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5e831d81db04554ad370dbf099ba58f | COc1c(Cl)cc(C)c2cn[nH]c12.O=S(=O)(Cl)c1ccccc1>>COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12 | ClC1=CC(=C2C=NNC2=C1OC)C.[H-].[Na+].C1(=CC=CC=C1)S(=O)(=O)Cl>>C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)C | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]2[cH:10][n:11][nH:12][c:22]12.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:9]2[cH:10][n:11][n:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]12 | COc1c(Cl)cc(C)c2cn[nH]c12.O=S(=O)(Cl)c1ccccc1 | COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12 | null | null | CCOC(=O)C.C1CCOC1 | Acylation | OtherReaction | 9ac2dd9da4cf023ae9acc8d8197a5ce03307f6588facb195f026e0f0c7cbe262 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1ccccc1)n1ncc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[#7;a:11]:[nH;D2;+0:12]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[#7;a:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | null | [] | 0 | CELSIUS | 10 | MINUTE | 6-Chloro-7-methoxy-4-methyl-1H-indazole (1.55 g, 9.2 mmol) is dissolved in THF (50 mL) and cooled to 0° C. Sodium hydride (60% in mineral oil, 0.40 g, 10 mmol) is added and the reaction is stirred 10 min. Benzenesulfonyl chloride (1.2 mL, 9.7 mmol) is added and the reaction is stirred 20 min. The reaction is diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2n[nH]cc2c1 | c1cc2n[nH]cc2cc1 | c1cc2n[nH]cc2cc1.c1ccccc1 | HCl | CCOC(=O)C.C1CCOC1 | 0 | 0.166667 | COc1c(Cl)cc(C)c2cn[nH]c12.O=S(=O)(Cl)c1ccccc1>CCOC(=O)C.C1CCOC1>COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efa69b70099d4206978f2bc3d9f4c70b | COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C1CCC(=O)N1Br>>COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12 | C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)CBr | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH3:8])[c:10]2[cH:11][n:12][n:13]([S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]12.O=C1CCC(=O)N1[Br:9]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH2:8][Br:9])[c:10]2[cH:11][n:12][n:13]([S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][... | COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C1CCC(=O)N1Br | COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | O=S(=O)(c1ccccc1)n1ncc2ccccc21 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]1:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]1:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | null | null | 1-Benzenesulfonyl-6-chloro-7-methoxy-4-methyl-1H-indazole (2.45 g, 7.3 mmol), recrystallized N-bromosuccinimide (1.36 g, 7.6 mmol) and benzoyl peroxide (90 mg, 0.37 mmol) are dissolved in carbon tetrachloride (25 mL). The reaction is degassed and then placed in a 80° C. bath. The reaction is heated (about 2 h) until no... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1cc2n[nH]cc2cc1.c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COc1c(Cl)cc(C)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fcc050a462145c7bb42d8662cfb0bda | COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1>>COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C(C1=CC=CC=C1)=NCC(=O)NCCCCC1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)CBr.[NH4+].[Cl-]>>C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)CC(C(=O)NCCCCC1=CC=CC=C1)N=C(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH2:8][c:7]1[cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:50]2[c:37]1[cH:38][n:39][n:40]2[S:41](=[O:42])(=[O:43])[c:44]1[cH:45][cH:46][cH:47][cH:48][cH:49]1.[CH2:9]([N:10]=[C:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:24](=[O:25])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][... | COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1 | COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 3eaaf72d0aea14ab64cbf2eaa034379ac1e018e2ca0aa69ec5bc55c38e063b81 | 5ea282f99a76ae0e99b6e606662ec1abb910dbc800826700b7b11b1baf068309 | O=C(NCCCCc1ccccc1)C(Cc1cccc2c1cnn2S(=O)(=O)c1ccccc1)N=C(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1.[C:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[#7:14]=[C:15](-[c:16])-[c:17]>>[C:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[#7:14]=[C:15](-[c:16])-[c:17])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | null | [] | -78 | CELSIUS | 15 | MINUTE | 2-(Diphenylmethylenamino)-N-(4-phenyl-butyl)-acetamide (7) (0.57 g, 1.5 mmol) is dissolved in dry THF (5 mL) and cooled to −78° C. A solution of KHMDS (0.5 M in PhMe, 3.0 mL, 1.5 mmol) is added slowly to the imide. The solution is warmed to 0° C. and then cooled to −78° C. A solution of 1-benzenesulfonyl-4-bromomethyl-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Substituted imine | Substituted imine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1cc2n[nH]cc2cc1.c1ccccc1 | HBr | C1CCOC1 | -78 | 0.25 | COc1c(Cl)cc(CBr)c2cnn(S(=O)(=O)c3ccccc3)c12.O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1>C1CCOC1>COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0db2ae4f7d5149f7b444cdd22e60ad48 | COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12>>COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | C1(=CC=CC=C1)S(=O)(=O)N1N=CC2=C(C=C(C(=C12)OC)Cl)CC(C(=O)NCCCCC1=CC=CC=C1)N=C(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>Cl.NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NN(C2=C(C(=C1)Cl)OC)S(=O)(=O)C1=CC=CC=C1 | c1ccc(C(c2ccccc2)=[N:10][CH:9]([CH2:8][c:7]2[cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:37]3[c:24]2[cH:25][n:26][n:27]3[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[C:11](=[O:12])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)cc1>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[c... | COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | null | null | CCOCC | Miscellaneous | OtherReaction | fe28e0513c54643a2e998df32fe9ad14c978580c0e1fa51268908e5a62d5d818 | 69d38cb38c5a54a23121b1c97287244fbbd5b6f97c6a1faf8cb1a05e149dd1cc | O=C(CCc1cccc2c1cnn2S(=O)(=O)c1ccccc1)NCCCCc1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[N;H0;D2;+0:7]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[NH2;D1;+0:7] | null | [] | null | null | null | null | 3-(1-Benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-2-(diphenylmethylenamino)-N-(4-phenyl-butyl)-propionamide (0.46 g, 0.65 mmol) is dissolved in Et2O (15 mL) and rapidly stirred with 2N HCl for 14 hours. The ether layer was decanted and the remaining aqueous layer was washed with Et2O. The aqueous layer was then ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1cc2n[nH]cc2cc1.c1ccccc1 | Other | CCOCC | null | null | COc1c(Cl)cc(CC(N=C(c2ccccc2)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12>CCOCC>COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0dd0762a70394299b19c9382db300680 | COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1>>COc1c(Cl)ccc2c(CC(NS(=O)(=O)c3ccccc3)C(=O)NCCCCc3ccccc3)nn(S(=O)(=O)c3ccccc3)c12 | Cl.NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NN(C2=C(C(=C1)Cl)OC)S(=O)(=O)C1=CC=CC=C1.N1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=NN(C2=C(C(=CC=C12)Cl)OC)S(=O)(=O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH2:10][CH:11]([NH2:12])[C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[c:8]2[cH:9][n:35][n:36]([S:37](=[O:38])(=[O:39])[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[c:46]12.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:1... | COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1 | COc1c(Cl)ccc2c(CC(NS(=O)(=O)c3ccccc3)C(=O)NCCCCc3ccccc3)nn(S(=O)(=O)c3ccccc3)c12 | null | null | ClCCl.CCOC(=O)C | Acylation | OtherReaction | 552b5ee834d5fd6842eb06ae8172e5b392b00560296acf79784aebb4778c0007 | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCCCc1ccccc1)C(Cc1nn(S(=O)(=O)c2ccccc2)c2ccccc12)NS(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#16:7]-[#7;a:8]1:[#7;a:9]:[cH;D2;+0:10]:[c:11]2:[c:12]:1:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:2-[CH2;D2;+0:17]-[C:18](-[NH2;D1;+0:19])-[C:20](=[O;D1;H0:21])-[#7:22]-[C:23]>>[#16:7]-[#7;a:8]1:[#7;a:9]:[c;H0;D3;+0:10](-[CH2;D2;+0:17]-[C:18](-[NH;D2;+0:19]... | null | [] | null | null | 18 | HOUR | 2-Amino-3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide hydrochloride (0.31 g, 0.54 mmol) is dissolved in a mixture of dichloromethane (4 mL) and pyridine (1.5 mL). Benzenesulfonyl chloride (0.12 mL, 0.9 mmol) is added portionwise and the reaction is allowed to stir for a total ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | c1cc2n[nH]cc2cc1 | c1cc2n[nH]cc2cc1 | c1ccccc1.c1ccccc1.c1cc2n[nH]cc2cc1.c1ccccc1 | HCl | ClCCl.CCOC(=O)C | null | 18 | COc1c(Cl)cc(CC(N)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1>ClCCl.CCOC(=O)C>COc1c(Cl)ccc2c(CC(NS(=O)(=O)c3ccccc3)C(=O)NCCCCc3ccccc3)nn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-945f0118a4544b1b9d86e075f4bc99d9 | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12>>COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NN(C2=C(C(=C1)Cl)OC)S(=O)(=O)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NNC2=C(C(=C1)Cl)OC | O=S(=O)(c1ccccc1)[n:36]1[n:35][cH:34][c:33]2[c:7]([CH2:8][CH:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[C:20](=[O:21])[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:37]21>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:... | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12 | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | null | null | CO | Reduction | OtherReaction | 5f3909121e327cf6bb6aee1b4f3390bb46be143d2b86e61210c3173691ea78ef | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ncc12)NS(=O)(=O)c1ccccc1 | O=S(=O)(-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | null | [] | null | null | 1 | HOUR | 2-Benzenesulfonylamino-3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide (0.17 g, 0.25 mmol) is dissolved in MeOH (2 mL) and K2CO3 is added and the reaction is stirred for 1 h. The reaction is quenched by the addition of 2 N HCl (0.1 mL) and then concentrated. The residue is disso... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cc2[nH]ncc2cc1 | c1ccc2n[nH]cc2c1 | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1 | HO- | CO | null | 1 | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cnn(S(=O)(=O)c3ccccc3)c12>CO>COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1f2beba88ac49209805ebde323201bc | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12>>O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NNC2=C(C(=C1)Cl)OC.Cl.[NH+]1=CC=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NNC2=C(C(=C1)Cl)O | C[O:21][c:20]1[c:18]([Cl:19])[cH:17][c:16]([CH2:15][CH:14]([C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[NH:27][S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[c:26]2[c:22]1[nH:23][n:24][cH:25]2>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][c... | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ncc12)NS(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[#7;a:6]:[c:7]:[c:8]:1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | 2-Benzenesulfonylamino-3-(6-chloro-7-methoxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide (0.10 g, 0.19 mmol) and pyridinium hydrochloride (ca. 0.7 g) are combined in a 2 mL pressure vial. The reaction is heated to obtain a melt (ca. 170° C. bath). After 50 min. the reaction is cooled and partitioned between EtOAc ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2[nH]ncc2c1.c1ccccc1 | Other | null | null | null | COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12>>O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dac15edfccee490a90f39607a30309f9 | COC(=O)CBr.O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1>>O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | C(=O)([O-])[O-].[K+].[K+].C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=NNC2=C(C(=C1)Cl)O.BrCC(=O)OC>>C1(=CC=CC=C1)S(=O)(=O)NC(CC1=C2C=NNC2=C(C(=C1)Cl)OCC(=O)O)C(NCCCCC1=CC=CC=C1)=O | C[O:3][C:2](=[O:1])[CH2:4]Br.[OH:5][c:6]1[c:7]([Cl:8])[cH:9][c:10]([CH2:11][CH:12]([NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23](=[O:24])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[c:36]2[cH:37][n:38][nH:39][c:40]12>>[O:1]=[C:2]([OH:3])[CH2:4][... | COC(=O)CBr.O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1 | O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | null | null | CN(C)C=O.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ncc12)NS(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[#7;a:9]:[#7;a:10]:[c:11]:[c:12]:1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[#7;a:9]:[#7;a:10]:[c:11]:[c:12]:1 | null | [] | null | null | 36 | HOUR | 2-Benzenesulfonylamino-3-(6-chloro-7-hydroxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide (30 mg, 0.057 mmol) is dissolved in DMF (1 mL) and K2CO3 is added followed by a slight excess of methyl bromoacetate (11 mg, 0.072 mmol). The reaction is allowed to stir for 36 h. The reaction is worked-up by diluting with EtO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1 | HBr | CN(C)C=O.CCOC(=O)C | null | 36 | COC(=O)CBr.O=C(NCCCCc1ccccc1)C(Cc1cc(Cl)c(O)c2[nH]ncc12)NS(=O)(=O)c1ccccc1>CN(C)C=O.CCOC(=O)C>O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07c91a5812cd47a1a871308ec1152428 | O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12>>O=C(O)COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | C1(=CC=CC=C1)S(=O)(=O)NC(CC1=C2C=NNC2=C(C(=C1)Cl)OCC(=O)O)C(NCCCCC1=CC=CC=C1)=O>>C1(=CC=CC=C1)S(=O)(=O)NC(CC1=C2C=NNC2=C(C=C1)OCC(=O)O)C(NCCCCC1=CC=CC=C1)=O | Cl[c:7]1[c:6]([O:5][CH2:4][C:2](=[O:1])[OH:3])[c:39]2[c:35]([c:9]([CH2:10][CH:11]([NH:12][S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:8]1)[cH:36][n:37][nH:38]2>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:... | O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | O=C(O)COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 5b5272366f02afef2e4988c85e194014363ac9ecbefdea542e560764e740c539 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ncc12)NS(=O)(=O)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2:[c:9]:1-[#8:10]>>[#8:10]-[c:9]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2:1 | null | [] | null | null | null | null | {4-[2-Benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-6-chloro-1H-indazol-7-yloxy}-acetic acid (8.0 mg, 0.014 mmol) is dissolved in MeOH (1.5 mL) and 10% Pd/C (5 mg) is added. The reaction is purged with N2 and then with H2. The reaction is rapidly stirred and monitored by HPLC until complete (approximately 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1 | Other | [Pd].CO | null | null | O=C(O)COc1c(Cl)cc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12>[Pd].CO>O=C(O)COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cn[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dcdc731f2cc84ee29c862d4a72fe44ae | COC(=O)c1ccc(OC)c2c1ccn2S(=O)(=O)c1ccccc1>>COc1ccc(CO)c2ccn(S(=O)(=O)c3ccccc3)c12 | [H-].C(C(C)C)[Al+]CC(C)C.COC(=O)C=1C=2C=CN(C2C(=CC1)OC)S(=O)(=O)C1=CC=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=C(C=CC(=C12)OC)CO | CO[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]2[c:9]1[cH:10][cH:11][n:12]2[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[cH:10][cH:11][n:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]12 | COC(=O)c1ccc(OC)c2c1ccn2S(=O)(=O)c1ccccc1 | COc1ccc(CO)c2ccn(S(=O)(=O)c3ccccc3)c12 | null | null | [C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O.[Na+].[K+].C(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 1 | HOUR | Diisobutylaluminum hydride (1.5 M toluene, 1.4 mL, 2.1 mmol) is added dropwise to a −78° C. solution of 1-benzenesulfonyl-7-methoxy-1H-indole-4-carboxylic acid methyl ester (0.34 g, 0.98 mmol, Santangelo, et. al., Synth. Commun. 1993, 23, 2717–2725) in CH2Cl2 (7 mL). After stirring for 1 h, the solution is diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cccc2[nH]ccc12.c1ccccc1 | Other | [C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O.[Na+].[K+].C(Cl)Cl | null | 1 | COC(=O)c1ccc(OC)c2c1ccn2S(=O)(=O)c1ccccc1>[C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O.[Na+].[K+].C(Cl)Cl>COc1ccc(CO)c2ccn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abb7f6e090d74c539d90ada5554ca473 | COc1ccc(CC(N)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1>>COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12 | CCN(C(C)C)C(C)C.[Cl-].NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CN(C2=C(C=C1)OC)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CN(C2=C(C=C1)OC)S(=O)(=O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8]([NH2:9])[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:32]2[cH:33][cH:34][n:35]([S:36](=[O:37])(=[O:38])[c:39]3[cH:40][cH:41][cH:42][cH:43][cH:44]3)[c:45]12.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:1... | COc1ccc(CC(N)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1 | COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12 | null | null | CCOCC.C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCCCc1ccccc1)C(Cc1cccc2c1ccn2S(=O)(=O)c1ccccc1)NS(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH2;D1;+0:13]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | 2 | HOUR | Hunig's base (2.1 g, 16 mmol) is added to a suspension of 2-amino-3-(1-benzenesulfonyl-7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide, hydrogen chloride salt (3.0 g, 5.6 mmol) in CH2Cl2. The resulting solution is cooled to 0° C. and benzenesulfonyl chloride (1.2 g, 6.9 mmol) is added. After being warmed to rt... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | HCl | CCOCC.C(Cl)Cl | 0 | 2 | COc1ccc(CC(N)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12.O=S(=O)(Cl)c1ccccc1>CCOCC.C(Cl)Cl>COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6fff82d4d9424ce1bcf30b2a374197da | COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12>>COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12 | C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CN(C2=C(C=C1)OC)S(=O)(=O)C1=CC=CC=C1.[OH-].[K+].[NH4+].[Cl-]>>C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CNC2=C(C=C1)OC | O=S(=O)(c1ccccc1)[n:35]1[cH:34][cH:33][c:32]2[c:6]([CH2:7][CH:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:5][cH:4][c:3]([O:2][CH3:1])[c:36]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7... | COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12 | COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12 | null | null | CO | Reduction | OtherReaction | 706bab53972d8bd3783a9b076a1c50a9aa5a0e0970c926686a27ee7263dbdbaf | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ccc12)NS(=O)(=O)c1ccccc1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | A mixture of 2-benzenesulfonylamino-3-(1-benzenesulfonyl-7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide (1.0 g, 1.6 mmol) and 2.5 M KOH (2.0 mL, 5.0 mmol) is refluxed in MeOH (9 mL) for 22 h. The resulting solution is poured into a saturated NH4Cl solution and extracted twice with EtOAc. The organics are drie... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | CO | null | null | COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2ccn(S(=O)(=O)c3ccccc3)c12>CO>COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1983935f784b4f378a92c5cece0120c6 | CCS.CCS.COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12.[NH4+]>>O=C(CNS(=O)(=O)c1ccccc1)NCCC(Cc1ccccc1)c1ccc(O)c2[nH]ccc12.O=C(NCCCCc1ccccc1)C(Cc1ccc(O)c2[nH]ccc12)NS(=O)(=O)c1ccccc1 | [NH4+].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].CCS.[Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CNC2=C(C=C1)OC.CCS>>C1(=CC=CC=C1)S(=O)(=O)NCC(=O)NCCC(CC1=CC=CC=C1)C1=C2C=CNC2=C(C=C1)O.C1(=CC=CC=C1)S(=O)(=O)NC(C(=O)NCCCCC1=CC=CC=C1)CC1=C2C=CNC2=C(C=C1)O | S[CH2:69][CH3:2].[CH3:52][CH2:53][SH:61].[O:1]=[S:5]([NH:4][CH:3]([C:36](=[O:35])[NH:37][CH2:38][CH2:39][CH2:40][CH2:41][c:42]1[cH:43][cH:44][cH:67][cH:46][cH:47]1)[CH2:49][c:50]1[cH:51][cH:27][c:28]([O:29][CH3:30])[c:55]2[nH:56][cH:57][cH:58][c:59]12)(=[O:6])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[NH4+:14]>>[O:1]=[... | CCS.CCS.COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12.[NH4+] | O=C(CNS(=O)(=O)c1ccccc1)NCCC(Cc1ccccc1)c1ccc(O)c2[nH]ccc12.O=C(NCCCCc1ccccc1)C(Cc1ccc(O)c2[nH]ccc12)NS(=O)(=O)c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 567b2db691f6ce3fb6b04d1424187c27634f6d754d36d9131d981ba9e97e8fd8 | 5226fb5d9ca42e1d50c8eb885034d36c77e02fc537477bcb9240e41162aeaea2 | O=C(CNS(=O)(=O)c1ccccc1)NCCC(Cc1ccccc1)c1cccc2[nH]ccc12.O=C(NCCCCc1ccccc1)C(Cc1cccc2[nH]ccc12)NS(=O)(=O)c1ccccc1 | S-[CH2;D2;+0:1]-[CH3;D1;+0:2].[CH3;D1;+0:3]-[CH2;D2;+0:4]-[SH;D1;+0:5].[C:6]-[#7:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[#7:11]-[S;H0;D4;+0:12](=[O;D1;H0:13])(=[O;H0;D1;+0:14])-[c:15](:[c:16]):[c:17])-[CH2;D2;+0:18]-[c:19]1:[cH;D2;+0:20]:[cH;D2;+0:21]:[c;H0;D3;+0:22](-[O;H0;D2;+0:23]-[CH3;D1;+0:24]):[c;H0;D3;+0... | null | [] | null | null | 3.5 | HOUR | Aluminum chloride (0.13 g, 0.99 mmol) is added to a 0° C. solution of 2-benzenesulfonylamino-3-(7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide (0.12 g, 0.25 mmol) and EtSH (0.061 g, 0.99 mmol). The mixture is stirred 3.5 h while being allowed to warm to rt. Additional AlCl3 (0.13 g, 0.99 mmol) and EtSH (0.061... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Secondary amide.Aliphatic thiol.Aliphatic thiol | Sulfonamide.Sulfonamide.Secondary amide.Secondary amide.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | 3.5 | CCS.CCS.COc1ccc(CC(NS(=O)(=O)c2ccccc2)C(=O)NCCCCc2ccccc2)c2cc[nH]c12.[NH4+]>>O=C(CNS(=O)(=O)c1ccccc1)NCCC(Cc1ccccc1)c1ccc(O)c2[nH]ccc12.O=C(NCCCCc1ccccc1)C(Cc1ccc(O)c2[nH]ccc12)NS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-403720b4bef8437f92fc3e9aee7e95fe | CC(C)(C)OC(=O)NCC(=O)O.NCCCCc1ccccc1>>CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1 | C1(=CC=CC=C1)CCCCN.N(CC(=O)O)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(NCC(NCCCCC1=CC=CC=C1)=O)=O | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]... | CC(C)(C)OC(=O)NCC(=O)O.NCCCCc1ccccc1 | CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1 | null | null | O1CCOCC1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+] | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | null | [] | null | null | 16 | HOUR | Phenylbutylamine (8.2 g, 52 mmol) is added to a mixture of BOC-Gly-PNB (14.82 g, 50 mmol) in dioxane (60 mL) and 1 M K2CO3 (60 mL). The mixture is stirred 16 h and then diluted with CH2Cl2 and washed with a saturated NaHCO3 solution until the organic phase is colorless. The organics are dried (MgSO4) and concentrated t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O1CCOCC1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+] | null | 16 | CC(C)(C)OC(=O)NCC(=O)O.NCCCCc1ccccc1>O1CCOCC1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c03b28059c94baea3e7e6a4addbc311 | CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1.Cl>>NCC(=O)NCCCCc1ccccc1.[Cl-] | C(C)(C)(C)OC(NCC(NCCCCC1=CC=CC=C1)=O)=O.Cl>>[Cl-].NCC(=O)NCCCCC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[ClH:16]>>[NH2:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[Cl-:16] | CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1.Cl | NCC(=O)NCCCCc1ccccc1.[Cl-] | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6].[ClH;D0;+0:7]>>[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1].[Cl-;H0;D0:7] | null | [] | null | null | null | null | The crude [(4-phenyl-butylcarbamoyl)-methyl]-carbamic acid tert-butyl ester is stirred in a solution of dioxane (150 mL) and HCl (4 M dioxane, 42 mL, 168 mmol) for 17 h. The volatiles are removed in vacuo to provide 2-amino-N-(4-phenyl-butyl)-acetamide, hydrogen chloride salt which is used as is without further purific... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | null | CC(C)(C)OC(=O)NCC(=O)NCCCCc1ccccc1.Cl>O1CCOCC1>NCC(=O)NCCCCc1ccccc1.[Cl-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0425835e9f904429b2a1ada31b068d43 | N=C(c1ccccc1)c1ccccc1.NCC(=O)NCCCCc1ccccc1>>O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1 | Cl.NCC(=O)NCCCCC1=CC=CC=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)=N>>C1(=CC=CC=C1)C(C1=CC=CC=C1)=NCC(=O)NCCCCC1=CC=CC=C1 | N=[C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[C:2]([CH2:3][NH2:4])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[C:2]([CH2:3][N:4]=[C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[N... | N=C(c1ccccc1)c1ccccc1.NCC(=O)NCCCCc1ccccc1 | O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5c2ecd1abe923724cb27d21ac6e885dd316245a236b29970f80eae667c9e6294 | d626c897c8bd63d92b2ec938ee0af3ccbc3842d02f981457c923654bacf119df | O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1 | N=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]-[NH2;D1;+0:13]>>[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12]-[N;H0;D2;+0:13]=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 2-Amino-N-(4-phenyl-butyl)-acetamide-hydrogen chloride salt is stirred with benzophenone imine (12.6 mL, 75 mmol) in CH2Cl2 (200 mL) for 24 h. The organics are then washed with water, dried (MgSO4), and concentrated to provide 2-(diphenylmethylenamino)-N-(4-phenyl-butyl)-acetamide (7) as a white solid which is used wit... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted imine.Primary amine | Substituted imine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | null | N=C(c1ccccc1)c1ccccc1.NCC(=O)NCCCCc1ccccc1>C(Cl)Cl>O=C(CN=C(c1ccccc1)c1ccccc1)NCCCCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc46d3f3c2e348ed877fbffad0cbf5b4 | Brc1ccccc1.O=C1CCC(=O)O1>>O=C(O)CCC(=O)c1ccc(Br)cc1 | [Al+3].[Cl-].[Cl-].[Cl-].C1(CCC(=O)O1)=O.BrC1=CC=CC=C1.Cl>>BrC1=CC=C(C=C1)C(CCC(=O)O)=O | [cH:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1.[O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | Brc1ccccc1.O=C1CCC(=O)O1 | O=C(O)CCC(=O)c1ccc(Br)cc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 95de0079bfd4d0e2b70eac1863ad8bac063c1a1557f674f5eb3c0cde67534555 | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccccc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:9]:[c:8] | 76.4 | [{"value": 76.4, "product": "BrC1=CC=C(C=C1)C(CCC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | AlCl3 (128.8 g, 0.97 mol) was added by portions within 20 min to a suspension of succinic anhydride (44.3 g, 0.44 mol) and bromobenzene (100 ml, 0.99 mol) in DCM (500 ml) while the reaction flask was cooled in a water bath. After 1 h 30 min at RT, the reaction mixture was refluxed for 2 h. After cooling, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | c1ccccc1.C1CCOC1 | c1ccccc1 | c1ccccc1 | null | C(Cl)Cl | null | 0.5 | Brc1ccccc1.O=C1CCC(=O)O1>C(Cl)Cl>O=C(O)CCC(=O)c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59f9547cfdad422da5017d291877cbf6 | CO.O=C(O)CCC(=O)c1ccc(Br)cc1>>COC(=O)CCC(=O)c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CCC(=O)O)=O.OS(=O)(=O)O.CO>>COC(CCC(=O)C1=CC=C(C=C1)Br)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1 | CO.O=C(O)CCC(=O)c1ccc(Br)cc1 | COC(=O)CCC(=O)c1ccc(Br)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | null | null | 4-(4-Bromophenyl)-4-oxobutyric acid (86.4 g, 0.336 mol) (Preparation 1) in MeOH (1.7 l) containing H2SO4 (86 ml) was refluxed for 21 h. After cooling, the light precipitate was filtered off and the reaction mixture concentrated to dryness. The obtained solid was placed in water and extracted twice with EtOAc. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)CCC(=O)c1ccc(Br)cc1>>COC(=O)CCC(=O)c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c37282cc8b64bfaa39e6296202f8b8f | Brc1ccccc1.O=C(Cl)CCBr>>O=C(CCBr)c1ccc(Br)cc1 | [Al+3].[Cl-].[Cl-].[Cl-].BrC1=CC=CC=C1.BrCCC(=O)Cl>>BrCCC(=O)C1=CC=C(C=C1)Br | [cH:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][Br:5]>>[O:1]=[C:2]([CH2:3][CH2:4][Br:5])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | Brc1ccccc1.O=C(Cl)CCBr | O=C(CCBr)c1ccc(Br)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 84.5 | [{"value": 84.5, "product": "BrCCC(=O)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | AlCl3 (23.8 g, 178 mmol) was added by portions to bromobenzene (155 ml, 1.47 mol) at 0° C. 3-Bromopropionyl chloride (25 g, 146 mmol) was added dropwise to the red solution kept at 0° C. over 30 min. After 1 h at RT, the reaction mixture was heated to 50° C. for 1 h. After cooling, the mixture was poured over ice/water... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | 50 | 0.5 | Brc1ccccc1.O=C(Cl)CCBr>>O=C(CCBr)c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf1a9a59f9ca487388bf4e396618b9aa | O=C(CCBr)c1ccc(Br)cc1>>OC(CCBr)c1ccc(Br)cc1 | [BH4-].[Na+].BrCCC(=O)C1=CC=C(C=C1)Br.Cl>>BrCCC(O)C1=CC=C(C=C1)Br | [O:1]=[C:2]([CH2:3][CH2:4][Br:5])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1>>[OH:1][CH:2]([CH2:3][CH2:4][Br:5])[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | O=C(CCBr)c1ccc(Br)cc1 | OC(CCBr)c1ccc(Br)cc1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 94.4 | [{"value": 94.4, "product": "BrCCC(O)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | NaBH4 (1.5 g, 39.7 mmol) was added by portions to a solution of 3-bromo-1-(4-bromophenyl)propan-1-one (11.7 g, 40 mmol) (Preparation 5) in MeOH while keeping the temperature below 10° C. After 1 h at RT, 1N aqueous hydrochloric acid was added at 5° C. to pH=1 and the mixture was concentrated in vacuum. The residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | CO | null | 1 | O=C(CCBr)c1ccc(Br)cc1>CO>OC(CCBr)c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-31b9b3e14509464ea943b6c60dbf1524 | CCOC(=O)CN.S=C=Nc1cc(Cl)cc(Cl)c1>>O=C1CNC(=S)N1c1cc(Cl)cc(Cl)c1 | ClC=1C=C(C=C(C1)Cl)N=C=S.Cl.NCC(=O)OCC>>ClC=1C=C(C=C(C1)Cl)N1C(NCC1=O)=S | CCO[C:2](=[O:1])[CH2:3][NH2:4].[C:5](=[S:6])=[N:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15]1>>[O:1]=[C:2]1[CH2:3][NH:4][C:5](=[S:6])[N:7]1[c:8]1[cH:9][c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15]1 | CCOC(=O)CN.S=C=Nc1cc(Cl)cc(Cl)c1 | O=C1CNC(=S)N1c1cc(Cl)cc(Cl)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 661d52a20ffc4dc07f0b42d6e71f02d6f2df62b907a8af0280f593fa5e8af5d9 | 1f7b20b438a0e6db92fae47a6dad1d97dbcb6314195567f1c56db0099cef8267 | O=C1CNC(=S)N1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[NH2;D1;+0:4].[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:6](=[S;D1;H0:5])-[N;H0;D3;+0:7]-1-[c:8](:[c:9]):[c:10] | 82.8 | [{"value": 82.8, "product": "ClC=1C=C(C=C(C1)Cl)N1C(NCC1=O)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | 3,5-Dichlorophenylisothiocyanate (5 g, 24.5 mmol) was added by portion to a suspension of the HCl salt of ethyl glycinate (3.4 g, 24.5 mmol) in a mixture of TEA (7.5 ml, 53.9 mmol) and dry DCM (40 ml) while cooling the flask in a water bath. After 60 h at RT, the solution was concentrated to dryness and partitioned bet... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Isothiocyanate | Thiourea.Tertiary amide | null | C1CNC[NH]1 | C1CNC[NH]1.c1ccccc1 | HO- | C(Cl)Cl | null | 60 | CCOC(=O)CN.S=C=Nc1cc(Cl)cc(Cl)c1>C(Cl)Cl>O=C1CNC(=S)N1c1cc(Cl)cc(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0f6abd673fe44b59f2198c705e4c686 | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=S>>CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CCCBr)Br.C(C)(C)(C)OC(=O)N1C(N(C(C1)=O)C1=CC(=CC(=C1)Cl)Cl)=S>>C(C)(C)(C)OC(=O)N1C(N(C([C@@]12[C@@H](CCC2)C2=CC=C(C=C2)Br)=O)C2=CC(=CC(=C2)Cl)Cl)=S | Br[CH2:23][CH2:24][CH2:25][CH:26](Br)[c:27]1[cH:28][cH:29][c:30]([Br:31])[cH:32][cH:33]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[S:10])[N:11]([c:12]2[cH:13][c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19]2)[C:20](=[O:21])[CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[S:10])[N... | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=S | CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | null | null | null | C-C Coupling | OtherReaction | f7705fcc55562dd1d514d37592f3026f1b985aed97988cbab983ce3221a43656 | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | O=C1N(c2ccccc2)C(=S)N[C@@]12CCC[C@H]2c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-Br)-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]1-[CH2;D2;+0:16]-[C:17](=[O;D1;H0:18])-[#7:19](-[c:20])-[C:21]-1=[S;D1;H0:22]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]1-[C... | null | [] | null | null | null | null | Using the same procedure as in Example 1 starting from 1-bromo-4-(1,4-dibromobutyl)benzene (423 mg, 1.1 mmol) (Preparation 4) and 3-(3,5-dichlorophenyl)-4-oxo-2-thioxoimidazolidine-1-carboxylic acid tert-butyl ester (361 mg, 1 mmol) (Preparation 9), (5R*,6S*)-6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1C[NH]C[NH]1 | C1CCC2(C1)C[NH]C[NH]2 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1 | HBr | null | null | null | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=S>>CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c24b3f2993e946fcbda0dfb1310bbbb5 | CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.N#Cc1ccc(C=O)cc1>>CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)/C1=C\c1ccc(C#N)cc1 | C(C)(C)(C)OC(=O)N1C(N(C(C1)=O)C1=CC(=CC(=C1)Cl)Cl)=O.C(#N)C1=CC=C(C=O)C=C1.CC(=O)[O-].[Na+]>>C(C)(=O)N\1C(N(C(/C1=C\C1=CC=C(C#N)C=C1)=O)C1=CC(=CC(=C1)Cl)Cl)=O | CC(C)(C)OC(=O)[N:4]1[C:5](=[O:6])[N:7]([c:8]2[cH:9][c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15]2)[C:16](=[O:17])[CH2:18]1.O=[CH:19][c:20]1[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[N:4]1[C:5](=[O:6])[N:7]([c:8]2[cH:9][c:10]([Cl:11])[cH:12][c:13]([Cl:14])[cH:15]2)[C:16](=[O:17])/[C:18]1=[CH... | CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.N#Cc1ccc(C=O)cc1 | CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)/C1=C\c1ccc(C#N)cc1 | null | null | CC(=O)OC(=O)C | Acylation | OtherReaction | c63cff6908ead9259865a72c3c86780707b1a88e0885e2beb31b19780f7a532b | 84427fcabd93888189c50bbfb7aecd65f7823243b9794dda39c8490a956075b6 | O=C1N/C(=C/c2ccccc2)C(=O)N1c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[c:6])-[C:7]-1=[O;D1;H0:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:13]-[C:14](=[O;D1;H0:15])-[N;H0;D3;+0:1]1-[C:7](=[O;D1;H0:8])-[#7:5](-[c:6])-[C:3](=[O;D1;H0:4])/[C;H0;D3;+0:2]-1=[CH;D2;+0:9]\[c:10](:[c:11]):[c:12] | 109.9 | [{"value": 109.9, "product": "C(C)(=O)N\\1C(N(C(/C1=C\\C1=CC=C(C#N)C=C1)=O)C1=CC(=CC(=C1)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester (3.45 g, 10 mmol) (Preparation 11), 4-cyanobenzaldehyde (1.31 g, 10 mmol) and NaOAc (0.82 g, 10 mmol) was refluxed for 3 h in Ac2O (50 ml). The solid obtained after concentration was taken into a mixture of ice/water and DCM. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Urea.Substituted dicarboximide.Boc | Enamine.Urea.Substituted dicarboximide | C1C[NH]C[NH]1 | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1ccccc1.c1ccccc1 | HO- | CC(=O)OC(=O)C | null | null | CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.N#Cc1ccc(C=O)cc1>CC(=O)OC(=O)C>CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)/C1=C\c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3b0ca61e6a744f0b37d526d63b480b5 | CCOC(=O)CNC.O=C=Nc1cc(Cl)nc(Cl)c1>>CN1CC(=O)N(c2cc(Cl)nc(Cl)c2)C1=O | Cl.C(C)OC(CNC)=O.ClC1=NC(=CC(=C1)N=C=O)Cl>>ClC1=NC(=CC(=C1)N1C(N(CC1=O)C)=O)Cl | CCO[C:4]([CH2:3][NH:2][CH3:1])=[O:5].[N:6]([c:7]1[cH:8][c:9]([Cl:10])[n:11][c:12]([Cl:13])[cH:14]1)=[C:15]=[O:16]>>[CH3:1][N:2]1[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([Cl:10])[n:11][c:12]([Cl:13])[cH:14]2)[C:15]1=[O:16] | CCOC(=O)CNC.O=C=Nc1cc(Cl)nc(Cl)c1 | CN1CC(=O)N(c2cc(Cl)nc(Cl)c2)C1=O | null | null | C(Cl)Cl | Acylation | OtherReaction | b625fb00e8984b3ab5a50595e831b3cf1c0e3d33ffe13b923a6e37bd004b081a | 14fc722b35388e650c3f1c11183dfc37a5a1b84b5dc579a69d8278216faa51d7 | O=C1CNC(=O)N1c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:5]-[N;H0;D3;+0:4]1-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:2)-[C;H0;D3;+0:7]-1=[O;D1;H0:6] | 155.4 | [{"value": 155.4, "product": "ClC1=NC(=CC(=C1)N1C(N(CC1=O)C)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 96 | HOUR | TEA (7.2 ml, 51 mmol) was added to a suspension of the HCl salt of sarcosine ethyl ester (3.4 g, 24.5 mmol) in dry DCM (80 ml). The formed triethylamine hydrochloride was filtered off and rinsed with DCM (20 ml). The filtrate was transferred into a 3-necked round bottom flask and cooled to 5° C. A solution of 2,6-dichl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Secondary amine | Urea.Substituted dicarboximide | null | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1ccncc1 | HO- | C(Cl)Cl | 5 | 96 | CCOC(=O)CNC.O=C=Nc1cc(Cl)nc(Cl)c1>C(Cl)Cl>CN1CC(=O)N(c2cc(Cl)nc(Cl)c2)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c368e0a839684f7b84c75961fa20ac31 | CCOC(=O)c1csc(C)n1.O=C1CCC(=O)N1Br>>CCOC(=O)c1csc(CBr)n1 | C(Cl)Cl.C(C)OC(=O)C=1N=C(SC1)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC=1SC=C(N1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9]([CH3:10])[n:12]1.O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][c:9]([CH2:10][Br:11])[n:12]1 | CCOC(=O)c1csc(C)n1.O=C1CCC(=O)N1Br | CCOC(=O)c1csc(CBr)n1 | null | null | ClCCCl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1cscn1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](-[CH3;D1;+0:8]):[#16;a:9]:[c:10]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](-[CH2;D2;+0:8]-[Br;H0;D1;+0:1]):[#16;a:9]:[c:10]:1 | 8 | [{"value": 8.0, "product": "BrCC=1SC=C(N1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of ethyl-2-methylthiazole 4-carboxylate (500 mg, 2.9 mmol), N-bromosuccinimide (877 mg, 4.9 mmol), and benzoyl peroxide (5–10 mg) in 1,2-DCE (3 mL) was heated at 70° C. for 85 h. After cooling to room temperature, DCM (10 ml) was added and washed with water (3 times). The organic layer was dried over Na2SO4 a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1cscn1 | HO- | ClCCCl | 70 | null | CCOC(=O)c1csc(C)n1.O=C1CCC(=O)N1Br>ClCCCl>CCOC(=O)c1csc(CBr)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d73a3046c0e481b980eb7c2a6a7655d | CC(C)(C)OC(=O)c1ccc(O)cc1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>CC(C)(C)OC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1 | O.FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.OC1=CC=C(C(=O)OC(C)(C)C)C=C1>>C(C)(C)(C)OC(C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:20][cH:21]1.O=S(=O)(O[S:13](=[O:14])(=[O:15])[C:16]([F:17])([F:18])[F:19])C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([O:12][S:13](=[O:14])(=[O:15])[C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1 | CC(C)(C)OC(=O)c1ccc(O)cc1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | CC(C)(C)OC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to triflate conversion | 934d625c86d5da305dd43240eee33b5e46f4d298c87ccdc218e9e2eb60c650b5 | 13e8f5cec02bd6a2d12ae535029c405c270682596231c5c8422ac50b2cb1ec74 | c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 87.1 | [{"value": 87.1, "product": "C(C)(C)(C)OC(C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Trifluoromethanesulfonic anhydride (1.04 ml, 6.2 mmol) was added to a cooled (5° C.) solution of tert-butyl 4-hydroxybenzoate (1 g, 5.1 mmol) in a mixture of DCM (25 ml) and TEA (1.1 ml, 7.8 mmol). After 4 h at 5° C., water was added. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The resi... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Aromatic alcohol | Triflate | null | null | c1ccccc1 | HF | C(Cl)Cl | null | 4 | CC(C)(C)OC(=O)c1ccc(O)cc1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>C(Cl)Cl>CC(C)(C)OC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05bc6480a1534adfa637df5896728945 | Cc1ccccc1-c1nnn[nH]1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>Cc1ccccc1-c1nnnn1C(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl.CC1=C(C=CC=C1)C1=NN=NN1>>C1(=C(C=CC=C1)C1=NN=NN1C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][n:10][n:11][nH:12]1.Cl[C:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][n:10][n:11][n:12]1[C:13]([c:14]1[cH:15][cH:16... | Cc1ccccc1-c1nnn[nH]1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | Cc1ccccc1-c1nnnn1C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c814b61f4411b43802c99c033287485a681b4494d43aabc070529707b2f4fba2 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | c1ccc(-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[c:11]-[c:12]1:[#7;a:13]:[#7;a:14]:[#7;a:15]:[nH;D2;+0:16]:1>>[c:3]:[c:2](-[C;H0;D4;+0:1](-[c:5](:[c:6]):[c:7])(-[c:8](:[c:9]):[c:10])-[n;H0;D3;+0:16]1:[#7;a:15]:[#7;a:14]:[#7;a:13]:[c:12]:1-[c:11]):[c:4] | 31.6 | [{"value": 31.6, "product": "C1(=C(C=CC=C1)C1=NN=NN1C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of triphenylmethyl chloride (348 mg, 1.25 mmol, 2 ml DCM) was added dropwise to a mixture of 5-(2-methylphenyl)-1H-tetrazole (200.5 mg, 1.25 mmol) and TEA (174 μl, 1.25 mmol) in 8 ml DCM. The reaction mixture was strirred overnight at RT, then washed with water (10 ml). The organic layer was dried over sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1nnn[nH]1 | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 8 | Cc1ccccc1-c1nnn[nH]1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>Cc1ccccc1-c1nnnn1C(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d213834817a045fc9c40e9442c732d6e | N#Cc1csc(C=O)c1.[N-]=[N+]=[N-]>>O=Cc1cc(-c2nnn[nH]2)cs1 | O.[N-]=[N+]=[N-].[Na+].C(=O)C1=CC(=CS1)C#N.Cl>>N1N=NN=C1C=1C=C(SC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:11][s:12]1.[N-:8]=[N+:9]=[N-:10]>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][n:8][n:9][nH:10]2)[cH:11][s:12]1 | N#Cc1csc(C=O)c1.[N-]=[N+]=[N-] | O=Cc1cc(-c2nnn[nH]2)cs1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1cc(-c2nnn[nH]2)cs1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[#16;a:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1>>[O;D1;H0:11]=[C:10]-[c:9]1:[#16;a:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]2:[n;H0;D2;+0:4]:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[nH;D2;+0:1]:2):[c:12]:1 | 20 | [{"value": 20.0, "product": "N1N=NN=C1C=1C=C(SC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (2.9 g, 44.6 mmol) and TEA hydrochloride (4.13 g, 30 mmol) were added to a solution of 5-formyl-thiophene-3-carbonitrile (2 g, 15 mmol, prepared according to Intern. application WO 02126718) in DMF (50 ml). The solution was refluxed for 12 h. After cooling to RT, water was added and the solution was carefu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccsc1.c1nnn[nH]1 | null | CN(C)C=O | null | null | N#Cc1csc(C=O)c1.[N-]=[N+]=[N-]>CN(C)C=O>O=Cc1cc(-c2nnn[nH]2)cs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-505d61d455ad42dea1fa0ca92d5dd593 | BrCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | O.[OH-].[K+].BrC1=CC=C(C=C1)C(CCCBr)Br.ClC=1C=C(C=C(C1)Cl)N1C(N(CC1=O)C)=O>>BrC1=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1 | Br[CH2:17][CH2:18][CH2:19][CH:20](Br)[c:21]1[cH:22][cH:23][c:24]([Br:25])[cH:26][cH:27]1.[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[CH2:16]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16]12[CH2:... | BrCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | f7705fcc55562dd1d514d37592f3026f1b985aed97988cbab983ce3221a43656 | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | O=C1N[C@@]2(CCC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-Br)-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[#7:9]1-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#7:13](-[c:14])-[C:15]-1=[O;D1;H0:16]>>[C;D1;H3:8]-[#7:9]1-[C:15](=[O;D1;H0:16])-[#7:13](-[c:14])-[C:11](=[O;D1;H0:12])-[C@;H0;D4;+0:10]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[C@H;D3;+0:4]-2-[c:5](:[c:6])... | 110.8 | [{"value": 110.8, "product": "BrC1=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | KOH flakes (1.3 g, 23.2 mmol) were added at RT to a solution of 1-bromo-4(1,4-dibromobutyl)benzene (4.08 g, 10.6 mmol) (Preparation 4) and 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione (2.5 g, 9.6 mmol, prepared according to Fujinami et al. cited above) in dry DMSO (40 ml). After 30 h at RT, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1C[NH]C[NH]1 | C1CCC2(C1)C[NH]C[NH]2 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1 | HBr | CS(=O)C | null | 30 | BrCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>CS(=O)C>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ba53f5111614be491e14902f7e9b2ca | CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.ClC(CCBr)c1ccc(Br)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CC[C@H]2c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CCBr)Cl.ClC=1C=C(C=C(C1)Cl)N1C(N(CC1=O)C)=O>>BrC1=CC=C(C=C1)[C@@H]1CC[C@@]12N(C(N(C2=O)C2=CC(=CC(=C2)Cl)Cl)=O)C | [CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[CH2:16]1.Cl[CH:19]([CH2:18][CH2:17]Br)[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16]12[CH2:17][CH2:... | CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.ClC(CCBr)c1ccc(Br)cc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CC[C@H]2c1ccc(Br)cc1 | null | null | null | C-C Coupling | OtherReaction | 633122e91d14da7e197b20d59ad495d86526fe11b8586f717e52f0c369568b4b | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | O=C1N[C@@]2(CC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH;D3;+0:3](-Cl)-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[#7:8]1-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#7:12](-[c:13])-[C:14]-1=[O;D1;H0:15]>>[C;D1;H3:7]-[#7:8]1-[C:14](=[O;D1;H0:15])-[#7:12](-[c:13])-[C:10](=[O;D1;H0:11])-[C@;H0;D4;+0:9]-12-[CH2;D2;+0:1]-[C:2]-[C@H;D3;+0:3]-2-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Using the same procedure as in Example 1 starting from 1-bromo-4-(3-bromo-1-chloropropyl)benzene (Preparation 7) and 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione, the above titled compound was obtained after reverse phase HPLC purification (gradient from CH3CN/H2O/TFA: 5/95/0.05 to CH3CN/H2O[[FA: 80/20/0.05).... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1C[NH]C[NH]1 | C1CC2(C1)C[NH]C[NH]2 | c1ccccc1.C1CC2(C1)C[NH]C[NH]2.c1ccccc1 | HCl.Br- | null | null | null | CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O.ClC(CCBr)c1ccc(Br)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CC[C@H]2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-37e8e7fbf64f43989d779c703b77e07e | BrCCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCCC[C@H]2c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CCCCBr)Br.ClC=1C=C(C=C(C1)Cl)N1C(N(CC1=O)C)=O>>BrC1=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCCC1 | Br[CH2:17][CH2:18][CH2:19][CH2:20][CH:21](Br)[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1.[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[CH2:16]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16... | BrCCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCCC[C@H]2c1ccc(Br)cc1 | null | null | null | C-C Coupling | OtherReaction | b5252ea826d331e6580a114bacf223f7ee0db41abb8410b94bbb79f77b0982ca | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | O=C1N[C@@]2(CCCC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH;D3;+0:5](-Br)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[#7:10]1-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#7:14](-[c:15])-[C:16]-1=[O;D1;H0:17]>>[C;D1;H3:9]-[#7:10]1-[C:16](=[O;D1;H0:17])-[#7:14](-[c:15])-[C:12](=[O;D1;H0:13])-[C@;H0;D4;+0:11]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C@H;D3;+0:5]-2... | null | [] | null | null | null | null | Using the same procedure as in Example 1 starting from 1-bromo-4-(1,5-dibromopentyl)benzene (4.2 g, 10.9 mmol) (Preparation 14) and 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione (2.59 g, 10 mmol), the above titled compound was obtained as a white solid (3.1 g, mp=118° C.). 1H NMR (CDCl3): 7.41 (2H, d, J=8.4 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1C[NH]C[NH]1 | C1CCC2(CC1)C[NH]C[NH]2 | c1ccccc1.C1CCC2(CC1)C[NH]C[NH]2.c1ccccc1 | HBr | null | null | null | BrCCCCC(Br)c1ccc(Br)cc1.CN1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCCC[C@H]2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-975e51b9a41b4311b50a080c893fcfdd | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>>CC(C)(C)OC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CCCBr)Br.C(C)(C)(C)OC(=O)N1C(N(C(C1)=O)C1=CC(=CC(=C1)Cl)Cl)=O>>C(C)(C)(C)OC(=O)N1C(N(C([C@@]12[C@@H](CCC2)C2=CC=C(C=C2)Br)=O)C2=CC(=CC(=C2)Cl)Cl)=O | Br[CH2:23][CH2:24][CH2:25][CH:26](Br)[c:27]1[cH:28][cH:29][c:30]([Br:31])[cH:32][cH:33]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[O:10])[N:11]([c:12]2[cH:13][c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19]2)[C:20](=[O:21])[CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C:9](=[O:10])[N... | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O | CC(C)(C)OC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 | null | null | null | C-C Coupling | OtherReaction | fcf323dbc98913cd643daae03149d5439e966c3e4b72498f18033d4ddeab87ee | f9ab306b4747162d02bd4f01c34c8064410ebdd862f2319d026ca31209db9bc0 | O=C1N[C@@]2(CCC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-Br)-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]1-[CH2;D2;+0:16]-[C:17](=[O;D1;H0:18])-[#7:19](-[c:20])-[C:21]-1=[O;D1;H0:22]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]1-[C... | null | [] | null | null | null | null | Using the same procedure as in Example 1 starting from 1-bromo-4-(1,4-dibromobutyl)benzene (153 mg, 0.4 mmol) (Preparation 4) and 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester (113 mg, 0.33 mmol) (Preparation 11), the above-titled compound was obtained (33 mg) as a white solid. 1H NMR... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide.Substituted dicarboximide | Substituted dicarboximide | C1C[NH]C[NH]1 | C1CCC2(C1)C[NH]C[NH]2 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1 | HBr | null | null | null | BrCCCC(Br)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O>>CC(C)(C)OC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-350aa061377f413b88ef248f811e4b96 | CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1>>O=C1N(c2cc(Cl)cc(Cl)c2)C(=S)NC12CCCC2c1ccc(Br)cc1 | C(C)(C)(C)OC(=O)N1C(N(C(C12C(CCC2)C2=CC=C(C=C2)Br)=O)C2=CC(=CC(=C2)Cl)Cl)=S.C(=O)(C(F)(F)F)O.C(Cl)Cl.O>>BrC1=CC=C(C=C1)C1C2(C(N(C(N2)=S)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1 | CC(C)(C)OC(=O)[N:14]1[C:12](=[S:13])[N:3]([c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11]2)[C:2](=[O:1])[C:15]12[CH2:16][CH2:17][CH2:18][CH:19]2[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1>>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11]2)[C:12](=[S:13])[NH:14][C:15]12[CH2:16][CH2:17]... | CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1 | O=C1N(c2cc(Cl)cc(Cl)c2)C(=S)NC12CCCC2c1ccc(Br)cc1 | null | null | null | Reduction | Boc amine deprotection | fe11bba53ba77b759f0c7fd3a8717a8b7b48968896e428499fd61e4892b39186 | a5b4fdded3cbffe70a4e1e726f93dd5004a2fc9b906892482e0785d7f6416d9f | O=C1N(c2ccccc2)C(=S)NC12CCCC2c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2](=[S;D1;H0:3])-[#7:4](-[c:5])-[C:6](=[O;D1;H0:7])-[C:8]-1(-[C:9])-[C:10]>>[C:9]-[C:8]1(-[C:10])-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4](-[c:5])-[C:6]-1=[O;D1;H0:7] | 60.4 | [{"value": 60.4, "product": "BrC1=CC=C(C=C1)C1C2(C(N(C(N2)=S)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (42 mg, 74 μmol) (Preparation 10) was added to a TFA/DCM/H2O (1/1/0.1) solution (1 ml) at RT. After 30 min the reaction mixture was concentrated to give a beige solid which was washed with pentane to yie... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Thiourea.Boc | Thiourea | C1CCC2(C1)C[NH]C[NH]2 | C1CCC2(C1)C[NH]CN2 | c1ccccc1.C1CCC2(C1)C[NH]CN2.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)N1C(=S)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1>>O=C1N(c2cc(Cl)cc(Cl)c2)C(=S)NC12CCCC2c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de085f3f17b64cf198ba4cd20b06db1d | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(C#N)cc1 | BrC1=CC=C(C=C1)C1C2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1.C(#N)[Cu].C(CN)N>>ClC=1C=C(C=C(C1)Cl)N1C(N([C@@]2(C1=O)[C@@H](CCC2)C2=CC=C(C#N)C=C2)C)=O | Br[c:24]1[cH:23][cH:22][c:21]([CH:20]2[C:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[CH2:17][CH2:18][CH2:19]2)[cH:28][cH:27]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16]12[CH2:17][CH2:18... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(C#N)cc1 | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=C1N[C@@]2(CCC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 180 | CELSIUS | null | null | A mixture of 6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (1 g, 2.1 mmol) (Example 1) and CuCN (0.45 g, 5 mmol) in NMP was heated to 180° C. for 6 h. After cooling, the reaction mixture was poured on a mixture of ice and ethylene diamine and extracted twice with DCM. The brown r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1 | Br- | CN1CCCC1=O | 180 | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)C12CCCC2c1ccc(Br)cc1>CN1CCCC1=O>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c46e7e76268b42ab83507814dbe2a19a | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccccc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccccc2)cc1 | BrC1=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1)C1=CC=CC=C1 | Br[c:24]1[cH:23][cH:22][c:21]([C@H:20]2[C@:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[CH2:17][CH2:18][CH2:19]2)[cH:32][cH:31]1.OB(O)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:1... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccccc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccccc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1N[C@@]2(CCC[C@H]2c2ccc(-c3ccccc3)cc2)C(=O)N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 25.3 | [{"value": 25.3, "product": "C1(=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of (5R*,6S*)-6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (80 mg, 0.17 mmol) (Example 1), phenylboronic acid (73 mg, 0.6 mmol), (Ph3P)4Pd (20 mg, 0.02 mmol) and K2CO3 (80 mg, 0.6 mmol) in a mixture of DME (1.5 ml) and water (50 μl) was heated at 80° C. for 12 h. The i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 80 | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-439a77c73ae7453d917a074aa8cfea94 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccc(F)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccc(F)cc2)cc1 | BrC1=CC=C(C=C1)[C@H]1[C@@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CCC1.FC1=CC=C(C=C1)B(O)O>>ClC=1C=C(C=C(C1)Cl)N1C(N([C@@]2(C1=O)[C@@H](CCC2)C2=CC=C(C=C2)C2=CC=C(C=C2)F)C)=O | Br[c:24]1[cH:23][cH:22][c:21]([C@H:20]2[C@:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[CH2:17][CH2:18][CH2:19]2)[cH:33][cH:32]1.OB(O)[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccc(F)cc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccc(F)cc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1N[C@@]2(CCC[C@H]2c2ccc(-c3ccccc3)cc2)C(=O)N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 14.6 | [{"value": 14.6, "product": "ClC=1C=C(C=C(C1)Cl)N1C(N([C@@]2(C1=O)[C@@H](CCC2)C2=CC=C(C=C2)C2=CC=C(C=C2)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 8 (5R*,6S*)-6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (80 mg, 0.17 mmol) (Example 1) was reacted with 4-fluorophenylboronic acid (71.4 mg, 0.51 mmol) to yield the above-titled compound (12 mg) as a white solid. 1H NMR (CDCl3) δ 7.45–7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1CCC2(C1)C[NH]C[NH]2.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(Br)cc1.OB(O)c1ccc(F)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CCC[C@H]2c1ccc(-c2ccc(F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08d22c3fc77948e883a615f5285a17f6 | CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1>>N#Cc1ccc([C@@H]2CN(Cc3ccccc3)C[C@@]23NC(=O)N(c2cc(Cl)cc(Cl)c2)C3=O)cc1 | C(C)(=O)N1C(N(C([C@]12CN(C[C@H]2C2=CC=C(C#N)C=C2)CC2=CC=CC=C2)=O)C2=CC(=CC(=C2)Cl)Cl)=O.N1CCCC1>>C(C1=CC=CC=C1)N1C[C@]2(C(N(C(N2)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C#N)C=C1 | CC(=O)[N:19]1[C@:18]2([C@H:7]([c:6]3[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:34][cH:33]3)[CH2:8][N:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17]2)[C:31](=[O:32])[N:22]([c:23]2[cH:24][c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30]2)[C:20]1=[O:21]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C@@H:7]2[CH2:8][N:9]([CH2:10]... | CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1 | N#Cc1ccc([C@@H]2CN(Cc3ccccc3)C[C@@]23NC(=O)N(c2cc(Cl)cc(Cl)c2)C3=O)cc1 | null | null | C1CCOC1 | Reduction | Hydrogenolysis of tertiary amines | cca8e3a2dc6c2eee6e2fdc484fec1d1448c5181def3e7a4e759da140ec931cff | b3d6f616fb24bef205baf1bc6e3966e3715bac59493272a22ddc34f831a5b118 | O=C1N[C@@]2(CN(Cc3ccccc3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | C-C(=O)-[N;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[C:6](=[O;D1;H0:7])-[C:8]-1(-[C:9])-[C:10]-[#7:11]>>[#7:11]-[C:10]-[C:8]1(-[C:9])-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[C:6]-1=[O;D1;H0:7] | 113.3 | [{"value": 113.3, "product": "C(C1=CC=CC=C1)N1C[C@]2(C(N(C(N2)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of Example 11 (8.9 g, 16.7 mmol), TEA (3.8 ml) and pyrrolidine (2.2 ml) in THF (270 ml) was refluxed for 2 h 30 min. The mixture was concentrated in vacuo and taken into DCM, then washed with water. The organic layer was dried over MgSO4 and concentrated. The resulting solid was chromatographed over silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Substituted dicarboximide | Urea | C1C[C@]2(C[NH]1)C[NH]C[NH]2 | C1C[C@]2(C[NH]1)C[NH]CN2 | c1ccccc1.c1ccccc1.C1C[C@]2(C[NH]1)C[NH]CN2.c1ccccc1 | HO- | C1CCOC1 | null | null | CC(=O)N1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1>C1CCOC1>N#Cc1ccc([C@@H]2CN(Cc3ccccc3)C[C@@]23NC(=O)N(c2cc(Cl)cc(Cl)c2)C3=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7cb9e9d519f0413c8a1628a32eb49f53 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1 | ClC(=O)OC(C)Cl.C(C1=CC=CC=C1)N1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C#N)C=C1>>ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O | c1ccc(C[N:18]2[CH2:17][C@@:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[C@H:20]([c:21]3[cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]3)[CH2:19]2)cc1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15]... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1 | null | null | C(Cl)Cl | Deprotection | Hydrogenolysis of tertiary amines | 86a93e9e2e1e54d1e9087e31670820a5e059aff13afceb12a5a20228453b2f67 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1N[C@@]2(CNC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | [#7:1]-[C:2]1(-[C:3]-[N;H0;D3;+0:4](-C-c2:c:c:c:c:c:2)-[C:5]-[C:6]-1)-[C:7](=[O;D1;H0:8])-[#7:9]>>[#7:1]-[C:2]1(-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1)-[C:7](=[O;D1;H0:8])-[#7:9] | 116.8 | [{"value": 116.8, "product": "ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-Chloroethyl chloroformate (4.4 ml, 40.3 mmol) was added to a cooled (5° C.) solution of Example 14 (5.1 g, 10.1 mmol) in DCM (250 ml). After 1 h at 5° C., the reaction mixture was stirred at RT for 20 h. The solution was concentrated to dryness and then refluxed in MeOH (350 ml) for 3 h. After concentration in vacuo,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2 | C1C[C@]2(CN1)C[NH]C[NH]2 | c1ccccc1.C1C[C@]2(CN1)C[NH]C[NH]2.c1ccccc1 | Other | C(Cl)Cl | null | 1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(C#N)cc1>C(Cl)Cl>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa608298f4e84e2c916e95bf0375dc9c | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 | ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O.ClS(=O)(=O)C=1C=C(C(=O)O)C=CC1.C([O-])(O)=O.[Na+]>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)S(=O)(=O)C=2C=C(C(=O)O)C=CC2 | [CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16]12[CH2:17][NH:18][CH2:31][C@H:32]2[c:33]1[cH:34][cH:35][c:36]([C:37]#[N:38])[cH:39][cH:40]1.Cl[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][c:26]([C:27](=[O:28])[OH:29])[cH:30]1>>[CH3:1][N:2]1[C:3](=[O:4... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 | null | null | O.CC(=O)C | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 1b2818293e715791db7c91df8d8a7422ce1fb5a109d0403b369edb71cf4e3394 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C1N[C@@]2(CN(S(=O)(=O)c3ccccc3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[C:8]1(-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#7:15]>>[#7:7]-[C:8]1(-[C:9]-[N;H0;D3;+0:10](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#7:15] | 77 | [{"value": 77.0, "product": "C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)S(=O)(=O)C=2C=C(C(=O)O)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 4-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile (Example 15a) (0.11 g, 0.26 mmol) and (3-(Chlorosulfonyl)benzoic acid (0.058 g, 0.26 mmol) in acetone and water (1:1 mL) was added sodium bicarbonate at room temperature. The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[C@]2(CN1)C[NH]C[NH]2 | C1C[C@]2(C[NH]1)C[NH]C[NH]2 | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1.c1ccccc1 | HCl | O.CC(=O)C | null | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1>O.CC(=O)C>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-35aad3b2b74b4113a221a93457d4b0e4 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=Cc1cc(C(=O)O)cs1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O.C(=O)C1=CC(=CS1)C(=O)O.S(=O)(=O)([O-])[O-].[Na+].[Na+]>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)O | [CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]2)[C:14](=[O:15])[C@:16]12[CH2:17][NH:18][CH2:28][C@H:29]2[c:30]1[cH:31][cH:32][c:33]([C:34]#[N:35])[cH:36][cH:37]1.O=[CH:19][c:20]1[cH:21][c:22]([C:23](=[O:24])[OH:25])[cH:26][s:27]1>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=Cc1cc(C(=O)O)cs1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 44097ca774a12d2e9795061525b666c24d17f0e2808f6b11d701443fa2eeefe0 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1N[C@@]2(CN(Cc3cccs3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[#7:6]-[C:7]1(-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1)-[C:12](=[O;D1;H0:13])-[#7:14]>>[#7:6]-[C:7]1(-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5])-[C:10]-[C:11]-1)-[C:12](=[O;D1;H0:13])-[#7:14] | 75 | [{"value": 75.0, "product": "C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of 4-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile (0.1 g, 0.24 mmol) (Example 15a) in 1,2-DCE (4 mL) were sequentially added 5-Formyl-3-thiophenecarboxylic acid (0.045 g, 0.29 mmol) and sodium sulfate (150 mgs) under a nitrogen atmosphere at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1C[C@]2(CN1)C[NH]C[NH]2 | C1C[C@]2(C[NH]1)C[NH]C[NH]2 | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccsc1.c1ccccc1 | Other | ClCCCl | null | 6 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=Cc1cc(C(=O)O)cs1>ClCCCl>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-484a0e8cb7574f20af85d49d661496c8 | CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1>>CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 | ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)CC)=O.ClS(=O)(=O)C=1C=C(C(=O)O)C=CC1.CCN(C(C)C)C(C)C>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2CC)=O)C2=CC(=CC(=C2)Cl)Cl)=O)S(=O)(=O)C=2C=C(C(=O)O)C=CC2 | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([Cl:10])[cH:11][c:12]([Cl:13])[cH:14]2)[C:15](=[O:16])[C@:17]12[CH2:18][NH:19][CH2:32][C@H:33]2[c:34]1[cH:35][cH:36][c:37]([C:38]#[N:39])[cH:40][cH:41]1.Cl[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31]1>>[CH3:1][CH2:2][N... | CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1 | CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 | null | null | C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 1b2818293e715791db7c91df8d8a7422ce1fb5a109d0403b369edb71cf4e3394 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C1N[C@@]2(CN(S(=O)(=O)c3ccccc3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[C:8]1(-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#7:15]>>[#7:7]-[C:8]1(-[C:9]-[N;H0;D3;+0:10](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#7:15] | 44.6 | [{"value": 44.6, "product": "C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2CC)=O)C2=CC(=CC(=C2)Cl)Cl)=O)S(=O)(=O)C=2C=C(C(=O)O)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a mixture of Example 50 (100 mg, 0.23 mmol) and 3-(chlorosulfonyl) benzoic acid (57 mg, 0.26 mmol) in THF (5 ml) was added DIEA (45 μl, 0.26 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 hours then concentrated under vacuum. The residue was partitioned between EtOAc and water... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[C@]2(CN1)C[NH]C[NH]2 | C1C[C@]2(C[NH]1)C[NH]C[NH]2 | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 24 | CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1.O=C(O)c1cccc(S(=O)(=O)Cl)c1>C1CCOC1>CCN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(S(=O)(=O)c1cccc(C(=O)O)c1)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b83e80f1a9644bf9b7f8fbb2a3be31c8 | CCOC(=O)CBr.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1>>CCOC(=O)CN1C[C@@H](c2ccc(C#N)cc2)[C@]2(C1)C(=O)N(c1cc(Cl)cc(Cl)c1)C(=O)N2C | ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O.CCOC(=O)CBr.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(CN1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)C#N)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[CH2:8][C@@H:9]([c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[C@:18]2([CH2:19]1)[C:20](=[O:21])[N:22]([c:23]1[cH:24][c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30]1)[C:31](=[O:32])[N:33]2[CH3:34]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][C@@H:9]([c:... | CCOC(=O)CBr.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1 | CCOC(=O)CN1C[C@@H](c2ccc(C#N)cc2)[C@]2(C1)C(=O)N(c1cc(Cl)cc(Cl)c1)C(=O)N2C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7756ee7a94ed7c5f836f75b7b27466db82f96ec3c12774686e48b30bc41fb738 | e09591825c4808efe257024fb4bbe3690a7cda9ee664fef9727988761bae5b4a | O=C1N[C@@]2(CNC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]1(-[#7:10])-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]1(-[#7:10])-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:13]-[C:14]-1 | 39.2 | [{"value": 39.2, "product": "C(C)OC(CN1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of Example 15 (100 mg, 0.24 mmol), ethyl bromo acetate (29 μl, 0.26 mmol) and K2CO3 (36.6 mg, 0.26 mmol) in toluene (2 ml) was heated to 100° C. for 5 h. After cooling to room temperature, the precipitate (unreacted starting material) was removed by filtration. The filtrate was concentrated and purified by ch... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester.Tertiary amine | C1C[C@]2(CN1)C[NH]C[NH]2 | C1C[C@]2(C[NH]1)C[NH]C[NH]2 | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | null | CCOC(=O)CBr.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1>C1(=CC=CC=C1)C>CCOC(=O)CN1C[C@@H](c2ccc(C#N)cc2)[C@]2(C1)C(=O)N(c1cc(Cl)cc(Cl)c1)C(=O)N2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2179b14edb1d4017bd86105da61999c7 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)OC(C)(C)C)C[C@H]2c1ccc(C#N)cc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1 | FC(C(=O)O)(F)F.C(C)(C)(C)OC(CN1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)C#N)=O>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC(=O)O | CC(C)(C)[O:22][C:20]([CH2:19][N:18]1[CH2:17][C@@:16]2([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]3[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]3)[C:14]2=[O:15])[C@H:24]([c:25]2[cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31][cH:32]2)[CH2:23]1)=[O:21]>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:1... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)OC(C)(C)C)C[C@H]2c1ccc(C#N)cc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1 | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1N[C@@]2(CNC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | Trifluoroacetic acid (4.8 ml, 59 mmol) was added to a solution of Example 63 (1.56 g, 2.95 mmol) in DCM (40 ml). The solution was refluxed for 3 h. It was then concentrated in vacuo and partitioned between EtOAc/aqueous NH4OH. The aqueous layer was acidified to pH=2 with SO2. The white precipitate was separated by filt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1 | Other | C(Cl)Cl | null | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)OC(C)(C)C)C[C@H]2c1ccc(C#N)cc1>C(Cl)Cl>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-824e14e2ee4142ac9fd082ec66eda74c | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(Br)cc1.[CH3][Sn]([CH3])([CH3])[c]1cncnc1>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(-c2cncnc2)cc1 | C(C1=CC=CC=C1)N1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)Br.C[Sn](C=1C=NC=NC1)(C)C>>C(C1=CC=CC=C1)N1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)C=1C=NC=NC1 | Br[c:31]1[cH:30][cH:29][c:28]([C@H:27]2[C@:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[CH2:17][N:18]([CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26]2)[cH:39][cH:38]1.[CH3][Sn]([CH3])([CH3])[c:32]1[cH:33][n:34][cH:35][n:36][cH:37]1>>[CH3:1][N... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(Br)cc1.[CH3][Sn]([CH3])([CH3])[c]1cncnc1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(-c2cncnc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 39e618932e02f216bb32f365d3d5cace861d61f943e27ad5f6a4e36b8af3ac81 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C1N[C@@]2(CN(Cc3ccccc3)C[C@H]2c2ccc(-c3cncnc3)cc2)C(=O)N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3]-[Sn](-[CH3])(-[CH3])-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1):[c:4]:[c:5] | null | [] | null | null | null | null | A mixture of Example 65 (2 g, 3.58 mmol), 5-trimethylstannyl-pyrimidine (1.3 g, 5.35 mmol, prepared according to patent WO 95/06636) and tetrakis(triphenylphosphine)palladium(0) (620 mg, 0.54 mmol) in toluene (50 ml) was refluxed for 10 h under a nitrogen atmosphere. After cooling to room temperature, the insoluble mat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1.c1ccccc1.c1cncnc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1ccccc1)C[C@H]2c1ccc(Br)cc1.[CH3][Sn]([CH3])([CH3])[c]1cncnc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56993d3e904b46e997c5ab995801993b | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1.N>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(N)=O)C[C@H]2c1ccc(C#N)cc1 | C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC(=O)O.CN1CCOCC1.N.ClC(=O)OCC(C)C>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC(=O)N | O[C:20]([CH2:19][N:18]1[CH2:17][C@@:16]2([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]3[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]3)[C:14]2=[O:15])[C@H:24]([c:25]2[cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31][cH:32]2)[CH2:23]1)=[O:22].[NH3:21]>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1.N | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(N)=O)C[C@H]2c1ccc(C#N)cc1 | null | null | O.C(Cl)Cl | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1N[C@@]2(CNC[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[NH3;D0;+0:5]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 55.3 | [{"value": 55.3, "product": "C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Isobutyl chloroformate (27 μl, 0.21 mmol) was added to a cooled (5° C.) suspension of Example 64 (90 mg, 0.19 mmol) and N-methyl morpholine (23 μl, 0.2 mmol) in DCM (4 ml). After 1 h, ammonia (420 μl, 0.5 M in dioxane, 0.21 mmol) was added. After 1 h at 5° C. and 3 h at RT, water (2 ml) was added. The organic layer was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1 | HO- | O.C(Cl)Cl | null | 1 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(=O)O)C[C@H]2c1ccc(C#N)cc1.N>O.C(Cl)Cl>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(CC(N)=O)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c8cc087949049a8ae08d344d04c36da | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.CS(N)(=O)=O>>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)NS(C)(=O)=O)cs1)C[C@H]2c1ccc(C#N)cc1 | CCN=C=NCCCN(C)C.C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)O.CS(=O)(=O)N.C(C)N(CC)CC>>C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)NS(=O)(=O)C | O[C:23]([c:22]1[cH:21][c:20]([CH2:19][N:18]2[CH2:17][C@@:16]3([N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]4[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[cH:13]4)[C:14]3=[O:15])[C@H:33]([c:34]3[cH:35][cH:36][c:37]([C:38]#[N:39])[cH:40][cH:41]3)[CH2:32]2)[s:31][cH:30]1)=[O:24].[NH2:25][S:26]([CH3:27])(=[O:28])=[O:29]>>[CH3:1][N:2]... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.CS(N)(=O)=O | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)NS(C)(=O)=O)cs1)C[C@H]2c1ccc(C#N)cc1 | null | CN(C)C=1C=CN=CC1 | O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C1N[C@@]2(CN(Cc3cccs3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1.[C;D1;H3:8]-[#16:9](-[NH2;D1;+0:10])(=[O;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:8]-[#16:9](=[O;D1;H0:11])(=[O;D1;H0:12])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1 | 34.2 | [{"value": 34.2, "product": "C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | EDCI (84 mg, 0.44 mmol) was added to a solution of Example 37 (100 mg, 0.18 mmol), methanesulfonamide (38 mg, 0.38 mmol), triethylamine (62 μl, 0.43 mmol) and a trace of DMAP in DCM (5 ml) at room temperature. After 48 h, water was added and the mixture was acidified by bubbling SO2. The organic layer was separated and... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccsc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.O.C(Cl)Cl | null | 48 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.CS(N)(=O)=O>CN(C)C=1C=CN=CC1.O.C(Cl)Cl>CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)NS(C)(=O)=O)cs1)C[C@H]2c1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-851aa17fb191445b8977f327b3ffde44 | CCOC(=O)CN=C=O.CN(C)C=O.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1>>NC(CO)(CO)CO.[N-]=C=O | ClC=1C=C(C=C(C1)Cl)N1C(N([C@]2(C1=O)CNC[C@H]2C2=CC=C(C#N)C=C2)C)=O.N(=C=O)CC(=O)OCC.C1CCOC1.CN(C)C=O>>C(C(CO)(CO)N)O.[N-]=C=O | C[CH2:7]O[C:3]([CH2:2][N:1]=[C:10]=[O:11])=[O:4].CN(C)[CH:5]=[O:6].CN1C(=[O:8])[N:9](c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1>>[NH2:1][C:2]([CH2:3][OH:4])([CH2:5][OH:6])[CH2:7][OH:8].[N-:9]=[C:10]=[O:11] | CCOC(=O)CN=C=O.CN(C)C=O.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1 | NC(CO)(CO)CO.[N-]=C=O | null | null | null | C-C Coupling | OtherReaction | 9db8d154f4f370a50652ea2322d698a91c7d9bf817cf458377313357946f97bf | 64caabfaa7c7fda5b99edeec4590e69b73ca1c2191ff1cff7f9d26fe5e85b1b5 | null | C-N(-C)-[CH;D2;+0:1]=[O;H0;D1;+0:2].C-N1-C(=[O;H0;D1;+0:3])-[N;H0;D3;+0:4](-c2:c:c(-Cl):c:c(-Cl):c:2)-C(=O)-[C@]-12-C-N-C-[C@@H]-2-c1:c:c:c(-C#N):c:c:1.C-[CH2;D2;+0:5]-O-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[CH2;D2;+0:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[N-;H0;D1:4]=[C;H0;D2;+0:10]=[O;D1;H0:11].[NH2;D1;+0:9]-[C;... | null | [] | null | null | 8 | HOUR | To a solution of Example 15 (24.9 mg, 0.06 mmol) in 1 ml THF/DMF (9/1), was added ethyl isocyanatoacetate (11.6 mg, 0.089 mmol), and the reaction mixture was stirred overnight at RT. The titled compound was obtained (33.3 mg) after treatment with PS-Trisamine (Argonaut, 73 mg, 0.267 mmol) and PS-Isocyanate (Argonaut, 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Urea.Substituted dicarboximide.Nitrile.Isocyanate.Tertiary amide.Secondary amine | Primary alcohol.Primary alcohol.Primary alcohol.Primary amine | c1ccccc1.C1C[C@]2(CN1)C[NH]CN2.c1ccccc1 | null | null | HCl | null | null | 8 | CCOC(=O)CN=C=O.CN(C)C=O.CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CNC[C@H]2c1ccc(C#N)cc1>>NC(CO)(CO)CO.[N-]=C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00de50691c634edaa9e1945831f94a76 | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)c1csc(CN2C[C@@H](c3ccc(C#N)cc3)[C@]3(C2)C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)N3C)c1 | OP(=O)(O)O.OP(=O)(O)O.C(#N)C1=CC=C(C=C1)[C@@H]1CN(C[C@]12C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)CC2=CC(=CS2)C(=O)O.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)C1=CSC(=C1)CN1C[C@]2(C(N(C(N2C)=O)C2=CC(=CC(=C2)Cl)Cl)=O)[C@@H](C1)C1=CC=C(C=C1)C#N | [OH:2][C:3](=[O:4])[c:5]1[cH:6][s:7][c:8]([CH2:9][N:10]2[CH2:11][C@@H:12]([c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C@:21]3([CH2:22]2)[C:23](=[O:24])[N:25]([c:26]2[cH:27][c:28]([Cl:29])[cH:30][c:31]([Cl:32])[cH:33]2)[C:34](=[O:35])[N:36]3[CH3:37])[cH:38]1.C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](... | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.C[Si](C)(C)C=[N+]=[N-] | COC(=O)c1csc(CN2C[C@@H](c3ccc(C#N)cc3)[C@]3(C2)C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)N3C)c1 | null | null | O.C(Cl)Cl.CO.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | O=C1N[C@@]2(CN(Cc3cccs3)C[C@H]2c2ccccc2)C(=O)N1c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[#16;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#16;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | null | [] | null | null | null | null | To a solution of 5-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carboxylic acid (example 37) (0.150 g, 0.27 mmol) in DCM/MeOH (5:1 mL) was added trimethylsilyldiazomethane (2.0 M solution in hexane, 0.33 mL, 0.67 mmol) over a period of three mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccsc1.c1ccccc1.C1C[C@]2(C[NH]1)C[NH]C[NH]2.c1ccccc1 | Other | O.C(Cl)Cl.CO.CO | null | null | CN1C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)[C@]12CN(Cc1cc(C(=O)O)cs1)C[C@H]2c1ccc(C#N)cc1.C[Si](C)(C)C=[N+]=[N-]>O.C(Cl)Cl.CO.CO>COC(=O)c1csc(CN2C[C@@H](c3ccc(C#N)cc3)[C@]3(C2)C(=O)N(c2cc(Cl)cc(Cl)c2)C(=O)N3C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d229ca0f699b42b4bc1c37a6d473d1ea | Brc1ccc2[nH]ccc2c1.OB(O)c1ccc(Cl)cc1>>Clc1ccc(-c2ccc3[nH]ccc3c2)cc1 | C(=O)([O-])[O-].[K+].[K+].BrC=1C=C2C=CNC2=CC1.ClC1=CC=C(C=C1)B(O)O>>ClC1=CC=C(C=C1)C=1C=C2C=CNC2=CC1 | Br[c:6]1[cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:13]2[cH:14]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:16][cH:15]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[nH:10][cH:11][cH:12][c:13]3[cH:14]2)[cH:15][cH:16]1 | Brc1ccc2[nH]ccc2c1.OB(O)c1ccc(Cl)cc1 | Clc1ccc(-c2ccc3[nH]ccc3c2)cc1 | null | null | O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 40.7 | [{"value": 40.7, "product": "ClC1=CC=C(C=C1)C=1C=C2C=CNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred slurry of 6.35 g (60 mmol) K2CO3, 2.94 g (15 mmol) 5-bromoindole, 2.50 g (16 mmol) 4-chlorophenylboronic acid, and 0.48 g (0.42 mmol) tetrakistriphenylphosphine palladium was heated to reflux for 2½ hours. The reaction mixture was allowed to cool and was then poured into 200 ml water and extracted with EtOAc.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr.B | O | null | null | Brc1ccc2[nH]ccc2c1.OB(O)c1ccc(Cl)cc1>O>Clc1ccc(-c2ccc3[nH]ccc3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adb93e0d0c2c49a4a0813f54e45fa3b2 | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>O=C1O[C@H]([C@@H](O)CO)C(O)=C1O | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>O=C1C(O)=C(O)[C@H](O1)[C@@H](O)CO | [O:1]=[CH:2][C@@H:11]([C@H:9]([C@H:4]([OH:3])[C@H:5]([OH:6])[CH2:7][OH:8])[OH:10])[OH:12]>>[O:1]=[C:2]1[O:3][C@H:4]([C@@H:5]([OH:6])[CH2:7][OH:8])[C:9]([OH:10])=[C:11]1[OH:12] | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | O=C1O[C@H]([C@@H](O)CO)C(O)=C1O | null | null | null | Oxidation | OtherReaction | 67e880f982e1ec20ff3e01ab27faa94976fdbdbfa80b39d1e5a327af5f5676c8 | bd2ab3fbcaddb67c8972abe9138d0a67a3d3cea6378334aebb0d07cc0e195b46 | O=C1C=CCO1 | [C:1]-[C:2](-[OH;D1;+0:3])-[C@H;D3;+0:4](-[O;D1;H1:5])-[C@@H;D3;+0:6](-[O;D1;H1:7])-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[C:2]1-[O;H0;D2;+0:3]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C;H0;D3;+0:6](-[O;D1;H1:7])=[C;H0;D3;+0:4]-1-[O;D1;H1:5] | null | [] | null | null | 17.5 | MINUTE | Isolation and Culture of Growth Plate Chondrocytes: Six- to eight-week old broiler chickens were obtained commercially, sacrificed by cervical displacement, and the tibiae harvested. Epiphyseal growth plate chondrocytes were obtained from the tibiae as described (Ali et al., 1970, Proc. Natl. Acad. Sci. USA 67: 1513–15... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol.Secondary alcohol.Secondary alcohol | Ester.Enol.Enol | null | C1=CCOC1 | C1=CCOC1 | null | null | null | 0.291667 | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>O=C1O[C@H]([C@@H](O)CO)C(O)=C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e19f693ac17d4f31bc9336f96c96004c | CC(C)(C)N.COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl>>COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C | Cl.C(C)(C)(C)N.ClS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-]>>C(C)(C)(C)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-] | [NH2:17][C:18]([CH3:19])([CH3:20])[CH3:21].Cl[S:14]([c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12]1)(=[O:15])=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[O:16])[NH:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CC(C)(C)N.COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]-[C:7](-[#8:8])=[O;D1;H0:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[NH2;D1;+0:14]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[C:11](-[C;D1;H3:10])(-[C;D1;H3:12])-[C;D1;H3:13]):[c:5] | null | [] | null | null | 2 | HOUR | At 0° C., 1.4 ml (13.3 mmol) of tert-butylamine are added dropwise to a solution of 1.00 g (3.58 mmol) of methyl 2-(chlorosulfonyl)-6-nitrobenzoate in 8 ml of dichloromethane, and the reaction mixture is then allowed to warm to room temperature. After 2 h, the reaction mixture is poured into ice-water, adjusted to pH 3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | ClCCl | null | 2 | CC(C)(C)N.COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl>ClCCl>COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea74c890f4544289b988a34632edf185 | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C>>COC(=O)c1c([N+](=O)[O-])cccc1S(N)(=O)=O | C(C)(C)(C)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-]>>NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-] | CC(C)(C)[NH:15][S:14]([c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12]1)(=[O:16])=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12][c:13]1[S:14]([NH2:15])(=[O:16])=[O:17] | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C | COC(=O)c1c([N+](=O)[O-])cccc1S(N)(=O)=O | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccccc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | 300 mg (0.948 mmol) of methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate in 8 ml of trifluoroacetic acid are stirred at room temperature for 4 h. The mixture is subsequently concentrated to dryness under reduced pressure and the residue is digested with diethyl ether. After filtration with suction and drying, 230 mg... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1 | Other | FC(C(=O)O)(F)F | null | null | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C>FC(C(=O)O)(F)F>COC(=O)c1c([N+](=O)[O-])cccc1S(N)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a5a0447e048426b955fee6516a6daf5 | CC(C)=O.COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C>>COC(=O)c1c(NC(C)C)cccc1S(=O)(=O)NC(C)(C)C | [BH4-].[Na+].CC(=O)C.N.NC1=C(C(=O)OC)C(=CC=C1)S(=O)(=O)NC(C)(C)C>>C(C)(C)(C)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)NC(C)C | O=[C:8]([CH3:9])[CH3:10].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:11][cH:12][cH:13][c:14]1[S:15](=[O:16])(=[O:17])[NH:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][CH:8]([CH3:9])[CH3:10])[cH:11][cH:12][cH:13][c:14]1[S:15](=[O:16])(=[O:17])[NH:18][C:19]([CH3:20])([CH3:21])[CH... | CC(C)=O.COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C | COC(=O)c1c(NC(C)C)cccc1S(=O)(=O)NC(C)(C)C | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:10] | null | [] | null | null | 1 | HOUR | At a temperature of 5-10° C., 925 mg (24.4 mmol) of sodium borohydride are stirred into 14 ml of acetic acid. After 1 h, this mixture is admixed first with 1.42 g (24.4 mmol) of acetone and then with 700 mg (2.44 mmol) of methyl 2-amino-6-[(tert-butylamino)sulfonyl]benzoate and stirred at 5-10° C. for 2.5 h. For work-u... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | C(C)(=O)O | null | 1 | CC(C)=O.COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C>C(C)(=O)O>COC(=O)c1c(NC(C)C)cccc1S(=O)(=O)NC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e109df869bcb46d5a4484519939d7541 | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C>>COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C | C(C)(C)(C)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-]>>NC1=C(C(=O)OC)C(=CC=C1)S(=O)(=O)NC(C)(C)C | O=[N+:7]([O-])[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([S:12](=[O:13])(=[O:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:10][cH:9][cH:8]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][cH:10][c:11]1[S:12](=[O:13])(=[O:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH3:19] | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C | COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 86 | [{"value": 86.0, "product": "NC1=C(C(=O)OC)C(=CC=C1)S(=O)(=O)NC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "NC1=C(C(=O)OC)C(=CC=C1)S(=O)(=O)NC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.00 g (25.3 mmol) of methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate is admixed with 3.2 g of palladium on activated carbon (5%) and hydrogenated at room temperature and under atmospheric pressure for 6 h. The reaction mixture is then filtered, the filtrate is concentrated to dryness and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd] | null | null | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(C)(C)C>[Pd]>COC(=O)c1c(N)cccc1S(=O)(=O)NC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da6af9e359ff40a1bbd60764a87e247b | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl.COc1nc(N)nc(OC)n1.N#C[O-]>>COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | ClS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-].NC1=NC(=NC(=N1)OC)OC.[O-]C#N.[Na+].N1=CC=CC=C1>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-] | Cl[S:14]([c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12]1)(=[O:15])=[O:16].[NH2:20][c:21]1[n:22][c:23]([O:24][CH3:25])[n:26][c:27]([O:28][CH3:29])[n:30]1.[N:17]#[C:18][O-:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[... | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl.COc1nc(N)nc(OC)n1.N#C[O-] | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | null | null | ClCCl.C(C)#N | Acylation | OtherReaction | 19bf7d753876392b4c2ac67bd5974bb402735841e5fbc22644f0435dcb2c464c | 3c780a65212b9deef596951b8d8a6ff51e2202acb785b2c2d65dd03dbc33bec4 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]-[C:7](-[#8:8])=[O;D1;H0:9].[N;H0;D1;+0:10]#[C;H0;D2;+0:11]-[O-;H0;D1:12].[NH2;D1;+0:13]-[c:14]1:[#7;a:15]:[c:16]:[#7;a:17]:[c:18]:[#7;a:19]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:10]-[C;H0;D3;+0:11... | null | [] | null | null | 7 | HOUR | At 55-60° C. and under argon, a solution of 5.0 g (17.9 mmol) of methyl 2-chlorosulfonyl-6-nitrobenzoate in 55 ml of dry dichloromethane is added dropwise over 2 h to a suspension of 2.79 g (17.9 mmol) of 2-amino-4,6-dimethoxy-1,3,5-triazine, 1.28 g (19.7 mmol) of sodium cyanate, 1.45 ml (17.9 mmol) of pyridine and 500... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Sulfonyl halide | Sulfonamide.Urea | null | null | c1ccccc1.c1ncncn1 | Other | ClCCl.C(C)#N | null | 7 | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)Cl.COc1nc(N)nc(OC)n1.N#C[O-]>ClCCl.C(C)#N>COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27ef5de7ff154d3ebc40d5c7ed2e1902 | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1>>COC(=O)c1c(N)cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C(=CC=C1)[N+](=O)[O-]>>NC1=C(C(=O)OC)C(=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(=N1)OC)OC | O=[N+:7]([O-])[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([S:12](=[O:13])(=[O:14])[NH:15][C:16](=[O:17])[NH:18][c:19]2[n:20][c:21]([O:22][CH3:23])[n:24][c:25]([O:26][CH3:27])[n:28]2)[cH:10][cH:9][cH:8]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][cH:10][c:11]1[S:12](=[O:13])(=[O:14])[NH:15][C:16](=[O:17... | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | COC(=O)c1c(N)cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | null | [Pd].[O-][V](=O)=O.[Na+] | CO.CN(C=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 10 | MINUTE | 50 mg (113 μmol) of methyl 2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]-carbonylamino)sulfonyl]-6-nitrobenzoate are suspended in a mixture of 3 ml of methanol/dimethylformamide (5:1), admixed with 10 mg of palladium on activated carbon (5%) and 1 mg (8.20 μmol) of sodium (meta)vanadate and hydrogenated under atmospher... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ncncn1 | Other | [Pd].[O-][V](=O)=O.[Na+].CO.CN(C=O)C | null | 0.166667 | COC(=O)c1c([N+](=O)[O-])cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1>[Pd].[O-][V](=O)=O.[Na+].CO.CN(C=O)C>COC(=O)c1c(N)cccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9223dc2964844701a6f6ccfee85268c6 | CCCCCCCCN.O=S(=O)(Cl)Cc1ccccc1>>NS(=O)(=O)Cc1ccccc1 | C1(=CC=CC=C1)CS(=O)(=O)Cl.C(CCCCCCC)N>>C1(=CC=CC=C1)CS(=O)(=O)N | CCCCCCCC[NH2:1].Cl[S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | CCCCCCCCN.O=S(=O)(Cl)Cc1ccccc1 | NS(=O)(=O)Cc1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | C-C-C-C-C-C-C-C-[NH2;D1;+0:1].Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[C:5]-[c:6]>>[NH2;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[C:5]-[c:6] | 93 | [{"value": 93.0, "product": "C1(=CC=CC=C1)CS(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "C1(=CC=CC=C1)CS(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The synthesis of the sulfonamide containing carboxylic acid precursor corresponding to the autoinducer analog 10 was accomplished by the two step sequence described below. Accordingly, a solution of α-toluenesulfonyl chloride (10 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of octylamine (20 mmol) in... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | CCCCCCCCN.O=S(=O)(Cl)Cc1ccccc1>C(Cl)Cl>NS(=O)(=O)Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61d100dc066b46178c90cd89026a6194 | CCOC(=O)CC1c2ccccc2C(=O)N1C.NC(N)=[NH2+]>>CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | Cl.[Cl-].NC(=[NH2+])N.CC(C)([O-])C.[K+].CN1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>CN1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:13]([CH2:12][CH:11]1[N:2]([CH3:1])[C:3](=[O:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21)=[O:14].[NH2:15][C:16]([NH2:17])=[NH2+:18]>>[CH3:1][N:2]1[C:3](=[O:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]1[CH2:12][C:13](=[O:14])[NH:15][C:16](=[NH:17])[NH2:18] | CCOC(=O)CC1c2ccccc2C(=O)N1C.NC(N)=[NH2+] | CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | O.CN(C=O)C | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 16.6 | [{"value": 16.6, "product": "CN1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 4.3 g of guanidinium chloride are added to a suspension of 5.2 g of potassium tertbutoxide in 100 cm3 of dimethylformamide. The reaction mixture is stirred under an inert atmosphere at a temperature in the region of 20° C. for 1 hour, followed by addition of a solution of 2 g of ethyl (2-methyl-3-oxo-2,3-dihydro-1H-iso... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O.CN(C=O)C | 20 | 1 | CCOC(=O)CC1c2ccccc2C(=O)N1C.NC(N)=[NH2+]>O.CN(C=O)C>CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6605c43fbed34c8ab0a97880ec653a0c | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.CN1C(=O)c2ccccc2C1O>>CCOC(=O)CC1c2ccccc2C(=O)N1C | C(C)OC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OC1N(C(C2=CC=CC=C12)=O)C>>CN1C(C2=CC=CC=C2C1=O)CC(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O[CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH3:17] | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.CN1C(=O)c2ccccc2C1O | CCOC(=O)CC1c2ccccc2C(=O)N1C | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 14c878cf46bb0acf53cb2263c3ebbadf4b36f4102a6ffade3bdc981212d4612e | ec740fdba0adc3c659d56447beb3ee7a35d222db2ebbeacae7f761e1e85567b3 | O=C1NCc2ccccc21 | O-[CH;D3;+0:1]1-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-1:[c:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D2;+0:13]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[CH;D3;+0:1]1-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-1:[c:8] | 63.7 | [{"value": 63.7, "product": "CN1C(C2=CC=CC=C2C1=O)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 11.5 g of ethoxycarbonylmethylenetriphenylphosphorane are added to a suspension of 4.5 g of 3-hydroxy-2-methyl-2,3-dihydroisoindol-1-one in 110 cm3 of toluene. The reaction mixture is refluxed with stirring for 16 hours and then cooled to a temperature in the region of 20° C. The mixture is then concentrated to dryness... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 20 | 16 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.CN1C(=O)c2ccccc2C1O>C1(=CC=CC=C1)C>CCOC(=O)CC1c2ccccc2C(=O)N1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-726e35a76abe402388792535b5c24847 | CN1C(=O)c2ccccc2C1=O>>CN1C(=O)c2ccccc2C1O | [BH4-].[K+].CN1C(C=2C(C1=O)=CC=CC2)=O.O>>OC1N(C(C2=CC=CC=C12)=O)C | [CH3:1][N:2]1[C:3](=[O:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]1=[O:12]>>[CH3:1][N:2]1[C:3](=[O:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]1[OH:12] | CN1C(=O)c2ccccc2C1=O | CN1C(=O)c2ccccc2C1O | null | null | CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C;D1;H3:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 44.4 | [{"value": 44.4, "product": "OC1N(C(C2=CC=CC=C12)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3.4 g of potassium borohydride are added slowly to a suspension of 10 g of N-methylphthalimide in 220 cm3 of methanol under an inert atmosphere. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by dropwise addition of 200 cm3 of distilled water. The solvent is then partial... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | CO | 20 | 20 | CN1C(=O)c2ccccc2C1=O>CO>CN1C(=O)c2ccccc2C1O |
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