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-d984914711904b51b3b77f5ad24366d3 | CSCc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(CS(C)(=O)=O)ccc23)n[nH]1 | OOS(=O)[O-].[K+].C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)CSC)=O.O1CCOCC1.O>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)CS(=O)(=O)C)=O | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([CH2:17][S:18][CH3:19])[cH:22][cH:23][c:24]23)[n:25][nH:26]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([CH2:17][S:18]([CH3:19])(=[O:20])=[O:21]... | CSCc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(CS(C)(=O)=O)ccc23)n[nH]1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[C:3]-[c:4]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:5])(=[O;D1;H0:6])-[C:3]-[c:4] | 20 | [{"value": 20.0, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)CS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Oxone (0.43 g, 0.7 mmol) was added in one portion to a stirred solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-methylsulfanylmethyl-2H-phthalazin-1-one (0.06 g, 0.17 mmol) in a 4:1 mixture of dioxane/water (1.2 ml) and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cn[nH]c1.c1ccc2cnncc2c1 | null | O | null | 1 | CSCc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1>O>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(CS(C)(=O)=O)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49332a5f9c03447d85bbd807a0c7d77e | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl>>COCC(=O)N(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | O.BrC1=NN(C(C2=CC(=CC=C12)NC)=O)C(C)C.[H-].[Na+].COCC(=O)Cl>>BrC1=NN(C(C2=CC(=CC=C12)N(C(COC)=O)C)=O)C(C)C | [NH:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([Br:13])[n:14][n:15]([CH:16]([CH3:17])[CH3:18])[c:19](=[O:20])[c:21]2[cH:22]1.Cl[C:4]([CH2:3][O:2][CH3:1])=[O:5]>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[N:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([Br:13])[n:14][n:15]([CH:16]([CH3:17])[CH3:18])[c:19](=[O:20])[c:21]2[cH:22]1 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl | COCC(=O)N(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=c1[nH]ncc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[c:7](:[c:8]):[c:9] | 76 | [{"value": 76.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(C(COC)=O)C)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(C(COC)=O)C)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.5 g, 1.69 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.19 g, 5.1 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then methoxyacetyl chloride (0.27 g, 2.5 mmol) was added dropwise and the reaction mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccc2cnncc2c1 | HCl | CN(C)C=O | null | 0.5 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl>CN(C)C=O>COCC(=O)N(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-089f47a9731b451f9cd7725d9a53b8a5 | CNc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl>>COCC(=O)N(C)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | O.C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)NC)=O.[H-].[Na+].COCC(=O)Cl>>C(C)(C)N1N=C(C2=CC=C(C=C2C1=O)N(C(COC)=O)C)NC1=NNC(=C1)C | [NH:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[nH:18][n:19]3)[n:20][n:21]([CH:22]([CH3:23])[CH3:24])[c:25](=[O:26])[c:27]2[cH:28]1.Cl[C:4]([CH2:3][O:2][CH3:1])=[O:5]>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[N:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]2[c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17... | CNc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl | COCC(=O)N(C)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[c:7](:[c:8]):[c:9] | 12 | [{"value": 12.0, "product": "C(C)(C)N1N=C(C2=CC=C(C=C2C1=O)N(C(COC)=O)C)NC1=NNC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.0, "product": "C(C)(C)N1N=C(C2=CC=C(C=C2C1=O)N(C(COC)=O)C)NC1=NNC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 2-Isopropyl-7-methylamino-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one (0.4 g, 1.3 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.1 g, 2.6 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 5 min then methoxyacetyl chloride (0.28 g, 2.6 mmol) was added dropwise and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1cn[nH]c1.c1ccc2cnncc2c1 | HCl | CN(C)C=O | null | 0.083333 | CNc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.COCC(=O)Cl>CN(C)C=O>COCC(=O)N(C)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-932f3e1266274b2f9fedfcdfd892c19b | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.O=C(Cl)CCCCl>>CC(C)n1nc(Br)c2ccc(NC(=O)CCCCl)cc2c1=O | ClCCCC(=O)Cl.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br>>BrC1=NN(C(C2=CC(=CC=C12)NC(CCCCl)=O)=O)C(C)C | [CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:19][c:20]2[c:21]1=[O:22].Cl[C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18])[cH:19][c:20]2[c:21]1=[O:22] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.O=C(Cl)CCCCl | CC(C)n1nc(Br)c2ccc(NC(=O)CCCCl)cc2c1=O | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1[nH]ncc2ccccc12 | 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] | 67 | [{"value": 67.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)NC(CCCCl)=O)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "BrC1=NN(C(C2=CC(=CC=C12)NC(CCCCl)=O)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 7-amino-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.5 g, 1.8 mmol) in DMF (8 ml), was added TEA (0.28 ml, 1.98 mmol). After 5 min, 4-chlorobutyryl chloride (0.22 ml, 2.0 mmol) was added and the solution was stirred at RT for 2 hours. After this time LC-MS indicated the complete consumption of starting m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2cnncc2c1 | HCl | CN(C)C=O | null | 0.083333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.O=C(Cl)CCCCl>CN(C)C=O>CC(C)n1nc(Br)c2ccc(NC(=O)CCCCl)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-481863679c4f49119ff75ba32ec07598 | C#COCC.CCCC(C)C(=O)Cl>>CCCC1(C)C(=O)C=C1OCC | CC(C(=O)Cl)CCC.C(C)OC#C.C(C)N(CC)CC>>C(C)OC1=CC(C1(CCC)C)=O | [CH:8]#[C:9][O:10][CH2:11][CH3:12].Cl[C:6]([CH:4]([CH2:3][CH2:2][CH3:1])[CH3:5])=[O:7]>>[CH3:1][CH2:2][CH2:3][C:4]1([CH3:5])[C:6](=[O:7])[CH:8]=[C:9]1[O:10][CH2:11][CH3:12] | C#COCC.CCCC(C)C(=O)Cl | CCCC1(C)C(=O)C=C1OCC | null | null | CCOCC | C-C Coupling | OtherReaction | a3cc8fa10bff2dd998a4f859b2aa4de74d55e3348bb806f1eac1ae52e0082e8c | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1C=CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C:5]-[C:6].[C:7]-[#8:8]-[C;H0;D2;+0:9]#[CH;D1;+0:10]>>[C:7]-[#8:8]-[C;H0;D3;+0:9]1=[CH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-1(-[C;D1;H3:4])-[C:5]-[C:6] | 77 | [{"value": 77.0, "product": "C(C)OC1=CC(C1(CCC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using a modification of the method of Wasserman, H. H. et al [J. Org. Chem, 38, 1451-1455, (1973)]; to a solution of 2-methyl pentanoyl chloride (3.91 ml) and ethyl ethynylether (5 g, 40% solution in hexanes, 28.6 mmol) in Et2O (35 ml) at room temperature was added triethylamine (9.9 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | null | C1=CCC1 | C1=CCC1 | HCl | CCOCC | null | null | C#COCC.CCCC(C)C(=O)Cl>CCOCC>CCCC1(C)C(=O)C=C1OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eaac26e6b1374dd39c62a819199bd155 | C#COCC.CCCC(CCC)C(=O)Cl>>CCCC1(CCC)C(=O)C=C1OCC | C(C)N(CC)CC.C(CC)C(C(=O)Cl)CCC.C(C)OC#C>>C(C)OC1=CC(C1(CCC)CCC)=O | [CH:10]#[C:11][O:12][CH2:13][CH3:14].Cl[C:8]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9]>>[CH3:1][CH2:2][CH2:3][C:4]1([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[CH:10]=[C:11]1[O:12][CH2:13][CH3:14] | C#COCC.CCCC(CCC)C(=O)Cl | CCCC1(CCC)C(=O)C=C1OCC | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | a3cc8fa10bff2dd998a4f859b2aa4de74d55e3348bb806f1eac1ae52e0082e8c | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1C=CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[C:8]-[#8:9]-[C;H0;D2;+0:10]#[CH;D1;+0:11]>>[C:8]-[#8:9]-[C;H0;D3;+0:10]1=[CH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-1(-[C:4]-[C:5])-[C:6]-[C:7] | 67 | [{"value": 67.0, "product": "C(C)OC1=CC(C1(CCC)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(C)OC1=CC(C1(CCC)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | The title compound was prepared using a modification of the method of Wasserman, H. H. et al, [J. Org. Chem, 38, 1451-1455, (1973)]; triethylamine (29 ml) was added dropwise at room temperature to a well-stirred solution of di-n-propylacetyl chloride (13.9 g, 85.8 mmol) and ethyl ethynylether (15 g, 40% solution in hex... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | null | C1=CCC1 | C1=CCC1 | HCl | C1(=CC=CC=C1)C | null | 48 | C#COCC.CCCC(CCC)C(=O)Cl>C1(=CC=CC=C1)C>CCCC1(CCC)C(=O)C=C1OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49a04347973442219de20d5520156b4d | CC(C)C(=O)Cl.CCCCCCC#COCC>>CCCCCCC1=C(OCC)C(C)(C)C1=O | C(C)N(CC)CC.C(C(C)C)(=O)Cl.C(C)OC#CCCCCCC>>C(C)OC1=C(C(C1(C)C)=O)CCCCCC | Cl[C:15]([CH:12]([CH3:13])[CH3:14])=[O:16].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][O:9][CH2:10][CH3:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1=[C:8]([O:9][CH2:10][CH3:11])[C:12]([CH3:13])([CH3:14])[C:15]1=[O:16] | CC(C)C(=O)Cl.CCCCCCC#COCC | CCCCCCC1=C(OCC)C(C)(C)C1=O | null | null | C(C)OCC | C-C Coupling | OtherReaction | a3cc8fa10bff2dd998a4f859b2aa4de74d55e3348bb806f1eac1ae52e0082e8c | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1C=CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[#8:7]-[C;H0;D2;+0:8]#[C;H0;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[#8:7]-[C;H0;D3;+0:8]1=[C;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-1(-[C;D1;H3:4])-[C;D1;H3:5] | 61 | [{"value": 61.0, "product": "C(C)OC1=C(C(C1(C)C)=O)CCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | The title compound was prepared using a modification of the method of Wasserman, H. H. et al, [J. Org. Chem, 38, 1451-1455, (1973)]; triethylamine (22 ml) was added dropwise at room temperature to a well-stirred solution of isobutyryl chloride (7.3 ml, 69 mmol) and 1-ethoxy-1-octyne [prepared according to the method of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | null | C1=CCC1 | C1=CCC1 | HCl | C(C)OCC | null | 96 | CC(C)C(=O)Cl.CCCCCCC#COCC>C(C)OCC>CCCCCCC1=C(OCC)C(C)(C)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c59bbb9f4fe42b38046928fe90a19db | CCOC(=O)[C@H](Cc1ccc(Nc2nccc3ccncc23)cc1)NC(=O)OC(C)(C)C>>CCOC(=O)[C@@H](N)Cc1ccc(Nc2nccc3ccncc23)cc1 | C(C)OC([C@H](CC1=CC=C(C=C1)NC1=NC=CC2=CC=NC=C12)NC(=O)OC(C)(C)C)=O.C(C)OC([C@H](CC1=CC=C(C=C1)N)NC(=O)OC(C)(C)C)=O.CO.C(Cl)Cl>>N[C@H](C(=O)OCC)CC1=CC=C(C=C1)NC1=NC=CC2=CC=NC=C12 | CC(C)(C)OC(=O)[NH:7][C@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][c:9]1[cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][cH:17][c:18]3[cH:19][cH:20][n:21][cH:22][c:23]23)[cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]([NH2:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][cH:17][c:18]3[cH:19]... | CCOC(=O)[C@H](Cc1ccc(Nc2nccc3ccncc23)cc1)NC(=O)OC(C)(C)C | CCOC(=O)[C@@H](N)Cc1ccc(Nc2nccc3ccncc23)cc1 | null | null | C(C)OC(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Nc2nccc3ccncc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of ethyl-(S)-3-[4-aminophenyl]-2-[t-butoxycarbonylamino]propanoate (638 mg, 2.07 mmol) and Intermediate 11 (310 mg, 1.88 mmol) in ethoxyethanol (2 ml) was stirred at 120° for 15 min and at 100° for 1 h under nitrogen. The volatiles were removed in vacuo and the dark residue partitioned between EtOAc (70 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cc2ccncc2cn1 | HO- | C(C)OC(C)O | null | null | CCOC(=O)[C@H](Cc1ccc(Nc2nccc3ccncc23)cc1)NC(=O)OC(C)(C)C>C(C)OC(C)O>CCOC(=O)[C@@H](N)Cc1ccc(Nc2nccc3ccncc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64c866725ddc4a1aaf0e3a25d6f22178 | COC(C)(OC)N(C)C.Cc1ccncc1C#N>>CC(=O)Cc1ccncc1C#N | CC1=C(C=NC=C1)C#N.COC(C)(N(C)C)OC>>C(C(=O)C)C1=C(C=NC=C1)C#N | CO[C:2](N(C)C)([CH3:1])[O:3]C.[CH3:4][c:5]1[cH:6][cH:7][n:8][cH:9][c:10]1[C:11]#[N:12]>>[CH3:1][C:2](=[O:3])[CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][c:10]1[C:11]#[N:12] | COC(C)(OC)N(C)C.Cc1ccncc1C#N | CC(=O)Cc1ccncc1C#N | null | null | CN(C)C=O | Acylation | OtherReaction | 7dc7b823acb76f2126a124819c3fc034848768949863bfa47d232efb87b8891e | 1c3b01f1b42dcb846348b2eb68044b34e6661d6bbb3f30c8846dbafef4eb6bd5 | c1ccncc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[O;H0;D2;+0:3]-C)-N(-C)-C.[CH3;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 69 | [{"value": 69.0, "product": "C(C(=O)C)C1=C(C=NC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "C(C(=O)C)C1=C(C=NC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-methyl-3-cyanopyridine (4 g, 33.9 mmol) and N,N-dimethylacetamide dimethylacetal (5.4 g, 40.6 mmol) in dry DMF (20 ml) was stirred at 130° for 7 h. The volatiles were removed in vacuo to afford a dark oil which solidified on standing. This material was chromatographed (SiO2; 50% EtOAc/Hexane-100% EtOAc)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amine | Ketone | null | null | c1ccncc1 | HO- | CN(C)C=O | null | null | COC(C)(OC)N(C)C.Cc1ccncc1C#N>CN(C)C=O>CC(=O)Cc1ccncc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24e2a20cd68f4c5da46c4ee69454c626 | O=P(Cl)(Cl)Cl.Oc1nccc2cnccc12>>Clc1nccc2cnccc12 | OC1=NC=CC2=CN=CC=C12.P(=O)(Cl)(Cl)Cl>>ClC1=NC=CC2=CN=CC=C12 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | O=P(Cl)(Cl)Cl.Oc1nccc2cnccc12 | Clc1nccc2cnccc12 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 2b7b7bc059bd0ff4138c613f1add62e6900147840b65bd3cc610f62eea9f3d7f | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cc2cnccc2cn1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Hydroxy-2,6-naphthyridine (550 mg) [prepared according to the method of Sakamoto, T. et al Chem, Pharm. Bull. 33, 626, (1985)] was stirred with phosphorous oxychloride (10 ml) at 110° for 5 h. The volatiles were removed in vacuo and the residue treated carefully with ice. After diluting with water (to ˜25 ml), solid ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cc2cnccc2cn1 | c1cc2cnccc2cn1 | c1cc2cnccc2cn1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1nccc2cnccc12>>Clc1nccc2cnccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04872a1546544a80904f2013986bb7fd | CCN(C(C)C)C(C)C.CCOC(=O)[C@H](Cc1ccc(N)cc1)NC(=O)OC(C)(C)C.CO>>CCOC(=O)[C@H](Cc1ccc(Nc2nccc3cnccc23)cc1)NC(=O)OC(C)(C)C | CO.C(Cl)Cl.NC1=CC=C(C=C1)C[C@@H](C(=O)OCC)NC(=O)OC(C)(C)C.CCN(C(C)C)C(C)C>>C(C)(C)(C)OC(=O)N[C@H](C(=O)OCC)CC1=CC=C(C=C1)NC1=NC=CC2=CN=CC=C12 | C[CH:17](C)[N:14]([CH:13]([CH3:21])[CH3:22])[CH2:15][CH3:16].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:23][cH:24]1)[NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].O[CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2... | CCN(C(C)C)C(C)C.CCOC(=O)[C@H](Cc1ccc(N)cc1)NC(=O)OC(C)(C)C.CO | CCOC(=O)[C@H](Cc1ccc(Nc2nccc3cnccc23)cc1)NC(=O)OC(C)(C)C | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 239c8e831ecc833ef19999c12e98b1a5766cd627c5ba17c5807eaf7f264d4d56 | 6edbeab18cd45f5a87542b41d3dbe5b30efaef7d29ddeb588d132bd64e6cd29b | c1ccc(Nc2nccc3cnccc23)cc1 | C-[CH;D3;+0:1](-C)-[N;H0;D3;+0:2](-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH;D3;+0:5](-[CH3;D1;+0:6])-[CH3;D1;+0:7].O-[CH3;D1;+0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:1]2:[c:13]:[#7;a:14]:[cH;D2;+0:8]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:... | 77.4 | [{"value": 42.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C(=O)OCC)CC1=CC=C(C=C1)NC1=NC=CC2=CN=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "C(C)(C)(C)OC(=O)N[C@H](C(=O)OCC)CC1=CC=C(C=C1)NC1=NC=CC2=CN=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl(S)-3-(4-aminophenyl)-2-[N-(t-butyloxycarbonyl)amino]propanoate (600 mg, 1.95 mmol), Intermediate 21 (350 mg, 2.13 mmol) and DIPEA (276 mg, 372 μl, 2.13 mmol) in 2-ethoxyethanol (0.5 ml) were stirred at 130° under N2 for several hours. The reaction was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine.Methanol | Secondary amine | null | c1cc2cnccc2cn1 | c1ccccc1.c1cc2cnccc2cn1 | HO- | C(C)OCCO | null | null | CCN(C(C)C)C(C)C.CCOC(=O)[C@H](Cc1ccc(N)cc1)NC(=O)OC(C)(C)C.CO>C(C)OCCO>CCOC(=O)[C@H](Cc1ccc(Nc2nccc3cnccc23)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-612d4aec17dd4244a22a36cf44ac3887 | C#COCC.CCN(CC)CC.CN(C)C=O.O=C(Cl)C(=O)Cl>>CCOC1=CC(=O)C12CCOCC2 | C(C)OC#C.C(C)N(CC)CC.CN(C)C=O.C(C(=O)Cl)(=O)Cl.C(Cl)Cl>>C(C)OC1=CC(C12CCOCC2)=O | [CH3:1][CH2:2][O:3][C:4]#[CH:5].CCN(C[CH3:9])[CH2:12][CH3:13].CN(C)C=[O:11].O=[C:8](Cl)[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]12[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2 | C#COCC.CCN(CC)CC.CN(C)C=O.O=C(Cl)C(=O)Cl | CCOC1=CC(=O)C12CCOCC2 | null | null | null | C-C Coupling | OtherReaction | 533a38594e71855da855aba13f2ccef9e3c5a7e996862363fc4f5e929b93cd57 | cf157086ea2771892d65bfac6ec25db68cc77d2db9212259f5a2861a16b9d8d2 | O=C1C=CC12CCOCC2 | C-C-N(-C-[CH3;D1;+0:1])-[CH2;D2;+0:2]-[CH3;D1;+0:3].C-N(-C)-C=[O;H0;D1;+0:4].Cl-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](-Cl)=O.[C:8]-[#8:9]-[C;H0;D2;+0:10]#[CH;D1;+0:11]>>[C:8]-[#8:9]-[C;H0;D3;+0:10]1=[CH;D2;+0:11]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D4;+0:7]-12-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[O;H0;D2;+0:4]-[C:12]-[CH2... | 59 | [{"value": 59.0, "product": "C(C)OC1=CC(C12CCOCC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 11 | DAY | Tetrahydropyranyl-4-carboxylic acid (14.7 g, 0.11 mol) and DMF (0.5 ml) in DCM (150 ml) was treated dropwise with oxalyl chloride (1.1 eq, 10.9 ml, 0.12 mol). After 1 h the reaction mixture was concentrated in vacuo and the residual slurry was diluted with Et2O (200 ml) and the resulting precipitate removed by filtrati... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Ether.Tertiary amide.Tertiary amine.Alkyne | Ketone.Ether.Ether | null | C1=CC2(C1)CCOCC2 | C1=CC2(C1)CCOCC2 | HCl | null | null | 264 | C#COCC.CCN(CC)CC.CN(C)C=O.O=C(Cl)C(=O)Cl>>CCOC1=CC(=O)C12CCOCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e23e903e13974e97a9e5a14168833a67 | C#COCC.O=C(Cl)C1CCCCCC1>>CCOC1CC(=O)C12CCCCCC2 | C1(CCCCCC1)C(=O)Cl.C(C)OC#C.C(C)N(CC)CC>>C(C)OC1CC(C12CCCCCC2)=O | [CH3:1][CH2:2][O:3][C:4]#[CH:5].Cl[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][CH2:2][O:3][CH:4]1[CH2:5][C:6](=[O:7])[C:8]12[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2 | C#COCC.O=C(Cl)C1CCCCCC1 | CCOC1CC(=O)C12CCCCCC2 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 3aa360b2ef6c5c73beffa87ad5d0db18c162839b34ddafa06351365e340f5590 | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1CCC12CCCCCC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[C:8]-[#8:9]-[C;H0;D2;+0:10]#[CH;D1;+0:11]>>[C:7]-[C:6]-[C;H0;D4;+0:3]1(-[C:4]-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:11]-[CH;D3;+0:10]-1-[#8:9]-[C:8] | 87.1 | [{"value": 87.0, "product": "C(C)OC1CC(C12CCCCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "C(C)OC1CC(C12CCCCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | A solution of cycloheptyl carbonyl chloride (10.0 g, 0.062 mol) and ethoxyacetylene (40% w/w solution in hexanes, 6.0 g, 0.083 mol, 12 ml) in diethylether (50 ml) was treated dropwise with triethylamine (20 ml, 0.14 mol) and the reaction stirred for 5 d at room temperature. Filtration and concentration of the filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | C1CCCCCC1 | C1CCCC2(CC1)CCC2 | C1CCCC2(CC1)CCC2 | Other | C(C)OCC | null | 120 | C#COCC.O=C(Cl)C1CCCCCC1>C(C)OCC>CCOC1CC(=O)C12CCCCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1f1cf96a691447386249bc1a58d5c3a | C#COCC.CC(=O)N1CCC(C(=O)Cl)CC1>>CCOC1=CC(=O)C12CCN(C(C)=O)CC2 | CCOC(=O)C.CCOC(=O)C.C(C)(=O)N1CCC(CC1)C(=O)Cl.C(C)OC#C.C(C)N(CC)CC>>C(C)(=O)N1CCC2(C(=CC2=O)OCC)CC1 | [CH3:1][CH2:2][O:3][C:4]#[CH:5].Cl[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([C:12]([CH3:13])=[O:14])[CH2:15][CH2:16]1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]12[CH2:9][CH2:10][N:11]([C:12]([CH3:13])=[O:14])[CH2:15][CH2:16]2 | C#COCC.CC(=O)N1CCC(C(=O)Cl)CC1 | CCOC1=CC(=O)C12CCN(C(C)=O)CC2 | null | null | CO.C1CCOC1 | C-C Coupling | OtherReaction | 34644e0f49da413295da033051c8f0e7e9df800696b9a4afe26f19d5cdd401ce | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1C=CC12CCNCC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5]-[#7:6]-[C:7]-[C:8]-1.[C:9]-[#8:10]-[C;H0;D2;+0:11]#[CH;D1;+0:12]>>[C:9]-[#8:10]-[C;H0;D3;+0:11]1=[CH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-12-[C:4]-[C:5]-[#7:6]-[C:7]-[C:8]-2 | 67.4 | [{"value": 67.0, "product": "C(C)(=O)N1CCC2(C(=CC2=O)OCC)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "C(C)(=O)N1CCC2(C(=CC2=O)OCC)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | A solution of 1-acetyl piperidine-4-carbonyl chloride (5.0 g, 26.4 mmol) and ethoxyacetylene (4.0 g, 55.5 mmol) in THF (60 ml) was treated dropwise with triethylamine (7.6 ml, 55.0 mmol). The resulting slurry was stirred at room temperature for 5 d prior to filtration and concentration of the filtrate in vacuo. Chromat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | C1CC[NH]CC1 | C1=CC2(C1)CC[NH]CC2 | C1=CC2(C1)CC[NH]CC2 | HCl | CO.C1CCOC1 | null | 120 | C#COCC.CC(=O)N1CCC(C(=O)Cl)CC1>CO.C1CCOC1>CCOC1=CC(=O)C12CCN(C(C)=O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbd3d5581419410aae766a25237d954d | C#COCC.COC1CCC(C(=O)Cl)CC1>>CCOC1=CC(=O)C12CCC(OC)CC2 | COC1CCC(CC1)C(=O)Cl.C(C)OC#C>>C(C)OC1=CC(C12CCC(CC2)OC)=O | [CH3:1][CH2:2][O:3][C:4]#[CH:5].Cl[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][CH:11]([O:12][CH3:13])[CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]12[CH2:9][CH2:10][CH:11]([O:12][CH3:13])[CH2:14][CH2:15]2 | C#COCC.COC1CCC(C(=O)Cl)CC1 | CCOC1=CC(=O)C12CCC(OC)CC2 | null | null | null | C-C Coupling | OtherReaction | f90806937c02ec5e3bc55be1e4430f4431c7c30a2c612eebac81543d071a4813 | 197d5ee1965d2ce73dd26e11727e6cf6f3795c1cc1c05a38f8b4443c26979a29 | O=C1C=CC12CCCCC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[C:8]-[#8:9]-[C;H0;D2;+0:10]#[CH;D1;+0:11]>>[C:7]-[C:6]-[C;H0;D4;+0:3]1(-[C:4]-[C:5])-[C;H0;D3;+0:10](-[#8:9]-[C:8])=[CH;D2;+0:11]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | Was prepared from 4-methoxy cyclohexanecarbonyl chloride (10 g, 52.1 mmol) and ethoxyacetylene (7.5 g, 0.10 mol) according to the method of Intermediate 1 to give the title compound as an approx. 1:1 mixture of isomers, as a pale yellow oil (7.2 g, 34.4 mmol, 65%). δH (CDCl3, 300K) 4.81-4.79 (1H, s), 4.22-4.20 (2H q, J... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ketone.Ether | C1CCCCC1 | C1=CC2(C1)CCCCC2 | C1=CC2(C1)CCCCC2 | HCl | null | null | null | C#COCC.COC1CCC(C(=O)Cl)CC1>>CCOC1=CC(=O)C12CCC(OC)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10dbb59b677040a6a09f5a4ba792023a | CC(=O)Cl.N[C@@H](CO)C(=O)[O-]>>CCOC(=O)[C@@H](N)CO.Cl | N[C@H](C(=O)[O-])CO.C(C)(=O)Cl>>Cl.N[C@H](C(=O)OCC)CO | [CH3:1][C:2](=[O:3])[Cl:10].[O-][C:4](=[O:5])[C@@H:6]([NH2:7])[CH2:8][OH:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]([NH2:7])[CH2:8][OH:9].[ClH:10] | CC(=O)Cl.N[C@@H](CO)C(=O)[O-] | CCOC(=O)[C@@H](N)CO.Cl | null | null | C(C)O | Acylation | OtherReaction | 12bc1c688a52b256183208ebc227b6be51386429494f86a80801e17ed96d3a2d | 74160603d2471b6dce676fdb61c753a80de32635d34da1c285b2b50abd3324f9 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:3])=[O;H0;D1;+0:4].[C:5]-[C:6](-[N;D1;H2:7])-[C;H0;D3;+0:8](-[O-])=[O;D1;H0:9]>>[C:5]-[C:6](-[N;D1;H2:7])-[C;H0;D3;+0:8](=[O;D1;H0:9])-[O;H0;D2;+0:4]-[CH2;D2;+0:2]-[C;D1;H3:1].[ClH;D0;+0:3] | 65.2 | [{"value": 65.0, "product": "Cl.N[C@H](C(=O)OCC)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "Cl.N[C@H](C(=O)OCC)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of (2S)-2-amino-3-hydroxypropanoate (25 g, 238 mmol) and acetyl chloride (34 ml, 476 mmol) in absolute ethanol (250 ml) was stirred at 50° for 18 hr. The volatiles were removed in vacuo until the volume was reduced to ˜100 ml. Upon cooling the resultant precipitate was collected, washed with ether and hexane ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ester | null | null | null | Other | C(C)O | null | 18 | CC(=O)Cl.N[C@@H](CO)C(=O)[O-]>C(C)O>CCOC(=O)[C@@H](N)CO.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee16093a9b7a4e13aea8a40dbf4284d0 | C#COCC.O=C(O)C1CCS(=O)(=O)CC1>>CCOC1=CC(=O)C12CCS(=O)(=O)CC2 | O=S1(CCC(CC1)C(=O)O)=O.CN(C)C=O.C(C(=O)Cl)(=O)Cl.C(C)OC#C>>C(C)OC1=CC(C12CCS(CC2)(=O)=O)=O | [CH3:1][CH2:2][O:3][C:4]#[CH:5].O[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][S:11](=[O:12])(=[O:13])[CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]12[CH2:9][CH2:10][S:11](=[O:12])(=[O:13])[CH2:14][CH2:15]2 | C#COCC.O=C(O)C1CCS(=O)(=O)CC1 | CCOC1=CC(=O)C12CCS(=O)(=O)CC2 | null | null | C(C)N(CC)CC.C(Cl)Cl.C1CCOC1 | C-C Coupling | OtherReaction | cc6c2e9108ce0b4228cc06b23244e707a0e090aad2d39a3af9d2b2825d44158c | dac41dc1e31f30afcf82042394adb16671be6d0e6e3e55a34dff0a46cdeb04af | O=C1C=CC12CCS(=O)(=O)CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5]-[#16:6]-[C:7]-[C:8]-1.[C:9]-[#8:10]-[C;H0;D2;+0:11]#[CH;D1;+0:12]>>[C:9]-[#8:10]-[C;H0;D3;+0:11]1=[CH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]-12-[C:4]-[C:5]-[#16:6]-[C:7]-[C:8]-2 | 67 | [{"value": 67.0, "product": "C(C)OC1=CC(C12CCS(CC2)(=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A solution of 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid (10.2 g, 57.3 mmol) [prepared according to the procedure of Org. Prep. Proc. Into 1977, 94] and DMF (0.3 ml) in DCM (120 ml) at rt, was treated dropwise with oxalyl chloride and the resulting slurry stirred for 3 d. The crude reaction was then concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Alkyne | Ketone.Ether | C1CCSCC1 | C1=CC2(C1)CCSCC2 | C1=CC2(C1)CCSCC2 | HO- | C(C)N(CC)CC.C(Cl)Cl.C1CCOC1 | null | 72 | C#COCC.O=C(O)C1CCS(=O)(=O)CC1>C(C)N(CC)CC.C(Cl)Cl.C1CCOC1>CCOC1=CC(=O)C12CCS(=O)(=O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f6e989318734b8a89e7730529b961dd | CCN(CC)CC.O=C(O)C1CC=CC1>>CCOC1=CC(=O)C12CC=CC2 | C(C)N(CC)CC.C1(CC=CC1)C(=O)O.CN(C)C=O.C(C(=O)Cl)(=O)Cl>>C(C)OC1=CC(C12CC=CC2)=O | CCN(CC)[CH2:2][CH3:1].[OH:3][C:4](=[O:7])[CH:8]1[CH2:9][CH:10]=[CH:11][CH2:12]1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]12[CH2:9][CH:10]=[CH:11][CH2:12]2 | CCN(CC)CC.O=C(O)C1CC=CC1 | CCOC1=CC(=O)C12CC=CC2 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | d94731a06c038c917274ebcf9771851539aa273c8d884944678324ec05bbc1d1 | a24328de03c104bb7da37f7e3c743a73679f810b1c8c02dab9ff18cc0b3b312d | O=C1C=CC12CC=CC2 | C-C-N(-C-C)-[CH2;D2;+0:1]-[C;D1;H3:2].[O;H0;D1;+0:3]=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[CH;D3;+0:6]1-[C:7]-[C:8]=[C:9]-[C:10]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C;H0;D3;+0:4]1=[C:11]-[C:12](=[O;H0;D1;+0:3])-[C;H0;D4;+0:6]-12-[C:7]-[C:8]=[C:9]-[C:10]-2 | 73 | [{"value": 73.0, "product": "C(C)OC1=CC(C12CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.7, "product": "C(C)OC1=CC(C12CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | A solution of cyclopent-3-ene carboxylic acid (4.0 g, 36.0 mmol) and DMF (0.25 ml) in DCM (30 ml) at 0° was treated dropwise with oxalyl chloride (3.5 ml, 39.0 mmol). After 2 h the reaction mixture was concentrated in vacuo, the residual slurry diluted with Et2O (100 ml) and the resulting precipitate removed by filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Ketone.Ether | C1=CCCC1 | C1=CCC2(C=CC2)C1 | C1=CCC2(C=CC2)C1 | Other | C(Cl)Cl | null | 168 | CCN(CC)CC.O=C(O)C1CC=CC1>C(Cl)Cl>CCOC1=CC(=O)C12CC=CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35ce76e5392747089e6b845de4ff1a2c | CC(C(=O)O)c1ccccc1.CCN(CC)CC.CN(C)C=O>>CCOC1=CC(=O)C1(C)c1ccccc1 | C1(=CC=CC=C1)C(C(=O)O)C.CN(C)C=O.C(Cl)Cl.C(C)N(CC)CC>>C(C)OC1=CC(C1(C1=CC=CC=C1)C)=O | O[C:6](=[O:7])[CH:8]([CH3:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.CCN(CC)[CH2:2][CH3:1].CN(C)[CH:4]=[O:3]>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][C:6](=[O:7])[C:8]1([CH3:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(C(=O)O)c1ccccc1.CCN(CC)CC.CN(C)C=O | CCOC1=CC(=O)C1(C)c1ccccc1 | null | C(C(=O)Cl)(=O)Cl | null | C-C Coupling | OtherReaction | 47bebffaa0a2ebb09e1edae0c3a3eedeb9e855f9b0cf1cebe7dd9829dadbc4ec | 89d1cff69fb36b3e8a85687fb42e89438fb23a3aa77edbd05fe39b114511e191 | O=C1C=CC1c1ccccc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[C;D1;H3:2].C-N(-C)-[CH;D2;+0:3]=[O;H0;D1;+0:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[C;D1;H3:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[C;H0;D3;+0:3]1=[C:12]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D4;+0:7]-1(-[C;D1;H3:8])-[c:9](:[c:10]):[c:11] | 45 | [{"value": 45.0, "product": "C(C)OC1=CC(C1(C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | A solution of (±)2-phenylpropionic acid (10.0 g, 0.66 mmol) and DMF (0.3 ml) in DCM (150 ml) was treated dropwise with oxalyl chloride (6.4 ml, 0.72 mmol). After 1 h the reaction mixture was concentrated in vacuo, the residual slurry diluted with Et2O (200 ml) and the resulting precipitate removed by filtration. The fi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Tertiary amine | Ketone.Ether | null | C1=CCC1 | C1=CCC1.c1ccccc1 | HO- | C(C(=O)Cl)(=O)Cl | null | 168 | CC(C(=O)O)c1ccccc1.CCN(CC)CC.CN(C)C=O>C(C(=O)Cl)(=O)Cl>CCOC1=CC(=O)C1(C)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dce8901bfd4746d6b2a681ec859933dd | BrCc1ccccc1.C#COCC>>CCOC#CCc1ccccc1 | C(C1=CC=CC=C1)Br.CN(C)P(=O)(N(C)C)N(C)C.C(C)OC#C.C(CCC)[Li]>>C(C)OC#CCC1=CC=CC=C1 | Br[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[CH3:1][CH2:2][O:3][C:4]#[CH:5]>>[CH3:1][CH2:2][O:3][C:4]#[C:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | BrCc1ccccc1.C#COCC | CCOC#CCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | a2902088eeffba8af7cde0e465024f8c5b6cd6239687cb7ab88d93a01519cd51 | 65c5c213019f4e08c3c32f7e1ced539ac3ff1efc4a39855e6d21bd16502eefc5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6]#[CH;D1;+0:7]>>[#8:5]-[C:6]#[C;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 99 | [{"value": 99.0, "product": "C(C)OC#CCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of ethoxy acetylene (9.95 g of 50% w/w. solution in hexanes, 70 mmol) in THF (100 ml) at −78° was added n-butyl lithium (31 ml of 2.5M solution in hexanes, 78 mmol). The mixture was stirred at this temperature for 2 h. prior to the addition of HMPA (20 ml), stirring was continued for a further 15 min. bef... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkyne | Alkyne | null | null | c1ccccc1 | HBr | C1CCOC1 | null | 2 | BrCc1ccccc1.C#COCC>C1CCOC1>CCOC#CCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8f295c03bc04286a9d255561101a4c3 | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1C=C(O)C12CCCCC2>>COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCCCC2 | N[C@H](C(=O)OC)CC1=CC(=C(C(=C1)OC)C1=CC=CC=C1)OC.O=C1C=C(C12CCCCC2)O>>O=C1C=C(C12CCCCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]([O:20][CH3:21])[cH:22]1)[NH2:23].O[C:24]1=[CH:25][C:26](=[O:27])[C:28]12[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][c:9]([O:10][CH3:11])... | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1C=C(O)C12CCCCC2 | COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCCCC2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 17ac8c2644828bfdfb238b1bb2ba1e9ab20745211d5e71bf450cafc1322a15fd | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1C=C(NCCc2ccc(-c3ccccc3)cc2)C12CCCCC2 | O-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-1(-[C:6])-[C:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:6]-[C:5]1(-[C:7])-[C:3](=[O;D1;H0:4])-[C:2]=[C;H0;D3;+0:1]-1-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14] | 93.4 | [{"value": 92.0, "product": "O=C1C=C(C12CCCCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "O=C1C=C(C12CCCCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution of methyl(2S)-2-amino-3-(2,6-dimethoxy[1,1′-biphenyl]-4-yl)propanoate (0.80 g, 2.5 mmol) in DCM (10 ml) at room temperature was added 1-keto-3-hydroxyspiro[3,5]-non-2-ene (0.38 g, 2.5 mmol) and the mixture stirred for 48 h. Volatiles were removed in vacuo and the residue purified by column chromatography ... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | C1=CC2(C1)CCCCC2 | C1=CC2(C1)CCCCC2 | c1ccccc1.c1ccccc1.C1=CC2(C1)CCCCC2 | HO- | C(Cl)Cl | null | 48 | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1C=C(O)C12CCCCC2>C(Cl)Cl>COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c850da0a55a4fd8a05538f92cc05245 | CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2=CC=CN(C)C2)C(=O)C12CCCCC2>>CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2CCCN(C)C2)C(=O)C12CCCCC2 | [I-].ClC1=C(C(=O)NC2=CC=C(C=C2)C[C@@H](C(=O)OCC)NC2=C(C(C23CCCCC3)=O)C=3CN(C=CC3)C)C(=CN=C1)Cl.[H][H]>>ClC1=C(C(=O)NC2=CC=C(C=C2)C[C@@H](C(=O)OCC)NC2=C(C(C23CCCCC3)=O)C3CN(CCC3)C)C(=CN=C1)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]2[c:16]([Cl:17])[cH:18][n:19][cH:20][c:21]2[Cl:22])[cH:23][cH:24]1)[NH:25][C:26]1=[C:27]([C:28]2=[CH:29][CH:30]=[CH:31][N:32]([CH3:33])[CH2:34]2)[C:35](=[O:36])[C:37]12[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2>>[CH3:1][... | CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2=CC=CN(C)C2)C(=O)C12CCCCC2 | CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2CCCN(C)C2)C(=O)C12CCCCC2 | null | [Pt](=O)=O | CCO | Reduction | OtherReaction | 51d8ec187963efacb1d62071530224679e3abfc3f8968b881ea6453b66a7d533 | 5013696d2eaf3ae5341916902d6a7d82a0bbf185f361a8c1eff4df8b05ab762b | O=C(Nc1ccc(CCNC2=C(C3CCCNC3)C(=O)C23CCCCC3)cc1)c1ccncc1 | [#7:1]-[C:2]1=[C:3](-[C;H0;D3;+0:4]2=[CH;D2;+0:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C:10]-2)-[C:11](=[O;D1;H0:12])-[C:13]-1>>[#7:1]-[C:2]1=[C:3](-[CH;D3;+0:4]2-[C:10]-[#7:8](-[C;D1;H3:9])-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-2)-[C:11](=[O;D1;H0:12])-[C:13]-1 | 100.1 | [{"value": 100.0, "product": "ClC1=C(C(=O)NC2=CC=C(C=C2)C[C@@H](C(=O)OCC)NC2=C(C(C23CCCCC3)=O)C3CN(CCC3)C)C(=CN=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "ClC1=C(C(=O)NC2=CC=C(C=C2)C[C@@H](C(=O)OCC)NC2=C(C(C23CCCCC3)=O)C3CN(CCC3)C)C(=CN=C1)Cl", "details": "CALCULATEDPERCENTYIE... | null | null | null | null | The compound of Example 86 (127 mg, 0.21 mmol) was dissolved in EtOH (10 ml) and hydrogenated over platinum dioxide (50 mg) at room temperature and 1 atmosphere hydrogen for 5 days. The catalyst was removed by evaporation in vacuo to afford the title compound as a yellow oil (129 mg, 100%). δH (DMSO d6) 10.48 (1H, br s... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Conjugated diene | null | C1=CC[NH]C=C1 | C1CC[NH]CC1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.C1=CC2(C1)CCCCC2 | null | [Pt](=O)=O.CCO | null | null | CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2=CC=CN(C)C2)C(=O)C12CCCCC2>[Pt](=O)=O.CCO>CCOC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cncc2Cl)cc1)NC1=C(C2CCCN(C)C2)C(=O)C12CCCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe87a3f2303146a9bbce8cc5f0dca776 | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1CC(=O)C12CCOCC2>>COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCOCC2 | N[C@H](C(=O)OC)CC1=CC(=C(C(=C1)OC)C1=CC=CC=C1)OC.C1(CC(C12CCOCC2)=O)=O>>O=C1C=C(C12CCOCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]([O:20][CH3:21])[cH:22]1)[NH2:23].O=[C:24]1[CH2:25][C:26](=[O:27])[C:28]12[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][c:9]([O:10][CH3:11])[... | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1CC(=O)C12CCOCC2 | COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCOCC2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 46b6ebd9d7fd3a8f9dbc9bafcd69df2fa897785fd81139fb1f89d2843be62c75 | 9b8ae7e5b30e191314c6441607ab55dc332b8bb8a66eba32f5a7b73c6f6f2034 | O=C1C=C(NCCc2ccc(-c3ccccc3)cc2)C12CCOCC2 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[C:5]-1(-[C:6])-[C:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:6]-[C:5]1(-[C:7])-[C:3](=[O;D1;H0:4])-[CH;D2;+0:2]=[C;H0;D3;+0:1]-1-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14] | 86 | [{"value": 86.0, "product": "O=C1C=C(C12CCOCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "O=C1C=C(C12CCOCC2)N[C@H](C(=O)OC)CC2=CC(=C(C(=C2)OC)C2=CC=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a similar procedure to that for the preparation the compound of Example 38 from methyl(2S)-2-amino-3-(2,6-dimethoxy[1,1′-biphenyl]-4-yl)propanoate (2.0 g, 6.3 mmol) and 7-oxaspiro[3.5]nonane-1,3-dione (1.1 g, 1.1 eq) in DCM (30 ml) was prepared the title compound as a white foam (2.4 g, 86%). δH (300 MHz, DMSO d6... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | Enamine | C1CC2(C1)CCOCC2 | C1=CC2(C1)CCOCC2 | c1ccccc1.c1ccccc1.C1=CC2(C1)CCOCC2 | HO- | C(Cl)Cl | null | null | COC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1.O=C1CC(=O)C12CCOCC2>C(Cl)Cl>COC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C12CCOCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99561aa460fb457586889e44f3f7103f | CC1(C)C(=O)C=C1O.CCOC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1>>CCOC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C1(C)C | N[C@H](C(=O)OCC)CC1=CC(=C(C(=C1)OC)C1=CC=CC=C1)OC.OC1=CC(C1(C)C)=O>>CC1(C(C=C1N[C@H](C(=O)OCC)CC1=CC(=C(C(=C1)OC)C1=CC=CC=C1)OC)=O)C | O[C:25]1=[CH:26][C:27](=[O:28])[C:29]1([CH3:30])[CH3:31].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][c:10]([O:11][CH3:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]([O:21][CH3:22])[cH:23]1)[NH2:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][c:10]([O:11][CH3:12])[c:13](-... | CC1(C)C(=O)C=C1O.CCOC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1 | CCOC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C1(C)C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 57260fa78c9f7bcaab387bba7dc29977a372c63ab9449fa266c84e16ab2c73dc | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1C=C(NCCc2ccc(-c3ccccc3)cc2)C1 | O-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-1(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH2;D1;+0:14]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH;D2;+0:14]-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-1(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | null | null | The title compound was prepared in a similar manner to that of the compound of Example 41 from ethyl(2S)-2-amino-3-(2,6-dimethoxy[1,1′-biphenyl]-4-yl)propanoate (1.5 g, 4.5 mol), and 3-hydroxy-4,4-dimethyl-2-cyclobutenone (0.5 g, 4.5 mmol) in DCM (15 ml) as a white foam (1.8 g, 93%). δH (300 MHz, DMSO d6) 8.68 (1H, d, ... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | C1=CCC1 | C1=CCC1 | c1ccccc1.c1ccccc1.C1=CCC1 | HO- | C(Cl)Cl | null | null | CC1(C)C(=O)C=C1O.CCOC(=O)[C@@H](N)Cc1cc(OC)c(-c2ccccc2)c(OC)c1>C(Cl)Cl>CCOC(=O)[C@H](Cc1cc(OC)c(-c2ccccc2)c(OC)c1)NC1=CC(=O)C1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-167c65b36ef045c2878dd95c113c12bc | O=C(O)N1CCCCC1.O=[N+]([O-])c1cccnc1Cl>>O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1 | CN1CCCC1=O.ClC1=NC=CC=C1[N+](=O)[O-].N1(CCCCC1)C(=O)O.C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C=1C(=NC=CC1)N1CCC(CC1)C(=O)O | [O:1]=[C:2]([OH:3])[N:7]1[CH2:6][CH2:5][CH2:4][CH2:18][CH2:17]1.Cl[c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[N+:14](=[O:15])[O-:16])[CH2:17][CH2:18]1 | O=C(O)N1CCCCC1.O=[N+]([O-])c1cccnc1Cl | O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1 | null | null | O | C-C Coupling | OtherReaction | 42d56df93a3e4e12deb7149eca4d733b256f10dfa62aae693f2005bdfe45d1dc | 8547c7c0f759e211ed067d629583b98e3ebffff0ca3dc4d0622bd64f5aa97315 | c1ccc(N2CCCCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-[O;D1;H1:9])-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[CH2;D2;+0:13]-[C:14]-[C:15]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[CH;D3;+0:13](-[C;H0;D3;+0:8](=[O;D1;H0:7])-[O;D1;H1:9])-[C:14]-[C:15]-1):[#7;a:2]:[c:3] | null | [] | 80 | CELSIUS | 2 | HOUR | The mixture consisting of 634 mg of 2-chloro-3-nitropyridine, 620 mg of piperidine carboxylic acid, 820 mg of potash and 3 ml of NMP was stirred at 80° C. for 2 hours. After allowing to cool, 30 ml of water of water were added and the crude product was extracted with 30 ml of ethyl acetate. After drying the organic pha... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic acid | Carboxylic acid.Tertiary amine | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HCl | O | 80 | 2 | O=C(O)N1CCCCC1.O=[N+]([O-])c1cccnc1Cl>O>O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad0cb22618c14d2a9255bd81c545f040 | O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1>>Nc1cccnc1N1CCC(C(=O)O)CC1 | [N+](=O)([O-])C=1C(=NC=CC1)N1CCC(CC1)C(=O)O.[Sn](Cl)Cl>>NC=1C(=NC=CC1)N1CCC(CC1)C(=O)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1 | O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1 | Nc1cccnc1N1CCC(C(=O)O)CC1 | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCCC2)nc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#7:5]):[#7;a:6]:[c:7]>>[#7:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 3 | HOUR | The solution of 850 mg of 3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid in 40 ml of ethyl acetate was admixed with 2.3 g of tin(II) chloride and stirred at room temperature for 3 hours. The mixture was then extracted with 50 ml of water, the aqueous phase was adjusted to pH=6 using sodium dihydroge... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.C1CC[NH]CC1 | Other | C(C)(=O)OCC | null | 3 | O=C(O)C1CCN(c2ncccc2[N+](=O)[O-])CC1>C(C)(=O)OCC>Nc1cccnc1N1CCC(C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b240956428b41c69bc0ee351e85c0e9 | O=C(NC(=O)c1cc(F)c(F)cc1Cl)Nc1cccnc1N1CCC(C(=O)O)CC1.[NH4+]>>NC(=O)C1CCN(c2ncccc2NC(=O)NC(=O)c2cc(F)c(F)cc2Cl)CC1 | CCN(C(C)C)C(C)C.ClC1=C(C(=O)NC(NC=2C(=NC=CC2)N2CCC(CC2)C(=O)O)=O)C=C(C(=C1)F)F.CN(C)C=O.[Cl-].[NH4+]>>ClC1=C(C(=O)NC(NC=2C(=NC=CC2)N2CCC(CC2)C(=O)N)=O)C=C(C(=C1)F)F | O[C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[NH:14][C:15](=[O:16])[NH:17][C:18](=[O:19])[c:20]2[cH:21][c:22]([F:23])[c:24]([F:25])[cH:26][c:27]2[Cl:28])[CH2:29][CH2:30]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[NH:14][C:15](=[O:... | O=C(NC(=O)c1cc(F)c(F)cc1Cl)Nc1cccnc1N1CCC(C(=O)O)CC1.[NH4+] | NC(=O)C1CCN(c2ncccc2NC(=O)NC(=O)c2cc(F)c(F)cc2Cl)CC1 | null | null | O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(NC(=O)c1ccccc1)Nc1cccnc1N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 2 | HOUR | The mixture consisting of 50 mg of 3′-[3-(2-chloro-4,5-difluorobenzoyl)ureido]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid, 0.5 ml of DMF, 6.1 mg of ammonium chlorid, 40 μl of Hunig's base and 37.3 mg of Totu was stirred at room temperature for 2 hours. Afterwards, it was diluted with 5 ml of water and th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HO- | O | null | 2 | O=C(NC(=O)c1cc(F)c(F)cc1Cl)Nc1cccnc1N1CCC(C(=O)O)CC1.[NH4+]>O>NC(=O)C1CCN(c2ncccc2NC(=O)NC(=O)c2cc(F)c(F)cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d53a21ed7ab44bd09fe0c7f4e788d4b5 | CCOC(=O)NN.Clc1nccc2ccc(Br)cc12>>O=c1[nH]nc2c3cc(Br)ccc3ccn12 | BrC1=CC=C2C=CN=C(C2=C1)Cl.C(NN)(=O)OCC>>BrC1=CC=C2C=CN3C(C2=C1)=NNC3=O | CCO[C:2](=[O:1])[NH:3][NH2:4].Cl[c:5]1[c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]1>>[O:1]=[c:2]1[nH:3][n:4][c:5]2[c:6]3[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]3[cH:13][cH:14][n:15]12 | CCOC(=O)NN.Clc1nccc2ccc(Br)cc12 | O=c1[nH]nc2c3cc(Br)ccc3ccn12 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 80bb0aab2bea056d6d1de1412089b1ac902955bd8d4cc08cce3251f276330616 | 7ea8a4abcfbf128ea24dc1847de0d89ffdd342d48377b983761322e60008422e | O=c1[nH]nc2c3ccccc3ccn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[NH2;D1;+0:4].Cl-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7]:[c:8]:[c:9]:[c:10]:1:[c:11]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]2:[c:10](:[c:11]):[c:9]:[c:8]:[c:7]:[n;H0;D3;+0:6]:1:2 | null | [] | null | null | null | null | 7-Bromo-1-chloroisoquinoline (1-1) (79 mg, 0.327 mmol, 1.0 equiv) and Ethyl carbazate (34 mg, 0.33 mmol, 1.0 equiv) were suspended in EtOH (1.5 mL). The reaction mixture was irradiated in microwave at 170° C. for 40 minutes. The crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aromatic halide.Carbamic ester.Ether | null | c1ccc2cnccc2c1 | c1ccc2ccn3cnnc3c2c1 | c1ccc2ccn3cnnc3c2c1 | HCl | CCO | null | null | CCOC(=O)NN.Clc1nccc2ccc(Br)cc12>CCO>O=c1[nH]nc2c3cc(Br)ccc3ccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03519a848bbe4761a45defd94301e86d | CC(C)(C)OC(=O)NCCBr.Oc1cnc(Cl)c2ccccc12>>CC(C)(C)OC(=O)NCCOc1cnc(Cl)c2ccccc12 | ClC1=NC=C(C2=CC=CC=C12)O.C(=O)([O-])[O-].[Cs+].[Cs+].BrCCNC(OC(C)(C)C)=O>>ClC1=NC=C(C2=CC=CC=C12)OCCNC(OC(C)(C)C)=O | Br[CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:11][c:12]1[cH:13][n:14][c:15]([Cl:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][n:14][c:15]([Cl:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CC(C)(C)OC(=O)NCCBr.Oc1cnc(Cl)c2ccccc12 | CC(C)(C)OC(=O)NCCOc1cnc(Cl)c2ccccc12 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2cnccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H0:5])-[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16] | null | [] | null | null | null | null | 1-chloro-4-hydroxyisoquinoline (50 mg, 0.28 mmol, 1.0 equiv), Cs2CO3 (454 mg, 1.39 mmol, 5.0 equiv.), and tert-butyl (2-bromoethyl)carbamate (2-2) (94 mg, 0.42 mmol, 1.5 equiv.) were suspended in anhydrous DMSO (2 mL) and stirred at room temperature. When LCMS indicated the reaction was complete, the crude reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2cnccc2c1 | HBr | CS(=O)C | null | null | CC(C)(C)OC(=O)NCCBr.Oc1cnc(Cl)c2ccccc12>CS(=O)C>CC(C)(C)OC(=O)NCCOc1cnc(Cl)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efc5cfcb18e3442fbfddda25730b794d | Clc1ccc2c(Br)cncc2c1>>[O-][n+]1cc(Br)c2ccc(Cl)cc2c1 | BrC1=CN=CC2=CC(=CC=C12)Cl.C1=CC(=CC(=C1)Cl)C(=O)OO.CCOCC>>BrC1=C[N+](=CC2=CC(=CC=C12)Cl)[O-] | [n:2]1[cH:3][c:4]([Br:5])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]2[cH:13]1>>[O-:1][n+:2]1[cH:3][c:4]([Br:5])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]2[cH:13]1 | Clc1ccc2c(Br)cncc2c1 | [O-][n+]1cc(Br)c2ccc(Cl)cc2c1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | e816787d3181379d6e882fc3df8c6c53f8584b001030fa5dbc8477f30a7e2118 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2c[nH+]ccc2c1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4]:[c:5] | null | [] | null | null | null | null | 4-bromo-7-chloroisoquinoline (3-6)(1 g, 4.12 mmol, 1.0 equiv.) was dissolved in anhydrous CH2Cl2 (8.2 mL) and treated with mCPBA (1.622 g, 9.40 mmol, 2.3 equiv.). The reaction mixture was stirred at room temperature, forming 3-7 as a white precipitate. Following dilution with Et2O, the solid was collected and used with... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2cnccc2c1 | C1=[NH+]C=c2ccccc2=C1 | C1=[NH+]C=c2ccccc2=C1 | null | C(Cl)Cl | null | null | Clc1ccc2c(Br)cncc2c1>C(Cl)Cl>[O-][n+]1cc(Br)c2ccc(Cl)cc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bd7798b5bd140359c3971cf33485571 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2ccc(Cl)cc2c1>>Clc1ccc2c(Br)cnc(Cl)c2c1 | BrC1=C[N+](=CC2=CC(=CC=C12)Cl)[O-].P(=O)(Cl)(Cl)Cl>>BrC1=CN=C(C2=CC(=CC=C12)Cl)Cl | O=P(Cl)(Cl)[Cl:11].[O-][n+:9]1[cH:8][c:6]([Br:7])[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:13][c:12]2[cH:10]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Br:7])[cH:8][n:9][c:10]([Cl:11])[c:12]2[cH:13]1 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2ccc(Cl)cc2c1 | Clc1ccc2c(Br)cnc(Cl)c2c1 | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC | Miscellaneous | OtherReaction | c1ddf9f61a552d85584c44bbda3ba3111579c62a279f9a96c290301ec90471a7 | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc2cnccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[c:5]:[c:6](:[c:7]):[cH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:2]:[c:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 66 | CELSIUS | 3 | HOUR | 4-bromo-7-chloroisoquinoline 2-oxide (3-7) (1.2 g, 4.64 mmol, 1.0 equiv.) was dissolved in anhydrous CHCl3 (20 mL) and treated dropwise with phosphorus oxychloride (0.649 mL, 6.96 mmol, 1.5 equiv.). The reaction mixture was refluxed at 66° C. LCMS after 3 hours showed only product. The reaction mixture was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=[NH+]C=c2ccccc2=C1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HCl | C(Cl)(Cl)Cl.C(C)(=O)OCC | 66 | 3 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2ccc(Cl)cc2c1>C(Cl)(Cl)Cl.C(C)(=O)OCC>Clc1ccc2c(Br)cnc(Cl)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d866d13c699e425cadf4e782d6af76db | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc(Cl)ccc3c(Br)cn12>>CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | BrC1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O.C(C)(C)(C)OC(NC\C=C\B1OC(C(O1)(C)C)(C)C)=O>>C(C)(C)(C)OC(NC\C=C\C1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)=O | CC1(C)OB(/[CH:11]=[CH:10]/[CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])OC1(C)C.Br[c:12]1[cH:13][n:14]2[c:15](=[O:16])[nH:17][n:18][c:19]2[c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9]/[CH:10]=[CH:11]/[c:12]1[cH:13][n:14]2[c:15](=[O:16]... | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc(Cl)ccc3c(Br)cn12 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | null | null | O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | C-C Coupling | Suzuki coupling with boronic esters | a0ff835bbc703e774eb2407533927c954789107a0ec16d40a5f24637791c01e5 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=c1[nH]nc2c3ccccc3ccn12 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]2:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1:[c:10].C-C1(-C)-O-B(/[CH;D2;+0:11]=[C:12]/[C:13]-[#7:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21])-O-C-1(-C)-C>>[C;D1;H3:19]-[C:18](-[C;D1;H3:20])(-[C;D1;H3:21])-[#8:17]-[C:15](=[O;D1;H0:16])-[#7:14]-... | null | [] | 100 | CELSIUS | 18 | HOUR | 6-bromo-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (3-9) (60 mg, 0.201 mmol, 1.0 equiv.) and tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (228 mg, 0.804 mmol, 4.0 equiv.) were dissolved in anhydrous 1,4-dioxane (0.6 ml) and 2 M K2CO3 aqueous solution (0.2 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccc2ccn3cnnc3c2c1 | c1ccc2ccn3cnnc3c2c1 | c1ccc2ccn3cnnc3c2c1 | HBr.B | O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | 100 | 18 | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc(Cl)ccc3c(Br)cn12>O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0f75c4e6bde457c863d63acf4a87886 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>>NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | C(C)(C)(C)OC(NC\C=C\C1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)=O>>NC/C=C/C1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O | CC(C)(C)OC(=O)[NH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7]2[c:8](=[O:9])[nH:10][n:11][c:12]2[c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]12>>[NH2:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7]2[c:8](=[O:9])[nH:10][n:11][c:12]2[c:13]2[cH:14][c:15]([Cl:16])[cH:17][cH:18][c:19]12 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | null | null | CC#N.C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1[nH]nc2c3ccccc3ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]/[C:3]=[C:4]/[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]/[C:4]=[C:3]/[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | tert-butyl[(2E)-3-(9-chloro-3-oxo-2,3-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (3-10) was dissolved in CH3CN (10 mL) with 0.1% TFA present. The resulted solution was irradiated in microwave at 150° C. for 5 minutes. LCMS showed only product. The crude mixture was purified with reverse phas... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2ccn3cnnc3c2c1 | HO- | CC#N.C(=O)(C(F)(F)F)O | null | null | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>CC#N.C(=O)(C(F)(F)F)O>NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-921ff8c7e2ab4625894cbbacc16e798f | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>>CC(C)(C)OC(=O)NCCCc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | C(C)(C)(C)OC(NC\C=C\C1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)=O.[H][H]>>C(C)(C)(C)OC(NCCCC1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9]/[CH:10]=[CH:11]/[c:12]1[cH:13][n:14]2[c:15](=[O:16])[nH:17][n:18][c:19]2[c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][c:12]1[cH:13][n:14]2[c:15](=[O:16])[nH:17][n:18][c:19]2... | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | CC(C)(C)OC(=O)NCCCc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | null | [OH-].[OH-].[Pd+2] | CCO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1[nH]nc2c3ccccc3ccn12 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]/[CH;D2;+0:10]=[CH;D2;+0:11]/[c:12](:[c:13]):[c:14]:[#7;a:15]1:[c:16]:[#7;a:17]:[#7;a:18]:[c:19]:1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:... | null | [] | null | null | null | null | To a solution of tert-butyl[(2E)-3-(9-chloro-3-oxo-2,3-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (3-10)(14 mg, 0.037 mmol, 1.0 equiv.) in EtOH (4 mL), was added Pd(OH)2/C (20% Pd, 1.3 mg, 0.002 mmol, 0.05 equiv.). The reaction mixture was stirred at room temperature for 1.5 hours under atmo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ccn3cnnc3c2c1 | null | [OH-].[OH-].[Pd+2].CCO | null | null | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>[OH-].[OH-].[Pd+2].CCO>CC(C)(C)OC(=O)NCCCc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa85eaad65b04089ba25b7f5b3de3c66 | C=CCO.[O-][n+]1cc(Br)c2ccccc2c1>>O=CCCc1c[n+]([O-])cc2ccccc12 | BrC1=C[N+](=CC2=CC=CC=C12)[O-].[Cl-].[Li+].C(C)N(CC)CC.C(C=C)O>>[O-][N+]1=CC2=CC=CC=C2C(=C1)CCC=O | [OH:1][CH2:2][CH:3]=[CH2:4].Br[c:5]1[cH:6][n+:7]([O-:8])[cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[O:1]=[CH:2][CH2:3][CH2:4][c:5]1[cH:6][n+:7]([O-:8])[cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | C=CCO.[O-][n+]1cc(Br)c2ccccc2c1 | O=CCCc1c[n+]([O-])cc2ccccc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | Acylation | OtherReaction | 3c39f25e8947e944e054e38557c220e4a5a8b82180f9232e10d1da792c38edcf | 41c2183cce55fcb3ca50640d2af54ecfcad21cf2ab1861841662332052c164bf | c1ccc2c[nH+]ccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a;+:3](-[O;-;D1;H0:4]):[c:5]:[c:6]:[c:7]:1:[c:8].[CH2;D1;+0:9]=[CH;D2;+0:10]-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[O;-;D1;H0:4]-[#7;a;+:3]1:[c:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH;D2;+0:11]=[O;H0;D1;+0:12]):[c:7](:[c:8]):[c:6]:[c:5]:1 | null | [] | 100 | CELSIUS | null | null | 4-bromoisoquinoline 2-oxide (5-2) (500 mg, 2.23 mmol, 1.0 equiv), lithium chloride (95 mg, 2.23 mmol, 1.0 equiv) and palladium(II) acetate (20.04 mg, 0.089 mmol, 0.04 equiv) were dissolved in anhydrous DMF (8.6 mL). To this orange solution, was added triethylamine (933 μl, 6.69 mmol, 3.0 equiv) and allyl alcohol (308 μ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Allyl | Aldehyde | C1=Cc2ccccc2C=[NH+]1 | C1=Cc2ccccc2C=[NH+]1 | C1=Cc2ccccc2C=[NH+]1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | 100 | null | C=CCO.[O-][n+]1cc(Br)c2ccccc2c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>O=CCCc1c[n+]([O-])cc2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2a95c90ae01410ab1c0282bc10143e6 | C=CCN.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=CCCc1c[n+]([O-])cc2cc(Cl)ccc12.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>>C=CCN(CC(F)Cc1c[n+]([O-])cc2cc(Cl)ccc12)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.ClC1=CC=C2C(=C[N+](=CC2=C1)[O-])CCC=O.C1=CC=C(C=C1)S(=O)(=O)N(F)S(=O)(=O)C2=CC=CC=C2.C(C=C)N.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].N1C(C(=O)O)CCC1>>C(C=C)N(C(OC(C)(C)C)=O)CC(CC1=C[N+](=CC2=CC(=CC=C12)Cl)[O-])F | [CH2:1]=[CH:2][CH2:3][NH2:4].CC(C)(C)OC(=O)O[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].O=[CH:5][CH2:6][CH2:8][c:9]1[cH:10][n+:11]([O-:12])[cH:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]12.O=S(=O)(c1ccccc1)N(S(=O)(=O)c1ccccc1)[F:7]>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]([F:7])[CH2:8][c:9]1[cH:10... | C=CCN.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=CCCc1c[n+]([O-])cc2cc(Cl)ccc12.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1 | C=CCN(CC(F)Cc1c[n+]([O-])cc2cc(Cl)ccc12)C(=O)OC(C)(C)C | null | null | C(C)(C)O.C1CCOC1 | Protection | OtherReaction | ac4523c96631043eb2f564e25ad424e28d9253f672dcc5affd2499bcdea892fc | a1dda3cd7c62e480de35344caf1334108de6b472a24d17c36b8a2b81043db3dd | c1ccc2c[nH+]ccc2c1 | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].O=S(=O)(-N(-[F;H0;D1;+0:8])-S(=O)(=O)-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[c:12]:[c:13]:[#7;a;+:14].[C;D1;H2:15]=[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a;+:14]:[c:13]:[c:12]-[C:11]-[CH;D3;+... | null | [] | null | null | 8 | HOUR | 3-(7-chloro-2-oxidoisoquinolin-4-yl)propanal (6-1)(300 mg, 1.27 mmol, 1.0 equiv) and N-fluorobenzenesulfonimide (442 mg, 1.40 mmol, 1.1 equiv) were dissolved in THF (11.6 mL) and isopropyl alcohol (1.16 mL). To this mixture, was added DL-proline (29.3 mg, 0.26 mmol, 0.2 equiv). The reaction mixture was stirred at room ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aldehyde.Carbonic Ester.Carbonic Ester.Primary amine.Tertiary amine.Boc.Boc | Secondary halide.Carbamic ester.Ether.Boc | c1ccccc1.c1ccccc1 | null | C1=Cc2ccccc2C=[NH+]1 | HO- | C(C)(C)O.C1CCOC1 | null | 8 | C=CCN.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=CCCc1c[n+]([O-])cc2cc(Cl)ccc12.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>C(C)(C)O.C1CCOC1>C=CCN(CC(F)Cc1c[n+]([O-])cc2cc(Cl)ccc12)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2926e3e4600e447a87afe72415ea8a63 | C=CCNCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>>NCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | C(C=C)NCC(CC1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)F.CC1=C2C=CC3=CC=CC=C3C2=C(C4=CC=CC=C14)C>>NCC(CC1=CN2C(C3=CC(=CC=C13)Cl)=NNC2=O)F | C=CC[NH:1][CH2:2][CH:3]([F:4])[CH2:5][c:6]1[cH:7][n:8]2[c:9](=[O:10])[nH:11][n:12][c:13]2[c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]12>>[NH2:1][CH2:2][CH:3]([F:4])[CH2:5][c:6]1[cH:7][n:8]2[c:9](=[O:10])[nH:11][n:12][c:13]2[c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]12 | C=CCNCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | NCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 | 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 | C(CCl)Cl | Deprotection | OtherReaction | a3a21d8317e51caa1765631e2a63c508a8bfb44420eeca60e42a65580e84713f | c8ba28e2215b4a1b1e014b5dacbfc5f8bf3624d2d1e715cad957d9e02f946a8a | O=c1[nH]nc2c3ccccc3ccn12 | C=C-C-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | 50 | CELSIUS | 5 | HOUR | 6-[3-(allylamino)-2-fluoropropyl]-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (6-4)(18 mg, 0.054 mmol, 1.0 equiv) and DMBA (25.2 mg, 0.16 mmol, 3.0equiv) and tetrakis(triphenylphosphine)palladium(0) (3 mg, 2.60 μmol, 0.05 equiv) were suspended in ClCH2CH2Cl (1 mL). The resulted yellow suspension was heated at 5... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Allyl | Primary amine | null | null | c1ccc2ccn3cnnc3c2c1 | Other | 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.C(CCl)Cl | 50 | 5 | C=CCNCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12>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.C(CCl)Cl>NCC(F)Cc1cn2c(=O)[nH]nc2c2cc(Cl)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fafcb209e0344b24b1ded107304c4640 | O=C(Cl)Oc1ccccc1.O=Cc1cncc(Br)c1.[Zn+][CH2]c1ccccc1>>O=CC1=CN(C(=O)Oc2ccccc2)C=C(Br)C1Cc1ccccc1 | [Cl-].[NH4+].C1(=CC=CC=C1)OC(=O)Cl.BrC=1C=NC=C(C=O)C1.[Br-].C(C1=CC=CC=C1)[Zn+]>>C(C1=CC=CC=C1)C1C(=CN(C=C1C=O)C(=O)OC1=CC=CC=C1)Br | Cl[C:6](=[O:7])[O:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[CH:2][c:3]1[cH:4][n:5][cH:15][c:16]([Br:17])[cH:18]1.[Zn+][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[CH:2][C:3]1=[CH:4][N:5]([C:6](=[O:7])[O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH:15]=[C:16]([Br:17])[CH:18]1[CH2:19][c:20]1[... | O=C(Cl)Oc1ccccc1.O=Cc1cncc(Br)c1.[Zn+][CH2]c1ccccc1 | O=CC1=CN(C(=O)Oc2ccccc2)C=C(Br)C1Cc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ea8e5d34db314555ec9923a8671f11f658222c748ebbd0cc3200c7db6822fc91 | 3be04b37ffda518a0178571703a37461151fdda4f82be096d0b307e692fb4735 | O=C(Oc1ccccc1)N1C=CC(Cc2ccccc2)C=C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[Br;D1;H0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[C:11]=[O;D1;H0:12]):[cH;D2;+0:13]:1.[Zn+]-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[Br;D1;H0:5]-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4])-[CH;D... | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of 5-bromonicotinaldehyde (7-1) (930 mg, 5 mmol, 1 eq) in anhydrous THF (10 ml) was cooled to 0° C. and treated with phenylchloroformate (783 mg, 5 mmol, 1eq). The reaction mixture was then stirred at this temperature for 1 h before the addition of benzylzinc bromide (0.5M in THF, 10 ml, 5 mmol, 1eq). The re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aldehyde.Ether | Enamine.Enamine.Alkenyl halide.Aldehyde.Carbamic ester.Ether | c1ccncc1 | C1=C[NH]C=CC1 | C1=C[NH]C=CC1.c1ccccc1.c1ccccc1 | Zn | C1CCOC1 | 0 | 0.5 | O=C(Cl)Oc1ccccc1.O=Cc1cncc(Br)c1.[Zn+][CH2]c1ccccc1>C1CCOC1>O=CC1=CN(C(=O)Oc2ccccc2)C=C(Br)C1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16e2d23641b344a287dd1fa5f719c490 | Brc1cncc2cc3ccccc3cc12>>[O-][n+]1cc(Br)c2cc3ccccc3cc2c1 | BrC1=CN=CC2=CC3=C(C=C12)C=CC=C3.C1=CC(=CC(=C1)Cl)C(=O)OO>>BrC1=C[N+](=CC2=CC3=C(C=C12)C=CC=C3)[O-] | [n:2]1[cH:3][c:4]([Br:5])[c:6]2[cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[cH:14][c:15]2[cH:16]1>>[O-:1][n+:2]1[cH:3][c:4]([Br:5])[c:6]2[cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[cH:14][c:15]2[cH:16]1 | Brc1cncc2cc3ccccc3cc12 | [O-][n+]1cc(Br)c2cc3ccccc3cc2c1 | null | null | ClCCl.CCOCC | Functional Group Interconversion | OtherReaction | 260c61d91180496a3c092bd9345b88e58a93308a22bdbfbe1f4b53db484f170e | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2cc3c[nH+]ccc3cc2c1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4]:[c:5] | null | [] | null | null | null | null | A solution of 4-bromobenzo[g]isoquinoline (7-3) (390 mg, 1.5 mmol, 1. eq) in dichloromethane (25 ml) was treated with mCPBA (˜70%, 559 mg, 2.27 mmol, 1.5 eq) and the reaction mixture was stirred at room temperature until LCMS showed complete conversion. The reaction mixture was diluted with ether, and the precipitate w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2cc3cnccc3cc2c1 | C1=[NH+]C=c2cc3ccccc3cc2=C1 | C1=[NH+]C=c2cc3ccccc3cc2=C1 | null | ClCCl.CCOCC | null | null | Brc1cncc2cc3ccccc3cc12>ClCCl.CCOCC>[O-][n+]1cc(Br)c2cc3ccccc3cc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a993729e79834ce3b754890ae7214468 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2cc3ccccc3cc2c1>>Clc1ncc(Br)c2cc3ccccc3cc12 | BrC1=C[N+](=CC2=CC3=C(C=C12)C=CC=C3)[O-].O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>>BrC1=CN=C(C2=CC3=C(C=C12)C=CC=C3)Cl | O=P(Cl)(Cl)[Cl:1].[O-][n+:3]1[cH:2][c:16]2[c:7]([c:5]([Br:6])[cH:4]1)[cH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[cH:15]2>>[Cl:1][c:2]1[n:3][cH:4][c:5]([Br:6])[c:7]2[cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15][c:16]12 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2cc3ccccc3cc2c1 | Clc1ncc(Br)c2cc3ccccc3cc12 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | efbeb27cae1a5e06b4583a1dcb000faa5a4508c74600893014d356fc6d378f93 | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccc2cc3cnccc3cc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[c:5]:[c:6](:[c:7]):[cH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:2]:[c:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 55 | CELSIUS | 2 | HOUR | 4-Bromo-benzo[g]isoquinoline 2-oxide (7-4) (380 mg, 1.39 mmol, 1 eq) was taken up in a ¼ v/v mixture of POCl3 and chloroform (20 ml) and the resulting solution was stirred at 55° C. for 2 hrs. The reaction mixture was then carefully poured into sat. aq. sodium bicarbonate, extracted with ethyl acetate, dried, and conce... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=Cc2cc3ccccc3cc2C=[NH+]1 | c1ccc2cc3cnccc3cc2c1 | c1ccc2cc3cnccc3cc2c1 | HCl | C(Cl)(Cl)Cl | 55 | 2 | O=P(Cl)(Cl)Cl.[O-][n+]1cc(Br)c2cc3ccccc3cc2c1>C(Cl)(Cl)Cl>Clc1ncc(Br)c2cc3ccccc3cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbe5aaabac674098a7b0bd0b478e03f5 | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc4ccccc4cc3c(Br)cn12>>CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 | C(C)(C)(C)OC(NC\C=C\B1OC(C(O1)(C)C)(C)C)=O.BrC1=CN2C(C3=CC4=C(C=C13)C=CC=C4)=NNC2=O.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(C)(C)OC(NC\C=C\C1=CN2C(C3=CC4=C(C=C13)C=CC=C4)=NNC2=O)=O | CC1(C)OB(/[CH:11]=[CH:10]/[CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])OC1(C)C.Br[c:12]1[cH:13][n:14]2[c:15](=[O:16])[nH:17][n:18][c:19]2[c:20]2[cH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[cH:28][c:29]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9]/[CH:10]=[CH:11]/[c:12]1[cH:13][... | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc4ccccc4cc3c(Br)cn12 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 | null | null | O.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic esters | 0967ab38e7cc0a5abb3b80d45bcd97a9972f23778b7ba3f6187a3f77a436f721 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=c1[nH]nc2c3cc4ccccc4cc3ccn12 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]2:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1:[c:10].C-C1(-C)-O-B(/[CH;D2;+0:11]=[C:12]/[C:13]-[#7:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21])-O-C-1(-C)-C>>[C;D1;H3:19]-[C:18](-[C;D1;H3:20])(-[C;D1;H3:21])-[#8:17]-[C:15](=[O;D1;H0:16])-[#7:14]-... | null | [] | 150 | CELSIUS | null | null | To a solution of tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (32.5 mg, 0.115 mmol, 4 eq) and 6-bromobenzo[g][1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (7-6) (9.0 mg, 0.029 mmol, 1 eq) in THF (0.5 ml) was added a solution of cesium carbonate (18.7 mg, 0.058 mmol, 2 eq) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cn2cnnc2c2cc3ccccc3cc12 | c1cn2cnnc2c2cc3ccccc3cc12 | c1cn2cnnc2c2cc3ccccc3cc12 | HBr.B | O.C1CCOC1 | 150 | null | CC(C)(C)OC(=O)NC/C=C/B1OC(C)(C)C(C)(C)O1.O=c1[nH]nc2c3cc4ccccc4cc3c(Br)cn12>O.C1CCOC1>CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4526d712568842058b2509899892207c | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12>>NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 | C(C)(C)(C)OC(NC\C=C\C1=CN2C(C3=CC4=C(C=C13)C=CC=C4)=NNC2=O)=O.C(=O)(C(F)(F)F)O>>NC/C=C/C1=CN2C(C3=CC4=C(C=C13)C=CC=C4)=NNC2=O.C(=O)(C(F)(F)F)O | CC(C)(C)OC(=O)[NH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7]2[c:8](=[O:9])[nH:10][n:11][c:12]2[c:13]2[cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21][c:22]12>>[NH2:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7]2[c:8](=[O:9])[nH:10][n:11][c:12]2[c:13]2[cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21][c:22]12 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 | NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1[nH]nc2c3cc4ccccc4cc3ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]/[C:3]=[C:4]/[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]/[C:4]=[C:3]/[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 15 | MINUTE | A solution of tert-butyl[(2E)-3-(3-oxo-2,3-dihydrobenzo[g][1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (7-7) (3.0 mg, 0.0077 mmol) in a ¼ mixture of dichloromethane and TFA (1.0 ml) was stirred at room temperature for 15 min and concentrated to dryness to give the deprotected material 7-8 as a TFA sa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cn2cnnc2c2cc3ccccc3cc12 | HO- | ClCCl | null | 0.25 | CC(C)(C)OC(=O)NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12>ClCCl>NC/C=C/c1cn2c(=O)[nH]nc2c2cc3ccccc3cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa87dad73ed14bc492504bd174026490 | NC(N)=O.Nc1cc2ccccc2cc1C(=O)O>>O=c1[nH]c(=O)c2cc3ccccc3cc2[nH]1 | NC=1C(=CC2=CC=CC=C2C1)C(=O)O.NC(=O)N.C1(=CC=CC=C1)O>>N1C(NC(C2=CC3=C(C=C12)C=CC=C3)=O)=O | N[C:2](=[O:1])[NH2:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14][c:15]1[NH2:16]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[c:6]2[cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[cH:14][c:15]2[nH:16]1 | NC(N)=O.Nc1cc2ccccc2cc1C(=O)O | O=c1[nH]c(=O)c2cc3ccccc3cc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1d79357f7c7239242afd250c297ba34777cd598ee8f644c1e3049f035cda8a47 | 29793ec3f3bfbe7b42772e4883b187282e69112be3962ee4c923f744133c810e | O=c1[nH]c(=O)c2cc3ccccc3cc2[nH]1 | N-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[O;D1;H0:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:3]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[c:8](:[c:10]):[c:6](:[c:7]):[c;H0;D3;+0:4](=[O;D1;H0:5]):[nH;D2;+0:2]:1 | null | [] | 185 | CELSIUS | null | null | A mixture of 3-amino-2-naphthoic acid (8-1,1.2 g, 6.6 mmol, 1 equiv), urea (2.0 g, 33 mmol, 5.0 equiv) and phenol (7.0 g, 74 mmol, 11 equiv) was heated at 160° C. for 0.5 h an 185° C. for an additional 1.5 h. The reaction was cooled and triturated with methanol (50 mL). The solid precipitate was filtered, washed with m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Urea.Primary amine | null | c1ccc2ccccc2c1 | c1ncc2cc3ccccc3cc2n1 | c1ncc2cc3ccccc3cc2n1 | HO- | null | 185 | null | NC(N)=O.Nc1cc2ccccc2cc1C(=O)O>>O=c1[nH]c(=O)c2cc3ccccc3cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc6f7ad8053149b7a4b6ec2cfc493544 | CC(C)(C)OC(=O)NCCCBr.CC(C)(C)OC(=O)n1nc2c3cc4ccccc4cc3[nH]c(=O)n2c1=O>>CC(C)(C)OC(=O)NCCCn1c(=O)n2c(=O)n(C(=O)OC(C)(C)C)nc2c2cc3ccccc3cc21 | O=C1N(N=C2N1C(NC=1C=C3C(=CC21)C=CC=C3)=O)C(=O)OC(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)(C)OC(NCCCBr)=O>>C(C)(C)(C)OC(=O)NCCCN1C(N2C(C=3C=C4C(=CC13)C=CC=C4)=NN(C2=O)C(=O)OC(C)(C)C)=O | Br[CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:12]1[c:13](=[O:14])[n:15]2[c:16](=[O:17])[n:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[n:26][c:27]2[c:28]2[cH:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]3[cH:36][c:37]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7... | CC(C)(C)OC(=O)NCCCBr.CC(C)(C)OC(=O)n1nc2c3cc4ccccc4cc3[nH]c(=O)n2c1=O | CC(C)(C)OC(=O)NCCCn1c(=O)n2c(=O)n(C(=O)OC(C)(C)C)nc2c2cc3ccccc3cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ad6101907d8918923c33bea255ae89fe898e3defd77f23e592d01c94a183e468 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]nc2c3cc4ccccc4cc3[nH]c(=O)n12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[nH;D2;+0:6]:[c:7](:[c:8]):[c:9]:[c:10]2:[#7;a:11]:[#7;a:12]:[c:13]:[#7;a:14]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:6]1:[c:5](=[O;D1;H0:4]):[#7;a:14]2:[c:13]:[#7;a:12]:[#7;a:11]:[c:10]:2:[c:9]:[c:7]:1:[c:8] | null | [] | 23 | CELSIUS | 16 | HOUR | A mixture of tert-butyl 3,5-dioxo-5,6-dihydrobenzo[g][1,2,4]triazolo[4,3-c]quinazoline-2(3H)-carboxylate (8-6, 28 mg, 0.079 mmol, 1 equiv), cesium carbonate (100 mg, 0.31 mmol, 3.8 equiv), and N-(3-bromopropyl)carbamic acid tert-butyl ester (50 mg, 0.21 mmol, 2.6 equiv) in DMF (3 mL) was stirred at 23° C. for 16 h. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc2c3cc4ccccc4cc3ncn12 | c1ccc2cc3c(cc2c1)ncn1cnnc31 | c1ccc2cc3c(cc2c1)ncn1cnnc31 | HBr | CN(C)C=O | 23 | 16 | CC(C)(C)OC(=O)NCCCBr.CC(C)(C)OC(=O)n1nc2c3cc4ccccc4cc3[nH]c(=O)n2c1=O>CN(C)C=O>CC(C)(C)OC(=O)NCCCn1c(=O)n2c(=O)n(C(=O)OC(C)(C)C)nc2c2cc3ccccc3cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-237717bf4dbc4636a0c4fa895c531924 | O=C(NCc1ccccn1)c1cccc2ccccc12>>c1ccc2c(-c3ncc4ccccn34)cccc2c1 | C([O-])([O-])=O.[K+].[K+].N1=C(C=CC=C1)CNC(=O)C1=CC=CC2=CC=CC=C12.O=P(Cl)(Cl)Cl>>C1(=CC=CC2=CC=CC=C12)C1=NC=C2N1C=CC=C2 | O=[C:6]([c:5]1[c:4]2[cH:3][cH:2][cH:1][cH:19][c:18]2[cH:17][cH:16][cH:15]1)[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5](-[c:6]3[n:7][cH:8][c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]34)[cH:15][cH:16][cH:17][c:18]2[cH:19]1 | O=C(NCc1ccccn1)c1cccc2ccccc12 | c1ccc2c(-c3ncc4ccccn34)cccc2c1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 1b4e55ff2e0f60e6a44cc161283eee0d751c452ef3ad342b3370f9f671cf0284 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | c1ccc2c(-c3ncc4ccccn34)cccc2c1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[n;H0;D2;+0:6]:[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14]>>[c:5]:[c:4]1:[cH;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14]):[n;H0;D3;+0:6]:1:[c:7]:[c:8] | 72.3 | [{"value": 72.0, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC=C2N1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC=C2N1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of naphthalene-1-carboxylic acid (pyridin-2-ylmethyl)-amide (2.80 g, 10.7 mmol) in toluene (100 mL) was added POCl3 (9 mL). The mixture was heated to 90° C. for 12 h. After this time the mixture was allowed to cool and poured slowly into 10% aqueous potassium carbonate (500 mL). The mixture was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccncc1 | c1ccn2cncc2c1 | c1ccn2cncc2c1.c1ccc2ccccc2c1 | HO- | C1(=CC=CC=C1)C | 90 | null | O=C(NCc1ccccn1)c1cccc2ccccc12>C1(=CC=CC=C1)C>c1ccc2c(-c3ncc4ccccn34)cccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e85b55bfbd644edb481e0577003a65c | CCCC(=O)Cl.c1ccc2c(-c3ncc4ccccn34)cccc2c1>>CCCC(=O)c1nc(-c2cccc3ccccc23)n2ccccc12 | C1(=CC=CC2=CC=CC=C12)C1=NC=C2N1C=CC=C2.C(CCC)(=O)Cl.[Cl-].[Cl-].[Cl-].[Al+3]>>C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(CCC)=O | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[cH:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[n:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[n:19]2[cH:20][cH:21][cH:... | CCCC(=O)Cl.c1ccc2c(-c3ncc4ccccn34)cccc2c1 | CCCC(=O)c1nc(-c2cccc3ccccc23)n2ccccc12 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 7e3083a795f0f1a2311102a499a72fc360598e51bd61eda8201497f129b9883a | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(-c3ncc4ccccn34)cccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[#7;a:6]1:[c:7]:[#7;a:8]:[cH;D2;+0:9]:[c:10]:1:[c:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[#7;a:6](:[c:5]):[c:10]:1:[c:11] | 8 | [{"value": 8.0, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.0, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of butyroylchloride (100 μL, 1.13 mmol) in dichloromethane (10 mL) was added aluminum trichloride (195 mg, 1.47 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-naphthalen-1-yl-imidazo[1,5-a]pyridine (276 mg, 1.13 mmol) in dichloromethane (5 mL) was added. The mixture was stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccc2ccccc2c1.c1ccn2cncc2c1 | HCl | ClCCl | null | 0.166667 | CCCC(=O)Cl.c1ccc2c(-c3ncc4ccccn34)cccc2c1>ClCCl>CCCC(=O)c1nc(-c2cccc3ccccc23)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bec8c995efc45d5bfada90c72dca714 | O=C(O)c1ccccc1I.c1ccc2c(-c3ncc4ccccn34)cccc2c1>>O=C(c1ccccc1I)c1nc(-c2cccc3ccccc23)n2ccccc12 | C1(=CC=CC2=CC=CC=C12)C1=NC=C2N1C=CC=C2.IC1=C(C(=O)O)C=CC=C1.[Cl-].[Cl-].[Cl-].[Al+3]>>IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)C2=CC=CC1=CC=CC=C21 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9].[cH:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]23)[n:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9])[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][... | O=C(O)c1ccccc1I.c1ccc2c(-c3ncc4ccccn34)cccc2c1 | O=C(c1ccccc1I)c1nc(-c2cccc3ccccc23)n2ccccc12 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 39831f2b87da8928d248907cc7532736d3826bbd4647f1e6be9bfa0e8ad4a019 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)c1nc(-c2cccc3ccccc23)n2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[#7;a:7]1:[c:8]:[#7;a:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[#7;a:7](:[c:6]):[c:11]:1:[c:12] | 18.4 | [{"value": 18.0, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)C2=CC=CC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.4, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)C2=CC=CC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 2-iodobenzoic acid (487 mg, 1.83 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (266 mg, 2.00 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-naphthalen-1-yl-imidazo[1,5-a]pyridine (212 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccn2cncc2c1 | HO- | ClCCCl | null | 0.166667 | O=C(O)c1ccccc1I.c1ccc2c(-c3ncc4ccccn34)cccc2c1>ClCCCl>O=C(c1ccccc1I)c1nc(-c2cccc3ccccc23)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ba2a1d370cb4c7aaf54abc6e7c021cb | O=C(c1nc(-c2cccc3ccccc23)n2ccccc12)C(F)(F)F.[OH-]>>O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12 | FC(C(=O)C=1N=C(N2C1C=CC=C2)C2=CC=CC1=CC=CC=C21)(F)F.[OH-].[K+]>>C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(=O)O | FC(F)(F)[C:2](=[O:1])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[n:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[n:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | O=C(c1nc(-c2cccc3ccccc23)n2ccccc12)C(F)(F)F.[OH-] | O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12 | null | null | CCO | Acylation | OtherReaction | 756646b5982ba7b2e2e932b5bd1ff8dac0e125212b25bd0438af537a84702fd6 | 56f806808680643dc41c682f53c8ec81d98ddc60c5b66ee62824a1ba9830c721 | c1ccc2c(-c3ncc4ccccn34)cccc2c1 | F-C(-F)(-F)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[OH-;D0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:10])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 55 | [{"value": 55.0, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,2,2-trifluoro-1-(3-naphthalen-1-yl-imidazo[1,5-a]pyridin-1-yl)-ethanone (260 mg, 0.76 mmol) in EtOH (10 mL) was added KOH (582 mg, 10.4 mmol) and the mixture was heated to reflux for 30 min. The mixture was allowed to cool and concentrated. The residue was dissolved in water (25 mL) and acidified to ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ketone | Carboxylic acid | null | null | c1ccc2ccccc2c1.c1ccn2cncc2c1 | Other | CCO | null | null | O=C(c1nc(-c2cccc3ccccc23)n2ccccc12)C(F)(F)F.[OH-]>CCO>O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8232e22aa0943378d95c5c298ee9d59 | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12>>O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2cccc3ccccc23)n2ccccc12 | C1(=CC=CC2=CC=CC=C12)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CCN(CC)CC.C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)C3=CC=CC2=CC=CC=C32 | [NH2:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:12]1)[CH2:13]2.O[C:2](=[O:1])[c:14]1[n:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]23)[n:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12>>[O:1]=[C:2]([NH:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH... | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12 | O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2cccc3ccccc23)n2ccccc12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2cccc3ccccc23)n2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])(-[C:13])-[C:14]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])(-[C:13])-[C:14] | 84 | [{"value": 84.0, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)C3=CC=CC2=CC=CC=C32", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)C3=CC=CC2=CC=CC=C32", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-naphthalen-1-yl-imidazo[1,5-a]pyridine-1-carboxylic acid (55 mg, 0.19 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1.c1ccn2cncc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(-c2cccc3ccccc23)n2ccccc12>CN(C)C=O.C(C)(=O)OCC>O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2cccc3ccccc23)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d2ea128900d4133b011c310b8a71f54 | CCCCC(=O)O.NCc1ccccn1>>CCCCC(=O)NCc1ccccn1 | NCC1=NC=CC=C1.C(CCCC)(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O>>N1=C(C=CC=C1)CNC(CCCC)=O | O[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1 | CCCCC(=O)O.NCc1ccccn1 | CCCCC(=O)NCc1ccccn1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 92 | [{"value": 92.0, "product": "N1=C(C=CC=C1)CNC(CCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of pentanoic acid (5.3 mL, 48.7 mmol) in THF (50 mL) was added EDC (11.2 g, 58.4 mmol) and HOBt (7.88 g, 58.4 mmol). The mixture was stirred for 10 min. then 2-(aminomethyl)pyridine (4.7 mL, 46.3 mmol) was added. The solution was allowed to stir for 3 h then quenched with water (100 mL). The mixture was e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.166667 | CCCCC(=O)O.NCc1ccccn1>C1CCOC1>CCCCC(=O)NCc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa586203693643e4a025d0751290fc85 | CCCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-]>>CCCCc1nc(C(=O)O)c2ccccn12 | C(CCC)C1=NC(=C2N1C=CC=C2)C(C(F)(F)F)=O.[OH-].[K+]>>C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O | FC(F)(F)[C:8]([c:7]1[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2)=[O:9].[OH-:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]12 | CCCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-] | CCCCc1nc(C(=O)O)c2ccccn12 | null | null | CCO | Acylation | OtherReaction | 756646b5982ba7b2e2e932b5bd1ff8dac0e125212b25bd0438af537a84702fd6 | 56f806808680643dc41c682f53c8ec81d98ddc60c5b66ee62824a1ba9830c721 | c1ccn2cncc2c1 | F-C(-F)(-F)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[OH-;D0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:10])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 62 | [{"value": 62.0, "product": "C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.9, "product": "C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of 1-(3-butyl-imidazo[1,5-a]pyridin-1-yl)-2,2,2-trifluoro-ethanone (400 mg, 1.48 mmol) in EtOH (10 mL) was added KOH (830 mg, 14.8 mmol). The mixture was stirred at ambient temperature for 15 h. After this time the mixture was concentrated, diluted with water (10 mL) and acidified to pH 3 with 2N HCl. The... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ketone | Carboxylic acid | null | null | c1ccn2cncc2c1 | Other | CCO | null | 15 | CCCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-]>CCO>CCCCc1nc(C(=O)O)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a33590c1095a438a9ae560b58fdf0d6a | CCCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2>>CCCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 | C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CCN(CC)CC.C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCCC | O[C:8]([c:7]1[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2)=[O:9].[NH2:10][C:11]12[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:18]3)[CH2:19]1)[CH2:20]2>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([C:8](=[O:9])[NH:10][C:11]23[CH2:12][CH:13]4[CH2:14][CH:15]([CH2:16][CH:17](... | CCCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2 | CCCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC12CC3CC(CC(C3)C1)C2)c1ncn2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])(-[C:13])-[C:14]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])(-[C:13])-[C:14] | 80 | [{"value": 80.0, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (150 mg, 0.56 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was stirred for 15 h the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccn2cncc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | CCCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2>CN(C)C=O.C(C)(=O)OCC>CCCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2be2ca97ad3e499caa174684a31156f4 | CCCC(=O)O.NCc1ccccn1>>CCCC(=O)NCc1ccccn1 | NCC1=NC=CC=C1.C(CCC)(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O>>N1=C(C=CC=C1)CNC(CCC)=O | O[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1 | CCCC(=O)O.NCc1ccccn1 | CCCC(=O)NCc1ccccn1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 67.1 | [{"value": 67.0, "product": "N1=C(C=CC=C1)CNC(CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "N1=C(C=CC=C1)CNC(CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of butyric acid (4.5 mL, 48.7 mmol) in THF (50 mL) was added EDC (11.2 g, 58.4 mmol) and HOBt (7.88 g, 58.4 mmol). The mixture was stirred for 10 min. then 2-(aminomethyl)pyridine (4.7 mL, 46.3 mmol) was added. The solution was allowed to stir for 3 h then quenched with water (100 mL). The mixture was ext... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.166667 | CCCC(=O)O.NCc1ccccn1>C1CCOC1>CCCC(=O)NCc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae8899dc610b4f739c22e27bf6b1eba5 | CCCc1ncc2ccccn12.O=C(Cl)c1cccc2ccccc12>>CCCc1nc(C(=O)c2cccc3ccccc23)c2ccccn12 | C(CC)C1=NC=C2N1C=CC=C2.C1(=CC=CC2=CC=CC=C12)C(=O)Cl.[Cl-].[Cl-].[Cl-].[Al+3]>>C(CC)C1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21 | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]12.Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[c:19]2[cH:20][cH:21][cH:22][... | CCCc1ncc2ccccn12.O=C(Cl)c1cccc2ccccc12 | CCCc1nc(C(=O)c2cccc3ccccc23)c2ccccn12 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 7e3083a795f0f1a2311102a499a72fc360598e51bd61eda8201497f129b9883a | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1cccc2ccccc12)c1ncn2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[c:7]1:[cH;D2;+0:8]:[#7;a:9]:[c:10]:[#7;a:11]:1:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[c:12]):[c:7]:1:[c:6] | 28 | [{"value": 28.0, "product": "C(CC)C1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.0, "product": "C(CC)C1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 1-naphthoyl chloride (409 ml, 2.70 mmol, 2 eq) in 1,2-dichloroethane (10 ml) was added aluminum trichloride (415 mg, 3.11 mmol, 2.3 eq). The reaction mixture was stirred at room temperature for 10 min., then a solution of 3-propyl-imidazo[1,5-a]pyridine (216 mg, 1.35 mmol) in 1,2-dichloroethane (5 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccc2ccccc2c1.c1ccn2cncc2c1 | HCl | ClCCCl | null | 0.166667 | CCCc1ncc2ccccn12.O=C(Cl)c1cccc2ccccc12>ClCCCl>CCCc1nc(C(=O)c2cccc3ccccc23)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-faea717aebe3405cab22275d2bcb28c8 | CCCc1ncc2ccccn12.O=C(O)c1ccccc1I>>CCCc1nc(C(=O)c2ccccc2I)c2ccccn12 | C(CC)C1=NC=C2N1C=CC=C2.IC1=C(C(=O)O)C=CC=C1.[Cl-].[Cl-].[Cl-].[Al+3]>>IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]12.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[I:15]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[I:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]12 | CCCc1ncc2ccccn12.O=C(O)c1ccccc1I | CCCc1nc(C(=O)c2ccccc2I)c2ccccn12 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 39831f2b87da8928d248907cc7532736d3826bbd4647f1e6be9bfa0e8ad4a019 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)c1ncn2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[c:7]1:[cH;D2;+0:8]:[#7;a:9]:[c:10]:[#7;a:11]:1:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[c:12]):[c:7]:1:[c:6] | 15 | [{"value": 15.0, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.7, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 2-iodobenzoic acid (487 mg, 1.83 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (266 mg, 2.00 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-propyl-imidazo[1,5-a]pyridine (139 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccccc1.c1ccn2cncc2c1 | HO- | ClCCCl | null | 0.166667 | CCCc1ncc2ccccn12.O=C(O)c1ccccc1I>ClCCCl>CCCc1nc(C(=O)c2ccccc2I)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7630696c714549eb85ab8648101cc6b9 | CCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-]>>CCCc1nc(C(=O)O)c2ccccn12 | FC(C(=O)C=1N=C(N2C1C=CC=C2)CCC)(F)F.[OH-].[K+]>>C(CC)C1=NC(=C2N1C=CC=C2)C(=O)O | FC(F)(F)[C:7]([c:6]1[n:5][c:4]([CH2:3][CH2:2][CH3:1])[n:15]2[c:10]1[cH:11][cH:12][cH:13][cH:14]2)=[O:8].[OH-:9]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]12 | CCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-] | CCCc1nc(C(=O)O)c2ccccn12 | null | null | CCO | Acylation | OtherReaction | 756646b5982ba7b2e2e932b5bd1ff8dac0e125212b25bd0438af537a84702fd6 | 56f806808680643dc41c682f53c8ec81d98ddc60c5b66ee62824a1ba9830c721 | c1ccn2cncc2c1 | F-C(-F)(-F)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[OH-;D0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:10])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 56.2 | [{"value": 56.0, "product": "C(CC)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "C(CC)C1=NC(=C2N1C=CC=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of 2,2,2-trifluoro-1-(3-propyl-imidazo[1,5-a]pyridin-1-yl)-ethanone (379 mg, 1.48 mmol) in EtOH (10 mL) was added KOH (830 mg, 14.8 mmol). The mixture was stirred at ambient temperature for 15 h. After this time the mixture was concentrated, diluted with water (10 mL) and acidified to pH 3 with 2N HCl. Th... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ketone | Carboxylic acid | null | null | c1ccn2cncc2c1 | Other | CCO | null | 15 | CCCc1nc(C(=O)C(F)(F)F)c2ccccn12.[OH-]>CCO>CCCc1nc(C(=O)O)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c7bfd9906674e61b8d3c6ee75ad351a | CCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2>>CCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 | C(CC)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CCN(CC)CC.C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCC | O[C:7]([c:6]1[n:5][c:4]([CH2:3][CH2:2][CH3:1])[n:25]2[c:20]1[cH:21][cH:22][cH:23][cH:24]2)=[O:8].[NH2:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:18]1)[CH2:19]2>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][C:10]23[CH2:11][CH:12]4[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]4)[CH2:1... | CCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2 | CCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC12CC3CC(CC(C3)C1)C2)c1ncn2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])(-[C:13])-[C:14]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])(-[C:13])-[C:14] | 79 | [{"value": 79.0, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-propyl-imidazo[1,5-a]pyridine-1-carboxylic acid (114 mg, 0.44 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was stirred for 15 h. t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccn2cncc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | CCCc1nc(C(=O)O)c2ccccn12.NC12CC3CC(CC(C3)C1)C2>CN(C)C=O.C(C)(=O)OCC>CCCc1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5233a06d34af41338ead7aec562398df | COC(=O)CCN1CCOCC1.NCc1ccccn1>>O=C(CCN1CCOCC1)NCc1ccccn1 | N1(CCOCC1)CCC(=O)OC.[OH-].[Na+].NCC1=NC=CC=C1.C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl>>N1(CCOCC1)CCC(=O)NCC1=NC=CC=C1 | CO[C:2](=[O:1])[CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.[NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1>>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1 | COC(=O)CCN1CCOCC1.NCc1ccccn1 | O=C(CCN1CCOCC1)NCc1ccccn1 | null | null | ClCCl.CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(CCN1CCOCC1)NCc1ccccn1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 79.1 | [{"value": 77.0, "product": "N1(CCOCC1)CCC(=O)NCC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "N1(CCOCC1)CCC(=O)NCC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl 4-morpholinepropionate (5.0 g, 28.9 mmol) in MeOH (25 mL) was added 2N NaOH (17.3 mL, 34.6 mmol). The mixture was stirred for 1 h then concentrated in vacuo. The residue was suspended in dichloromethane (125 mL) and DMF (30 μL) was added followed by oxalylchloride (10 mL, 115.6 mmol). The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccncc1 | HO- | ClCCl.CO | null | 1 | COC(=O)CCN1CCOCC1.NCc1ccccn1>ClCCl.CO>O=C(CCN1CCOCC1)NCc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4303cc0898b432ea7c687346ea67b50 | O=C(CCN1CCOCC1)NCc1ccccn1>>c1ccn2c(CCN3CCOCC3)ncc2c1 | N1(CCOCC1)CCC(=O)NCC1=NC=CC=C1.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>>N1(CCOCC1)CCC1=NC=C2N1C=CC=C2 | O=[C:5]([CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)[NH:14][CH2:15][c:16]1[n:4][cH:3][cH:2][cH:1][cH:17]1>>[cH:1]1[cH:2][cH:3][n:4]2[c:5]([CH2:6][CH2:7][N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][cH:15][c:16]2[cH:17]1 | O=C(CCN1CCOCC1)NCc1ccccn1 | c1ccn2c(CCN3CCOCC3)ncc2c1 | null | null | ClCCCl | Aromatic Heterocycle Formation | OtherReaction | 1b4e55ff2e0f60e6a44cc161283eee0d751c452ef3ad342b3370f9f671cf0284 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | c1ccn2c(CCN3CCOCC3)ncc2c1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 78 | [{"value": 78.0, "product": "N1(CCOCC1)CCC1=NC=C2N1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 3-morpholin-4-yl-N-pyridin-2-ylmethyl-propionamide (5.4 g, 21.7 mmol) in 1,2-dichloroethane (100 mL), cooled in an ice bath, was added POCl3 (12 mL). The mixture was heated to 80° C. for 3 h. After this time the mixture was allowed to cool and poured slowly into 10% aqueous potassium carbonate (500 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccncc1 | c1ccn2cncc2c1 | C1COCC[NH]1.c1ccn2cncc2c1 | HO- | ClCCCl | 80 | null | O=C(CCN1CCOCC1)NCc1ccccn1>ClCCCl>c1ccn2c(CCN3CCOCC3)ncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a2e32fd45894d59a095857b914e8044 | O=C(Cl)c1cccc2ccccc12.c1ccn2c(CCN3CCOCC3)ncc2c1>>O=C(c1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | N1(CCOCC1)CCC1=NC=C2N1C=CC=C2.C1(=CC=CC2=CC=CC=C12)C(=O)Cl.[Cl-].[Cl-].[Cl-].[Al+3]>>N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12.[cH:13]1[n:14][c:15]([CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[n:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[c:13]1[n:14][c:15]([CH2:16][CH2:1... | O=C(Cl)c1cccc2ccccc12.c1ccn2c(CCN3CCOCC3)ncc2c1 | O=C(c1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 7e3083a795f0f1a2311102a499a72fc360598e51bd61eda8201497f129b9883a | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[#7;a:7]1:[c:8]:[#7;a:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[#7;a:7](:[c:6]):[c:11]:1:[c:12] | 48 | [{"value": 48.0, "product": "N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)C2=CC=CC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of naphthoylchloride (0.28 mL, 1.85 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (300 mg, 2.25 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (200 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccc2ccccc2c1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | ClCCCl | null | 0.166667 | O=C(Cl)c1cccc2ccccc12.c1ccn2c(CCN3CCOCC3)ncc2c1>ClCCCl>O=C(c1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-beccbf8452fd44c99978798d51b6cc77 | O=C(O)c1ccccc1I.c1ccn2c(CCN3CCOCC3)ncc2c1>>O=C(c1ccccc1I)c1nc(CCN2CCOCC2)n2ccccc12 | N1(CCOCC1)CCC1=NC=C2N1C=CC=C2.IC1=C(C(=O)O)C=CC=C1.[Cl-].[Cl-].[Cl-].[Al+3]>>IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9].[cH:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[n:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9])[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]... | O=C(O)c1ccccc1I.c1ccn2c(CCN3CCOCC3)ncc2c1 | O=C(c1ccccc1I)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | ClCCCl | C-C Coupling | Friedel-Crafts acylation | 39831f2b87da8928d248907cc7532736d3826bbd4647f1e6be9bfa0e8ad4a019 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[#7;a:7]1:[c:8]:[#7;a:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[#7;a:7](:[c:6]):[c:11]:1:[c:12] | 16 | [{"value": 16.0, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.7, "product": "IC1=C(C=CC=C1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 2-iodobenzoic acid (487 mg, 1.83 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (266 mg, 2.00 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (201 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccn2cncc2c1 | c1ccn2cncc2c1 | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HO- | ClCCCl | null | 0.166667 | O=C(O)c1ccccc1I.c1ccn2c(CCN3CCOCC3)ncc2c1>ClCCCl>O=C(c1ccccc1I)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23bed56f44c34dd1986e6ea1335d3c57 | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(CCN2CCOCC2)n2ccccc12 | N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CCN(CC)CC.C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3 | [NH2:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:12]1)[CH2:13]2.O[C:2](=[O:1])[c:14]1[n:15][c:16]([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[n:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[O:1]=[C:2]([NH:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:12]1)[CH... | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(CCN2CCOCC2)n2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])(-[C:13])-[C:14]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])(-[C:13])-[C:14] | 89 | [{"value": 89.0, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "C12(CC3CC(CC(C1)C3)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carboxylic acid (150 mg, 0.54 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccn2cncc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | NC12CC3CC(CC(C3)C1)C2.O=C(O)c1nc(CCN2CCOCC2)n2ccccc12>CN(C)C=O.C(C)(=O)OCC>O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-801206734ac849569f2eb03cc6b2c1c4 | NN1CCCCC1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(NN1CCCCC1)c1nc(CCN2CCOCC2)n2ccccc12 | NN1CCCCC1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>N1(CCCCC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1.Cl[C:2](=[O:1])[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[n:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[O:1]=[C:2]([NH:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][... | NN1CCCCC1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(NN1CCCCC1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 76e474c9dcce40e7c35c8f78d834149480d3c5d1f85bb22ed583a932a8f908b5 | 63b8330ebf088c16fa42481d4df221c4a2a7081161aafbc66cd44502eb8a31d9 | O=C(NN1CCCCC1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[#7:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[#7:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])-[C:13] | 34.2 | [{"value": 34.0, "product": "N1(CCCCC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "N1(CCCCC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-aminopiperidine (0.060 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h. then washed with sat. aq. NaHCO3 (2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Acylhydrazine | null | null | C1CC[NH]CC1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | NN1CCCCC1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(NN1CCCCC1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df22b0681f7946eb800817677107cacc | Nc1cccc(Cl)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(Nc1cccc(Cl)c1)c1nc(CCN2CCOCC2)n2ccccc12 | ClC=1C=C(N)C=CC1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>ClC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[cH:10]1.Cl[C:2](=[O:1])[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[n:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[cH:10]1)[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][... | Nc1cccc(Cl)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(Nc1cccc(Cl)c1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 35.2 | [{"value": 35.0, "product": "ClC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.2, "product": "ClC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-chloroaniline (0.060 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | Nc1cccc(Cl)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(Nc1cccc(Cl)c1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62535478035b4277b4d3fd555068c463 | C1COCCN1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(c1nc(CCN2CCOCC2)n2ccccc12)N1CCOCC1 | N1CCOCC1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>N1(CCOCC1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1.Cl[C:2](=[O:1])[c:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[O:1]=[C:2]([c:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12)[N:2... | C1COCCN1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(c1nc(CCN2CCOCC2)n2ccccc12)N1CCOCC1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b2821ffedb27fdb32ee8909e6c37f5667f3a9287b29ba6c49c7967ceba44bfc3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1nc(CCN2CCOCC2)n2ccccc12)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1)-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 55 | [{"value": 55.0, "product": "N1(CCOCC1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "N1(CCOCC1)C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of morpholine (0.050 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccn2cncc2c1.C1COCC[NH]1 | HCl | C(Cl)Cl | null | 1 | C1COCCN1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(c1nc(CCN2CCOCC2)n2ccccc12)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2a611103444467fa6aa8fa54051b481 | NCc1ccc(Cl)cc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(NCc1ccc(Cl)cc1)c1nc(CCN2CCOCC2)n2ccccc12 | ClC1=CC=C(CN)C=C1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>ClC1=CC=C(CNC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3)C=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1.Cl[C:2](=[O:1])[c:12]1[n:13][c:14]([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[n:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[c:12]1[n:13][c:14]([CH2:15][CH2:16][N:17]2[... | NCc1ccc(Cl)cc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(NCc1ccc(Cl)cc1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 47.4 | [{"value": 47.0, "product": "ClC1=CC=C(CNC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.4, "product": "ClC1=CC=C(CNC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-chlorobenzylamine (0.080 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | NCc1ccc(Cl)cc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(NCc1ccc(Cl)cc1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15ed0b16e08a4af98179572a7066b8aa | CNc1ccccc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>CN(C(=O)c1nc(CCN2CCOCC2)n2ccccc12)c1ccccc1 | CNC1=CC=CC=C1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>CN(C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2)C2=CC=CC=C2 | [CH3:1][NH:2][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.Cl[C:3](=[O:4])[c:5]1[n:6][c:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][N:2]([C:3](=[O:4])[c:5]1[n:6][c:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]2[cH:17][cH:18]... | CNc1ccccc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | CN(C(=O)c1nc(CCN2CCOCC2)n2ccccc12)c1ccccc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C;D1;H3:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9])-[c:12](:[c:13]):[c:14] | 64 | [{"value": 64.0, "product": "CN(C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "CN(C(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of n-methylaniline (0.060 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | C1COCC[NH]1.c1ccn2cncc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | CNc1ccccc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>CN(C(=O)c1nc(CCN2CCOCC2)n2ccccc12)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e3b7f50d4a4490ca488a7f86b6bb077 | Nc1cccc(F)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(Nc1cccc(F)c1)c1nc(CCN2CCOCC2)n2ccccc12 | FC=1C=C(N)C=CC1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>FC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([F:9])[cH:10]1.Cl[C:2](=[O:1])[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[n:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([F:9])[cH:10]1)[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:... | Nc1cccc(F)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(Nc1cccc(F)c1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 18.1 | [{"value": 18.0, "product": "FC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.1, "product": "FC=1C=C(C=CC1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-fluoroaniline (0.052 mL, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | Nc1cccc(F)c1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(Nc1cccc(F)c1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-633e267ffa8f495e9d4e6e640639302f | Nc1cccnc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(Nc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | NC=1C=NC=CC1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>N1=CC(=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1.Cl[C:2](=[O:1])[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[n:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:... | Nc1cccnc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(Nc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 32 | [{"value": 32.0, "product": "N1=CC(=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.6, "product": "N1=CC(=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-aminopyridine (0.051 g, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 mL... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | Nc1cccnc1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(Nc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bb66c627985473abead64a2bfa9e38c | NCc1ccccn1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(NCc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | NCC1=NC=CC=C1.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>N1=CC(=CC=C1)CNC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:10][n:9]1.Cl[C:2](=[O:1])[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[n:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:... | NCc1ccccn1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(NCc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | OtherReaction | 76ee741894d73d8b89ab254c3dac1c10a435e06f304694c213450d1a231674fc | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[C:11]-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[n;H0;D2;+0:17]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[n;H0;D2;+0:17]:[cH;D2;+0:16]:1)-[c:3]1:[... | 32 | [{"value": 32.0, "product": "N1=CC(=CC=C1)CNC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.6, "product": "N1=CC(=CC=C1)CNC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(aminomethyl)pyridine (0.052 g, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | NCc1ccccn1.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(NCc1cccnc1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d66ee03b78c44c5bb4aabb7d442f349 | Nc1cccc2ccccc12.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>>O=C(Nc1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | C1=CC=C2C(=C1)C=CC=C2N.C(C)N(CC)CC.Cl.N1(CCOCC1)CCC1=NC(=C2N1C=CC=C2)C(=O)Cl>>C1(=CC=CC2=CC=CC=C12)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.Cl[C:2](=[O:1])[c:14]1[n:15][c:16]([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[n:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12)[c:14]1[n:15][c:16](... | Nc1cccc2ccccc12.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12 | O=C(Nc1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | 32.2 | [{"value": 32.0, "product": "C1(=CC=CC2=CC=CC=C12)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "C1(=CC=CC2=CC=CC=C12)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-naphylamine (0.077 g, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1.C1COCC[NH]1.c1ccn2cncc2c1 | HCl | C(Cl)Cl | null | 1 | Nc1cccc2ccccc12.O=C(Cl)c1nc(CCN2CCOCC2)n2ccccc12>C(Cl)Cl>O=C(Nc1cccc2ccccc12)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a887097a529414d9485b425ba8bbeba | CC12CC3CC(C)(C1)CC(N)(C3)C2.CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.On1nnc2ccccc21>>CC12CC3CC(C)(C1)CC(NC(=O)c1nc(CCN4CCOCC4)n4ccccc14)(C3)C2 | C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.C(C)N(C(C)C)C(C)C.Cl.CC12CC3(CC(CC(C1)(C3)C)C2)N>>CC12CC3(CC(CC(C1)(C3)C)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3 | [CH3:1][C:2]12[CH2:3][CH:4]3[CH2:5][C:6]([CH3:7])([CH2:8]1)[CH2:9][C:10]([NH2:11])([CH2:31]3)[CH2:32]2.CC[CH2:18][CH2:17][c:16]1[n:15][c:14]([C:12](O)=[O:13])[c:30]2[n:25]1[cH:26][cH:27][cH:28][cH:29]2.CC(C)[N:19](C(C)C)[CH2:24][CH3:23].c1ccc2c(c1)nnn2[OH:22]>>[CH3:1][C:2]12[CH2:3][CH:4]3[CH2:5][C:6]([CH3:7])([CH2:8]1)... | CC12CC3CC(C)(C1)CC(N)(C3)C2.CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.On1nnc2ccccc21 | CC12CC3CC(C)(C1)CC(NC(=O)c1nc(CCN4CCOCC4)n4ccccc14)(C3)C2 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | OtherReaction | 0a9d6b17b2dfa5a763c85c30f557af13e903a0fd6def0793e8e9259dff2c63b7 | b71b9d9710804babc9f5f922e705141d250c7502472ef78f21dd8c70ea1821a2 | O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(CCN2CCOCC2)n2ccccc12 | C-C(-C)-[N;H0;D3;+0:1](-[C:2]-[CH3;D1;+0:3])-C(-C)-C.C-C-[CH2;D2;+0:4]-[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C;H0;D3;+0:9](-O)=[O;D1;H0:10]):[c:11](:[c:12]):[#7;a:13]:1:[c:14].[C:15]-[C:16](-[NH2;D1;+0:17])(-[C:18])-[C:19].[OH;D1;+0:20]-n1:n:n:c2:c:c:c:c:c:2:1>>[C:15]-[C:16](-[NH;D2;+0:17]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:8]1:... | 16 | [{"value": 16.0, "product": "CC12CC3(CC(CC(C1)(C3)C)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.7, "product": "CC12CC3(CC(CC(C1)(C3)C)C2)NC(=O)C=2N=C(N3C2C=CC=C3)CCN3CCOCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (200 mg, 0.73 mmol) in DMF (5 mL) was added EDC (182 mg, 0.95 mmol), HOBt, (129 mg, 0.95 mmol) and iPr2EtN (0.22 mL, 1.31 mmol). The mixture was allowed to stir for 10 min. and 3,5-dimethyl-1-aminoadamantane hydrochloride (187 mg, 0.88 mmol) was added. T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine | Ether.Secondary amide.Tertiary amine | c1ccc2[nH]nnc2c1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccn2cncc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | CC12CC3CC(C)(C1)CC(N)(C3)C2.CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.On1nnc2ccccc21>CN(C)C=O.C(C)(=O)OCC>CC12CC3CC(C)(C1)CC(NC(=O)c1nc(CCN4CCOCC4)n4ccccc14)(C3)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72c381f4ae17497ea9d0f6d9784fd8ee | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.Nc1ccccc1.On1nnc2ccccc21>>O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.C(C)N(C(C)C)C(C)C.NC1=CC=CC=C1>>C1(=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | CCC[CH2:13][c:12]1[n:11][c:10]([C:2](O)=[O:1])[c:26]2[n:21]1[cH:22][cH:23][cH:24][cH:25]2.CC(C)[N:15](C(C)[CH3:19])[CH2:14][CH3:20].[NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.c1ccc2c(c1)nnn2[OH:18]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][c:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:1... | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.Nc1ccccc1.On1nnc2ccccc21 | O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | OtherReaction | 0a9d6b17b2dfa5a763c85c30f557af13e903a0fd6def0793e8e9259dff2c63b7 | b71b9d9710804babc9f5f922e705141d250c7502472ef78f21dd8c70ea1821a2 | O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | C-C(-C)-[N;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH3;D1;+0:3])-C(-C)-[CH3;D1;+0:4].C-C-C-[CH2;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8](-[C;H0;D3;+0:9](-O)=[O;D1;H0:10]):[c:11](:[c:12]):[#7;a:13]:1:[c:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18].[OH;D1;+0:19]-n1:n:n:c2:c:c:c:c:c:2:1>>[O;D1;H0:10]=[C;H0;D3;+0:9](-[NH;D2;+0:15]-[c:16](:[c:17]):... | 16 | [{"value": 16.0, "product": "C1(=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.6, "product": "C1(=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (200 mg, 0.73 mmol) in DMF (5 mL) was added EDC (182 mg, 0.95 mmol), HOBt, (129 mg, 0.95 mmol) and iPr2EtN (0.22 mL, 1.31 mmol). The mixture was allowed to stir for 10 min. and aniline (0.080 mL, 0.88 mmol) was added. The mixture was stirred for 15 h the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine | Ether.Secondary amide.Tertiary amine | c1ccc2[nH]nnc2c1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.Nc1ccccc1.On1nnc2ccccc21>CN(C)C=O.C(C)(=O)OCC>O=C(Nc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b302df757bf4a429cfee724706eadec | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.NCc1ccccc1.On1nnc2ccccc21>>O=C(NCc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | C(CCC)C1=NC(=C2N1C=CC=C2)C(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.C(C)N(C(C)C)C(C)C.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2 | CCC[CH2:14][c:13]1[n:12][c:11]([C:2](O)=[O:1])[c:27]2[n:22]1[cH:23][cH:24][cH:25][cH:26]2.CC(C)[N:16]([CH2:15][CH3:20])[CH:21](C)C.[NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.c1ccc2c(c1)nnn2[OH:19]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[n:12][c:13]([CH2:14][CH2:15][N:16]2[CH2:... | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.NCc1ccccc1.On1nnc2ccccc21 | O=C(NCc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | OtherReaction | 0a9d6b17b2dfa5a763c85c30f557af13e903a0fd6def0793e8e9259dff2c63b7 | b71b9d9710804babc9f5f922e705141d250c7502472ef78f21dd8c70ea1821a2 | O=C(NCc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 | C-C(-C)-[N;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH3;D1;+0:3])-[CH;D3;+0:4](-C)-C.C-C-C-[CH2;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8](-[C;H0;D3;+0:9](-O)=[O;D1;H0:10]):[c:11](:[c:12]):[#7;a:13]:1:[c:14].[NH2;D1;+0:15]-[C:16]-[c:17].[OH;D1;+0:18]-n1:n:n:c2:c:c:c:c:c:2:1>>[O;D1;H0:10]=[C;H0;D3;+0:9](-[NH;D2;+0:15]-[C:16]-[c:17])-[c:8]1:[#7;... | 17 | [{"value": 17.0, "product": "C(C1=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.9, "product": "C(C1=CC=CC=C1)NC(=O)C=1N=C(N2C1C=CC=C2)CCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (200 mg, 0.73 mmol) in DMF (5 mL) was added EDC (182 mg, 0.95 mmol), HOBt, (129 mg, 0.95 mmol) and iPr2EtN (0.22 mL, 1.31 mmol). The mixture was allowed to stir for 10 min. and benzylamine (0.096 mL, 0.88 mmol) was added. The mixture was stirred for 15 h... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine | Ether.Secondary amide.Tertiary amine | c1ccc2[nH]nnc2c1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1ccn2cncc2c1 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 0.166667 | CCCCc1nc(C(=O)O)c2ccccn12.CCN(C(C)C)C(C)C.NCc1ccccc1.On1nnc2ccccc21>CN(C)C=O.C(C)(=O)OCC>O=C(NCc1ccccc1)c1nc(CCN2CCOCC2)n2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddbc6e5a49d544f9a50fc63ba8bdaf1c | COc1cccc(C(=O)CBr)c1.Nc1nccs1>>COc1cccc(-c2cn3ccsc3n2)c1 | NC=1SC=CN1.BrCC(=O)C1=CC(=CC=C1)OC.[OH-].[NH4+]>>COC=1C=C(C=CC1)C=1N=C2SC=CN2C1 | O=[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16]1)[CH2:9]Br.[n:10]1[cH:11][cH:12][s:13][c:14]1[NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][cH:12][s:13][c:14]3[n:15]2)[cH:16]1 | COc1cccc(C(=O)CBr)c1.Nc1nccs1 | COc1cccc(-c2cn3ccsc3n2)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fc4245e28231e2acdadf0a109add94d7bcbb15727aa9b3c4274dbbacfc4598a4 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccsc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[n;H0;D2;+0:13]:1>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:13]2:[c:12]:[c:11]:[#16;a:10]:[c:9]:2:[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 82.9 | [{"value": 81.0, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a mixture of 2-aminothiazole (2.7 g, 26.7 mmol) and 2-bromo-3′-methoxyacetophenone (6.0 g, 0.0262 mol) was added absolute ethanol (100 ml). The reaction was allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture was reduced to half its original volume in vacuo. The remaining li... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1cscn1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HBr | C(C)O | null | 18 | COc1cccc(C(=O)CBr)c1.Nc1nccs1>C(C)O>COc1cccc(-c2cn3ccsc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1335e176c04444f29e6d6404fe72b4b0 | COc1cccc(-c2nc3sccn3c2C(C)=O)c1>>COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1 | COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C(C)=O>>CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2[C:16](=[O:17])[CH3:18])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2[C:16](=[O:17])[CH:18]=[CH:19][N:20]([CH3:21])[CH3:22])[cH:23]1 | COc1cccc(-c2nc3sccn3c2C(C)=O)c1 | COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1 | null | null | COC(N(C)C)OC | Functional Group Addition | OtherReaction | 0d5311ecd80009424fc95ec0c1e1de1c0fa876a3bfe24e4a46e66a7cdd1602d1 | 6230731b070dd3e80e820430f3c2d37c21f8df4c00e299dfe083db33f2adb1d0 | c1ccc(-c2cn3ccsc3n2)cc1 | [#7;a:1]:[c:2](-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]):[c:6]:[#7;a:7]>>[#7:8]-[C:9]=[CH;D2;+0:4]-[C:3](=[O;D1;H0:5])-[c:2](:[#7;a:1]):[c:6]:[#7;a:7] | 165.7 | [{"value": 165.7, "product": "CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 100 ml round bottom flask was charged with the 1-[6-(3-methoxyphenyl)imidazo [2,1-b][1,3]thiazol-5-yl]ethanone (17.95 g, 62 mmol) and dimethylformamide dimethylacetal (120 ml). The mixture was refluxed for 72 hours and then cooled to room temperature. The mixture was concentrated in vacuo and the residue was purified... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Enamine.Ketone | null | null | c1ccccc1.c1cn2ccsc2n1 | Other | COC(N(C)C)OC | null | null | COc1cccc(-c2nc3sccn3c2C(C)=O)c1>COC(N(C)C)OC>COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1a8089dfcd943e1bc3475841cbcbb9f | COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1>>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)c1 | [O-]CC.[Na+].CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C.Cl.N/C(=N/[H])/N[C@H]1CN(CCC1)C(=O)OC(C)(C)C>>COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C | CN(C)[CH:18]=[CH:17][C:16](=O)[c:15]1[c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36]2)[n:9][c:10]2[s:11][cH:12][cH:13][n:14]21.[H]/[N:19]=[C:20](\[NH:21][C@@H:22]1[CH2:23][CH2:24][CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1)[NH2:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7... | COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[#7;a:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[c:12].[C:13]-[#7:14]/[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[N;H0;D2;+0:17]\[H]>>[C:13]-[#7:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:17]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[#7;a:5]3:... | 93 | [{"value": 93.0, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(dimethylamino)-1-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]prop-2-en-1-one (5.0 g, 15.3 mmol) and tert-butyl (3R)-3-{[(Z)-amino(imino)methyl]amino}piperidine-1-carboxylate hydrochloride (5.28 g, 18.95 mmol) was diluted with 60 ml of absolute ethanol and treated with 1.15 eq. of a 21% w/w solut... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1 | HO- | C(C)O | null | null | COc1cccc(-c2nc3sccn3c2C(=O)C=CN(C)C)c1.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1>C(C)O>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c25133a0db040a5a477ace4e9b5271a | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1>>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | Cl.COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1.CCN(C(C)C)C(C)C.ClC1=CC=C(C=C1)S(=O)(=O)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2-[c:16]2[cH:17][cH:18][n:19][c:20]([NH:21][C@@H:22]3[CH2:23][CH2:24][CH2:25][NH:26][CH2:37]3)[n:38]2)[cH:39]1.Cl[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6]... | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11] | 85 | [{"value": 85.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 30 | MINUTE | The 4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[(3R)-piperidin-3-yl]pyrimidin-2-amine hydrochloride (6.81 g, 14.2 mmol) in methylene chloride (DCM) (60 ml) was cooled to 0° C. and was treated with Hunig's base (9.9 ml, 56.8 mmol). The mixture was kept at 0° C. for 30 minutes then the 4-chlorophenylsulfony... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1>C(Cl)Cl>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44a367ad8742466c80c2d374be86b968 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 | B(Br)(Br)Br.ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)O | C[O:29][c:28]1[cH:27][cH:26][cH:25][c:24](-[c:23]2[c:22](-[c:21]3[cH:20][cH:19][n:18][c:17]([NH:16][C@@H:15]4[CH2:14][CH2:13][CH2:12][N:11]([S:2](=[O:1])(=[O:3])[c:4]5[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]5)[CH2:38]4)[n:37]3)[n:36]3[c:32]([n:31]2)[s:33][cH:34][cH:35]3)[cH:30]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:... | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | The N-{(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}-4-[6-(3-methoxy-phenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (6.98 g, 12.03 mmol) in methylene chloride (100 ml) was cooled to −78° C. and slowly treated with 1 molar solution of boron tribromide in methylene chloride (65 ml). The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | Other | C(Cl)Cl | null | 1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>C(Cl)Cl>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8799287d4d7444818b0c364e181e36be | Nc1ncco1.O=C(CBr)c1ccc(F)cc1>>Br.N=c1occn1CC(=O)c1ccc(F)cc1 | NC=1OC=CN1.BrCC(=O)C1=CC=C(C=C1)F>>Br.FC1=CC=C(C=C1)C(CN1C(OC=C1)=N)=O | [NH2:2][c:3]1[o:4][cH:5][cH:6][n:7]1.[Br:1][CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[BrH:1].[NH:2]=[c:3]1[o:4][cH:5][cH:6][n:7]1[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | Nc1ncco1.O=C(CBr)c1ccc(F)cc1 | Br.N=c1occn1CC(=O)c1ccc(F)cc1 | null | null | C(C)#N.C1CCOC1 | Protection | OtherReaction | e59ba20c48f14515fa5c22ea780ae8faed56db186c989d61962c80af34e0e76f | 3e0b0a35c2a7c4c0b7c118f4bde50e6141fa63de0c1d3b86bd90b0c63d0ce094 | N=c1occn1CC(=O)c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5].[NH2;D1;+0:6]-[c;H0;D3;+0:7]1:[#8;a:8]:[c:9]:[c:10]:[n;H0;D2;+0:11]:1>>[BrH;D0;+0:1].[NH;D1;+0:6]=[c;H0;D3;+0:7]1:[#8;a:8]:[c:9]:[c:10]:[n;H0;D3;+0:11]:1-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 72 | [{"value": 72.0, "product": "Br.FC1=CC=C(C=C1)C(CN1C(OC=C1)=N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "Br.FC1=CC=C(C=C1)C(CN1C(OC=C1)=N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 2-amino-oxazole (14.9 g, 0.179 mol) in acetonitrile (100 ml) was slowly added over a period of 20 minutes to a solution of 2-bromo-1-(4-fluorophenyl)ethanone (57.6 g, 0.36 mol) in THF (150 ml). The reaction mixture was stirred at room temperature for 24 hrs then cooled to 0° C. A precipitate formed and wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | Ketone | c1cocn1 | c1cocn1 | c1cocn1.c1ccccc1 | null | C(C)#N.C1CCOC1 | null | 24 | Nc1ncco1.O=C(CBr)c1ccc(F)cc1>C(C)#N.C1CCOC1>Br.N=c1occn1CC(=O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5527e0450a5544249024ffb86820fa8c | N=c1occn1CC(=O)c1ccc(F)cc1>>Fc1ccc(-c2cn3ccoc3n2)cc1 | Br.FC1=CC=C(C=C1)C(CN1C(OC=C1)=N)=O>>FC1=CC=C(C=C1)C=1N=C2OC=CN2C1 | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:15][cH:14]1)[CH2:7][n:8]1[cH:9][cH:10][o:11][c:12]1=[NH:13]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8]3[cH:9][cH:10][o:11][c:12]3[n:13]2)[cH:14][cH:15]1 | N=c1occn1CC(=O)c1ccc(F)cc1 | Fc1ccc(-c2cn3ccoc3n2)cc1 | null | Cl[Ti](Cl)(Cl)Cl | null | Aromatic Heterocycle Formation | OtherReaction | f00f362e14414a67734378e05c301aaa7b3d6763aba3b993d26d42be8352f609 | a8967c9eacb418e0bc7f9cb97db3a9e26ef1bbc7a8b0098b1f7ac06e3777d85a | c1ccc(-c2cn3ccoc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[#7;a:3]1:[c:4]:[c:5]:[#8;a:6]:[c;H0;D3;+0:7]:1=[NH;D1;+0:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[#7;a:3]2:[c:4]:[c:5]:[#8;a:6]:[c;H0;D3;+0:7]:2:[n;H0;D2;+0:8]:1):[c:12]:[c:13] | 10.6 | [{"value": 10.6, "product": "FC1=CC=C(C=C1)C=1N=C2OC=CN2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | The 1-(4-fluorophenyl)-2-(2-iminooxazol-3-yl)-ethanone hydrobromide salt (10.0 g, 0.32 mol) was introduced in a two-neck flask, fitted with a condenser, and flushed with nitrogen. Anhydrous toluene (100 ml) was added and the mixture was cooled to −10° C. TiCl4 (17.5 ml, 0.16 mol) was added over a period of 30 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1cocn1 | c1cn2ccoc2n1 | c1ccccc1.c1cn2ccoc2n1 | HO- | Cl[Ti](Cl)(Cl)Cl | -10 | 1 | N=c1occn1CC(=O)c1ccc(F)cc1>Cl[Ti](Cl)(Cl)Cl>Fc1ccc(-c2cn3ccoc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b818454fd0940c896fa7fd5a9a53ce8 | CC(=O)OC(C)=O.Fc1ccc(-c2cn3ccoc3n2)cc1>>CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | FC1=CC=C(C=C1)C=1N=C2OC=CN2C1.C(C)(=O)OC(C)=O>>FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[n:13][c:14]2[o:15][cH:16][cH:17][n:18]12>>[CH3:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[n:13][c:14]2[o:15][cH:16][cH:17][n:18]12 | CC(=O)OC(C)=O.Fc1ccc(-c2cn3ccoc3n2)cc1 | CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | null | S(O)(O)(=O)=O | null | C-C Coupling | Friedel-Crafts acylation | 3b733bfc184370077bda5e0d21496a90945e19bc3adca5b1c367a06d365b28b1 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccc(-c2cn3ccoc3n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]2:[#8;a:8]:[c:9]:[c:10]:[#7;a:11]:2:[cH;D2;+0:12]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:12]1:[#7;a:11]2:[c:10]:[c:9]:[#8;a:8]:[c:7]:2:[#7;a:6]:[c:5]:1-[c:4] | 72.6 | [{"value": 72.6, "product": "FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole (2.5 g, 0.0124 mol) in acetic anhydride (60 ml) was heated to 140° C. and then treated with concentrated sulfuric acid (5 drops). After 15 minute at that temperature, HPLC showed clean conversion and the reaction mixture was quenched by the addition of ice cold wat... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1cn2ccoc2n1 | c1cn2ccoc2n1 | c1ccccc1.c1cn2ccoc2n1 | HO- | S(O)(O)(=O)=O | null | 0.25 | CC(=O)OC(C)=O.Fc1ccc(-c2cn3ccoc3n2)cc1>S(O)(O)(=O)=O>CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-790c0f95a01d44d585155e8649d27c2e | CC(=O)c1c(-c2ccc(F)cc2)nc2occn12>>CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C(C)=O>>CN(C=CC(=O)C1=C(N=C2OC=CN21)C2=CC=C(C=C2)F)C | [cH:1]1[c:13]([F:14])[cH:12][cH:11][c:10](-[c:9]2[c:8]([C:6]([CH3:5])=[O:7])[n:2]3[c:18]([n:17]2)[o:19][cH:20][cH:21]3)[cH:16]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6](=[O:7])[c:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[n:17][c:18]2[o:19][cH:20][cH:21][n:22]12 | CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | null | null | COC(N(C)C)OC | Functional Group Addition | OtherReaction | ca6848dc1fbe2ebc8d6b6f4abe620f1899ee9ae344909fa3f835401969575517 | 2e24cd796006f232a2b6ce7a6a32c27678f1760f3709a542cbd48850bce3e2db | c1ccc(-c2cn3ccoc3n2)cc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5](-[c:6]2:[c:7]:[c:8]:[c;H0;D3;+0:9](-[F;D1;H0:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:2):[#7;a:13]:[c;H0;D3;+0:14]2:[#8;a:15]:[c:16]:[cH;D2;+0:17]:[n;H0;D3;+0:18]:2:1>>[C;D1;H3:19]-[N;H0;D3;+0:18](-[CH3;D1;+0:11])-[C:20]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[#... | null | [] | null | null | null | null | A solution of 1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (0.0374 g, 0.000153 mol) in N,N-dimethylformamide dimethyl acetal (3.0 ml) was heated to 100° C. for 24 hrs. HPLC showed complete consumption of the starting material. The volatiles were removed in vacuo, yielding a brown solid (0.046 g, quantit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Enamine.Aromatic halide.Ketone | c1ccccc1.c1cn2ccoc2n1 | c1ccccc1.c1cn2ccoc2n1 | c1ccccc1.c1cn2ccoc2n1 | Other | COC(N(C)C)OC | null | null | CC(=O)c1c(-c2ccc(F)cc2)nc2occn12>COC(N(C)C)OC>CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c53ef980bc6841fa899ade986d5382c8 | CC(C)(C)OC(=O)N1CCC(N)CC1.N=C(N)c1cc[nH]n1>>CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1 | NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.N1N=C(C=C1)C(=N)N.CCN(C(C)C)C(C)C>>Cl.NC(=N)NC1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH2:12])[CH2:16][CH2:17]1.c1cc([C:13](=[NH:14])[NH2:15])n[nH]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][C:13](=[NH:14])[NH2:15])[CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N1CCC(N)CC1.N=C(N)c1cc[nH]n1 | CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | fc40081018b37da8451450064d8784be1219df3f09b9877dca11163275b8a8c2 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | C1CCNCC1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4].[N;D1;H1:5]=[C;H0;D3;+0:6](-[N;D1;H2:7])-c1:c:c:[nH]:n:1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:6](=[N;D1;H1:5])-[N;D1;H2:7])-[C:4] | null | [] | 60 | CELSIUS | 2 | HOUR | To a mixture of tert-butyl 4-aminopiperidine-1-carboxylate (8.93 g, 44.6 mmol) and pyrazole carbox-amidine hydrochloride (6.536 g, 44.6 mmol) was added Hunig's base (7.77 ml, 44.6 mmol) and DMF (25 ml). The reaction was heated at 60° C. for 15 hours. The reaction was then cooled to room temperature and quenched by addi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1cn[nH]c1 | null | C1CC[NH]CC1 | Other | CN(C)C=O | 60 | 2 | CC(C)(C)OC(=O)N1CCC(N)CC1.N=C(N)c1cc[nH]n1>CN(C)C=O>CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ff1923098a748439b8056f3c337bda7 | CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1.CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12>>CC(C)(C)OC(=O)N1CCC(Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)CC1 | [O-]CC.[Na+].CN(C=CC(=O)C1=C(N=C2OC=CN21)C2=CC=C(C=C2)F)C.Cl.NC(=N)NC1CCN(CC1)C(=O)OC(C)(C)C>>FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][C:13]([NH2:14])=[NH:33])[CH2:34][CH2:35]1.CN(C)[CH:15]=[CH:16][C:17](=O)[c:18]1[c:19](-[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[n:27][c:28]2[o:29][cH:30][cH:31][n:32]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1... | CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1.CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | CC(C)(C)OC(=O)N1CCC(Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)CC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2nc3occn3c2-c2ccnc(NC3CCNCC3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[#7;a:5]2:[c:6]:[c:7]:[#8;a:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[c:12].[C:13]-[#7:14]-[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[NH;D1;+0:17]>>[C:13]-[#7:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[#7;a:5]3:[c:6]:[... | 65.3 | [{"value": 65.0, "product": "FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one (4.24 g, 14.2 mmol) and tert-butyl 4-{[amino(imino)methyl]amino}-piperidine-1-carboxylate hydrochloride (5.92 g, 21.2 mmol) was diluted with 40 ml of absolute ethanol and treated with 1.35 eq. of a 21% w/w solution of sod... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccoc2n1 | HO- | C(C)O | null | null | CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1.CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12>C(C)O>CC(C)(C)OC(=O)N1CCC(Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32a67e0def91432ab509dd4b57a85004 | Fc1ccc(-c2nc3sccn3c2-c2ccnc(NC3CCCNC3)n2)cc1.O=Cc1ccc(F)cc1>>Fc1ccc(CN2CCCC(Nc3nccc(-c4c(-c5ccc(F)cc5)nc5sccn45)n3)C2)cc1 | Cl.FC1=CC=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CNCCC1.ClCCCl.CN(C)C=O.C(C)N(CC)CC.FC1=CC=C(C=O)C=C1>>FC1=CC=C(CN2CC(CCC2)NC2=NC=CC(=N2)C2=C(N=C3SC=CN32)C3=CC=C(C=C3)F)C=C1 | [NH:7]1[CH2:8][CH2:9][CH2:10][CH:11]([NH:12][c:13]2[n:14][cH:15][cH:16][c:17](-[c:18]3[c:19](-[c:20]4[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]4)[n:27][c:28]4[s:29][cH:30][cH:31][n:32]34)[n:33]2)[CH2:34]1.O=[CH:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:36][cH:35]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2... | Fc1ccc(-c2nc3sccn3c2-c2ccnc(NC3CCCNC3)n2)cc1.O=Cc1ccc(F)cc1 | Fc1ccc(CN2CCCC(Nc3nccc(-c4c(-c5ccc(F)cc5)nc5sccn45)n3)C2)cc1 | null | null | ClCCCl.CN(C)C=O | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCCC(Nc3nccc(-c4c(-c5ccccc5)nc5sccn45)n3)C2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | 56.2 | [{"value": 56.0, "product": "FC1=CC=C(CN2CC(CCC2)NC2=NC=CC(=N2)C2=C(N=C3SC=CN32)C3=CC=C(C=C3)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "FC1=CC=C(CN2CC(CCC2)NC2=NC=CC(=N2)C2=C(N=C3SC=CN32)C3=CC=C(C=C3)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | The racemic 4-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[piperidin-3-yl]pyrimidin-2-amine hydrochloride (70 mg g, 0.15 mmol) was dissolved in a 80/20 mixture of DCE and DMF (1.2 ml) and treated with three equivalent of triethylamine (63 uL). The 4-fluorobenzaldehyde (19 mg, 0.15 mmol) was added, followed by... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | Other | ClCCCl.CN(C)C=O | null | 18 | Fc1ccc(-c2nc3sccn3c2-c2ccnc(NC3CCCNC3)n2)cc1.O=Cc1ccc(F)cc1>ClCCCl.CN(C)C=O>Fc1ccc(CN2CCCC(Nc3nccc(-c4c(-c5ccc(F)cc5)nc5sccn45)n3)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac96b095864a48c1a97f17234f1daa49 | O=[N+]([O-])c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)[N+](=O)[O-].Cl>>NC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[s:10][cH:11][cH:12][n:13]3[c:14]2-[c:15]2[cH:16][cH:17][n:18][c:19]([NH:20][C@@H:21]3[CH2:22][CH2:23][CH2:24][N:25]([S:26](=[O:27])(=[O:28])[c:29]4[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]4)[CH2:36]3)[n:37]2)[cH:38]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](... | O=[N+]([O-])c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 100 | CELSIUS | 1 | HOUR | N-{(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}-4-[6-(3-nitrophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (1.05 g, 1.76 mmol) was dissolved in ethanol 95% (10 ml) and water (2.5 ml). The solution was treated with irn powder (1 g, 17.6 mmol) and concentrated HCl (200 uL). The reaction mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | Other | O.C(C)O | 100 | 1 | O=[N+]([O-])c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>O.C(C)O>Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc6414b4a673402f8deae24fb908797d | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | NC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl.C(C)(C)(C)OC(=O)NCC(=O)O.CCN(C(C)C)C(C)C.[Cl-].ClC=1N(C=C[N+]1C)C>>C(C)(C)(C)OC(NCC(=O)NC1=CC(=CC=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl)=O | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][c:20]3[s:21][cH:22][cH:23][n:24]3[c:25]2-[c:26]2[cH:27][cH:28][n:29][c:30]([NH:31][C@@H:32]3[CH2:33][CH2:34][CH2:35][N:36]([S:37](=[O:38])(=[O:39])[c:40]4[cH:41][cH:42][c:43]([Cl:44])[... | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | 55.5 | [{"value": 55.5, "product": "C(C)(C)(C)OC(NCC(=O)NC1=CC(=CC=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | The 4-[6-(3-aminophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-{(3R)-1-[(4-chlorophenyl)-sulfonyl]piperidin-3-yl}pyrimidin-2-amine (0.1 g, 0.177 mmol) and N-(tert-butoxycarbonyl)glycine (34 mg, 0.194 mmol) were dissolved in DCM (5 ml) and treated with Hunig's base (92 uL, 0.53 mmol) and 2-chloro-1,3-dimethyl-1H-imidazol-3-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | C(Cl)Cl | null | 1.5 | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>C(Cl)Cl>CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8a3ad10a4654756a8ddb4f676f9b8b7 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | C(C)(C)(C)OC(NCC(=O)NC1=CC(=CC=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl)=O.Cl>>Cl.ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)NC(CN)=O | CC(C)(C)OC(=O)[NH:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][c:14]3[s:15][cH:16][cH:17][n:18]3[c:19]2-[c:20]2[cH:21][cH:22][n:23][c:24]([NH:25][C@@H:26]3[CH2:27][CH2:28][CH2:29][N:30]([S:31](=[O:32])(=[O:33])[c:34]4[cH:35][cH:36][c:37]([Cl:38])[cH:39][cH:40]4)[CH2:41]3)[n:42]2)[cH:43]1>>... | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]>>[NH2;D1;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | 201.1 | [{"value": 201.1, "product": "Cl.ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)NC(CN)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | The tert-butyl{2-[(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)-pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)amino]-2-oxoethyl}carbamate (71 mg, 0.098 mmol) was dissolved in dioxane (3 ml) and treated with a 4N HCl solution in dioxane (1 ml). The mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | O1CCOCC1 | null | 3 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>O1CCOCC1>NCC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c7e22b71814474ab8c58219646be72f | CC(=O)Cl.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>CC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | NC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)S(=O)(=O)C1=CC=C(C=C1)Cl.CCN(C(C)C)C(C)C.C(C)(=O)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[s:13][cH:14][cH:15][n:16]3[c:17]2-[c:18]2[cH:19][cH:20][n:21][c:22]([NH:23][C@@H:24]3[CH2:25][CH2:26][CH2:27][N:28]([S:29](=[O:30])(=[O:31])[c:32]4[cH:33][cH:34][c:35]([Cl:36])[cH:37][cH:38]4)[CH2:39]3)[n:40]2)[cH:41]1>>[CH3:1][C:2](=[O:3... | CC(=O)Cl.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | CC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 90.1 | [{"value": 90.1, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The 4-[6-(3-aminophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-{(3R)-1-[(4-chlorophenyl)-sulfonyl]piperidin-3-yl}pyrimidin-2-amine (0.1 g, 0.177 mmol) was dissolved in DCM (5 ml) and treated sequentially with Hunig's base (46 uL, 0.265 mmol) and acetyl chloride (15 uL, 0.212 mmol). The mixture was kept at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CC(=O)Cl.Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>C(Cl)Cl>CC(=O)Nc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b9ef12bac9d499db99b9775ca0b332b | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.Cc1ccc(S(=O)(=O)OC[C@@H]2COC(C)(C)O2)cc1>>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1 | CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]1OC(OC1)(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[K+].[K+].Cl.COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1>>CC1(OC[C@H](O1)CN1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2-[c:16]2[cH:17][cH:18][n:19][c:20]([NH:21][C@@H:22]3[CH2:23][CH2:24][CH2:25][NH:26][CH2:35]3)[n:36]2)[cH:37]1.Cc1ccc(S(=O)(=O)O[CH2:27][C@@H:28]2[CH2:29][O:30][C:31]([CH3:32])([CH3:33])[O:34]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH... | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.Cc1ccc(S(=O)(=O)OC[C@@H]2COC(C)(C)O2)cc1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | eea6f10dbbd1f6788b047d78092cba8a768c0aea4874e4d0fb62b27a28862459 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COCO4)C3)n2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-[#8:5]-[C:6]-2):c:c:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[#8:5]-[C:6]-1)-[C:10]-[C:11] | 64 | [{"value": 64.0, "product": "CC1(OC[C@H](O1)CN1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "CC1(OC[C@H](O1)CN1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | 130 | CELSIUS | 5 | HOUR | The 4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[(3R)-piperidin-3-yl]-pyrimidin-2-amine hydrochloride (310 mg, 0.7 mmol) was dissolved in DMF (15 ml) and was treated successively with Hunig's base (240 uL, 1.4 mmol), potassium carbonate (192 mg, 0.7 mmol) and terabutylammonium iodide (26 mg, 0.07 mmol). Th... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | C1CC[NH]CC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.C1COCO1 | TsOH.HO- | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 130 | 5 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.Cc1ccc(S(=O)(=O)OC[C@@H]2COC(C)(C)O2)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39add21eac73415d98cd6896ebf24499 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1>>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1 | C([O-])([O-])=O.[K+].[K+].O.FC(C(=O)O)(F)F.CC1(OC[C@H](O1)CN1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)OC)C>>COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O | CC1(C)[O:29][C@H:28]([CH2:27][N:26]2[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:21][c:20]3[n:19][cH:18][cH:17][c:16](-[c:15]4[c:8](-[c:7]5[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34]5)[n:9][c:10]5[s:11][cH:12][cH:13][n:14]54)[n:33]3)[CH2:32]2)[CH2:30][O:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11... | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1 | null | null | CO | Deprotection | Acetal hydrolysis to diol | 5f7e1daa6b91d1ca6716348acae46f804565b19cb8bd8a05be2ed6c083743e87 | d0de49ebcb43eafba55a762f6d5237c53d7a87b3a882d6753f793a17a3c3a120 | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[O;H0;D2;+0:5]-1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[OH;D1;+0:5] | 87 | [{"value": 87.0, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 18 | HOUR | The N-((3R)-1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}piperidin-3-yl)-4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (150 mg, 0.288 mmol) was dissolved in MeOH (10 ml) and water (1.2 ml) and treated with trifluoroacetic acid (90 uL). The mixture was stirred at 50° C. overnight (18 hours). ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Secondary alcohol | C1COCO1 | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1 | Other | CO | 50 | 18 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H]4COC(C)(C)O4)C3)n2)c1>CO>COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18ed9a8a01804039ac8711f3f5f8358a | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1>>OC[C@H](O)CN1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 | B(Br)(Br)Br.COC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O>>OC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O | C[O:24][c:23]1[cH:22][cH:21][cH:20][c:19](-[c:18]2[c:17](-[c:16]3[cH:15][cH:14][n:13][c:12]([NH:11][C@@H:10]4[CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C@H:3]([CH2:2][OH:1])[OH:4])[CH2:33]4)[n:32]3)[n:31]3[c:27]([n:26]2)[s:28][cH:29][cH:30]3)[cH:25]1>>[OH:1][CH2:2][C@H:3]([OH:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][C@@H:10]([NH:... | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1 | OC[C@H](O)CN1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49 | [{"value": 49.0, "product": "OC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.8, "product": "OC=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C[C@H](CO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The (2R)-3-[(3R)-3-({4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidin-1-yl]propane-1,2-diol (150 mg, 0.312 mmol) in methylene chloride (10 ml) was cooled to −78° C. and slowly treated with 1 molar solution of boron tribromide in methylene chloride (2.5 ml). The reaction mixture was k... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | Other | C(Cl)Cl | null | 1 | COc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C[C@@H](O)CO)C3)n2)c1>C(Cl)Cl>OC[C@H](O)CN1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(O)c4)nc4sccn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14475ac02d574b14977a89ed6f061e41 | Fc1ccc(-c2nc3occn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=C(Cl)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)C1 | FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1.CCN(C(C)C)C(C)C.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)Cl | [NH:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([NH:9][c:10]2[n:11][cH:12][cH:13][c:14](-[c:15]3[c:16](-[c:17]4[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]4)[n:24][c:25]4[o:26][cH:27][cH:28][n:29]34)[n:30]2)[CH2:31]1.ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)[Cl:3])=[O:1]>>[O:1]=[C:2]([Cl:3])[N:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([NH:9][c:10]2[n:11... | Fc1ccc(-c2nc3occn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=C(Cl)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)C1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 928ca241f6336c02cec71c4c980225fdfbac397020a13ce7787b1de82c29f1c9 | c5674cad8f50e137418323e673c87f500d3f14758d6a3111a9ca9e5c866850a2 | c1ccc(-c2nc3occn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-[Cl;H0;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:3])=[O;D1;H0:2])-[C:7]-[C:8] | 95.8 | [{"value": 95.8, "product": "FC1=CC=C(C=C1)C=1N=C2OC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]-N-[(3R)-piperidin-3-yl]pyrimidin-2-amine (200 mg, 0.45 mmol) and Hunig's base (145 μL, 0.90 mmol) in 10 mL DCM was added a solution of triphosgene (660 mg; 2.25 mmol) in 10 mL DCM dropwise over 10 min with stirring. The mixture was allowed to stir at... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary amine | Acyl halide.Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccoc2n1 | HCl | C(Cl)Cl | null | null | Fc1ccc(-c2nc3occn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C(Cl)Cl>O=C(Cl)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2497737102b64838b6c521fcd40fd95e | COc1cc(C(=O)CBr)ccc1F.Nc1nccs1>>COc1cc(-c2cn3ccsc3n2)ccc1F | NC=1SC=CN1.BrCC(=O)C1=CC(=C(C=C1)F)OC.[OH-].[NH4+]>>FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1)OC | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:16]([F:17])[cH:15][cH:14]1)[CH2:7]Br.[n:8]1[cH:9][cH:10][s:11][c:12]1[NH2:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8]3[cH:9][cH:10][s:11][c:12]3[n:13]2)[cH:14][cH:15][c:16]1[F:17] | COc1cc(C(=O)CBr)ccc1F.Nc1nccs1 | COc1cc(-c2cn3ccsc3n2)ccc1F | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fc4245e28231e2acdadf0a109add94d7bcbb15727aa9b3c4274dbbacfc4598a4 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccsc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[n;H0;D2;+0:13]:1>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:13]2:[c:12]:[c:11]:[#16;a:10]:[c:9]:2:[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 66 | [{"value": 66.0, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a mixture of 2-aminothiazole (0.976 g, 9.74 mmol) and 2-bromo-1-(4-fluoro-3-methoxy-phenyl)-ethanone (2.4 g, 9.74 mmol) was added absolute ethanol (100 ml). The reaction was allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture was reduced to half its original volume in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1cscn1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HBr | C(C)O | null | 18 | COc1cc(C(=O)CBr)ccc1F.Nc1nccs1>C(C)O>COc1cc(-c2cn3ccsc3n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84734a6e0d0b4a9993a1fa8ca8aa0f7c | CC(=O)OC(C)=O.COc1cc(-c2cn3ccsc3n2)ccc1F>>COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F | S(O)(O)(=O)=O.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1)OC.C(C)(=O)OC(C)=O.S(O)(O)(=O)=O>>FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C(C)=O)OC | CC(=O)O[C:14]([CH3:15])=[O:16].[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[cH:13]2)[cH:17][cH:18][c:19]1[F:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2[C:14]([CH3:15])=[O:16])[cH:17][cH:18][c:19]1[F:20] | CC(=O)OC(C)=O.COc1cc(-c2cn3ccsc3n2)ccc1F | COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F | null | null | O | C-C Coupling | Friedel-Crafts acylation | 20e4fc8dbd319e0c49a94d48e9c26d09ea69cb91c825364825442124ee99bcaa | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccc(-c2cn3ccsc3n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]2:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:2:[cH;D2;+0:12]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:12]1:[#7;a:11]2:[c:10]:[c:9]:[#16;a:8]:[c:7]:2:[#7;a:6]:[c:5]:1-[c:4] | 96 | [{"value": 96.0, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C(C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 1 | HOUR | To a mixture of 6-(4-fluoro-3-methoxyphenyl)-imidazo[2,1-b]thiazole (1.0 g, 4.03 mmol) and acetic anhydride (25 ml), heated to 140° C., was added 43 μl of concentrated sulfuric acid. The reaction mixture was heated at 140° C. for 1 hour. The reaction was monitored by HPLC. After one hour, only 10% product was observed.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1cn2ccsc2n1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HO- | O | 140 | 1 | CC(=O)OC(C)=O.COc1cc(-c2cn3ccsc3n2)ccc1F>O>COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a740da2163041bda748483667e07a22 | COC(OC)N(C)C.COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F>>COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F | FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C(C)=O)OC.COC(N(C)C)OC>>CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC)C | CO[CH:17](OC)[N:18]([CH3:19])[CH3:20].[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2[C:14](=[O:15])[CH3:16])[cH:21][cH:22][c:23]1[F:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2[C:14](=[O:15])[CH:16]=[CH:17][N:18]([CH3:19])[CH3:20])[cH:21][cH:2... | COC(OC)N(C)C.COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F | null | null | null | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | c1ccc(-c2cn3ccsc3n2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7;a:5]:[c:6](-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]):[c:10]:[#7;a:11]>>[#7;a:5]:[c:6](-[C:7](=[O;D1;H0:9])-[CH;D2;+0:8]=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:10]:[#7;a:11] | 85 | [{"value": 85.0, "product": "CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 100 ml round bottom flask was charged with the 1-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]ethanone (1.12 g, 3.86 mmol) and dimethylformamide dimethylacetal (25 ml). The mixture was refluxed for 20 hours and then cooled to room temperature. The mixture was concentrated in vacuo and the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.c1cn2ccsc2n1 | HO- | null | null | null | COC(OC)N(C)C.COc1cc(-c2nc3sccn3c2C(C)=O)ccc1F>>COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30951136747f4a7ebbca4f4cc3e2b2ef | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1>>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F | Cl.N/C(=N/[H])/N[C@H]1CN(CCC1)C(=O)OC(C)(C)C.CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC)C.Cl.N/C(=N/[H])/N[C@H]1CN(CCC1)C(=O)OC(C)(C)C.[O-]CC.[Na+].[O-]CC.[Na+]>>FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C)OC | CN(C)[CH:16]=[CH:15][C:14](=O)[c:13]1[c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:36]([F:37])[cH:35][cH:34]2)[n:7][c:8]2[s:9][cH:10][cH:11][n:12]21.[H]/[N:17]=[C:18](\[NH:19][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1)[NH2:33]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c... | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[#7;a:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[c:12].[C:13]-[#7:14]/[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[N;H0;D2;+0:17]\[H]>>[C:13]-[#7:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:17]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[#7;a:5]3:... | 86 | [{"value": 86.0, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(dimethylamino)-1-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]prop-2-en-1-one (0.6 g, 1.74 mmol) and tert-butyl (3R)-3-{[(Z)-amino (imino)methyl]amino}piperidine-1-carboxylate hydrochloride (0.726 g, 2.61 mmol) was diluted with 13 ml of absolute ethanol and treated with 1.35 eq. of a 21%... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1 | HO- | C(C)O | null | null | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)N[C@@H]1CCCN(C(=O)OC(C)(C)C)C1>C(C)O>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98091fa893bc409c8047f1664579c518 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F>>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F | FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C)OC.Cl>>Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1)OC | CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:19][c:18]2[n:17][cH:16][cH:15][c:14](-[c:13]3[c:6](-[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28][cH:27]4)[n:7][c:8]4[s:9][cH:10][cH:11][n:12]43)[n:26]2)[CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2-[c:14]2[... | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F | null | null | O1CCOCC1.CCOCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 95 | [{"value": 95.0, "product": "Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The tert-butyl (3R)-3-({4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.785 g, 1.50 mmol) was dissolved in 15 ml of dioxane and treated with 7.5 ml of anhydrous 4N HCl in dioxane at room temperature. The reaction mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CCNCC1 | HO- | O1CCOCC1.CCOCC | null | 2 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)n2)ccc1F>O1CCOCC1.CCOCC>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6a59214d34c4dcab59d2f49f778d980 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F.O=S(=O)(Cl)c1ccc(Cl)cc1>>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)ccc1F | Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1)OC.CCN(C(C)C)C(C)C.ClC1=CC=C(C=C1)S(=O)(=O)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2-[c:14]2[cH:15][cH:16][n:17][c:18]([NH:19][C@@H:20]3[CH2:21][CH2:22][CH2:23][NH:24][CH2:35]3)[n:36]2)[cH:37][cH:38][c:39]1[F:40].Cl[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-... | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F.O=S(=O)(Cl)c1ccc(Cl)cc1 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)ccc1F | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11] | 94 | [{"value": 94.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC", "details": "CALCULATEDPERCENTYIE... | null | null | 30 | MINUTE | The 4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[(3R)-piperidin-3-yl]pyrimidin-2-amine hydrochloride (0.25 g, 0.50 mmol) in methylene chloride (DCM) (12 ml) was cooled to 0° C. and was treated with Hunig's base (440 μl, 2.5 mmol). The mixture was kept at 0° C. for 30 minutes then the 4-chloropheny... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)ccc1F.O=S(=O)(Cl)c1ccc(Cl)cc1>C(Cl)Cl>COc1cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)ccc1F |
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