dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13431698043b4429b5d25f1e893bb8f6 | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccccc2Cl)CC1>>N#CC1(c2ccccc2Cl)CCNCC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C#N)C1=C(C=CC=C1)Cl.Cl.O1CCOCC1>>Cl.ClC1=C(C=CC=C1)C1(CCNCC1)C#N | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][C:4]([C:3]#[N:2])([c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[CH2:16][CH2:15]1>>[N:2]#[C:3][C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Cl:11])[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1 | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccccc2Cl)CC1 | N#CC1(c2ccccc2Cl)CCNCC1 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(C2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 200 | [{"value": 100.0, "product": "Cl.ClC1=C(C=CC=C1)C1(CCNCC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 200.0, "product": "Cl.ClC1=C(C=CC=C1)C1(CCNCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of HCl in dioxane (4M, 200 mL, 800 mmol) was added to the Boc-protected amine 18.15 (18.4 g, 57.4 mmol). After 1.5 h the solvent was evaporated and the residue dried in vacuo, giving 14.8 g (57.4 mmol, 100%) of 7.15, colorless solid, mp 241-243° C. (decomp.). 1H NMR (200 MHz, CDCl3): δ=2.5-2.8 (brm, 4H), 3.4... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccccc2Cl)CC1>>N#CC1(c2ccccc2Cl)CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-40dfc95fe54d4561abf036588c7acd5a | Nc1cc(Cl)nc(-c2ccccc2)n1.O=C(Br)CBr>>O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1 | ClC1=CC(=NC(=N1)C1=CC=CC=C1)N.BrCC(=O)Br.C(C)(C)N(C(C)C)CC>>BrCC(=O)NC1=NC(=NC(=C1)Cl)C1=CC=CC=C1 | [NH2:5][c:6]1[cH:7][c:8]([Cl:9])[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][c:6]1[cH:7][c:8]([Cl:9])[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1 | Nc1cc(Cl)nc(-c2ccccc2)n1.O=C(Br)CBr | O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2ncccn2)cc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | null | [] | null | null | 1 | HOUR | 6-chloro-2-phenylpyrimidin-4-amine (4) (830 mg) was dissolved in anhydrous DCM (50 ml). To this was added dropwise a solution of bromoacetylbromide (1.05 ml in 10 ml DCM), forming a precipitate after 10 min. To this was then added dropwise a solution of N,N-diisopropylethylamine (1.06 ml in 10 ml DCM) and the solution ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cncnc1.c1ccccc1 | HBr | C(Cl)Cl | null | 1 | Nc1cc(Cl)nc(-c2ccccc2)n1.O=C(Br)CBr>C(Cl)Cl>O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a1633353a8548bcacaced3e44db6cac | C1CCNCC1.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1>>O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | BrCC(=O)NC1=NC(=NC(=C1)Cl)C1=CC=CC=C1.N1CCCCC1>>ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCCCC1)=O | [NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1.Br[CH2:3][C:2](=[O:1])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[n:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[NH:10][c:11]1[cH:12][c:13]([Cl:14])[n:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:... | C1CCNCC1.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1 | O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCCCC1)Nc1ccnc(-c2ccccc2)n1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[#7;a:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;a:6]:[c:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | 1.5 | HOUR | 2-Bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide (28 mg) was dissolved in acetonitrile (2 ml) and piperidine added (23 μl in 500 μl acetonitrile). The mixture was left to stir for 1.5 hr after which time the solvent was removed in vacuo. Purification using a short silica plug, eluting with a mixture of ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cncnc1.c1ccccc1 | HBr | C(C)#N | null | 1.5 | C1CCNCC1.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1>C(C)#N>O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c6c184e1d684d56a0e5c98b1dbafb7f | O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1.O=[N+]([O-])c1cc(C(F)(F)F)ccc1N1CCNCC1>>O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | BrCC(=O)NC1=NC(=NC(=C1)Cl)C1=CC=CC=C1.FC(C1=CC(=C(C=C1)N1CCNCC1)[N+](=O)[O-])(F)F>>ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCCCC1)=O | Br[CH2:3][C:2](=[O:1])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[n:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1.O=[N+]([O-])c1c[c:7](C(F)(F)F)ccc1[N:4]1[CH2:5][CH2:6]N[CH2:8][CH2:9]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[NH:10][c:11]1[cH:12][c:13]([Cl:14])[n:15][c:16](-[c:17]2[cH:1... | O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1.O=[N+]([O-])c1cc(C(F)(F)F)ccc1N1CCNCC1 | O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | ed2a776df84198d1a92de276bc523f3c5e8287fe975562aa8e8d94ed8e26c757 | 79c4558b7d67ee64432cce07554c99d85d6c5ed415728734500b678feedcc09d | O=C(CN1CCCCC1)Nc1ccnc(-c2ccccc2)n1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[#7;a:6].F-C(-F)(-F)-[c;H0;D3;+0:7]1:c:c:c(-[N;H0;D3;+0:8]2-[C:9]-[CH2;D2;+0:10]-N-[CH2;D2;+0:11]-[C:12]-2):c(-[N+](=O)-[O-]):c:1>>[#7;a:6]:[c:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:7]-[CH2;D2;+0:11]-[C:12]-1 | null | [] | null | null | 8 | HOUR | 2-Bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide (100 mg) was dissolved in acetonitrile (5 ml) and (4-trifluromethyl-2-nitrophenyl)piperazine (253 mg) added. The solution was stirred overnight at room temperature. After this time the solvent was removed in vacuo. Purification by flash chromatography on silica gel e... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Primary halide.Nitro group.Secondary amine.Tertiary amine | Tertiary amine | c1ccccc1.C1C[NH]CCN1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cncnc1.c1ccccc1 | HF.Br- | C(C)#N | null | 8 | O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1.O=[N+]([O-])c1cc(C(F)(F)F)ccc1N1CCNCC1>C(C)#N>O=C(CN1CCCCC1)Nc1cc(Cl)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-672ef598fb674a0f9bd424ca5278f4f3 | C(=C/c1ccccc1)\CN1CCNCC1.CC#N.CCN(C(C)C)C(C)C.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1>>CC(C)(C)c1ccc(CN2CCN(CC(=O)Nc3cc(Cl)nc(-c4ccccc4)n3)CC2)cc1 | BrCC(=O)NC1=NC(=NC(=C1)Cl)C1=CC=CC=C1.C1(=CC=CC=C1)/C=C/CN1CCNCC1.C(C)(C)N(C(C)C)CC.C(C)#N>>C(C)(C)(C)C1=CC=C(CN2CCN(CC2)CC(=O)NC2=NC(=NC(=C2)Cl)C2=CC=CC=C2)C=C1 | [CH:2](\[CH2:4][N:13]1[CH2:12][CH2:11][NH:10][CH2:32][CH2:31]1)=[CH:9]/[c:8]1[cH:7][cH:6][cH:5][cH:34][cH:33]1.N#C[CH3:1].CCN(C(C)C)C(C)[CH3:3].Br[CH2:14][C:15](=[O:16])[NH:17][c:18]1[cH:19][c:20]([Cl:21])[n:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[n:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7]... | C(=C/c1ccccc1)\CN1CCNCC1.CC#N.CCN(C(C)C)C(C)C.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1 | CC(C)(C)c1ccc(CN2CCN(CC(=O)Nc3cc(Cl)nc(-c4ccccc4)n3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 70f2a0b43ac9faa91d509f06067a4a04fc8f6b89843dea8def1b3ebcf67d5c00 | 64cd2998c91b9dd28fdab8512224366c34774301f2a5f5c753c4c77c6ce63c37 | O=C(CN1CCN(Cc2ccccc2)CC1)Nc1ccnc(-c2ccccc2)n1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[#7;a:6].C-C-N(-C(-C)-C)-C(-C)-[CH3;D1;+0:7].N#C-[CH3;D1;+0:8].[C:9]1-[C:10]-[N;H0;D3;+0:11](-[CH2;D2;+0:12]/[CH;D2;+0:13]=[CH;D2;+0:14]/[c:15]2:[c:16]:[c:17]:[cH;D2;+0:18]:[c:19]:[c:20]:2)-[C:21]-[C:22]-[NH;D2;+0:23]-1>>[#7;a:6]:[c:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2... | null | [] | null | null | 3 | HOUR | To a stirred solution of 2-bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide (0.80 g in 40 ml acetonitrile) was added [(2E)-3-phenylprop-2-enyl]piperazine (0.50 g in 10 ml acetonitrile). After 3 hrs, N,N-diisopropylethylamine was added (428 μl in 10 ml acetonitrile) and the reaction stirred for a further 2 hrs after w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile.Secondary amine.Tertiary amine.Tertiary amine | Tertiary amine.Tertiary amine | C1C[NH]CCN1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccccc1 | HBr | null | null | 3 | C(=C/c1ccccc1)\CN1CCNCC1.CC#N.CCN(C(C)C)C(C)C.O=C(CBr)Nc1cc(Cl)nc(-c2ccccc2)n1>>CC(C)(C)c1ccc(CN2CCN(CC(=O)Nc3cc(Cl)nc(-c4ccccc4)n3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3083b2053c424e5ba82e6f94ce0f42f1 | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)OC)=O>>C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)O)=O | C[O:16][C:14]([C:12]([NH:11][c:10]1[cH:9][c:8]([NH:7][CH2:6][CH2:5][NH:4][C:2]([CH3:1])=[O:3])[n:25][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:17]1)=[O:13])=[O:15]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH:11][C:12](=[O:13])[C:14](=[O:15])[OH:16])[n:17][c:18](-[c:19]2[cH:20][cH:2... | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1 | CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ncccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | Methyl [(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)amino](oxo)acetate (10 mg) was dissolved in anhydrous THF (1.5 ml) and potassium trimethylsilanate (4 mg) added. The reaction was left for 3 hrs after which time a precipitate of the title compound was visible which was filtered (10 mg).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | C1CCOC1 | null | null | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>C1CCOC1>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3af1703d66fa4d3686b2ee715a5614b2 | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)OC)=O.C(C1=CC=CC=C1)C1CCNCC1>>C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)O)=O | C[O:16][C:14]([C:12]([NH:11][c:10]1[cH:9][c:8]([NH:7][CH2:6][CH2:5][NH:4][C:2]([CH3:1])=[O:3])[n:25][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:17]1)=[O:13])=[O:15]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH:11][C:12](=[O:13])[C:14](=[O:15])[OH:16])[n:17][c:18](-[c:19]2[cH:20][cH:2... | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1 | CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | null | null | CS(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ncccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 68.7 | [{"value": 68.7, "product": "C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl [(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)amino](oxo)acetate (50 mg) was dissolved in DMSO (420 μl) with stirring. To this were added 4-benzylpiperidine (74 μl) and activated powdered 4 angstrom molecular sieves and the mixture left to stir at room temperature for 5 hrs. After this time the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | CS(=O)C | null | null | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>CS(=O)C>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b37195723c8b43a3b72b2487af64c3c4 | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)OC)=O.C1(=CC=CC=C1)N1CCNCC1.ClCCl>>C(C)(=O)NCCNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(C(=O)O)=O | C[O:16][C:14]([C:12]([NH:11][c:10]1[cH:9][c:8]([NH:7][CH2:6][CH2:5][NH:4][C:2]([CH3:1])=[O:3])[n:25][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:17]1)=[O:13])=[O:15]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][c:10]([NH:11][C:12](=[O:13])[C:14](=[O:15])[OH:16])[n:17][c:18](-[c:19]2[cH:20][cH:2... | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1 | CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 | null | null | CS(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ncccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | To a well of a 96 well microtitre plate were added methyl [(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)amino](oxo)acetate (30 μl of a 0.3M solution in anhydrous DMSO) and 4-phenylpiperazine (30 μl of a 1.5M solution). This solution was left to shake on a plate shaker for 16 hrs. After this time 800 μl of di... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | CS(=O)C | null | 16 | COC(=O)C(=O)Nc1cc(NCCNC(C)=O)nc(-c2ccccc2)n1>CS(=O)C>CC(=O)NCCNc1cc(NC(=O)C(=O)O)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dd16eab2b6941edbbcb5c059d77f0a9 | CCOC(=O)CC(=O)OCC.N=C(N)c1ccc(Cl)cc1>>Oc1cc(O)nc(-c2ccc(Cl)cc2)n1 | Cl.[O-]CC.[Na+].ClC1=CC=C(C(=N)N)C=C1.C(CC(=O)OCC)(=O)OCC>>ClC1=CC=C(C=C1)C1=NC(=CC(=N1)O)O | CCO[C:2](=[O:1])[CH2:3][C:4](OCC)=[O:5].[NH2:6][C:7]([c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)=[NH:15]>>[OH:1][c:2]1[cH:3][c:4]([OH:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[n:15]1 | CCOC(=O)CC(=O)OCC.N=C(N)c1ccc(Cl)cc1 | Oc1cc(O)nc(-c2ccc(Cl)cc2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C.[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[NH;D1;+0:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]... | null | [] | 40 | CELSIUS | 96 | HOUR | To sodium ethoxide (48 ml of a 21% wt solution in ethanol diluted with a further 130 ml ethanol) was added 4-chlorobenzamidine (8 g) and diethyl malonate (6.67 ml) and the solution left to stir at 40° C. for 96 hrs. The reaction mixture was subsequently cooled to 5° C. and acidified cautiously to pH 2 using concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O | 40 | 96 | CCOC(=O)CC(=O)OCC.N=C(N)c1ccc(Cl)cc1>C(C)O>Oc1cc(O)nc(-c2ccc(Cl)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0dfd7bcacc594fe0b4289174cbdf87f8 | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccccc1>>Cc1c(O)nc(-c2ccccc2)nc1O | Cl.[O-]CC.[Na+].Cl.C(C1=CC=CC=C1)(=N)N.C(C)OC(C(C(=O)OCC)C)=O>>CC=1C(=NC(=NC1O)C1=CC=CC=C1)O | CCO[C:3]([CH:2]([CH3:1])[C:14](OCC)=[O:15])=[O:4].[NH2:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[NH:13]>>[CH3:1][c:2]1[c:3]([OH:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]1[OH:15] | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccccc1 | Cc1c(O)nc(-c2ccccc2)nc1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-O-C-C.[NH2;D1;+0:7]-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[n;H0;D2;+0:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13... | null | [] | 40 | CELSIUS | 22 | HOUR | To ethanol (180 ml) was added sodium ethoxide solution (38 ml of a 21% wt solution in ethanol), benzamidine hydrochloride (5.0 g) and diethylmethylmalonate (4.91 ml). The suspension was stirred at 40° C. in an inert atmosphere for 22 hrs after which time it was cooled to 5° C. (ice bath) and treated dropwise with conce... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O | 40 | 22 | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccccc1>C(C)O>Cc1c(O)nc(-c2ccccc2)nc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-965dbecc980844109c13adeaf733f50f | CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCN)c1C.O=C(O)c1ccc2ccccc2n1>>CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCNC(=O)c2ccc3ccccc3n2)c1C | NCCNC1=C(C(=NC(=N1)C1=CC=CC=C1)NCCNC(C)=O)C.C(C1=NC2=CC=CC=C2C=C1)(=O)O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>C(C)(=O)NCCNC1=C(C(=NC(=N1)C1=CC=CC=C1)NCCNC(=O)C1=NC2=CC=CC=C2C=C1)C | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]([NH:19][CH2:20][CH2:21][NH2:22])[c:35]1[CH3:36].O[C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[n:34]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][c:10... | CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCN)c1C.O=C(O)c1ccc2ccccc2n1 | CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCNC(=O)c2ccc3ccccc3n2)c1C | null | null | CN1CCCC1=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCNc1ccnc(-c2ccccc2)n1)c1ccc2ccccc2n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 12 | HOUR | A solution of quinaldic acid (30 μl of a 0.3M solution in NMP), HATU (30 μl of a 0.3M solution in NMP) and diisopropylethylamine (30 μl of a 0.3M solution in NMP) was shaken at ambient temperature in a well of a 96 position microtitre plate for 45 min. N-[2-({6-[(2-aminoethyl)amino]-5-methyl-2-phenylpyrimidin-4-yl}amin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.c1ccccc1.c1ccc2ncccc2c1 | HO- | CN1CCCC1=O | null | 12 | CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCN)c1C.O=C(O)c1ccc2ccccc2n1>CN1CCCC1=O>CC(=O)NCCNc1nc(-c2ccccc2)nc(NCCNC(=O)c2ccc3ccccc3n2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d013e6bfa1a4d4fb5cc408a88ba8a9a | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccc(Cl)cc1>>Cc1c(O)nc(-c2ccc(Cl)cc2)nc1O | Cl.[O-]CC.[Na+].Cl.ClC1=CC=C(C(=N)N)C=C1.C(C)OC(C(C(=O)OCC)C)=O>>ClC1=CC=C(C=C1)C1=NC(=C(C(=N1)O)C)O | CCO[C:3]([CH:2]([CH3:1])[C:15](OCC)=[O:16])=[O:4].[NH2:5][C:6]([c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)=[NH:14]>>[CH3:1][c:2]1[c:3]([OH:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[n:14][c:15]1[OH:16] | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccc(Cl)cc1 | Cc1c(O)nc(-c2ccc(Cl)cc2)nc1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-O-C-C.[NH2;D1;+0:7]-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[n;H0;D2;+0:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13... | null | [] | 40 | CELSIUS | 44 | HOUR | To ethanol (20 ml) was added sodium ethoxide solution (7.76 ml of a 21% wt solution in ethanol), 4-chlorobenzamidine hydrochloride (1.0 g) and diethylmethylmalonate (0.89 ml). The suspension was stirred at 40° C. in an inert atmosphere for 44 hrs after which time it was cooled to 5° C. and treated dropwise with concent... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O | 40 | 44 | CCOC(=O)C(C)C(=O)OCC.N=C(N)c1ccc(Cl)cc1>C(C)O>Cc1c(O)nc(-c2ccc(Cl)cc2)nc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4ac9264e02d439eaec8cf29e5ca99ed | CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCN)c1C.O=C(O)c1cc2ccccc2cn1>>CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCNC(=O)c2cc3ccccc3cn2)c1C | NCCNC1=C(C(=NC(=N1)C1=CC=C(C=C1)Cl)NCCNC(C)=O)C.C1=NC(=CC2=CC=CC=C12)C(=O)O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>C(C)(=O)NCCNC1=C(C(=NC(=N1)C1=CC=C(C=C1)Cl)NCCNC(=O)C=1N=CC2=CC=CC=C2C1)C | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[n:18][c:19]([NH:20][CH2:21][CH2:22][NH2:23])[c:36]1[CH3:37].O[C:24](=[O:25])[c:26]1[cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[cH:34][n:35]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][c:8]1[n... | CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCN)c1C.O=C(O)c1cc2ccccc2cn1 | CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCNC(=O)c2cc3ccccc3cn2)c1C | null | null | CN1CCCC1=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCNc1ccnc(-c2ccccc2)n1)c1cc2ccccc2cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 12 | HOUR | A solution of 3-isoquinoline carboxylic acid (60 μl of a 0.3M solution in NMP), HATU (60 μl of a 0.3M solution in NMP) and diisopropylethylamine (60 μl of a 0.3M solution in NMP) was shaken at ambient temperature in a well of a 96 position microtitre plate for 20 min. N-{2-[6-(2-Aminoethylamino)-2-(4-chlorophenyl)-5-me... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.c1ccccc1.c1ccc2cnccc2c1 | HO- | CN1CCCC1=O | null | 12 | CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCN)c1C.O=C(O)c1cc2ccccc2cn1>CN1CCCC1=O>CC(=O)NCCNc1nc(-c2ccc(Cl)cc2)nc(NCCNC(=O)c2cc3ccccc3cn2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-585a8db0485945a99143e53538042ebb | NCC(N)=O.O=C(CN1CCN(C/C=C/c2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1>>NC(=O)CNc1cc(NC(=O)CN2CCN(C/C=C/c3ccccc3)CC2)nc(-c2ccccc2)n1 | ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCN(CC1)C\C=C\C1=CC=CC=C1)=O.C(C)(C)N(C(C)C)CC.Cl.NCC(=O)N>>C1(=CC=CC=C1)C1=NC(=CC(=N1)NCC(=O)N)NC(CN1CCN(CC1)C\C=C\C1=CC=CC=C1)=O | [NH2:1][C:2](=[O:3])[CH2:4][NH2:5].Cl[c:6]1[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:17]/[CH:18]=[CH:19]/[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[n:28][c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36]1>>[NH2:1][C:2](=[O:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([... | NCC(N)=O.O=C(CN1CCN(C/C=C/c2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | NC(=O)CNc1cc(NC(=O)CN2CCN(C/C=C/c3ccccc3)CC2)nc(-c2ccccc2)n1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(CN1CCN(C/C=C/c2ccccc2)CC1)Nc1ccnc(-c2ccccc2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1.[N;D1;H2:11]-[C:12](=[O;D1;H0:13])-[C:14]-[NH2;D1;+0:15]>>[N;D1;H2:11]-[C:12](=[O;D1;H0:13])-[C:14]-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1 | 3.9 | [{"value": 3.9, "product": "C1(=CC=CC=C1)C1=NC(=CC(=N1)NCC(=O)N)NC(CN1CCN(CC1)C\\C=C\\C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a crude sample of N-(6-chloro-2-phenylpyrimidin-4-yl)-2-{4-[(2E)-3-phenylprop-2-enyl]piperazin-1-yl}acetamide (22.54) (0.75 g in 60 ml DMSO) were added glycinamide hydrochloride (1.85 g in 10 ml DMSO) and N,N-diisopropylethylamine (2.96 ml) and the mixture heated to 100° C. for 16 hrs. The solvent was then removed i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | null | 100 | null | NCC(N)=O.O=C(CN1CCN(C/C=C/c2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1>>NC(=O)CNc1cc(NC(=O)CN2CCN(C/C=C/c3ccccc3)CC2)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a0a39dd53a4470291acef8ebdbb327d | NCC(N)=O.O=C(CN1CCC(Cc2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1>>NC(=O)CNc1cc(NC(=O)CN2CCC(Cc3ccccc3)CC2)nc(-c2ccccc2)n1 | ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCC(CC1)CC1=CC=CC=C1)=O.C(C)(C)N(C(C)C)CC.Cl.NCC(=O)N>>NC(CNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCC(CC1)CC1=CC=CC=C1)=O)=O | [NH2:1][C:2](=[O:3])[CH2:4][NH2:5].Cl[c:6]1[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[n:34]1>>[NH2:1][C:2](=[O:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]([NH:9][C:10](=[O:... | NCC(N)=O.O=C(CN1CCC(Cc2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1 | NC(=O)CNc1cc(NC(=O)CN2CCC(Cc3ccccc3)CC2)nc(-c2ccccc2)n1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(CN1CCC(Cc2ccccc2)CC1)Nc1ccnc(-c2ccccc2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1.[N;D1;H2:11]-[C:12](=[O;D1;H0:13])-[C:14]-[NH2;D1;+0:15]>>[N;D1;H2:11]-[C:12](=[O;D1;H0:13])-[C:14]-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1 | 39.9 | [{"value": 39.9, "product": "NC(CNC1=CC(=NC(=N1)C1=CC=CC=C1)NC(CN1CCC(CC1)CC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a crude sample of N-(6-chloro-2-phenylpyrimidin-4-yl)-2-(4-benzylpiperidin-1-yl)acetamide (22.55) (0.75 g in 60 ml DMSO) were added glycinamide hydrochloride (1.85 g in 10 ml DMSO) and N,N-diisopropylethylamine (2.96 ml) and the mixture heated to 100° C. for 16 hrs. The solvent was then removed in vacuo and the resi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | 100 | null | NCC(N)=O.O=C(CN1CCC(Cc2ccccc2)CC1)Nc1cc(Cl)nc(-c2ccccc2)n1>>NC(=O)CNc1cc(NC(=O)CN2CCC(Cc3ccccc3)CC2)nc(-c2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d5f062294bb489fbc316ee938c82274 | C1COCCN1.Cc1cc(Br)cc(C)c1N>>Cc1cc(N2CCOCC2)cc(C)c1N | C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[K+].N1CCOCC1.BrC1=CC(=C(N)C(=C1)C)C>>CC1=C(C(=CC(=C1)N1CCOCC1)C)N | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:14]([NH2:15])[c:12]([CH3:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH2:15] | C1COCCN1.Cc1cc(Br)cc(C)c1N | Cc1cc(N2CCOCC2)cc(C)c1N | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 41 | [{"value": 41.0, "product": "CC1=C(C(=CC(=C1)N1CCOCC1)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Bis(dibenzylideneacetone)palladium (2.88 g) and (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.69 g) were added to dry toluene (175 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (7.06 g), morpholine (8.7 mL) and 4-bromo-2,6-dimethylaniline (10.03 g) were added subsequently. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1(=CC=CC=C1)C | null | 0.25 | C1COCCN1.Cc1cc(Br)cc(C)c1N>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1(=CC=CC=C1)C>Cc1cc(N2CCOCC2)cc(C)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fcb70df1cfb485f943a7f33cd533dfd | Cc1cc(Br)cc(C)c1N.O=C(Cl)CC1CCCC1>>Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1 | BrC1=CC(=C(N)C(=C1)C)C.C1(CCCC1)CC(=O)Cl>>BrC1=CC(=C(C(=C1)C)NC(CC1CCCC1)=O)C | [CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([CH3:8])[c:9]1[NH2:10].Cl[C:11](=[O:12])[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | Cc1cc(Br)cc(C)c1N.O=C(Cl)CC1CCCC1 | Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1 | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 92 | [{"value": 92.0, "product": "BrC1=CC(=C(C(=C1)C)NC(CC1CCCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 4-Bromo-2,6-dimethylaniline (5.92 g) and cyclopentylacetyl chloride (4.87 mL) were dissolved in acetonitrile (26 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0° C., the product filtered off and washed with cold acetonitrile (50 mL) affording 8.43 g (92% yield) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCC1 | HCl | C(C)#N | 150 | null | Cc1cc(Br)cc(C)c1N.O=C(Cl)CC1CCCC1>C(C)#N>Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb0397acdf094dd49207fab7ba10a240 | BrBr.Nc1ccc([N+](=O)[O-])cc1C(F)(F)F>>Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F | BrBr.[N+](=O)([O-])C1=CC(=C(C=C1)N)C(F)(F)F.O>>BrC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N | Br[Br:4].[NH2:1][c:2]1[cH:3][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | BrBr.Nc1ccc([N+](=O)[O-])cc1C(F)(F)F | Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 91 | [{"value": 91.0, "product": "BrC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | Bromine (0.60 mL) dissolved in acetic acid (11 mL) was added dropwise to a solution of 4-nitro-2-trifluoromethyl-phenylamine (2.4 g) in acetic acid (12 mL). The reaction mixture was heated to 120° C. for 2½ hours, poured into water (400 mL) and filtered. The collected solid was washed with water (200 mL) and dried in v... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | 120 | null | BrBr.Nc1ccc([N+](=O)[O-])cc1C(F)(F)F>C(C)(=O)O>Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37c3ef9d66dc4b4da4af6741431ccf80 | Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F>>Nc1cc(Br)c(N)c(C(F)(F)F)c1 | Cl.BrC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N>>BrC1=C(C(=CC(=C1)N)C(F)(F)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[c:6]([NH2:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[c:6]([NH2:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1 | Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F | Nc1cc(Br)c(N)c(C(F)(F)F)c1 | null | [Zn] | O1CCCC1 | 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] | 99.2 | [{"value": 98.0, "product": "BrC1=C(C(=CC(=C1)N)C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "BrC1=C(C(=CC(=C1)N)C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Aqueous hydrochloric acid (2 M, 45 mL) was added slowly to a mixture of zinc dust (8.6 g) and 2-bromo-4-nitro-6-trifluoromethyl-phenylamine (2.5 g) in tetrahydrofuran (50 mL). The reaction mixture was stirred for 1 hour, filtered and neutralized with saturated aqueous sodium bicarbonate (100 mL). Water (100 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Zn].O1CCCC1 | null | 1 | Nc1c(Br)cc([N+](=O)[O-])cc1C(F)(F)F>[Zn].O1CCCC1>Nc1cc(Br)c(N)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09a39be68a3e4680bc801c01ced3ec31 | BrCCOCCBr.Nc1cc(Br)c(N)c(C(F)(F)F)c1>>Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F | C([O-])(O)=O.BrC1=C(C(=CC(=C1)N)C(F)(F)F)N.BrCCOCCBr.C(C)(C)N(C(C)C)CC>>BrC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N | Br[CH2:8][CH2:9][O:10][CH2:11][CH2:12]Br.[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([NH2:7])[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | BrCCOCCBr.Nc1cc(Br)c(N)c(C(F)(F)F)c1 | Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(N2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 63 | [{"value": 63.0, "product": "BrC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | 2-Bromo-6-trifluoromethyl-benzene-1,4-diamine (2.21 g), bis-(2-bromoethyl)ether (1.30 mL) and N,N-diisopropyl-ethylamine (4.64 mL) were mixed in N,N-dimethylformamide (19 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (100 mL) was added and the crude mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | CN(C=O)C | 180 | null | BrCCOCCBr.Nc1cc(Br)c(N)c(C(F)(F)F)c1>CN(C=O)C>Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fcb9c1fa95643e1be8fa5a015f8cef2 | N#Cc1cc([N+](=O)[O-])cc(Cl)c1N>>N#Cc1cc(N)cc(Cl)c1N | Cl.NC1=C(C#N)C=C(C=C1Cl)[N+](=O)[O-].C([O-])([O-])=O.[Na+].[Na+]>>NC1=C(C#N)C=C(C=C1Cl)N | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([C:2]#[N:1])[c:10]([NH2:11])[c:8]([Cl:9])[cH:7]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][c:8]([Cl:9])[c:10]1[NH2:11] | N#Cc1cc([N+](=O)[O-])cc(Cl)c1N | N#Cc1cc(N)cc(Cl)c1N | null | [Zn] | O1CCCC1 | 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] | 99 | [{"value": 99.0, "product": "NC1=C(C#N)C=C(C=C1Cl)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "NC1=C(C#N)C=C(C=C1Cl)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Aqueous hydrochloric acid (12 M, 5.3 mL) was added slowly to a mixture of zinc dust (2.01 g) and 2-amino-3-chloro-5-nitro-benzonitrile (0.50 g) in tetrahydrofuran (40 mL). The reaction mixture was stirred for 2 hours, neutralized with saturated aqueous sodium carbonate (50 mL), and extracted with ethyl acetate (3×50 mL... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Zn].O1CCCC1 | null | 2 | N#Cc1cc([N+](=O)[O-])cc(Cl)c1N>[Zn].O1CCCC1>N#Cc1cc(N)cc(Cl)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cecd1ec4350a412f9ee76876ab2f7cab | BrCCOCCBr.N#Cc1cc(N)cc(Cl)c1N>>N#Cc1cc(N2CCOCC2)cc(Cl)c1N | C([O-])(O)=O.NC1=C(C#N)C=C(C=C1Cl)N.BrCCOCCBr.C(C)(C)N(C(C)C)CC>>NC1=C(C#N)C=C(C=C1Cl)N1CCOCC1 | Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[cH:12][c:13]([Cl:14])[c:15]1[NH2:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([Cl:14])[c:15]1[NH2:16] | BrCCOCCBr.N#Cc1cc(N)cc(Cl)c1N | N#Cc1cc(N2CCOCC2)cc(Cl)c1N | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(N2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 91 | [{"value": 91.0, "product": "NC1=C(C#N)C=C(C=C1Cl)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | 2,5-Diamino-3-chloro-benzonitrile (387 mg), bis-(2-bromoethyl)ether (0.35 mL) and N,N-diisopropyl-ethylamine (1.25 mL) were mixed in N,N-dimethylformamide (4 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (20 mL) was added and the crude mixture was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | CN(C=O)C | 180 | null | BrCCOCCBr.N#Cc1cc(N)cc(Cl)c1N>CN(C=O)C>N#Cc1cc(N2CCOCC2)cc(Cl)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-965ceeb189724deca33cd3653589b454 | C=Cc1ccc(F)cc1.CC(C)(C)OC(N)=O>>CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1 | ClOC(C)(C)C.P(=O)([O-])([O-])[O-].[OH-].[Na+].FC1=CC=C(C=C)C=C1.C(C)(C)(C)OC(N)=O>>C(C)(C)(C)OC(NCC(O)C1=CC=C(C=C1)F)=O | [CH2:9]=[CH:10][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | C=Cc1ccc(F)cc1.CC(C)(C)OC(N)=O | CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1 | null | O.O.[O-][Os](=O)(=O)[O-].[K+].[K+] | O.C(C)#N | Functional Group Addition | OtherReaction | 343f99300470b98849d71651d2e82d6c9edacd4c68421a204dfc04370ba1a1a5 | aa86d9adfff8b4301422489db74dbfc5ba2c2de99ec7ca2eb8abb8343061789f | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](-[NH2;D1;+0:7])=[O;D1;H0:8].[CH2;D1;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:8])-[NH;D2;+0:7]-[CH2;D2;+0:9]-[CH;D3;+0:10](-[O;D1;H1:14])-[c:11](:[c:12]):[c:13] | 57 | [{"value": 57.0, "product": "C(C)(C)(C)OC(NCC(O)C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | To a stirred solution of carbamic acid tert-butyl ester (0.22 g) in acetonitrile (6 mL) was added in sequence at 0° C.: Sodium hydroxide (52 mg) in water (5 mL); after 2 minutes tert-butyl hypochlorite (139 μL); after 10 minutes potassium osmate(VI) dihydrate (9 mg) in water (1 mL); after 1 minute hydroquinine (anthraq... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Vinyl | Carbamic ester.Secondary alcohol | null | null | c1ccccc1 | Other | O.O.[O-][Os](=O)(=O)[O-].[K+].[K+].O.C(C)#N | 0 | 3 | C=Cc1ccc(F)cc1.CC(C)(C)OC(N)=O>O.O.[O-][Os](=O)(=O)[O-].[K+].[K+].O.C(C)#N>CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-250062c19e314a8eaf3c96965828ede1 | CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1>>Fc1ccc(C2CNCCO2)cc1 | C(C)(C)(C)OC(NCC(O)C1=CC=C(C=C1)F)=O.ClCCl>>FC1=CC=C(C=C1)C1CNCCO1 | CC(C)(C)O[C:9](=O)[NH:8][CH2:7][CH:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:13][cH:12]1)[OH:11]>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][O:11]2)[cH:12][cH:13]1 | CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1 | Fc1ccc(C2CNCCO2)cc1 | null | null | FC(C(=O)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | 022fd6e7610a4bfc782fb7f6e2f059d36ee5269228ea0e457b1bfe06a8cc55f7 | 689122b84622cdd3ad3005e68e3a042fc56aae50665b37e1f5dc7a38f5fe3697 | c1ccc(C2CNCCO2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[c:6]>>[c:6]-[C:4]1-[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:7]-[O;H0;D2;+0:5]-1 | 94 | [{"value": 94.0, "product": "FC1=CC=C(C=C1)C1CNCCO1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1.5 | HOUR | A solution of [2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (90 mg) in dichloromethane (1 mL) and trifluoroacetic acid (1 mL) was stirred at 25° C. for 1 hour and then concentrated in vacuo. The residue was partitioned between ethyl acetate (5 mL) and saturated aqueous potassium carbonate (5 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary alcohol.Boc | Ether | null | C1COCCN1 | c1ccccc1.C1COCCN1 | HO- | FC(C(=O)O)(F)F | 25 | 1.5 | CC(C)(C)OC(=O)NCC(O)c1ccc(F)cc1>FC(C(=O)O)(F)F>Fc1ccc(C2CNCCO2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65f6ee47b2704f1a9cc633e1faf63866 | COc1cccc(C)c1N.O=C1CCC(=O)N1Br>>COc1cc(Br)cc(C)c1N | COC1=C(C(=CC=C1)C)N.BrN1C(CCC1=O)=O>>BrC1=CC(=C(C(=C1)C)N)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:7][c:8]([CH3:9])[c:10]1[NH2:11].O=C1CCC(=O)N1[Br:6]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH3:9])[c:10]1[NH2:11] | COc1cccc(C)c1N.O=C1CCC(=O)N1Br | COc1cc(Br)cc(C)c1N | null | null | C(C)#N | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 26 | [{"value": 26.0, "product": "BrC1=CC(=C(C(=C1)C)N)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.6, "product": "BrC1=CC(=C(C(=C1)C)N)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 145 | CELSIUS | null | null | To 2-methoxy-6-methyl-phenylamine (10.0 g) dissolved in acetonitrile (200 mL) was added N-bromosuccinimide (14.3 g) and the reaction mixture was heated to 145° C. for 15 minutes in a sealed microwave process vessel. The crude mixture was filtered through Celite, diluted with diethyl ether (200 mL) and washed with sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | C(C)#N | 145 | null | COc1cccc(C)c1N.O=C1CCC(=O)N1Br>C(C)#N>COc1cc(Br)cc(C)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-031ab1a7e01641a985696960ab2eb1a4 | C1COCCN1.COc1cc(Br)cc(C)c1N>>COc1cc(N2CCOCC2)cc(C)c1N | C1(CCCCC1)P(C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)C1CCCCC1.CC(C)([O-])C.[K+].N1CCOCC1.BrC1=CC(=C(C(=C1)C)N)OC>>COC1=C(C(=CC(=C1)N1CCOCC1)C)N | [NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:15]([NH2:16])[c:13]([CH3:14])[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([CH3:14])[c:15]1[NH2:16] | C1COCCN1.COc1cc(Br)cc(C)c1N | COc1cc(N2CCOCC2)cc(C)c1N | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 29 | [{"value": 29.0, "product": "COC1=C(C(=CC(=C1)N1CCOCC1)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Bis(dibenzylideneacetone)palladium (0.63 g) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (0.68 g) were added to dry toluene (100 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (3.70 g), morpholine (4.0 mL) and 4-bromo-2-methoxy-6-methyl-phenylamine (3.40 g) were ad... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1(=CC=CC=C1)C | null | 0.25 | C1COCCN1.COc1cc(Br)cc(C)c1N>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].C1(=CC=CC=C1)C>COc1cc(N2CCOCC2)cc(C)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa09eba90a414382af1c6fb125c70708 | C1COCCN1.O=[N+]([O-])c1c(F)cc(F)cc1F>>O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F | FC1=C(C(=CC(=C1)F)F)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].N1CCOCC1>>FC=1C=C(C=C(C1[N+](=O)[O-])F)N1CCOCC1 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.F[c:8]1[cH:7][c:5]([F:6])[c:4]([N+:2](=[O:1])[O-:3])[c:16]([F:17])[cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([F:6])[cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]1[F:17] | C1COCCN1.O=[N+]([O-])c1c(F)cc(F)cc1F | O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 37 | [{"value": 37.0, "product": "FC=1C=C(C=C(C1[N+](=O)[O-])F)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 16 | HOUR | 2,4,6-Trifluoronitrobenzene (4.95 g) and potassium carbonate (4.63 g) were mixed in dry dimethyl sulfoxide (40 mL) and cooled to 10° C. under argon. Morpholine (2.56 mL) was added and the reaction mixture was allowed to warm to 25° C. and stirred under argon for 16 hours. The reaction mixture was concentrated in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HF | CS(=O)C | 10 | 16 | C1COCCN1.O=[N+]([O-])c1c(F)cc(F)cc1F>CS(=O)C>O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8cb2a4d1c5c492d885e976a8f9d15c2 | O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F>>Nc1c(F)cc(N2CCOCC2)cc1F | Cl.FC=1C=C(C=C(C1[N+](=O)[O-])F)N1CCOCC1>>FC1=C(C(=CC(=C1)N1CCOCC1)F)N | O=[N+:1]([O-])[c:2]1[c:3]([F:4])[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[F:15]>>[NH2:1][c:2]1[c:3]([F:4])[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[F:15] | O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F | Nc1c(F)cc(N2CCOCC2)cc1F | null | [Zn] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "FC1=C(C(=CC(=C1)N1CCOCC1)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "FC1=C(C(=CC(=C1)N1CCOCC1)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Concentrated hydrochloric acid (4.2 mL) was added slowly to a mixture of zinc dust (3.3 g) and 4-(3,5-difluoro-4-nitro-phenyl)-morpholine (2.49 g) in tetrahydrofuran (40 mL) cooled to 0° C. The reaction mixture was then stirred for 1 hour at 0° C. and 2 hours at 25° C. The reaction mixture was filtered through Celite (... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Zn].O1CCCC1 | 0 | 2 | O=[N+]([O-])c1c(F)cc(N2CCOCC2)cc1F>[Zn].O1CCCC1>Nc1c(F)cc(N2CCOCC2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65064098cc944640a30038fea2b7af32 | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.O=C1CCC(=O)N1Cl>>Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F | [N+](=O)([O-])C1=CC(=C(C=C1)N)C(F)(F)F.ClN1C(CCC1=O)=O.C(C)(=O)OCC>>ClC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N | [NH2:1][c:2]1[cH:3][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15].O=C1CCC(=O)N1[Cl:4]>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.O=C1CCC(=O)N1Cl | Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F | null | null | C(C)#N | Functional Group Interconversion | Chlorination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 75 | [{"value": 75.0, "product": "ClC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "ClC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 4-Nitro-2-trifluoromethyl-phenylamine (5.6 g) and N-chlorosuccinimide (4.0 g) were suspended in acetonitrile (15 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Ethyl acetate (80 mL) was added and the organic phase was washed with 5% aqueous NaOH (2×50 mL), water (2×50 mL) and brine (2×50 m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | C(C)#N | 150 | null | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.O=C1CCC(=O)N1Cl>C(C)#N>Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-043fdd206af64f83ba1b370e4f747c34 | Cc1cc([N+](=O)[O-])cc(Cl)c1N.O=C(Cl)CC1CCCC1>>Cc1cc([N+](=O)[O-])cc(Cl)c1NC(=O)CC1CCCC1 | ClC1=C(C(=CC(=C1)[N+](=O)[O-])C)N.C1(CCCC1)CC(=O)Cl>>ClC1=C(C(=CC(=C1)[N+](=O)[O-])C)NC(CC1CCCC1)=O | [CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([Cl:10])[c:11]1[NH2:12].Cl[C:13](=[O:14])[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([Cl:10])[c:11]1[NH:12][C:13](=[O:14])[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1 | Cc1cc([N+](=O)[O-])cc(Cl)c1N.O=C(Cl)CC1CCCC1 | Cc1cc([N+](=O)[O-])cc(Cl)c1NC(=O)CC1CCCC1 | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 58 | [{"value": 58.0, "product": "ClC1=C(C(=CC(=C1)[N+](=O)[O-])C)NC(CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC1=C(C(=CC(=C1)[N+](=O)[O-])C)NC(CC1CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 2-Chloro-6-methyl-4-nitro-phenylamine (6.0 g) and cyclopentylacetyl chloride (5.1 g) were dissolved in acetonitrile (45 mL) and heated to 150° C. for 20 minutes in a sealed microwave process vessel. The reaction mixture was cooled to 0° C. and the precipitated product collected by filtration and washed with cold aceton... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCC1 | HCl | C(C)#N | 150 | null | Cc1cc([N+](=O)[O-])cc(Cl)c1N.O=C(Cl)CC1CCCC1>C(C)#N>Cc1cc([N+](=O)[O-])cc(Cl)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ebbb9c8c9e4423ba80206e6ba59430c | Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F>>Nc1cc(Cl)c(N)c(C(F)(F)F)c1 | C(C)(=O)O.ClC1=C(C(=CC(=C1)[N+](=O)[O-])C(F)(F)F)N>>ClC1=C(C(=CC(=C1)N)C(F)(F)F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1 | Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F | Nc1cc(Cl)c(N)c(C(F)(F)F)c1 | null | [Zn] | O1CCCC1 | 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] | 83 | [{"value": 83.0, "product": "ClC1=C(C(=CC(=C1)N)C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "ClC1=C(C(=CC(=C1)N)C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Acetic acid (13 mL) was added slowly to a mixture of zinc dust (12.4 g) and 2-chloro-4-nitro-6-trifluoromethyl-phenylamine (4 g) in tetrahydrofuran (40 mL). The reaction mixture was stirred for 1 hour, filtered through silica and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Zn].O1CCCC1 | null | 1 | Nc1c(Cl)cc([N+](=O)[O-])cc1C(F)(F)F>[Zn].O1CCCC1>Nc1cc(Cl)c(N)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb8cb8cbcc9d49f2b2bd7a8dd9118a36 | ClCCOCCCl.Nc1cc(Cl)c(N)c(C(F)(F)F)c1>>Nc1c(Cl)cc(N2CCOCC2)cc1C(F)(F)F | ClC1=C(C(=CC(=C1)N)C(F)(F)F)N.ClCCOCCCl.[I-].[Na+]>>ClC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N | Cl[CH2:8][CH2:9][O:10][CH2:11][CH2:12]Cl.[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([NH2:7])[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | ClCCOCCCl.Nc1cc(Cl)c(N)c(C(F)(F)F)c1 | Nc1c(Cl)cc(N2CCOCC2)cc1C(F)(F)F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(N2CCOCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 24 | [{"value": 24.0, "product": "ClC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}] | 165 | CELSIUS | null | null | 2-Chloro-6-trifluoromethyl-benzene-1,4-diamine (2.9 g), bis-(2-chloroethyl)ether (1.7 mL) and sodium iodide (516 mg) were mixed in acetonitrile (45 mL) and heated to 165° C. for 1 hour in a sealed microwave process vessel. The crude mixture was concentrated in vacuo, redissolved in ethyl acetate (100 mL) and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HCl | C(C)#N | 165 | null | ClCCOCCCl.Nc1cc(Cl)c(N)c(C(F)(F)F)c1>C(C)#N>Nc1c(Cl)cc(N2CCOCC2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdac82b42e4044e798cf58bba4e84266 | Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc([N+](=O)[O-])cc2C(C)C)cc1>>Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1 | C(C)(C)C1=C(C(=CC(=C1)[N+](=O)[O-])C(C)C)NS(=O)(=O)C1=CC=C(C=C1)C.[OH-].[Na+]>>NC1=CC(=C(C(=C1)C(C)C)NS(=O)(=O)C1=CC=C(C=C1)C)C(C)C | O=[N+:17]([O-])[c:16]1[cH:15][c:11]([CH:12]([CH3:13])[CH3:14])[c:10]([NH:9][S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]2)(=[O:7])=[O:8])[c:19]([CH:20]([CH3:21])[CH3:22])[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][c:10]2[c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][c:16]([NH2:17])[cH:18][c:19... | Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc([N+](=O)[O-])cc2C(C)C)cc1 | Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1 | null | null | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 76 | [{"value": 76.0, "product": "NC1=CC(=C(C(=C1)C(C)C)NS(=O)(=O)C1=CC=C(C=C1)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "NC1=CC(=C(C(=C1)C(C)C)NS(=O)(=O)C1=CC=C(C=C1)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of N-(2,6-diisopropyl-4-nitro-phenyl)-4-methyl-benzenesulfonamide (3.72 g) in ethanol (50 mL) was added stannous(II) chloride dihydrate (11.2 g) and the mixture was heated to 80° C. for 1.5 hour. It was then poured onto ice (300 mL), made strongly basic with solid sodium hydroxide (20 g) and diluted wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.C(C)O | 80 | null | Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc([N+](=O)[O-])cc2C(C)C)cc1>C(C)(=O)OCC.C(C)O>Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bcb9e4423d34fa0b69962431bccb5b7 | BrCCOCCBr.Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1>>CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N | NC1=CC(=C(C(=C1)C(C)C)NS(=O)(=O)C1=CC=C(C=C1)C)C(C)C.BrCCOCCBr.C(C)(C)N(C(C)C)CC.CN1CCCC1>>C(C)(C)C1=C(C(=CC(=C1)N1CCOCC1)C(C)C)N | Br[CH2:8][CH2:9][O:10][CH2:11][CH2:12]Br.Cc1ccc(S(=O)(=O)[NH:19][c:18]2[c:4]([CH:2]([CH3:1])[CH3:3])[cH:5][c:6]([NH2:7])[cH:13][c:14]2[CH:15]([CH3:16])[CH3:17])cc1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[c:18]1[NH2:19] | BrCCOCCBr.Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1 | CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 3fe2cc49141015d2943c1e66414072573b8365671fdc19a3cb604d4d4ddc57eb | 6512170477587dad35bf5996e96073bacf6d26cb0464d8d5ed5d3effb56dd351 | c1ccc(N2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.C-c1:c:c:c(-S(=O)(=O)-[NH;D2;+0:6]-[c:7]2:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]:[c:13]:2):c:c:1>>[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[N;H0;D3;+0:11]2-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-2):[c:12]:[c:13]:1 | 99 | [{"value": 99.0, "product": "C(C)(C)C1=C(C(=CC(=C1)N1CCOCC1)C(C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 3 | HOUR | A mixture of N-(4-amino-2,6-diisopropyl-phenyl)-4-methyl-benzenesulfonamide (346 mg), bis-(2-bromoethyl)ether (151 μL), N,N-diisopropyl-ethylamine (0.53 mL) and N-methylpyrrolidine (1.0 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washe... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Tosylate.Primary halide.Primary halide.Primary amine | Primary amine.Tertiary amine | c1ccccc1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | TsOH.HBr | C(C)(=O)OCC | 180 | 3 | BrCCOCCBr.Cc1ccc(S(=O)(=O)Nc2c(C(C)C)cc(N)cc2C(C)C)cc1>C(C)(=O)OCC>CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6932b139f88d4c50b5443388b3a5686b | CCc1cc([N+](=O)[O-])cc(CC)c1NS(=O)(=O)c1ccc(C)cc1>>CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | S(=O)([O-])S(=O)[O-].[Na+].[Na+].C(C)C1=C(C(=CC(=C1)[N+](=O)[O-])CC)NS(=O)(=O)C1=CC=C(C=C1)C.C([O-])([O-])=O.[K+].[K+]>>NC1=CC(=C(C(=C1)CC)NS(=O)(=O)C1=CC=C(C=C1)C)CC | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:11]([NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([CH3:20])[cH:21][cH:22]2)[c:8]([CH2:9][CH3:10])[cH:7]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][c:8]([CH2:9][CH3:10])[c:11]1[NH:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([CH3:20])[cH:21][... | CCc1cc([N+](=O)[O-])cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | null | null | O1CCCC1.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Nc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "NC1=CC(=C(C(=C1)CC)NS(=O)(=O)C1=CC=C(C=C1)C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.8, "product": "NC1=CC(=C(C(=C1)CC)NS(=O)(=O)C1=CC=C(C=C1)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 20 | HOUR | A solution of sodium dithionite (772 mg) in water (6 mL) was added to a solution of N-(2,6-diethyl-4-nitro-phenyl)-4-methyl-benzenesulfonamide (309 mg) in tetrahydrofuran (6 mL) and the resulting mixture was stirred at 50° C. for 20 hours. After cooling, the water was saturated with potassium carbonate and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.O | 50 | 20 | CCc1cc([N+](=O)[O-])cc(CC)c1NS(=O)(=O)c1ccc(C)cc1>O1CCCC1.O>CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9e8fdfc834b4946b7d476ba1a26e87f | BrCCOCCBr.CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1>>CCc1cc(N2CCOCC2)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | NC1=CC(=C(C(=C1)CC)NS(=O)(=O)C1=CC=C(C=C1)C)CC.BrCCOCCBr.C(C)(C)N(C(C)C)CC.CN1CCCC1>>C(C)C1=C(C(=CC(=C1)N1CCOCC1)CC)NS(=O)(=O)C1=CC=C(C=C1)C | Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.[CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[cH:12][c:13]([CH2:14][CH3:15])[c:16]1[NH:17][S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([CH3:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][c:13]([CH2:14][CH3:15])[c:16]1[NH:... | BrCCOCCBr.CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | CCc1cc(N2CCOCC2)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | O=S(=O)(Nc1ccc(N2CCOCC2)cc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 91 | [{"value": 91.0, "product": "C(C)C1=C(C(=CC(=C1)N1CCOCC1)CC)NS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of N-(4-amino-2,6-diethyl-phenyl)-4-methyl-benzenesulfonamide (70 mg), bis-(2-bromoethyl)ether (33 μL), N,N-diisopropyl-ethylamine (115 μL) and N-methylpyrrolidine (0.3 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccccc1 | HBr | C(C)(=O)OCC | 180 | null | BrCCOCCBr.CCc1cc(N)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1>C(C)(=O)OCC>CCc1cc(N2CCOCC2)cc(CC)c1NS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26c94bd826b04d9c9a95a4833d3e9118 | O=C(O)Cc1ccc(F)c(F)c1.O=S(Cl)Cl>>O=C(Cl)Cc1ccc(F)c(F)c1 | FC=1C=C(C=CC1F)CC(=O)O.S(=O)(Cl)Cl>>FC=1C=C(C=CC1F)CC(=O)Cl | O[C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1 | O=C(O)Cc1ccc(F)c(F)c1.O=S(Cl)Cl | O=C(Cl)Cc1ccc(F)c(F)c1 | null | null | ClCCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5] | 100 | [{"value": 100.0, "product": "FC=1C=C(C=CC1F)CC(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To (3,4-difluoro-phenyl)-acetic acid (2.0 g) dissolved in 1,2-dichloroethane (5 mL) was added thionyl chloride (5 mL) and the mixture was refluxed for 16 hours under argon. The crude mixture was concentrated in vacuo to furnish 2.2 g (100%) of the title compound as a yellow oil. 1H NMR (500 MHz, CDCl3): 4.10 (s, 2H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | ClCCCl | null | null | O=C(O)Cc1ccc(F)c(F)c1.O=S(Cl)Cl>ClCCCl>O=C(Cl)Cc1ccc(F)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b4fd8f361d640e4ab0811af31b04b92 | Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.O=C(Cl)Cc1ccc(F)cc1>>O=C(Cc1ccc(F)cc1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F | BrC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N.FC1=CC=C(C=C1)CC(=O)Cl.O>>BrC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)NC(CC1=CC=C(C=C1)F)=O | [NH2:11][c:12]1[c:13]([Br:14])[cH:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[cH:23][c:24]1[C:25]([F:26])([F:27])[F:28].Cl[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[NH:11][c:12]1[c:13]([Br:14])[cH:15][c:16]([N:17]2[CH2... | Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.O=C(Cl)Cc1ccc(F)cc1 | O=C(Cc1ccc(F)cc1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1ccc(N2CCOCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 9 | [{"value": 9.0, "product": "BrC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)NC(CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 2-Bromo-4-morpholin-4-yl-6-trifluoromethyl-phenylamine (0.236 g) and 4-fluorophenylacetyl chloride (0.105 mL) were dissolved in acetonitrile (5 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Water (25 mL) was added and the product was extracted with ethyl acetate (3×25 mL). The organic pha... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1COCC[NH]1 | HCl | C(C)#N | 150 | null | Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.O=C(Cl)Cc1ccc(F)cc1>C(C)#N>O=C(Cc1ccc(F)cc1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-244288c6908c4f758195da94539616c5 | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)CC1CCCC1>>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 | CC1=C(C(=CC(=C1)N1CCOCC1)C)N.C1(CCCC1)CC(=O)Cl.O>>C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C)N1CCOCC1)C | [CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH2:15].Cl[C:16](=[O:17])[CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][CH:19]1[CH2:20][CH... | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)CC1CCCC1 | Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 20 | [{"value": 20.0, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C)N1CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 2,6-Dimethyl-4-morpholin-4-yl-phenylamine (0.50 g) and cyclopentylacetyl chloride (0.53 mL) were dissolved in acetonitrile (5 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Water (25 mL) was added and the product was extracted with ethyl acetate (3×25 mL). The organic phases were washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.C1CCCC1 | HCl | C(C)#N | 150 | null | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)CC1CCCC1>C(C)#N>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ea1b7f4019d4fcab8f0d829e7210ab6 | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)OCc1ccccc1>>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)OCc1ccccc1 | ClC(=O)OCC1=CC=CC=C1.CC1=C(C(=CC(=C1)N1CCOCC1)C)N.C(C)(C)N(C(C)C)CC>>C(C1=CC=CC=C1)OC(NC1=C(C=C(C=C1C)N1CCOCC1)C)=O | [CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH2:15].Cl[C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH:15][C:16](=[O:17])[O:18][CH2:19][c:20... | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)OCc1ccccc1 | Cc1cc(N2CCOCC2)cc(C)c1NC(=O)OCc1ccccc1 | null | null | ClCCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccc(N2CCOCC2)cc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 47 | [{"value": 47.0, "product": "C(C1=CC=CC=C1)OC(NC1=C(C=C(C=C1C)N1CCOCC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Benzyl chloroformate (32 mg) was added to a solution of 0.15 M 2,6-dimethyl-4-morpholin-4-yl-phenylamine and 0.30 M N,N-diisopropyl-ethylamine in 1,2-dichloroethane (1 mL). The vial was shaken for 16 hours and concentrated in vacuo. Aqueous sodium hydroxide (1 M, 2 mL) was added and the crude mixture was extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1 | HCl | ClCCCl | null | 16 | Cc1cc(N2CCOCC2)cc(C)c1N.O=C(Cl)OCc1ccccc1>ClCCCl>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70b7f9e8e896453db39b8050c826a880 | CCCCC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N>>CCCCC(=O)Nc1c(C)cc(N2CCOCC2)cc1C | CC1=C(C(=CC(=C1)N1CCOCC1)C)N.C(CCCC)(=O)O.C(C)(C)N(C(C)C)CC.C(C)(=O)OCC>>CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CCCC)=O | O[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[c:9]([CH3:10])[cH:11][c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19][c:20]1[CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[cH:11][c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19][c:20]1[CH3:21] | CCCCC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N | CCCCC(=O)Nc1c(C)cc(N2CCOCC2)cc1C | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(N2CCOCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 40 | [{"value": 40.0, "product": "CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | MINUTE | Pentanoic acid (0.37 g), N,N-diisopropyl-ethylamine (1.51 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (1.66 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2,6-Dimethyl-4-morpholin-4-yl-phenylami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 0.033333 | CCCCC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N>CN(C=O)C>CCCCC(=O)Nc1c(C)cc(N2CCOCC2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5211cc71422745739d3aa7d204c09c02 | CCC(CC)CC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N>>CCC(CC)CC(=O)Nc1c(C)cc(N2CCOCC2)cc1C | C(C)C(CC(=O)O)CC.S(=O)(Cl)Cl.CC1=C(C(=CC(=C1)N1CCOCC1)C)N.C([O-])(O)=O.[Na+].[Cl-].[Na+].O.O>>CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC(CC)CC)=O | O[C:7]([CH2:6][CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:8].[NH2:9][c:10]1[c:11]([CH3:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[c:11]([CH3:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[... | CCC(CC)CC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N | CCC(CC)CC(=O)Nc1c(C)cc(N2CCOCC2)cc1C | null | null | C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(N2CCOCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 30.5 | [{"value": 30.0, "product": "CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC(CC)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.5, "product": "CC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC(CC)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | 3-Ethylpentanoic acid (0.79 g) and thionyl chloride (0.44 mL) were mixed-in acetonitrile (10 mL) and heated to 110° C. for 5 minutes in a sealed microwave process vial. 2,6-Dimethyl-4-morpholin-4-yl-phenylamine (1:25 g) dissolved in acetonitrile (10 mL) was added to the reaction mixture and heated to 150° C. for 15 min... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1 | HO- | C(C)#N | 110 | null | CCC(CC)CC(=O)O.Cc1cc(N2CCOCC2)cc(C)c1N>C(C)#N>CCC(CC)CC(=O)Nc1c(C)cc(N2CCOCC2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ece7f9c6febb462db1b38004d1cc89cf | O=C(CC1CCCC1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.OB(O)c1cccnc1>>O=C(CC1CCCC1)Nc1c(-c2cccnc2)cc(N2CCOCC2)cc1C(F)(F)F | C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)Br.N1=CC(=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C=1C=NC=CC1 | Br[c:11]1[c:10]([NH:9][C:2](=[O:1])[CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[c:27]([C:28]([F:29])([F:30])[F:31])[cH:26][c:19]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[cH:18]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[NH:9][c:10]1[c:11](-[c:12]2[c... | O=C(CC1CCCC1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.OB(O)c1cccnc1 | O=C(CC1CCCC1)Nc1c(-c2cccnc2)cc(N2CCOCC2)cc1C(F)(F)F | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CC(=O)C | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1-c1cccnc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]-[C:6]=[O;D1;H0:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:7]=[C:6]-[#7:5]-[c:4](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:2]:[c:3] | 18.1 | [{"value": 18.0, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.1, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | 2-Cyclopentyl-N-(2-bromo-6-trifluoromethyl-4-morpholin-4-yl-phenyl)-acetamide (1b, 15 mg), 3-pyridylboronic acid (21 mg), aqueous potassium carbonate (5 M, 90 μL) and palladium(II) acetate (1 mg) were mixed in acetone (2 mL) and heated to 130° C. for 20 minutes in a sealed microwave process vial. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccncc1.c1ccccc1 | C1CCCC1.c1ccncc1.c1ccccc1.C1COCC[NH]1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CC(=O)C | 130 | null | O=C(CC1CCCC1)Nc1c(Br)cc(N2CCOCC2)cc1C(F)(F)F.OB(O)c1cccnc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CC(=O)C>O=C(CC1CCCC1)Nc1c(-c2cccnc2)cc(N2CCOCC2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb7d3289f07d45a68a72d0c8777a54f7 | CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N.O=C(Cl)CC1CCCC1>>CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1NC(=O)CC1CCCC1 | C(C)(C)C1=C(C(=CC(=C1)N1CCOCC1)C(C)C)N.N1=CC=CC=C1.C1(CCCC1)CC(=O)Cl>>C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(C)C)N1CCOCC1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[c:18]1[NH2:19].Cl[C:20](=[O:21])[CH2:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]([CH:15]([CH3:1... | CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N.O=C(Cl)CC1CCCC1 | CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1NC(=O)CC1CCCC1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 33 | [{"value": 33.0, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(C)C)N1CCOCC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1 | HOUR | To a solution of 2,6-diisopropyl-4-morpholin-4-yl-phenylamine (279 mg) and pyridine (245 μL) in tetrahydrofuran (2 mL) was added cyclopentylacetyl chloride (210 μL) and the mixture was stirred for 1 hour at 25° C. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with 10% aqueous sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.C1CCCC1 | HCl | O1CCCC1.C(C)(=O)OCC | 25 | 1 | CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1N.O=C(Cl)CC1CCCC1>O1CCCC1.C(C)(=O)OCC>CC(C)c1cc(N2CCOCC2)cc(C(C)C)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69e7c1a160fc48618e4222b3b56292b9 | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(Cl)CC1CCCC1>>O=C(CC1CCCC1)Nc1c(F)cc(N2CCOCC2)cc1F | FC1=C(C(=CC(=C1)N1CCOCC1)F)N.C1(CCCC1)CC(=O)Cl>>C1(CCCC1)CC(=O)NC1=C(C=C(C=C1F)N1CCOCC1)F | [NH2:9][c:10]1[c:11]([F:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23].Cl[C:2](=[O:1])[CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1>>[O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[NH:9][c:10]1[c:11]([F:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21... | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(Cl)CC1CCCC1 | O=C(CC1CCCC1)Nc1c(F)cc(N2CCOCC2)cc1F | null | null | C(C)#N | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 75 | [{"value": 75.0, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1F)N1CCOCC1)F", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 2,6-Difluoro-4-morpholin-4-yl-phenylamine (0.20 g) and cyclopentylacetyl chloride (149 μL) were dissolved in acetonitrile (4 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo and purified by flash chromatography to furnish 228 mg (75%) of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccccc1.C1COCC[NH]1 | HCl | C(C)#N | 150 | null | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(Cl)CC1CCCC1>C(C)#N>O=C(CC1CCCC1)Nc1c(F)cc(N2CCOCC2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ed907889b4e49d1bd440dd340a6a0f3 | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(O)CC1C=CCC1>>O=C(CC1C=CCC1)Nc1c(F)cc(N2CCOCC2)cc1F | FC1=C(C(=CC(=C1)N1CCOCC1)F)N.C1(C=CCC1)CC(=O)O.C(C)(C)N(C(C)C)CC.C(C)(=O)OCC>>C1(C=CCC1)CC(=O)NC1=C(C=C(C=C1F)N1CCOCC1)F | [NH2:9][c:10]1[c:11]([F:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c:22]1[F:23].O[C:2](=[O:1])[CH2:3][CH:4]1[CH:5]=[CH:6][CH2:7][CH2:8]1>>[O:1]=[C:2]([CH2:3][CH:4]1[CH:5]=[CH:6][CH2:7][CH2:8]1)[NH:9][c:10]1[c:11]([F:12])[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[cH:21][c... | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(O)CC1C=CCC1 | O=C(CC1C=CCC1)Nc1c(F)cc(N2CCOCC2)cc1F | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC1C=CCC1)Nc1ccc(N2CCOCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]=[C:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 71 | [{"value": 71.0, "product": "C1(C=CCC1)CC(=O)NC1=C(C=C(C=C1F)N1CCOCC1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | MINUTE | Cyclopent-2-enylacetic acid (0.17 mL), N,N-diisopropyl-ethylamine (0.50 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.55 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2,6-Difluoro-4-morpholin-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1=CCCC1.c1ccccc1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 0.033333 | Nc1c(F)cc(N2CCOCC2)cc1F.O=C(O)CC1C=CCC1>CN(C=O)C>O=C(CC1C=CCC1)Nc1c(F)cc(N2CCOCC2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4b6d09f88be45b3b2aa7bfd9f304cb3 | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(O)CC1CC2CCC1C2>>Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CC2CCC1C2 | CC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N.C12C(CC(CC1)C2)CC(=O)O.C(C)(C)N(C(C)C)CC.C(C)(=O)OCC>>C12C(CC(CC1)C2)CC(=O)NC2=C(C=C(C=C2C(F)(F)F)N2CCOCC2)C | [CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]1[NH2:18].O[C:19](=[O:20])[CH2:21][CH:22]1[CH2:23][CH:24]2[CH2:25][CH2:26][CH:27]1[CH2:28]2>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[... | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(O)CC1CC2CCC1C2 | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CC2CCC1C2 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC1CC2CCC1C2)Nc1ccc(N2CCOCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 6 | [{"value": 6.0, "product": "C12C(CC(CC1)C2)CC(=O)NC2=C(C=C(C=C2C(F)(F)F)N2CCOCC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.8, "product": "C12C(CC(CC1)C2)CC(=O)NC2=C(C=C(C=C2C(F)(F)F)N2CCOCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | MINUTE | Bicyclo[2.2.1]hept-2-yl-acetic acid (160 mg), N,N-diisopropyl-ethylamine (0.44 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.47 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2-Methyl-4-morphol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC2CCC1C2.c1ccccc1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 0.033333 | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(O)CC1CC2CCC1C2>CN(C=O)C>Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CC2CCC1C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b6a52156dac4313b101d9167201ce36 | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(Cl)CC1CCCC1>>Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CCCC1 | CC1=C(C(=CC(=C1)N1CCOCC1)C(F)(F)F)N.C1(CCCC1)CC(=O)Cl>>C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C | [CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]1[NH2:18].Cl[C:19](=[O:20])[CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]1[NH:18][C... | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(Cl)CC1CCCC1 | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CCCC1 | null | null | C(C)#N.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 52 | [{"value": 52.0, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "C1(CCCC1)CC(=O)NC1=C(C=C(C=C1C(F)(F)F)N1CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 2-Methyl-4-morpholin-4-yl-6-trifluoromethyl-phenylamine (0.18 g) and cyclopentylacetyl chloride (112 mg) were dissolved in acetonitrile (4 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL) and brine (1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.C1CCCC1 | HCl | C(C)#N.C(C)(=O)OCC | 150 | null | Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1N.O=C(Cl)CC1CCCC1>C(C)#N.C(C)(=O)OCC>Cc1cc(N2CCOCC2)cc(C(F)(F)F)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e4617c4ca0b4100ad6fc4e651a16091 | Cc1cc(N)cc(Cl)c1NC(=O)Cc1cccc(F)c1.ClCCOCCCl>>Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)Cc1cccc(F)c1 | C([O-])(O)=O.[Na+].NC1=CC(=C(C(=C1)C)NC(CC1=CC(=CC=C1)F)=O)Cl.ClCCOCCCl.[I-].[K+]>>ClC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC1=CC(=CC=C1)F)=O | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:11][c:12]([Cl:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]1.Cl[CH2:6][CH2:7][O:8][CH2:9][CH2:10]Cl>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([Cl:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][c:19]1[cH:... | Cc1cc(N)cc(Cl)c1NC(=O)Cc1cccc(F)c1.ClCCOCCCl | Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)Cc1cccc(F)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | O=C(Cc1ccccc1)Nc1ccc(N2CCOCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 31 | [{"value": 31.0, "product": "ClC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC1=CC(=CC=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | N-(4-Amino-2-chloro-6-methyl-phenyl)-2-(3-fluoro-phenyl)-acetamide (616 mg), bis-(2-chloroethyl)ether (260 μL) and potassium iodide (400 mg) were mixed in dry N,N-dimethylformamide (11 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. 5% aqueous sodium bicarbonate (100 mL) was added and the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccccc1 | HCl | CN(C=O)C | 180 | null | Cc1cc(N)cc(Cl)c1NC(=O)Cc1cccc(F)c1.ClCCOCCCl>CN(C=O)C>Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)Cc1cccc(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd7578946f024f4d8de8d7c2e329bb7d | Cc1cc(N)cc(Cl)c1NC(=O)CC1CCCC1.ClCCOCCCl>>Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)CC1CCCC1 | NC1=CC(=C(C(=C1)C)NC(CC1CCCC1)=O)Cl.ClCCOCCCl.[I-].[K+]>>ClC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC1CCCC1)=O | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:11][c:12]([Cl:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.Cl[CH2:6][CH2:7][O:8][CH2:9][CH2:10]Cl>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([Cl:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][CH:19]1[CH2:20][CH2... | Cc1cc(N)cc(Cl)c1NC(=O)CC1CCCC1.ClCCOCCCl | Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)CC1CCCC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 41 | [{"value": 41.0, "product": "ClC1=C(C(=CC(=C1)N1CCOCC1)C)NC(CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | N-(4-Amino-2-chloro-6-methyl-phenyl)-2-cyclopentyl-acetamide (830 mg), bis-(2-chloroethyl)ether (3.35 mL) and potassium iodide (470 mg) were mixed in absolute ethanol (33 mL) and heated to 170° C. for 1 hour in a sealed microwave process vial. The crude mixture was concentrated in vacuo and purified by flash chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.C1CCCC1 | HCl | C(C)O | 170 | null | Cc1cc(N)cc(Cl)c1NC(=O)CC1CCCC1.ClCCOCCCl>C(C)O>Cc1cc(N2CCOCC2)cc(Cl)c1NC(=O)CC1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39b98bd20bf342e696ee6a5bad97b8d0 | Clc1nc2ccccc2nc1Cl.N#Cc1nc2ccccc2nc1Cc1ccccc1>>Clc1nc2ccccc2nc1Cc1ccccc1 | C=1C=CC=2C(C1)=NC=3C(=NNC3N2)N.C(C1=CC=CC=C1)[Mg]Cl.C(C1=CC=CC=C1)C1=NC2=CC=CC=C2N=C1C#N.ClC1=NC2=CC=CC=C2N=C1Cl>>C(C1=CC=CC=C1)C1=NC2=CC=CC=C2N=C1Cl | Clc1nc2ccccc2nc1[Cl:1].N#C[c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10][c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[Cl:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10][c:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Clc1nc2ccccc2nc1Cl.N#Cc1nc2ccccc2nc1Cc1ccccc1 | Clc1nc2ccccc2nc1Cc1ccccc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 34dd55ba7b01d1c12ce36eabfae058a31305aff73795be952668d7b25e2cef93 | 07b7b788ad65039b4d7a1268818a84100b9ec71d6cde6c3476df8d8b650b7287 | c1ccc(Cc2cnc3ccccc3n2)cc1 | Cl-c1:n:c2:c:c:c:c:c:2:n:c:1-[Cl;H0;D1;+0:1].N#C-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1-[C:8]>>[C:8]-[c:7]1:[#7;a:6]:[c:5]:[c:4]:[#7;a:3]:[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | Intermediate 3 can be prepared from the starting material 2,3-dichloroquinoxaline 1 following the reaction in Scheme 1. In this manner, quinoxaline 1 can be reacted with benzylmagnesium chloride in THF to afford 2-benzyl-3-chloroquinoxaline 2. 2-Benzylquinoxalines can also be prepared by reaction with alternative alkyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitrile | Aromatic halide | c1ccc2nccnc2c1.c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1.c1ccccc1 | HCl | C1CCOC1 | null | null | Clc1nc2ccccc2nc1Cl.N#Cc1nc2ccccc2nc1Cc1ccccc1>C1CCOC1>Clc1nc2ccccc2nc1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6ffcff6f31e4e339a3265be4b192216 | Clc1nc2ccccc2nc1Cc1ccccc1.[C-]#N>>N#Cc1nc2ccccc2nc1Cc1ccccc1 | C(C1=CC=CC=C1)[Li].C(C1=CC=CC=C1)C1=NC2=CC=CC=C2N=C1Cl.[C-]#N>>C(C1=CC=CC=C1)C1=NC2=CC=CC=C2N=C1C#N | Cl[c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[N:1]#[C-:2]>>[N:1]#[C:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | Clc1nc2ccccc2nc1Cc1ccccc1.[C-]#N | N#Cc1nc2ccccc2nc1Cc1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 53e76cb2c979967a434ecf085a6d6985ac0504f1b7b5b2af0e532407da06c0e3 | 2549b026e730aedabd9d1c88337e10b7987bb7b86597cabf3fd7fef1a79c8a9a | c1ccc(Cc2cnc3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7].[C-;H0;D1:8]#[N;D1;H0:9]>>[C:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:8]#[N;D1;H0:9] | null | [] | null | null | null | null | Intermediate 3 can be prepared from the starting material 2,3-dichloroquinoxaline 1 following the reaction in Scheme 1. In this manner, quinoxaline 1 can be reacted with benzylmagnesium chloride in THF to afford 2-benzyl-3-chloroquinoxaline 2. 2-Benzylquinoxalines can also be prepared by reaction with alternative alkyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1.c1ccccc1 | Other | null | null | null | Clc1nc2ccccc2nc1Cc1ccccc1.[C-]#N>>N#Cc1nc2ccccc2nc1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cb813fa1afc453b986fe24bc8525349 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1>>Cc1ccc(C(=O)N(CCCN)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1 | C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C1CC1)C1=NC2=CC=CC=C2N=C1CC1=CC=CC=C1)=O.Cl.CCOCC>>Cl.NCCCN(C(C1=CC=C(C=C1)C)=O)C(C1CC1)C1=NC2=CC=CC=C2N=C1CC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:12][CH2:11][CH2:10][CH2:9][N:8]([C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]1)=[O:7])[CH:13]([c:14]1[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[n:22][c:23]1[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[CH:31]1[CH2:32][CH2:33]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH2... | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1 | Cc1ccc(C(=O)N(CCCN)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(NC(c1nc2ccccc2nc1Cc1ccccc1)C1CC1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 90 | [{"value": 90.0, "product": "Cl.NCCCN(C(C1=CC=C(C=C1)C)=O)C(C1CC1)C1=NC2=CC=CC=C2N=C1CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of (±)-{3-[[(3-benzylquinoxalin-2-yl)cyclopropylmethyl]-(4-methyl-benzoyl)-amino]-propyl}carbamic acid tert-butyl ester 7 (0.40 g, 0.71 mmol) in dioxane (5 mL) at rt was added 4 N HCl in dioxane (2.0 mL, 8 mmol). The reaction mixture was stirred overnight. It was added with Et2O and the precipitated solid wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2nccnc2c1.c1ccccc1.C1CC1 | HO- | O1CCOCC1 | null | 8 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1>O1CCOCC1>Cc1ccc(C(=O)N(CCCN)C(c2nc3ccccc3nc2Cc2ccccc2)C2CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd29ce28e6c140db85e5cc95b038e023 | CN(c1nc2cc(Cl)ccc2nc1Cc1ccccc1)C1CC1.N#Cc1nc2cc(Cl)ccc2nc1Cc1ccccc1>>Clc1ccc2nc(Cc3ccccc3)c(CNC3CC3)nc2c1 | C(=O)(C(F)(F)F)O.C(C1=CC=CC=C1)C=1C(=NC2=CC(=CC=C2N1)Cl)N(C)C1CC1.C(C1=CC=CC=C1)C=1C(=NC2=CC(=CC=C2N1)Cl)C#N.C1(CC1)[Mg]Br>>C(C1=CC=CC=C1)C=1C(=NC2=CC(=CC=C2N1)Cl)CNC1CC1 | Clc1ccc2nc(Cc3ccccc3)c([N:17]([CH3:16])[CH:18]3[CH2:19][CH2:20]3)nc2c1.N#C[c:15]1[c:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:6][c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:23][c:22]2[n:21]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15]([CH2:16][NH:17][CH:18]3[CH... | CN(c1nc2cc(Cl)ccc2nc1Cc1ccccc1)C1CC1.N#Cc1nc2cc(Cl)ccc2nc1Cc1ccccc1 | Clc1ccc2nc(Cc3ccccc3)c(CNC3CC3)nc2c1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 85c5bd04daf968854f19ef102f861f8cdca5b497c49fd6e6307c1a7d9609f4bd | e57444645ba26124f13ae60bf9e9d06ce0df8c4514dec8b6702f6337d15976f1 | c1ccc(Cc2nc3ccccc3nc2CNC2CC2)cc1 | Cl-c1:c:c:c2:n:c(-C-c3:c:c:c:c:c:3):c(-[N;H0;D3;+0:1](-[CH3;D1;+0:2])-[C:3]3-[C:4]-[C:5]-3):n:c:2:c:1.N#C-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1-[C:12]>>[C:12]-[c:11]1:[#7;a:10]:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:1-[CH2;D2;+0:2]-[NH;D2;+0:1]-[C:3]1-[C:4]-[C:5]-1 | null | [] | -60 | CELSIUS | 40 | MINUTE | (±)-(3-Benzyl-7-chloroquinoxalin-2-yl)-cyclopropyl-methylamine (16): To a stirred solution of 3-benzyl-7-chloro-2-cyanoquinoxaline (4.0 g, 14.3 mmol) in anhydrous CH2Cl2 (80 mL) at −64° C. under nitrogen was added dropwise cyclopropylmagnesium bromide (0.76 M in THF, 52 mL, 39.5 mmol). The reaction mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrile.Tertiary amine | Secondary amine | c1ccc2nccnc2c1.c1ccccc1.c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1.c1ccccc1.C1CC1 | HCl | C(Cl)Cl | -60 | 0.666667 | CN(c1nc2cc(Cl)ccc2nc1Cc1ccccc1)C1CC1.N#Cc1nc2cc(Cl)ccc2nc1Cc1ccccc1>C(Cl)Cl>Clc1ccc2nc(Cc3ccccc3)c(CNC3CC3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fa89c549ef74665a64b70e2202ff80b | CCOC(=O)c1ccc(N2CCNCC2)cc1.Cc1ccc(N=C=O)cc1>>CCOC(=O)c1ccc(N2CCN(C(=O)Nc3ccc(C)cc3)CC2)cc1 | N1(CCNCC1)C1=CC=C(C(=O)OCC)C=C1.C(C)N(CC)CC.N(=C=O)C1=CC=C(C=C1)C>>CC1=CC=C(C=C1)NC(=O)N1CCN(CC1)C1=CC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][NH:13][CH2:24][CH2:25]2)[cH:26][cH:27]1.[C:14](=[O:15])=[N:16][c:17]1[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][c... | CCOC(=O)c1ccc(N2CCNCC2)cc1.Cc1ccc(N=C=O)cc1 | CCOC(=O)c1ccc(N2CCN(C(=O)Nc3ccc(C)cc3)CC2)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 6fdae4b903e981d8b7a376762a2f4ccd0c6fe7e77f0529898c101f9e9062d1aa | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(Nc1ccccc1)N1CCN(c2ccccc2)CC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 2.7 | [{"value": 2.7, "product": "CC1=CC=C(C=C1)NC(=O)N1CCN(CC1)C1=CC=C(C(=O)OCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A solution of 1-isocyanato-4-methyl-benzene (0.051 mol) in DCM p.a. (75 ml) was added dropwise to a solution of 4-(1-piperazinyl)-benzoic acid, ethyl ester (0.043 mol) and triethylamine (0.051 mol) in DCM p.a. (75 ml) while stirring at 0° C. (ice) for 20 minutes. The reaction mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | 0 | 0.333333 | CCOC(=O)c1ccc(N2CCNCC2)cc1.Cc1ccc(N=C=O)cc1>C(Cl)Cl>CCOC(=O)c1ccc(N2CCN(C(=O)Nc3ccc(C)cc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-378770d071f84d5e9f27fd124c0f46de | COCOc1cnccc1C1=NOC(CO)C1CO>>OCC1ON=C(c2ccncc2O)C1CO | OCC1C(=NOC1CO)C1=C(C=NC=C1)OCOC>>OCC1C(=NOC1CO)C1=C(C=NC=C1)O | COC[O:13][c:12]1[c:7]([C:6]2=[N:5][O:4][CH:3]([CH2:2][OH:1])[CH:14]2[CH2:15][OH:16])[cH:8][cH:9][n:10][cH:11]1>>[OH:1][CH2:2][CH:3]1[O:4][N:5]=[C:6]([c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[OH:13])[CH:14]1[CH2:15][OH:16] | COCOc1cnccc1C1=NOC(CO)C1CO | OCC1ON=C(c2ccncc2O)C1CO | null | null | FC(C(=O)O)(F)F.C(Cl)Cl | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1cc(C2=NOCC2)ccn1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 150.4 | [{"value": 150.4, "product": "OCC1C(=NOC1CO)C1=C(C=NC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of intermediate compound 12 (3.8 g, 0.0142 mol) in 100 ml of DCM, 25 ml of triflouroacetic acid were added portionwise at room temperature. The reaction was stirred overnight at room temperature. The solvent was evaporated and the residue was co-evaporated with ethanol. Yielding 4.79 g (100, crude product... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=NOCC1.c1ccncc1 | HO- | FC(C(=O)O)(F)F.C(Cl)Cl | null | 8 | COCOc1cnccc1C1=NOC(CO)C1CO>FC(C(=O)O)(F)F.C(Cl)Cl>OCC1ON=C(c2ccncc2O)C1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff1b9824571941e48737c951367a5bc9 | Fc1cccc2[nH]ccc12.O=C(Cl)C(=O)Cl>>O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12 | FC1=C2C=CNC2=CC=C1.C(C(=O)Cl)(=O)Cl>>FC1=C2C(=CNC2=CC=C1)C(C(=O)Cl)=O | [cH:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]12.Cl[C:4]([C:2](=[O:1])[Cl:3])=[O:5]>>[O:1]=[C:2]([Cl:3])[C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]12 | Fc1cccc2[nH]ccc12.O=C(Cl)C(=O)Cl | O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12 | null | null | CCOCC | C-C Coupling | Friedel-Crafts acylation | bc61c2f3c4095d2339fbb0f834e9655112dfadeca9b866efcca6455903db578f | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2[nH]ccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])=[O;D1;H0:5].[c:6]:[c:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[Cl;D1;H0:4]-[C:3](=[O;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c:7](:[c:6]):[c:11]:1:[c:12] | 78 | [{"value": 78.0, "product": "FC1=C2C(=CNC2=CC=C1)C(C(=O)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "FC1=C2C(=CNC2=CC=C1)C(C(=O)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of 4-fluoroindole (2.00 g, 14.8 mmol) in ether (15 mL), at 0° C. under Ar, was added oxalyl chloride (1.55 mL, 17.8 mmol) dropwise. The resulting suspension was stirred at room temperature for 1 h and then it was filtered and the filtercake was washed with ether. The resulting solid was dried in v... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | CCOCC | null | 1 | Fc1cccc2[nH]ccc12.O=C(Cl)C(=O)Cl>CCOCC>O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24fc9d4575e24c72add2703e98910e41 | CC(C)Oc1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O.CNC>>CN(C)c1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O | CNC.FC1=C2C(=CNC2=CC=C1)C(C(=O)N1CCN(CC1)C=1C(C(C1OC(C)C)=O)=O)=O>>FC1=C2C(=CNC2=CC=C1)C(C(=O)N1CCN(CC1)C=1C(C(C1N(C)C)=O)=O)=O | CC(C)O[c:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[C:12](=[O:13])[c:14]3[cH:15][nH:16][c:17]4[cH:18][cH:19][cH:20][c:21]([F:22])[c:23]34)[CH2:24][CH2:25]2)[c:26](=[O:27])[c:28]1=[O:29].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[c:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[C:12](=[O:13])[c:14]3[cH:15][... | CC(C)Oc1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O.CNC | CN(C)c1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by secondary amine | 5cdfe7ea62d2ded02dec5c538b96c37c00d3ce780e4ef5bf43f938759584aae8 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | O=C(C(=O)N1CCN(c2cc(=O)c2=O)CC1)c1c[nH]c2ccccc12 | C-C(-C)-O-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:1-[#7:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[#7:6]-[c:5]1:[c:4]:[c:2](=[O;D1;H0:3]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9] | 99 | [{"value": 99.0, "product": "FC1=C2C(=CNC2=CC=C1)C(C(=O)N1CCN(CC1)C=1C(C(C1N(C)C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a saturated solution of dimethylamine in ethanol (2 mL), cooled at 5° C. under Ar, was added 3-[4-[2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl]piperazin1-yl]-4-isopropoxy-cyclobut-3-ene-1,2-dione (0.020 g, 0.048 mmol) and the mixture was then allowed to stir at room temperature for 2 h. The volatiles were then removed in... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | C1=CC=C1 | C1=CC=C1 | C1=CC=C1.C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | HO- | C(C)O | null | 2 | CC(C)Oc1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O.CNC>C(C)O>CN(C)c1c(N2CCN(C(=O)C(=O)c3c[nH]c4cccc(F)c34)CC2)c(=O)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c85563ae20744998fe7eb3cad8fa76e | COc1cnc(O)c2[nH]ccc12.O=P(Br)(Br)Br>>COc1cnc(Br)c2[nH]ccc12 | OC=1N=CC(=C2C=CNC12)OC.C1(=CC=CC=C1)OC.P(=O)(Br)(Br)Br>>BrC=1N=CC(=C2C=CNC12)OC | O[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[c:12]2[c:8]1[nH:9][cH:10][cH:11]2.O=P(Br)(Br)[Br:7]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Br:7])[c:8]2[nH:9][cH:10][cH:11][c:12]12 | COc1cnc(O)c2[nH]ccc12.O=P(Br)(Br)Br | COc1cnc(Br)c2[nH]ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 41fd6ec7090bce24ee71874a07300f89eea57a34fa0a080938cd56e1f1e58e63 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cc2cc[nH]c2cn1 | Br-P(-Br)(=O)-[Br;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8] | 27.4 | [{"value": 27.0, "product": "BrC=1N=CC(=C2C=CNC12)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.4, "product": "BrC=1N=CC(=C2C=CNC12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | To a flask containing 7-hydroxy-4-methoxy-6-azaindole (0.200 g, 1.22 mmol) was added anisole (3 mL) and then POBr3 (1.57 g, 6.09 mmol). The system was purged with Ar and then it was heated at 160° C. (oil bath temperature) for 1 h. The reaction mixture was then allowed to cool to room temperature, quenched with 2M HBr ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | HBr | null | 160 | null | COc1cnc(O)c2[nH]ccc12.O=P(Br)(Br)Br>>COc1cnc(Br)c2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4c6cf1b3e0f477bacc26e5b6b4800c6 | COC(=O)C(=O)c1c[nH]c2c(Br)ncc(OC)c12>>COc1cnc(Br)c2[nH]cc(C(=O)C(=O)O)c12 | BrC=1N=CC(=C2C(=CNC12)C(C(=O)OC)=O)OC.C(=O)([O-])[O-].[K+].[K+]>>BrC=1N=CC(=C2C(=CNC12)C(C(=O)O)=O)OC | C[O:16][C:14]([C:12]([c:11]1[cH:10][nH:9][c:8]2[c:6]([Br:7])[n:5][cH:4][c:3]([O:2][CH3:1])[c:17]21)=[O:13])=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Br:7])[c:8]2[nH:9][cH:10][c:11]([C:12](=[O:13])[C:14](=[O:15])[OH:16])[c:17]12 | COC(=O)C(=O)c1c[nH]c2c(Br)ncc(OC)c12 | COc1cnc(Br)c2[nH]cc(C(=O)C(=O)O)c12 | null | null | O.CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc2cc[nH]c2cn1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 59.3 | [{"value": 59.0, "product": "BrC=1N=CC(=C2C(=CNC12)C(C(=O)O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "BrC=1N=CC(=C2C(=CNC12)C(C(=O)O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate (0.083 g, 0.265 mmol) in MeOH—H2O (3:1, 3 mL) was added 1M aqueous K2CO3 (1.1 mL, 1.1 mmol). The mixture was stirred at room temperature for 14 h and then it was diluted with H2O (2 mL). The volatiles were removed under reduced pressure and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2cc[nH]c2cn1 | Other | O.CO.O | null | 14 | COC(=O)C(=O)c1c[nH]c2c(Br)ncc(OC)c12>O.CO.O>COc1cnc(Br)c2[nH]cc(C(=O)C(=O)O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a802b3ca9524f2a8f42c6e306d1dcbd | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccn1.COc1cnc(Br)c2[nH]cc(C(=O)C(=O)N3CCN(c4c(-c5ccccc5)c(=O)c4=O)CC3)c12>>COc1cnc(-c2cnccn2)c2[nH]cc(C(=O)C(=O)N3CCN(c4c(-c5ccccc5)c(=O)c4=O)CC3)c12 | BrC=1N=CC(=C2C(=CNC12)C(C(=O)N1CCN(CC1)C=1C(C(C1C1=CC=CC=C1)=O)=O)=O)OC.C(CCC)[Sn](C1=NC=CN=C1)(CCCC)CCCC>>N1=C(C=NC=C1)C=1N=CC(=C2C(=CNC12)C(C(=O)N1CCN(CC1)C=1C(C(C1C1=CC=CC=C1)=O)=O)=O)OC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:7]1[cH:8][n:9][cH:10][cH:11][n:12]1.Br[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[c:39]2[c:13]1[nH:14][cH:15][c:16]2[C:17](=[O:18])[C:19](=[O:20])[N:21]1[CH2:22][CH2:23][N:24]([c:25]2[c:26](-[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[c:33](=[O:34])[c:35]2=[O:36])[CH2:37][CH2:38]1>>[CH3:1][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccn1.COc1cnc(Br)c2[nH]cc(C(=O)C(=O)N3CCN(c4c(-c5ccccc5)c(=O)c4=O)CC3)c12 | COc1cnc(-c2cnccn2)c2[nH]cc(C(=O)C(=O)N3CCN(c4c(-c5ccccc5)c(=O)c4=O)CC3)c12 | 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 | O1CCOCC1.CCOC(=O)C | C-C Coupling | Stille reaction_aryl | df3ce359ef1fcd56719a5a51db9f4372e4c005194f1fe10ad92263b439434db9 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C(C(=O)N1CCN(c2c(-c3ccccc3)c(=O)c2=O)CC1)c1c[nH]c2c(-c3cnccn3)nccc12 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1>>[c:7]:[#7;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1):[#7;a:2]:[c:3] | 7 | [{"value": 7.0, "product": "N1=C(C=NC=C1)C=1N=CC(=C2C(=CNC12)C(C(=O)N1CCN(CC1)C=1C(C(C1C1=CC=CC=C1)=O)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.7, "product": "N1=C(C=NC=C1)C=1N=CC(=C2C(=CNC12)C(C(=O)N1CCN(CC1)C=1C(C(C1C1=CC=CC=C1)=O)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 90 | CELSIUS | null | null | A solution of 3-[4-[2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetyl]piperazin-1-yl]-4-phenyl-cyclobut-3-ene-1,2-dione (0.030 g, 0.057 mmol) and 2-tributylstannylpyrazine (0.025 g, 0.069 mmol) in dioxane (3 mL) was purged with Ar and then Pd(PPh3)4 (0.020 g, 0.017 mmol) was added, the reactor was sealed and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cnccn1.c1cc2cc[nH]c2cn1 | c1cnccn1.c1cc2cc[nH]c2cn1 | c1cnccn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1.C1=CC=C1 | 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.O1CCOCC1.CCOC(=O)C | 90 | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccn1.COc1cnc(Br)c2[nH]cc(C(=O)C(=O)N3CCN(c4c(-c5ccccc5)c(=O)c4=O)CC3)c12>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.O1CCOCC1.CCOC(=O)C>COc1cnc(-c2cnccn2)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67bc241e82b741dfbd05c329de930cf6 | COc1cnc(Cl)c2[nH]ccc12.c1nc[nH]n1>>COc1cnc(-n2cncn2)c2[nH]ccc12 | ClC=1N=CC(=C2C=CNC12)OC.N1N=CN=C1.[OH-].[K+]>>COC1=C2C=CNC2=C(N=C1)N1N=CN=C1 | Cl[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[c:16]2[c:12]1[nH:13][cH:14][cH:15]2.[nH:7]1[cH:8][n:9][cH:10][n:11]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[n:7]2[cH:8][n:9][cH:10][n:11]2)[c:12]2[nH:13][cH:14][cH:15][c:16]12 | COc1cnc(Cl)c2[nH]ccc12.c1nc[nH]n1 | COc1cnc(-n2cncn2)c2[nH]ccc12 | null | [Cu] | CO | Heteroatom Alkylation and Arylation | OtherReaction | bc1f300bbe9c7ae93a5c6ff6b34386ab7684995eb1e247adc6f74ede48e73ab2 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cc2cc[nH]c2c(-n2cncn2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[nH;D2;+0:12]:1>>[c:7]:[#7;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[n;H0;D3;+0:12]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1):[#7;a:2]:[c:3] | 58 | [{"value": 58.0, "product": "COC1=C2C=CNC2=C(N=C1)N1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "COC1=C2C=CNC2=C(N=C1)N1N=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A mixture of 7-chloro-4-methoxy-6-azaindole (1.029 g, 5.62 mmol), 1,2,4-triazole (11.6 g, 30 equiv), copper bronze (0.72 g, 11.2 mgatom) and finely pulverized KOH (0.63 g, 11.2 mmol) was heated in a sealed tube at 160° C. (oil bath temperature) for 18 h. The cooled mixture was taken up in MeOH and the resulting slurry ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc2cc[nH]c2cn1.c1nc[nH]n1 | c1nc[nH]n1.c1cc2cc[nH]c2cn1 | c1nc[nH]n1.c1cc2cc[nH]c2cn1 | HCl | [Cu].CO | 160 | null | COc1cnc(Cl)c2[nH]ccc12.c1nc[nH]n1>[Cu].CO>COc1cnc(-n2cncn2)c2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76e2c5df80054f8cb169491b502ba6d8 | CC(=O)[O-].CCOC(C)=O.COc1cnc(-n2cncn2)c2[nH]ccc12>>COC(=O)C(=O)c1c[nH]c2c(-n3cncn3)ncc(OC)c12 | [Al+3].[Cl-].[Cl-].[Cl-].COC1=C2C=CNC2=C(N=C1)N1N=CN=C1.C(C)(=O)[O-].[NH4+].CCOC(=O)C>>COC(C(=O)C1=CNC2=C(N=CC(=C12)OC)N1N=CN=C1)=O | [O-:2][C:3](=[O:4])[CH3:5].CCOC([CH3:1])=[O:6].[cH:7]1[cH:8][nH:9][c:10]2[c:11](-[n:12]3[cH:13][n:14][cH:15][n:16]3)[n:17][cH:18][c:19]([O:20][CH3:21])[c:22]12>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][nH:9][c:10]2[c:11](-[n:12]3[cH:13][n:14][cH:15][n:16]3)[n:17][cH:18][c:19]([O:20][CH3:21])[c:22]12 | CC(=O)[O-].CCOC(C)=O.COc1cnc(-n2cncn2)c2[nH]ccc12 | COC(=O)C(=O)c1c[nH]c2c(-n3cncn3)ncc(OC)c12 | null | null | C(Cl)Cl.C[N+](=O)[O-] | C-C Coupling | OtherReaction | 864419f71ecea5e7b7db9cf3cdd250f407bbf3a11ceb0de604aae827aa9baf4f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1cc2cc[nH]c2c(-n2cncn2)n1 | C-C-O-C(-[CH3;D1;+0:1])=[O;H0;D1;+0:2].[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:2:[c:10]:[c:11]:1.[CH3;D1;+0:12]-[C:13](-[O-;H0;D1:14])=[O;D1;H0:15]>>[CH3;D1;+0:1]-[O;H0;D2;+0:14]-[C:13](=[O;D1;H0:15])-[C;H0;D3;+0:12](=[O;H0;D1;+0:2])-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5]2:[c:4]:[#7;a:3]:[c:11]:[c:10]:[c... | 46 | [{"value": 46.0, "product": "COC(C(=O)C1=CNC2=C(N=CC(=C12)OC)N1N=CN=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a mixture of AlCl3 (0.665 g, 5.0 mmol) in 4 mL of CH2Cl2-MeNO2 (4:1) was added 4-methoxy-7-(1,2,4-triazol-1-yl)-6-azaindole (0.108 g, 0.50 mmol) as a solid. To the resulting solution was added methyl oxalyl chloride (0.185 mL, 2.0 mmol) dropwise and then the mixture was stirred at room temperature for 16 h. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Ester | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | c1nc[nH]n1.c1cc2cc[nH]c2cn1 | HO- | C(Cl)Cl.C[N+](=O)[O-] | null | 16 | CC(=O)[O-].CCOC(C)=O.COc1cnc(-n2cncn2)c2[nH]ccc12>C(Cl)Cl.C[N+](=O)[O-]>COC(=O)C(=O)c1c[nH]c2c(-n3cncn3)ncc(OC)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9365148b5e944b79005cd3dbb68b919 | NC1CC1.O=C(Cl)c1ccc(CCl)cc1>>O=C(NC1CC1)c1ccc(CCl)cc1 | C(C)(=O)OCC.ClCC1=CC=C(C(=O)Cl)C=C1.C1(CC1)N.CCN(C(C)C)C(C)C>>ClCC1=CC=C(C(=O)NC2CC2)C=C1 | [NH2:3][CH:4]1[CH2:5][CH2:6]1.Cl[C:2](=[O:1])[c:7]1[cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13][cH:14]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13][cH:14]1 | NC1CC1.O=C(Cl)c1ccc(CCl)cc1 | O=C(NC1CC1)c1ccc(CCl)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NC1CC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]1-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4-Chloromethyl-benzoyl chloride (2.82 g, 15 mmol) and cyclopropylamine (1.26 ml, 18 mmol) were reacted in CH2Cl2 (30 ml) and in the presence of Hünig's base (3.1 ml, 18 mmol) for 1 h. A precipitate was formed which was resolubilized by adding ethyl acetate. The reaction mixture was washed with a 5% KHSO4/10% K2SO4 solu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC1.c1ccccc1 | HCl | C(Cl)Cl | null | null | NC1CC1.O=C(Cl)c1ccc(CCl)cc1>C(Cl)Cl>O=C(NC1CC1)c1ccc(CCl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7c652ff3ffd4450bec666a767506163 | COC(=O)c1ccc(OC)nc1>>COc1ccc(CO)cn1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=NC=C(C(=O)OC)C=C1>>COC1=CC=C(C=N1)CO | CO[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:10][cH:9]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][n:10]1 | COC(=O)c1ccc(OC)nc1 | COc1ccc(CO)cn1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | 2 | HOUR | To lithium aluminium hydride (0.68 g, 18 mmol) suspended in dry THF (10 ml) was added dropwise a solution of methyl 6-methoxynicotinate (1 g, 6 mmol) in dry THF (5 ml). The reaction mixture was stirred for 2 h at r.t. then cooled (ice-bath) and quenched with water (2 ml) followed by the further addition of 1 N NaOH (6 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 2 | COC(=O)c1ccc(OC)nc1>C1CCOC1>COc1ccc(CO)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c66eddc371c43c7a53c3ee05b304da1 | C=CCC(NC(=O)OC(C)(C)C)C(=O)O.C=CCNCc1ccc(OC)cc1OC>>C=CC[C@@H](NC(=O)OC(C)(C)C)C(=O)N(CC=C)Cc1ccc(OC)cc1OC | CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CC(C)(C)OC(=O)NC(CC=C)C(=O)O.C1CCC(CC1)NC2CCCCC2.C(C=C)NCC1=C(C=C(C=C1)OC)OC>>C(C)(C)(C)OC(N[C@H](CC=C)C(N(CC1=C(C=C(C=C1)OC)OC)CC=C)=O)=O | O[C:13]([CH:4]([CH2:3][CH:2]=[CH2:1])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:14].[NH:15]([CH2:16][CH:17]=[CH2:18])[CH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][c:27]1[O:28][CH3:29]>>[CH2:1]=[CH:2][CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])... | C=CCC(NC(=O)OC(C)(C)C)C(=O)O.C=CCNCc1ccc(OC)cc1OC | C=CC[C@@H](NC(=O)OC(C)(C)C)C(=O)N(CC=C)Cc1ccc(OC)cc1OC | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[#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]=[C;D1;H2:14].[C;D1;H2:15]=[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[c:20]>>[C;D1;H2:15]=[C:16]-[C:17]-[N;H0;D3;+0:18](-[C:19]-[c:20])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@H;D3;+0:3](-[#7:4]... | null | [] | null | null | 8 | HOUR | (R)-N-Boc-allylglycine (2.3 g, 9.9 mmol) was dissolved in dimethylformamide (20 ml) and activated with the coupling reagent TATU (3.5 g, 10.9 mmol) and Hünig's base (3.8 ml, 21.9 mmol) for 2 min. Allyl-(2,4-dimethoxy-benzyl)-amine (2.1 g, 9.9 mmol) dissolved in dimethylformamide (20 ml) was added to the chilled (ice-wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | null | 8 | C=CCC(NC(=O)OC(C)(C)C)C(=O)O.C=CCNCc1ccc(OC)cc1OC>CN(C=O)C>C=CC[C@@H](NC(=O)OC(C)(C)C)C(=O)N(CC=C)Cc1ccc(OC)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dcedabcac5534c418b6e92f382b85b8e | COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1>>COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1 | C(C)(C)(C)OC(N[C@H]1C(N(CC(CC1)=O)CC1=C(C=C(C=C1)OC)OC)=O)=O.C(C)(C)(C)OC(N[C@H]1C(N(CCC(C1)=O)CC1=C(C=C(C=C1)OC)OC)=O)=O.C(C)(C)(C)OC(N[C@H]1C(N(CC=CC1)CC1=C(C=C(C=C1)OC)OC)=O)=O>>C(C)(C)(C)OC(N[C@H]1C(N(CCC(C1)=O)CC1=C(C=C(C=C1)OC)OC)=O)=O.C(C)(C)(C)OC(N[C@H]1C(N(CC(CC1)=O)CC1=C(C=C(C=C1)OC)OC)=O)=O | [CH3:29][O:30][c:31]1[cH:32][cH:33][c:34]([CH2:35][N:36]2[CH2:37][CH2:38][C:39](=[O:40])[CH2:41][C@@H:42]([NH:43][C:44](=[O:45])[O:46][C:47]([CH3:48])([CH3:49])[CH3:50])[C:51]2=[O:52])[c:53]([O:54][CH3:55])[cH:56]1>>[CH3:29][O:30][c:31]1[cH:32][cH:33][c:34]([CH2:35][N:36]2[CH2:37][CH2:38][C:39](=[O:40])[CH2:41][C@@H:42... | COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1 | COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1 | null | null | O.CN(C)C=O.O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCC(=O)N(Cc2ccccc2)CC1 | null | null | [] | 50 | CELSIUS | null | null | [(R)-1-(2,4-Dimethoxy-benzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]-carbamic acid tert-butyl ester (5.4 g, 14.3 mmol) was dissolved in DMF/water (10:1 v/v) and then Pd(II)Cl2 (1 g, 5.7 mmol) and Cu(I)Cl (7.2 g, 72.4 mmol) were added. The reaction mixture was evacuated and saturated with O2 and then heated at 50° C. ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CCC[NH]CC1 | null | O.CN(C)C=O.O | 50 | null | COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1>O.CN(C)C=O.O>COc1ccc(CN2CCC(=O)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3bb5e9cfc8546aeb6a1f6aa91b6e90b | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cc3)C2=O)c(OC)c1>>O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | FC(C(=O)O)(F)F.FC(S(=O)(=O)O)(F)F.ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(N(CCC(C1)(F)F)CC1=C(C=C(C=C1)OC)OC)=O>>ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O | COc1ccc(C[N:3]2[C:2](=[O:1])[C@H:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[CH2:9][C:6]([F:7])([F:8])[CH2:5][CH2:4]2)c(OC)c1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cc3)C2=O)c(OC)c1 | O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of tertiary amines | 79b08332c5c21e9adef36d66611fe6b82c22e57d08f56bf4970d6f853fe1c8ec | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1NCCCC[C@H]1NS(=O)(=O)c1ccccc1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]):c(-O-C):c:1>>[C:6]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A cocktail containing 40% trifluoroacetic acid, 1% trifluoromethanesulfonic acid in CH2Cl2 (20 ml) was added to 4-chloro-N-[(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-benzenesulfonamide (0.5 g, 1.0 mmol). After 30 min the reaction mixture was concentrated and the residue was dissolved in ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cc3)C2=O)c(OC)c1>C(Cl)Cl>O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab4db7aaf0e0490e9940c0a17b51a6fc | BrCc1ccc(-c2ccno2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(-c2ccno2)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.BrCC1=CC=C(C=C1)C1=CC=NO1>>ClC1=CC=C(C=C1)S(=O)(=O)N(CC1=CC=C(C=C1)C1=CC=NO1)[C@H]1C(NCCC(C1)(F)F)=O | Br[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][n:20][o:21]2)[cH:22][cH:23]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:... | BrCc1ccc(-c2ccno2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(-c2ccno2)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccc(-c2ccno2)cc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15]>>[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 5-(4-bromomethyl-phenyl)-isoxazole analogous to Example 1 to afford 4-chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-N-(4-isoxazol-5-yl-benzyl)-benzenesulfonamide: MS: m/e=496.0 (MH+), 513.2 (MNH4+).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCNCC1.c1ccccc1.c1cnoc1.c1ccccc1 | HBr | null | null | null | BrCc1ccc(-c2ccno2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(-c2ccno2)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-444b98a42e1f4af097dffdb2308daee7 | COc1ccc(CBr)c(F)c1F.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1F | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.BrCC1=C(C(=C(C=C1)OC)F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C(=C(C=C1)OC)F)F | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([F:32])[c:29]1[F:30].[NH:8]([C@@H:9]1[CH2:10][C:11]([F:12])([F:13])[CH2:14][CH2:15][NH:16][C:17]1=[O:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][C:11]([F:12])([F:1... | COc1ccc(CBr)c(F)c1F.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1F | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 1-bromomethyl-2,3-difluoro-4-methoxy-benzene analogous to Example 1 to afford 4-chloro-N-(2,3-difluoro-4-methoxy-benzyl)-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | HBr | null | null | null | COc1ccc(CBr)c(F)c1F.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9479442081a4abe8b88415a5b1ed629 | COc1ccc(CO)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.FC1=C(C=CC(=C1)OC)CO>>ClC1=CC=C(C=C1)S(=O)(=O)N(CC1=C(C=C(C=C1)OC)F)[C@H]1C(NCCC(C1)(F)F)=O | O[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:29]1[F:30].[NH:8]([C@@H:9]1[CH2:10][C:11]([F:12])([F:13])[CH2:14][CH2:15][NH:16][C:17]1=[O:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][C:11]([F:12])([F:13])[CH2:... | COc1ccc(CO)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu_sulfonamide | 0bda68210bc1a4edc8064b140a39ccb3ef813b89c5267469bd545dded6906cd4 | 2497efd1dadfa61592e966deb414dc4463866875b7ffd693ba98c7592e2a7ec2 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was reacted with (2-fluoro-4-methoxy-phenyl)-methanol analogous to Example 3a to afford 4-chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-N-(2-fluoro-4-methoxy-benzyl)-benzenesulfonamide:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | HO- | null | null | null | COc1ccc(CO)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58e77ba3623241b6b11cddc9118496ca | COC(=O)c1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.COC(C1=CC(=C(C=C1)CBr)F)=O>>COC(C1=CC(=C(C=C1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl)F)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:33][c:31]1[F:32].[NH:10]([C@@H:11]1[CH2:12][C:13]([F:14])([F:15])[CH2:16][CH2:17][NH:18][C:19]1=[O:20])[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH2... | COC(=O)c1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 4-bromomethyl-3-fluoro-benzoic acid methyl ester analogous to Example 1 to afford 4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester: MS: m/e=504.9 (MH+), 522.1(MNH4+... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | HBr | null | null | null | COC(=O)c1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c961f12561c042328103a558b7a58f69 | COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>>O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | COC(C1=CC(=C(C=C1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl)F)=O.[OH-].[Na+]>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C=C(C(=O)O)C=C1)F | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([C@@H:10]2[CH2:11][C:12]([F:13])([F:14])[CH2:15][CH2:16][NH:17][C:18]2=[O:19])[S:20](=[O:21])(=[O:22])[c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[c:30]([F:31])[cH:32]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([C@@H:10]2[CH2:11][C:12]([F:13... | COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | null | null | C1CCOC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester (130 mg, 0.26 mmol) was dissolved in THF/MeOH (5 ml) and treated with 1 N NaOH (1.2 ml) for 1.5 h. The reaction mixture was concentrated under reduced pressure diluted using water and extracted with die... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | Other | C1CCOC1.CO | null | null | COC(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>C1CCOC1.CO>O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-903a00b6940a4f14a328e8c3828555f4 | NN1CCCC1.O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>>O=C(NN1CCCC1)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O.CCN(C(C)C)C(C)C.ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C=C(C(=O)O)C=C1)F.Cl.NN1CCCC1.CCN(C(C)C)C(C)C>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C=C(C(=O)NN2CCCC2)C=C1)F | [NH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1.O[C:2](=[O:1])[c:9]1[cH:10][cH:11][c:12]([CH2:13][N:14]([C@@H:15]2[CH2:16][C:17]([F:18])([F:19])[CH2:20][CH2:21][NH:22][C:23]2=[O:24])[S:25](=[O:26])(=[O:27])[c:28]2[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]2)[c:35]([F:36])[cH:37]1>>[O:1]=[C:2]([NH:3][N:4]1[CH2:5][CH2:6][CH2:... | NN1CCCC1.O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | O=C(NN1CCCC1)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | O=C(NN1CCCC1)c1ccc(CN([C@@H]2CCCCNC2=O)S(=O)(=O)c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[#7:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | null | [] | null | null | null | null | 4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid (50 mg, 0.10 mmol) was dissolved in DMF (1 ml) and activated with the coupling reagent TPTU (33 mg, 0.11 mmol) and Hünig's base (0.03 ml, 0.26 mmol) for 2 min. 1-Aminopyrrolidine hydrochloride (0.013 g, 0.22 mmol) a... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | C1CC[NH]C1.c1ccccc1.C1CCCNCC1.c1ccccc1 | HO- | CN(C)C=O | null | null | NN1CCCC1.O=C(O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>CN(C)C=O>O=C(NN1CCCC1)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9f36f134803413dbdbdf24989ec456e | CS(=O)(=O)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CS(=O)(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.CS(=O)(=O)C1=CC=C(CBr)C=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N(CC1=CC=C(C=C1)S(=O)(=O)C)[C@H]1C(NCCC(C1)(F)F)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:32][cH:31]1.[NH:10]([C@@H:11]1[CH2:12][C:13]([F:14])([F:15])[CH2:16][CH2:17][NH:18][C:19]1=[O:20])[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH... | CS(=O)(=O)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | CS(=O)(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 4-methylsulphonylbenzyl bromide analogous to Example 1 to afford 4-chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-N-(4-methanesulfonylbenzyl)-benzenesulfonamide: MS: m/e=507.2 (MH+), 524.1(MNH4+).
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | HBr | null | null | null | CS(=O)(=O)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CS(=O)(=O)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1de4c1a5b9304387a449bb70004cc337 | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.FC(OC1=CC=C(CBr)C=C1)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=CC=C(C=C1)OC(F)F | Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:12][c:13... | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15]>>[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 4-(difluoromethoxy)benzyl bromide analogous to Example 1 to afford 4-chloro-N-(4-difluoromethoxy-benzyl)-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCNCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5aa9f9ae3284910bd874e669028f008 | FC(F)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(C(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.BrCC1=CC=C(C=C1)C(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=CC=C(C=C1)C(F)F | Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([CH:17]([F:18])[F:19])[cH:20][cH:21]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:12][c:13]1[cH:... | FC(F)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(C(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15]>>[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 1-bromomethyl-4-difluoromethyl-benzene analogous to Example 1 to afford 4-chloro-N-(4-difluoromethyl-benzyl)-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCNCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)c1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(C(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9ec1de09acc45cbb7a8c4c2532e7033 | Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.C(C)(C)(C)OC(=O)N1CCC(CC1)COS(=O)(=O)C1=CC=C(C=C1)C>>C(C)(C)(C)OC(=O)N1CCC(CC1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl | Cc1ccc(S(=O)(=O)O[CH2:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:35][CH2:34]2)cc1.[NH:13]([C@@H:14]1[CH2:15][C:16]([F:17])([F:18])[CH2:19][CH2:20][NH:21][C:22]1=[O:23])[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O... | Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e744aaec43d4cae0f62ffc033588ec8c1162aa614027d68ba7b84bcec4663fb | 67298390bbcc11d70c41987c4ac06c2607123196b8179aab003bf84a312a9881 | O=C1NCCCC[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:6](-[C:5])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:4] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester analogous to Example 1 to afford 4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Tosylate | Tertiary amine | c1ccccc1 | null | C1CC[NH]CC1.C1CCCNCC1.c1ccccc1 | TsOH.HO- | null | null | null | Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98f4c402d5914ae9b2c415fb2d1d732c | CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1>>O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1 | C(C)(C)(C)OC(=O)N1CCC(CC1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N(CC1CCNCC1)[C@H]1C(NCCC(C1)(F)F)=O | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][N:11]([C@H:10]2[C:2](=[O:1])[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9]2)[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:18][CH2:17]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:12][CH:13]1[CH2:... | CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1 | O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1NCCCC[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 94 | [{"value": 94.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N(CC1CCNCC1)[C@H]1C(NCCC(C1)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N(CC1CCNCC1)[C@H]1C(NCCC(C1)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (0.105 g, 0.2 mmol) was dissolved in a mixture of trifluoroacetic acid and dichloromethane (1:1) and stirred overnight. After extraction with aqueous sodium bicarbonate solution the organic l... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCCNCC1.C1CCNCC1.c1ccccc1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 8 | CC(C)(C)OC(=O)N1CCC(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)CC1>ClCCl.FC(C(=O)O)(F)F>O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9fca5523fdbe41458e37906910fc45ca | O=C(Cl)c1ccccc1.O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1>>O=C1NCCC(F)(F)C[C@H]1N(CC1CCN(C(=O)c2ccccc2)CC1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N(CC1CCNCC1)[C@H]1C(NCCC(C1)(F)F)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)N1CCC(CC1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1C(NCCC(C1)(F)F)=O | Cl[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:25][CH2:26]1)[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])... | O=C(Cl)c1ccccc1.O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1 | O=C1NCCC(F)(F)C[C@H]1N(CC1CCN(C(=O)c2ccccc2)CC1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1NCCCC[C@H]1N(CC1CCN(C(=O)c2ccccc2)CC1)S(=O)(=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | 59.7 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1C(NCCC(C1)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1C(NCCC(C1)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 8 | HOUR | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-N-piperidin-4-ylmethyl-benzenesulfonamide (0.04 g, 0.09 mmol) and triethylamine (19 mg, 0.18 mmol) were dissolved in dichloromethane (1.5 ml). Then benzoyl chloride (0.018 g, 0.13 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CCCNCC1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 8 | O=C(Cl)c1ccccc1.O=C1NCCC(F)(F)C[C@H]1N(CC1CCNCC1)S(=O)(=O)c1ccc(Cl)cc1>ClCCl>O=C1NCCC(F)(F)C[C@H]1N(CC1CCN(C(=O)c2ccccc2)CC1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37aa036b7fcb4f0ab3d34ba3b30cc187 | N#Cc1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1C(NCCC(C1)(F)F)=O.BrCC1=C(C=C(C#N)C=C1)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C=C(C=C1)C#N)F | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:31][c:29]1[F:30].[NH:8]([C@@H:9]1[CH2:10][C:11]([F:12])([F:13])[CH2:14][CH2:15][NH:16][C:17]1=[O:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][C:11]([F:12])([F:13])[CH2:1... | N#Cc1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15] | null | [] | null | null | null | null | 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 4-bromomethyl-3-fluoro-benzonitrile analogous to Example 1 to afford 4-chloro-N-(4-cyano-2-fluoro-benzyl)-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide:MS: m/e=472.2 (MH+).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(CBr)c(F)c1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c2fa5f091a84e0c9ee9814151a9b65d | CCO.N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>>CCOC(=N)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1.Cl | ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=C(C=C(C=C1)C#N)F.C(C)O>>Cl.C(C)OC(C1=CC(=C(C=C1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl)F)=N | [CH3:1][CH2:2][OH:3].[C:4](#[N:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([C@@H:12]2[CH2:13][C:14]([F:15])([F:16])[CH2:17][CH2:18][NH:19][C:20]2=[O:21])[S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[c:32]([F:33])[cH:34]1>>[CH3:1][CH2:2][O:3][C:4](=[NH:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N:1... | CCO.N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1 | CCOC(=N)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1.Cl | null | null | null | Acylation | OtherReaction | e564e96d7d2f965b49edf364feccacb527e51024ce8a97adfccc27d77cbffea1 | 515b5097d48e8822f99e612a636ab28d5c6d3dcc515412839570278fb17e2efd | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | [C;D1;H3:1]-[C:2]-[OH;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[NH;D1;+0:4])-[c:6](:[c:7]):[c:8] | null | [] | 0 | CELSIUS | 20 | HOUR | 4-Chloro-N-(4-cyano-2-fluoro-benzyl)-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide (0.23 g, 0.49 mmol) was suspended in dry ethanol (10 ml) and cooled to 0° C. Dry HCl gas was gently bubbled over 30 min into this suspension. The light red reaction mixture was stirred at room temperature for 20 h. A clear ye... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Ether | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | Other | null | 0 | 20 | CCO.N#Cc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1>>CCOC(=N)c1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)c(F)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f2e800efc1d45beb78286d4b4663b8b | COC(=O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1>>O=C(O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | Cl.[Li+].[OH-].O.COC(CCC1=CC=C(C=C1)CN([C@H]1C(NCCC(C1)(F)F)=O)S(=O)(=O)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1C(NCCC(C1)(F)F)=O)CC1=CC=C(C=C1)CCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([C@@H:12]2[CH2:13][C:14]([F:15])([F:16])[CH2:17][CH2:18][NH:19][C:20]2=[O:21])[S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[cH:32][cH:33]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([C@@H... | COC(=O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | O=C(O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | CO.C(C)(=O)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | 3-(4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-propionic acid methyl ester (65 mg, 0.13 mmol) was dissolved in methanol (0.5 ml) and treated with 2 N LiOH in water (0.25 ml, 0.5 mmol) overnight at 40° C. The reaction mixture was distributed between 4 N HCl and ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CCCNCC1.c1ccccc1 | Other | CO.C(C)(=O)OCC | null | null | COC(=O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1>CO.C(C)(=O)OCC>O=C(O)CCc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdb5fc0982a645b89c3170eee4de6216 | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)CCC(F)(F)F>>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 | FC(CCS(=O)(=O)Cl)(F)F.C(C)(C)(C)OC(N[C@H]1C(N(CCC(C1)(F)F)CC1=C(C=C(C=C1)OC)OC)=O)=O.Cl.O1CCOCC1.CCN(C(C)C)C(C)C>>COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)CCC(F)(F)F)=O)C=CC(=C1)OC | CC(C)(C)OC(=O)[NH:16][C@@H:15]1[CH2:14][C:11]([F:12])([F:13])[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:28]2[O:29][CH3:30])[C:26]1=[O:27].Cl[S:17](=[O:18])(=[O:19])[CH2:20][CH2:21][C:22]([F:23])([F:24])[F:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]([F:12])... | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)CCC(F)(F)F | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 | null | null | ClCCl.C(Cl)Cl | Acylation | OtherReaction | e5e0353ed7860f5f3e39514139f051e4d6492a60eb2b5be38d0840e87639dc1b | cf59b7e4d6547a1ecb903c2113fc2917df8195614c8f97dab060eab217c2f6c5 | O=C1CCCCCN1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8].Cl-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[C:12]-[C:13]>>[C:3]-[C:2](-[NH;D2;+0:1]-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[C:12]-[C:13])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8] | null | [] | null | null | null | null | [(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.85 g, 1.85 mmol) was dissolved in 38 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Sulfonamide | null | null | c1ccccc1.C1CCC[NH]CC1 | HCl | ClCCl.C(Cl)Cl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)CCC(F)(F)F>ClCCl.C(Cl)Cl>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e703a008be9493abeef0a61165c3243 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1.COc1ccc(CO)cn1>>COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 | COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)CCC(F)(F)F)=O)C=CC(=C1)OC.COC1=CC=C(C=N1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>COC1=C(CN2C([C@@H](CC(CC2)(F)F)N(S(=O)(=O)CCC(F)(F)F)CC=2C=NC(=CC2)OC)=O)C=CC(=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]([F:12])([F:13])[CH2:14][C@@H:15]([NH:16][S:26](=[O:27])(=[O:28])[CH2:29][CH2:30][C:31]([F:32])([F:33])[F:34])[C:35]2=[O:36])[c:37]([O:38][CH3:39])[cH:40]1.O[CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[n:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c... | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1.COc1ccc(CO)cn1 | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu_sulfonamide | 0bda68210bc1a4edc8064b140a39ccb3ef813b89c5267469bd545dded6906cd4 | 2497efd1dadfa61592e966deb414dc4463866875b7ffd693ba98c7592e2a7ec2 | O=C1[C@H](NCc2cccnc2)CCCCN1Cc1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[C:8](-[NH;D2;+0:9]-[#16:10](-[C:11])(=[O;D1;H0:12])=[O;D1;H0:13])-[C:14](=[O;D1;H0:15])-[#7:16](-[C:17])-[C:18]>>[C:7]-[C:8](-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[#16:10](-[C:11])(=[O;D1;H0:12])=[O;D1;H0:13])-[C:14](=[O;D1;H0:15])-[... | null | [] | null | null | 1 | HOUR | 3,3,3-Trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide (0.15 g, 0.31 mmol), (6-methoxy-pyridin-3-yl)-methanol (0.06 g, 0.38 mmol), triphenyl phosphine (0.17 g, 0.62 mmol) were dissolved in dry THF (15 ml) at 0-5° C. (ice-water bath) under an argon atmosphere followed... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | c1ccccc1.C1CCC[NH]CC1.c1ccncc1 | HO- | C1CCOC1 | null | 1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1.COc1ccc(CO)cn1>C1CCOC1>COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82a6a5a1bb6445d28ca1c7d6942feb56 | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)CCC(F)(F)F)cn1 | FC(C(=O)O)(F)F.FC(S(=O)(=O)O)(F)F.COC1=C(CN2C([C@@H](CC(CC2)(F)F)N(S(=O)(=O)CCC(F)(F)F)CC=2C=NC(=CC2)OC)=O)C=CC(=C1)OC>>FC1(C[C@H](C(NCC1)=O)N(S(=O)(=O)CCC(F)(F)F)CC=1C=NC(=CC1)OC)F | COc1ccc(C[N:16]2[CH2:15][CH2:14][C:11]([F:12])([F:13])[CH2:10][C@@H:9]([N:8]([CH2:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[n:29][cH:28]3)[S:19](=[O:20])(=[O:21])[CH2:22][CH2:23][C:24]([F:25])([F:26])[F:27])[C:17]2=[O:18])c(OC)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][C:11]([F:12])([F:13])[CH... | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1 | COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)CCC(F)(F)F)cn1 | null | null | ClCCl | Reduction | Hydrogenolysis of tertiary amines | 79b08332c5c21e9adef36d66611fe6b82c22e57d08f56bf4970d6f853fe1c8ec | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1NCCCC[C@H]1NCc1cccnc1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]):c(-O-C):c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 0.76 ml) was added to 3,3,3-trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide (0.2 g, 0.24 mmol) in dichloromethane (10 ml). After 2 h the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | c1ccncc1.C1CCCNCC1 | HO- | ClCCl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)CCC(F)(F)F)C2=O)c(OC)c1>ClCCl>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)CCC(F)(F)F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ee4173d9ead4250a3904aea770d4184 | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)s1>>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 | ClC1=CC=C(S1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@H]1C(N(CCC(C1)(F)F)CC1=C(C=C(C=C1)OC)OC)=O)=O.Cl.O1CCOCC1.CCN(C(C)C)C(C)C>>COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)C=2SC(=CC2)Cl)=O)C=CC(=C1)OC | CC(C)(C)OC(=O)[NH:16][C@@H:15]1[CH2:14][C:11]([F:12])([F:13])[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:28]2[O:29][CH3:30])[C:26]1=[O:27].Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[s:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]([F:12])(... | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)s1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 | null | null | ClCCl.C(Cl)Cl | Acylation | OtherReaction | e5e0353ed7860f5f3e39514139f051e4d6492a60eb2b5be38d0840e87639dc1b | cf59b7e4d6547a1ecb903c2113fc2917df8195614c8f97dab060eab217c2f6c5 | O=C1[C@H](NS(=O)(=O)c2cccs2)CCCCN1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8].Cl-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12](:[c:13]):[#16;a:14]:[c:15]>>[C:3]-[C:2](-[NH;D2;+0:1]-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12](:[c:13]):[#16;a:14]:[c:15])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8] | null | [] | null | null | null | null | [(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.85 g, 1.85 mmol) was dissolved in 38 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Sulfonamide | null | null | c1ccccc1.C1CCC[NH]CC1.c1ccsc1 | HCl | ClCCl.C(Cl)Cl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)s1>ClCCl.C(Cl)Cl>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23f47b7a2fdc4ab9b979f6540c9278d9 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1.COc1ccc(CO)cn1>>COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 | COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)C=2SC(=CC2)Cl)=O)C=CC(=C1)OC.COC1=CC=C(C=N1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>COC1=C(CN2C([C@@H](CC(CC2)(F)F)N(S(=O)(=O)C=2SC(=CC2)Cl)CC=2C=NC(=CC2)OC)=O)C=CC(=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]([F:12])([F:13])[CH2:14][C@@H:15]([NH:16][S:26](=[O:27])(=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[s:34]3)[C:35]2=[O:36])[c:37]([O:38][CH3:39])[cH:40]1.O[CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[n:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1.COc1ccc(CO)cn1 | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu_sulfonamide | 0bda68210bc1a4edc8064b140a39ccb3ef813b89c5267469bd545dded6906cd4 | 2497efd1dadfa61592e966deb414dc4463866875b7ffd693ba98c7592e2a7ec2 | O=C1[C@H](N(Cc2cccnc2)S(=O)(=O)c2cccs2)CCCCN1Cc1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[#16;a:7]:[c:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:12]-[C:13](-[C:14])-[C:15](=[O;D1;H0:16])-[#7:17](-[C:18])-[C:19]>>[#16;a:7]:[c:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:13](-[C:14])-[... | null | [] | null | null | 1 | HOUR | 5-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide (0.20 g, 0.40 mmol), (6-methoxy-pyridin-3-yl)-methanol (0.07 g, 0.48 mmol), triphenyl phosphine (0.22 g, 0.80 mmol) were dissolved in dry THF (15 ml) at 0-5° C. (ice-water bath) under an argon atmosphere followed by t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | c1ccccc1.C1CCC[NH]CC1.c1ccncc1.c1ccsc1 | HO- | C1CCOC1 | null | 1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1.COc1ccc(CO)cn1>C1CCOC1>COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-062a2d5b66be42e89939bac9741e1198 | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1>>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)s2)cn1 | FC(C(=O)O)(F)F.FC(S(=O)(=O)O)(F)F.COC1=C(CN2C([C@@H](CC(CC2)(F)F)N(S(=O)(=O)C=2SC(=CC2)Cl)CC=2C=NC(=CC2)OC)=O)C=CC(=C1)OC>>FC1(C[C@H](C(NCC1)=O)N(S(=O)(=O)C=1SC(=CC1)Cl)CC=1C=NC(=CC1)OC)F | COc1ccc(C[N:16]2[CH2:15][CH2:14][C:11]([F:12])([F:13])[CH2:10][C@@H:9]([N:8]([CH2:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[n:29][cH:28]3)[S:19](=[O:20])(=[O:21])[c:22]3[cH:23][cH:24][c:25]([Cl:26])[s:27]3)[C:17]2=[O:18])c(OC)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][C:11]([F:12])([F:13])[CH2... | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1 | COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)s2)cn1 | null | null | ClCCl | Reduction | Hydrogenolysis of tertiary amines | 79b08332c5c21e9adef36d66611fe6b82c22e57d08f56bf4970d6f853fe1c8ec | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1NCCCC[C@H]1N(Cc1cccnc1)S(=O)(=O)c1cccs1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]):c(-O-C):c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 0.62 ml) was added to 5-chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide (0.17 g, 0.19 mmol) in dichloromethane (10 ml). After 2 h the reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | c1ccncc1.C1CCCNCC1.c1ccsc1 | HO- | ClCCl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](N(Cc3ccc(OC)nc3)S(=O)(=O)c3ccc(Cl)s3)C2=O)c(OC)c1>ClCCl>COc1ccc(CN([C@@H]2CC(F)(F)CCNC2=O)S(=O)(=O)c2ccc(Cl)s2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a3793eb74b648518e3d9254a1bc78bb | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)cn1>>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1 | ClC=1C=CC(=NC1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@H]1C(N(CCC(C1)(F)F)CC1=C(C=C(C=C1)OC)OC)=O)=O.Cl.O1CCOCC1.CCN(C(C)C)C(C)C>>COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)C2=NC=C(C=C2)Cl)=O)C=CC(=C1)OC | CC(C)(C)OC(=O)[NH:16][C@@H:15]1[CH2:14][C:11]([F:12])([F:13])[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:29]2[O:30][CH3:31])[C:27]1=[O:28].Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]([... | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)cn1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1 | null | null | ClCCl.C(Cl)Cl | Acylation | OtherReaction | e5e0353ed7860f5f3e39514139f051e4d6492a60eb2b5be38d0840e87639dc1b | cf59b7e4d6547a1ecb903c2113fc2917df8195614c8f97dab060eab217c2f6c5 | O=C1[C@H](NS(=O)(=O)c2ccccn2)CCCCN1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8].Cl-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12](:[c:13]):[#7;a:14]:[c:15]>>[C:3]-[C:2](-[NH;D2;+0:1]-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12](:[c:13]):[#7;a:14]:[c:15])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8] | null | [] | null | null | null | null | [(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.46 g, 1.0 mmol) was dissolved in 20 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Sulfonamide | null | null | c1ccccc1.C1CCC[NH]CC1.c1ccncc1 | HCl | ClCCl.C(Cl)Cl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](NC(=O)OC(C)(C)C)C2=O)c(OC)c1.O=S(=O)(Cl)c1ccc(Cl)cn1>ClCCl.C(Cl)Cl>COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a767e2cc465548bba826aba987932013 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1>>O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1 | FC(C(=O)O)(F)F.FC(S(=O)(=O)O)(F)F.COC1=C(CN2C([C@@H](CC(CC2)(F)F)NS(=O)(=O)C2=NC=C(C=C2)Cl)=O)C=CC(=C1)OC>>FC1(C[C@H](C(NCC1)=O)NS(=O)(=O)C1=NC=C(C=C1)Cl)F | COc1ccc(C[N:3]2[C:2](=[O:1])[C@H:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][n:21]3)[CH2:9][C:6]([F:7])([F:8])[CH2:5][CH2:4]2)c(OC)c1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][n:21]1 | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1 | O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1 | null | null | ClCCl | Reduction | Hydrogenolysis of tertiary amines | 79b08332c5c21e9adef36d66611fe6b82c22e57d08f56bf4970d6f853fe1c8ec | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1NCCCC[C@H]1NS(=O)(=O)c1ccccn1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]):c(-O-C):c:1>>[C:6]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 2.44 ml) was added to 5-chloro-pyridine-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide (0.37 g, 0.76 mmol) in dichloromethane (20 ml). After 2 h the reaction mixture was concentrated under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1.c1ccncc1 | HO- | ClCCl | null | null | COc1ccc(CN2CCC(F)(F)C[C@@H](NS(=O)(=O)c3ccc(Cl)cn3)C2=O)c(OC)c1>ClCCl>O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6873cfde16ff470a95b2f71e5fbab44a | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1>>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cn1 | FC1(C[C@H](C(NCC1)=O)NS(=O)(=O)C1=NC=C(C=C1)Cl)F.FC(OC1=CC=C(CBr)C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>FC(OC1=CC=C(CN(S(=O)(=O)C2=NC=C(C=C2)Cl)[C@H]2C(NCCC(C2)(F)F)=O)C=C1)F | Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[NH:11][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][n:32]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([F:7])([F:8])[CH2:9][C@H:10]1[N:11]([CH2:12][c:13]... | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1 | O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C1NCCCC[C@H]1N(Cc1ccccc1)S(=O)(=O)c1ccccn1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[NH;D2;+0:10]-[C:11](-[C:12])-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16]>>[#7;a:5]:[c:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11](-[C:12])-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16] | null | [] | 65 | CELSIUS | 3 | HOUR | 5-Chloro-pyridine-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amide (0.21 g, 0.61 mmol), 4-(difluoromethoxy)benzyl bromide (0.23 g, 0.91 mmol), K2CO3 (0.85 g, 6.08 mmol), KI (0.02 g, 0.12 mmol) were added to dry DMF (10 ml) and the resultant reaction mixture was stirred for 1.5 h at 65° C. and for additional 3... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCNCC1.c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | 65 | 3 | FC(F)Oc1ccc(CBr)cc1.O=C1NCCC(F)(F)C[C@H]1NS(=O)(=O)c1ccc(Cl)cn1>CN(C)C=O>O=C1NCCC(F)(F)C[C@H]1N(Cc1ccc(OC(F)F)cc1)S(=O)(=O)c1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de8ad8713eec4f30805385a65bb90772 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]2C(=O)OCc2ccccc2)ccn1>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1 | C(C)(=O)O.[Si](C)(C)(C(C)(C)C)N1[C@@H]([C@H](C1=O)CC1=CC(=NC=C1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OCC1=CC=CC=C1.[F-].[NH4+]>>C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C | CC(C)(C)[Si](C)(C)[N:23]1[C:21](=[O:22])[C@H:20]([CH2:19][c:18]2[cH:17][c:16]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:37][cH:36][cH:35]2)[C@H:24]1[C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]2C(=O)OCc2ccccc2)ccn1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1 | null | null | C([O-])(O)=O.[Na+].CO.C(C)(=O)OCC | Deprotection | Hydrogenolysis of tertiary amines | 164bd7804d1ccf9d137b2eb7c529a664cfdd2d5444ce897bf38b5e9691c9e7a9 | c090f428d51b6df82e29f4cd328a9a4394669333cd0963969691f2a783f35cdc | O=C(OCc1ccccc1)[C@H]1NC(=O)[C@@H]1Cc1ccncc1 | C-C(-C)(-C)-[Si](-C)(-C)-[N;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-1 | 70.4 | [{"value": 69.0, "product": "C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 8 | HOUR | Ester 18 (127 mg, 0.20 mmol) was dissolved in 1 mL dry methanol at room temperature. 1 mL of a 0.5 M solution of ammonium fluoride in methanol (0.5 mmol, 2.5 equiv.) was added, then 60 mg acetic acid (1 mmol, 5 equiv). The reaction was stirred overnight under argon, diluted with 20 mL ethyl acetate and 20 mL saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Silyl protective group | Secondary amide | C1C[NH]C1 | C1CNC1 | c1ccncc1.C1CNC1.c1ccccc1 | Other | C([O-])(O)=O.[Na+].CO.C(C)(=O)OCC | null | 8 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]2C(=O)OCc2ccccc2)ccn1>C([O-])(O)=O.[Na+].CO.C(C)(=O)OCC>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09f34667e2ad4d39845b49384f16c557 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1.CCN(CC)CC.[N-]=C=O>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1 | C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C.C(C)N(CC)CC.[N-]=C=O>>C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[cH:17][c:18]([CH2:19][C@H:20]2[C:21](=[O:22])[NH:23][C@@H:33]2[C:34](=[O:35])[O:36][CH2:37][c:38]2[cH:39][cH:40][cH:41][cH:42][cH:43]2)[cH:44][cH:45][n:46]1.N([CH2:27][CH3:28])([CH2:29][CH3:30])[CH2:32][... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1.CCN(CC)CC.[N-]=C=O | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | e4e9947e2fbbecd0f8a314af6baf13edb024aeea7b2cb6310cfe2a9ec59fc5fb | 9e13493cfd71d6ef13cede2cefbb1f8d719919b82b670255d6765613a3d77fc9 | O=C(OCc1ccccc1)[C@@H]1[C@@H](Cc2ccncc2)C(=O)N1C(=O)Nc1ccccc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[C:13](=[O;D1;H0:14])-[NH;D2;+0:15]-1.[N-;H0;D1:16]=[C;H0;D2;+0:17]=[O;D1;H0:18]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[C:13](=[O;D1;H0:14])-[N;H0;D3;+0:15]-1-[C;H0;D3;+0:... | 169.9 | [{"value": 85.0, "product": "C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 169.9, "product": "C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C", "... | null | null | 8 | HOUR | Deprotected lactam 19 (72 mg, 0.14 mmol) was dissolved in 4 mL dry THF at room temperature. Triethylamine (71 mg, 5 equiv.) was added, then 42 mg (2.5 equiv.) of the isocyanate. The reaction was stirred overnight under argon and concentrated in vacuo. The residue was purified by column chromatography eluting with methy... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amine | Urea.Substituted dicarboximide | C1CNC1 | C1C[NH]C1.c1ccccc1 | c1ccncc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 8 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)OCc2ccccc2)ccn1.CCN(CC)CC.[N-]=C=O>C1CCOC1>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2a8676c2be04af68bf78a251ae2b299 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)O)ccn1 | C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)O)C(=O)OC(C)(C)C | c1ccc(C[O:36][C:34]([C@@H:33]2[C@@H:20]([CH2:19][c:18]3[cH:17][c:16]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:39][cH:38][cH:37]3)[C:21](=[O:22])[N:23]2[C:24](=[O:25])[NH:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)=[O:35])cc1>>[CH3:1][C:2]([CH3:... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)O)ccn1 | null | [Pd] | CO.C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)N1C[C@@H](Cc2ccncc2)C1=O | [#7:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[#7:1]-[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5] | null | [] | null | null | 8 | HOUR | Acylated lactam ester 20 (56 mg, 0.089 mmol) was dissolved in 2 mL of 1:1 methanol-ethyl acetate in a 20 mL glass vial. 10% palladium on carbon catalyst (10 mg) was added, and the solution was stirred under an atmosphere of hydrogen at room temperature overnight under argon, filtered, and then concentrated in vacuo. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccncc1.C1C[NH]C1.c1ccccc1 | Other | [Pd].CO.C(C)(=O)OCC | null | 8 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)OCc2ccccc2)ccn1>[Pd].CO.C(C)(=O)OCC>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N(C(=O)Nc3ccccc3)[C@@H]2C(=O)O)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b77a079ee394e79b7077d74f01c6326 | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CI>>C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | CI.[Si](C)(C)(C(C)(C)C)N1[C@@H](CC1=O)C(=O)O.[Li+].CC(C)[N-]C(C)C>>[Si](C)(C)(C(C)(C)C)N1[C@@H]([C@H](C1=O)C)C(=O)O | [CH2:2]1[C:3](=[O:4])[N:5]([Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C@@H:13]1[C:14](=[O:15])[OH:16].I[CH3:1]>>[CH3:1][C@H:2]1[C:3](=[O:4])[N:5]([Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C@@H:13]1[C:14](=[O:15])[OH:16] | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CI | C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_secondary | 17914f03dac77d406ac0228390584524824f878e5f66fc96c5f00224ec0c6df4 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1CCN1 | I-[CH3;D1;+0:1].[C:2]-[#14:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]1-[C:7](-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[CH2;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[C:2]-[#14:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#7:6]1-[C:7](-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[C@@H;D3;+0:11](-[CH3;D1;+0:1])-[C:12]-1=[O;D1;H0:13] | null | [] | -78 | CELSIUS | 20 | MINUTE | To a solution of (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid 4 (2.00 g, 8.73 mmol.) in THF (30 ml) at −78° C. was added LDA (19 ml, 2.0 eq.). After the solution was stirred for 20 min. at −78° C., it was warmed to 0° C. for 5 min. The solution was re-cooled to −78° C. and methyl iodide (3.10 g, 2.5... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1 | HI | C1CCOC1 | -78 | 0.333333 | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CI>C1CCOC1>C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f36e59fb3184c3a9cf914e071e4f31f | C=CCBr.C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O>>C=CC[C@@]1(C)C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | C(C=C)Br.[Si](C)(C)(C(C)(C)C)N1[C@@H]([C@H](C1=O)C)C(=O)O.[Li+].CC(C)[N-]C(C)C>>C(C=C)[C@@]1([C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)O)C | Br[CH2:3][CH:2]=[CH2:1].[C@H:4]1([CH3:5])[C:6](=[O:7])[N:8]([Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[C@@H:16]1[C:17](=[O:18])[OH:19]>>[CH2:1]=[CH:2][CH2:3][C@@:4]1([CH3:5])[C:6](=[O:7])[N:8]([Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[C@@H:16]1[C:17](=[O:18])[OH:19] | C=CCBr.C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | C=CC[C@@]1(C)C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 0a0a074f1918cc59cb0c863af61776848c3701f3ba90ca3fc9defcc58ffb3db6 | 4e1ce4e19860a9931e6216ba313479e4494dc60a286d9f70a4527814b3cbb3e2 | O=C1CCN1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C@@H;D3;+0:13](-[C;D1;H3:14])-[C:15]-1=[O;D1;H0:16]>>[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C@@;H0;D4;+0:13](-[C;D1;H3:14])(-[CH2;D2;+0:... | null | [] | -20 | CELSIUS | 20 | MINUTE | To a solution of compound 47 (0.200 g, 0.823 mmol) in THF (5 ml) at −78° C. was added a solution of LDA (1.10 ml, 2.4 eq.). The reaction solution was stirred for 20 min. at that temperature, warmed to −20° C. and allyl bromide (0.138 Ml, 2.0 eq.) was added slowly. Reaction mixture was warmed to 0° C. for 30 min. and qu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1 | HBr | C1CCOC1 | -20 | 0.333333 | C=CCBr.C[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O>C1CCOC1>C=CC[C@@]1(C)C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4809683c9824c2c94be36c1adc9232f | C=CCBr.CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O>>C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | [Si](C)(C)(C(C)(C)C)N1[C@@H](CC1=O)C(=O)O.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.C(C=C)Br>>C(C=C)[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)O | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]1[C:5](=[O:6])[N:7]([Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[C@@H:15]1[C:16](=[O:17])[OH:18]>>[CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[N:7]([Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[C@@H:15]1[C:16](=[O:17])[OH:18] | C=CCBr.CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 0a0a074f1918cc59cb0c863af61776848c3701f3ba90ca3fc9defcc58ffb3db6 | 4e1ce4e19860a9931e6216ba313479e4494dc60a286d9f70a4527814b3cbb3e2 | O=C1CCN1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[CH2;D2;+0:13]-[C:14]-1=[O;D1;H0:15]>>[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C@@H;D3;+0:13](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:14]-1=[O... | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid (4) (2.00 g, 8.73 mmol.) in anhydrous THF (20 mL) at −78° C. was added 1.0 M solution of LiHMDS (20 ml, 20.1 mmol, 2.3 eq.) in THF. After the solution was stirred for 30 min. at −78° C., it was warmed to 0° C. for 10 min. The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1 | HBr | C1CCOC1 | -78 | 0.5 | C=CCBr.CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O>C1CCOC1>C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd3714c40d89410691f4cfe1b050b370 | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O.COc1ccc(CO)cc1>>C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1 | C(C=C)[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)O.CCN=C=NCCCN(C)C.Cl.COC1=CC=C(CO)C=C1>>COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)[Si](C)(C)C(C)(C)C)C=C1 | O[C:16]([C@@H:15]1[C@@H:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[N:7]1[Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])=[O:17].[OH:18][CH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]1>>[CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[N:7]([Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[... | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O.COc1ccc(CO)cc1 | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C1C[C@@H](C(=O)OCc2ccccc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-1-[#14:8](-[C:9])(-[C;D1;H3:10])-[C;D1;H3:11].[OH;D1;+0:12]-[C:13]-[c:14]>>[C:9]-[#14:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#7:7]1-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:4]-[C:5]-1=[O;D1;H0:6] | 49 | [{"value": 49.0, "product": "COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)[Si](C)(C)C(C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)[Si](C)(C)C(C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 900 mg of crude compound 57 (3.34 mmol) above, EDC hydrochloride salt (1.34 g, 7.01 mmol), DMAP (83 mg, 0.67 mmol) and 4-methoxybenzyl alcohol (1.40 g, 10.1 mmol) in dichloromethane (9 mL) was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1C[NH]C1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 8 | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O.COc1ccc(CO)cc1>CN(C)C=1C=CN=CC1.ClCCl>C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4be8430d39044e3ab8d1d14f53eb25f | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1>>C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1 | [F-].[NH4+].COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)[Si](C)(C)C(C)(C)C)C=C1.C(C)(=O)O>>COC1=CC=C(COC(=O)[C@H]2NC([C@@H]2CC=C)=O)C=C1 | CC(C)(C)[Si](C)(C)[N:7]1[C:5](=[O:6])[C@H:4]([CH2:3][CH:2]=[CH2:1])[C@H:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[NH:7][C@@H:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]1 | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1 | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1 | null | null | CO | Deprotection | Hydrogenolysis of tertiary amines | 164bd7804d1ccf9d137b2eb7c529a664cfdd2d5444ce897bf38b5e9691c9e7a9 | c090f428d51b6df82e29f4cd328a9a4394669333cd0963969691f2a783f35cdc | O=C1C[C@@H](C(=O)OCc2ccccc2)N1 | C-C(-C)(-C)-[Si](-C)(-C)-[N;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-1 | null | [] | null | null | 2 | HOUR | A solution of 6.2 mL of 0.5 M ammonium fluoride in methanol (3.1 mmol) was added to a mixture of compound 58 (1.0 g, 2.57 mmol), acetic acid (530 uL, 9.0 mmol) and methanol (25 mL). The mixture was stirred at room temperature for 2 h. The solvent was removed and the residue was taken up in toluene (2˜3 mL) to assist re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Silyl protective group | Secondary amide | C1C[NH]C1 | C1CNC1 | C1CNC1.c1ccccc1 | Other | CO | null | 2 | C=CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1C(=O)OCc1ccc(OC)cc1>CO>C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1 |
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