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-03ba810b7f464a06b5d8787af2e8b64e | ord-0f09a2bb51314285b6f991b9d512a73d | CC(C)(C)OC(=O)N1CCC(=O)CC1.CI>>CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1 | C(C)(C)(C)OC(=O)N1CCC(CC1)=O.O1CCCC1.[H-].[Na+].CI>>C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:16]1.I[CH3:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH2:16]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CI | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1 | null | null | null | C-C Coupling | OtherReaction | adac5963216d307b6de224f49f25d68455d025ace9329a773c47c2937f141090 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1CCNCC1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9]1-[C:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[C:14]-[C:15]-1>>[C;D1;H3:16]-[C;H0;D4;+0:11]1(-[CH3;D1;+0:1])-[C:10]-[#7:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C:3](-[C;D1;H3:2])(-[C;D1;H3:4])-[C;D1;H3:5])-[C:15]-[C:14]-[C:12]-1=[O;D... | 32 | [{"value": 32.0, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | 4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL) and the resulting solution was cooled to 0° C. Sodium hydride (60% in mineral oil, 2.10 g, 53 mmol) was added to the cooled solution in a single portion, and the resulting cloudy mixture was allowed to stir 10 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | null | null | 0 | 0.166667 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CI>>CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-56dffb8badf046c4b6812a170c7583af | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1>>CC1(C)CNCCC1=O | C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)(C)C.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F>>CC1(CNCCC1=O)C | CC(C)(C)OC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[C:8](=[O:9])[CH2:7][CH2:6]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH2:6][CH2:7][C:8]1=[O:9] | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1 | CC1(C)CNCCC1=O | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1>>[O;D1;H0:5]=[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-1 | null | [] | null | null | 2 | HOUR | The 3,3-dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester thus prepared (450 mg, 1.97 mmol) was dissolved in methylene chloride (10 mL). Trifluoroacetic acid was added (305 uL) and the resulting solution stirred at room temperature 2 h. Additional trifluoroacetic acid was added (300 uL) and the reaction stir... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | HO- | C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1>C(Cl)Cl>CC1(C)CNCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8f1b7bacbef04f158bc05613acb1e601 | COC(=O)c1c(N)c([N+](=O)[O-])cc(B2OC(C)(C)C(C)(C)O2)c1F.Cn1ccc(OS(=O)(=O)C(F)(F)F)cc1=O>>COC(=O)c1c(N)c([N+](=O)[O-])cc(-c2ccn(C)c(=O)c2)c1F | CN1C(C=C(C=C1)OS(=O)(=O)C(F)(F)F)=O.[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+].COC(C1=C(C(=CC(=C1F)B1OC(C(O1)(C)C)(C)C)[N+](=O)[O-])N)=O>>COC(C1=C(C(=CC(=C1F)C1=CC(N(C=C1)C)=O)[N+](=O)[O-])N)=O | CC1(C)OB([c:13]2[cH:12][c:8]([N+:9](=[O:10])[O-:11])[c:6]([NH2:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:22]2[F:23])OC1(C)C.O=S(=O)(O[c:14]1[cH:15][cH:16][n:17]([CH3:18])[c:19](=[O:20])[cH:21]1)C(F)(F)F>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13](-[c:14]2[cH:15][cH:16][n:17]([CH... | COC(=O)c1c(N)c([N+](=O)[O-])cc(B2OC(C)(C)C(C)(C)O2)c1F.Cn1ccc(OS(=O)(=O)C(F)(F)F)cc1=O | COC(=O)c1c(N)c([N+](=O)[O-])cc(-c2ccn(C)c(=O)c2)c1F | null | null | COCCOC | C-C Coupling | Suzuki coupling with boronic esters OTf | a3d570e4e0fd76e9f22489a70a6350782719cf47be069d1c7a3ebdc884544e3b | c376e10fbe6bc6c372c1e0d96cbf0a9d9ea35ea77075840731f29cc7280d2ecc | O=c1cc(-c2ccccc2)cc[nH]1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]-[C:7](-[#8:8])=[O;D1;H0:9])-O-C-1(-C)-C.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13](-[C;D1;H3:14]):[c:15](=[O;D1;H0:16]):[c:17]:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[c:11]:[c:12]... | 25 | [{"value": 25.0, "product": "COC(C1=C(C(=CC(=C1F)C1=CC(N(C=C1)C)=O)[N+](=O)[O-])N)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 18 | HOUR | To a solution of 2-amino-5-bromo-6-fluoro-3-nitro-benzoic acid methyl ester (1.0 g, 3.4 mmol) in dioxane (25 mL), under nitrogen atmosphere, was added bispinacoladaboron (1.3 g, 5.1 mmol), dichloro[1,1′-bis(diphenylphosphine)ferrocene]palladium (II) dichlormethane adduct (0.125 g, 0.17 mmol), and potassium acetate (1.0... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | TfOH.HO-.B | COCCOC | 90 | 18 | COC(=O)c1c(N)c([N+](=O)[O-])cc(B2OC(C)(C)C(C)(C)O2)c1F.Cn1ccc(OS(=O)(=O)C(F)(F)F)cc1=O>COCCOC>COC(=O)c1c(N)c([N+](=O)[O-])cc(-c2ccn(C)c(=O)c2)c1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e16e26ba504e42cea01239161cdd285d | Nc1c(C(=O)C2CCCCC2)cc(Br)cc1[N+](=O)[O-].c1cncc(B2OCCCO2)c1>>Nc1c(C(=O)C2CCCCC2)cc(-c2cccnc2)cc1[N+](=O)[O-] | C(=O)(O)[O-].[Na+].B1(OCCCO1)C2=CN=CC=C2.NC1=C(C=C(C=C1[N+](=O)[O-])Br)C(=O)C1CCCCC1>>NC1=C(C=C(C=C1[N+](=O)[O-])C=1C=NC=CC1)C(=O)C1CCCCC1 | Br[c:13]1[cH:12][c:3]([C:4](=[O:5])[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[c:2]([NH2:1])[c:21]([N+:22](=[O:23])[O-:24])[cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][n:18][cH:... | Nc1c(C(=O)C2CCCCC2)cc(Br)cc1[N+](=O)[O-].c1cncc(B2OCCCO2)c1 | Nc1c(C(=O)C2CCCCC2)cc(-c2cccnc2)cc1[N+](=O)[O-] | null | null | CCOC(=O)C.COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 24090aed37a48c66cce36a374df588b856a5a96d58744799fd5f32d2bb560bf0 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(c1cccc(-c2cccnc2)c1)C1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].C1-C-O-B(-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:2)-O-C-1>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1):[c:6]:[c:7] | 89 | [{"value": 89.0, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])C=1C=NC=CC1)C(=O)C1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])C=1C=NC=CC1)C(=O)C1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a solution of (2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone (600 mg, 1.83 mmol) in DME (25 mL) was added, successively, pyridine-3-boronic acid 1,3-propanediol cyclic ester (388 mg, 2.38 mmol), (tetrakistriphenylphosphine) palladium(0) (212 mg, 0.18 mmol), and 1N NaHCO3 (3.7 mL, 3.7 mmol). The resulting mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.B1OCCCO1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.C1CCCCC1.c1ccncc1 | HBr.B | CCOC(=O)C.COCCOC | null | 1.5 | Nc1c(C(=O)C2CCCCC2)cc(Br)cc1[N+](=O)[O-].c1cncc(B2OCCCO2)c1>CCOC(=O)C.COCCOC>Nc1c(C(=O)C2CCCCC2)cc(-c2cccnc2)cc1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-becf597f931c48eab6d0ab9385f0ebff | BrBr.COC(=O)c1cccc([N+](=O)[O-])c1N>>COC(=O)c1cc(Br)cc([N+](=O)[O-])c1N | COC(C1=C(C(=CC=C1)[N+](=O)[O-])N)=O.BrBr>>COC(C1=C(C(=CC(=C1)Br)[N+](=O)[O-])N)=O | Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[NH2:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[NH2:15] | BrBr.COC(=O)c1cccc([N+](=O)[O-])c1N | COC(=O)c1cc(Br)cc([N+](=O)[O-])c1N | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[c:8]:[c:9] | 87.4 | [{"value": 82.0, "product": "COC(C1=C(C(=CC(=C1)Br)[N+](=O)[O-])N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "COC(C1=C(C(=CC(=C1)Br)[N+](=O)[O-])N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2.23 g (10.4 mmol) of 2-amino-3-nitro-benzoic acid methyl ester in 12 mL of acetic acid was added dropwise over 5 minutes a solution of 0.53 mL (10.4 mmol, 1 eq) of bromine in 2 mL of acetic acid. The mixture was stirred at room temperature for 30 minutes and poured into 100 grams of ice. The precipita... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 0.5 | BrBr.COC(=O)c1cccc([N+](=O)[O-])c1N>C(C)(=O)O>COC(=O)c1cc(Br)cc([N+](=O)[O-])c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a1eedacf1b8549838884bd4e41b128f0 | COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc([N+](=O)[O-])c1N.Cc1cccnc1-n1c(C)cc(OS(=O)(=O)C(F)(F)F)cc1=O>>COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N | COC(C1=C(C(=CC(=C1)B1OC(C(O1)(C)C)(C)C)[N+](=O)[O-])N)=O.CC=1C(=NC=CC1)N1C(C=C(C=C1C)OS(=O)(=O)C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>>COC(C1=C(C(=CC(=C1)C1=CC(C(C(=C1)C)CC1=NC=CC=C1)=O)[N+](=O)[O-])N)=O | CC1(C)OB([c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:28]([NH2:29])[c:24]([N+:25](=[O:26])[O-:27])[cH:23]2)O[C:12]1(C)C.O=S(=O)(O[c:8]1[cH:9][c:10](=[O:11])n(-[c:14]2[c:15]([CH3:13])[cH:16][cH:17][cH:18][n:19]2)[c:20]([CH3:21])[cH:22]1)C(F)(F)F>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]2=[CH:9][C:10](=[O:11])[... | COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc([N+](=O)[O-])c1N.Cc1cccnc1-n1c(C)cc(OS(=O)(=O)C(F)(F)F)cc1=O | COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | COCCOC | C-C Coupling | OtherReaction | ff374bc0f966ac2c660c8c98edfc5f1bde6d27ce574152e42066dfdfcefbf961 | edd4560b8a1be426237062e9a97abe24adb8300f6c980bf4d4d1bfac5151ff0f | O=C1C=C(c2ccccc2)C=CC1Cc1ccccn1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8])-O-[C;H0;D4;+0:9]-1(-C)-C.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[C;D1;H3:13]):n(-[c;H0;D3;+0:14]2:[#7;a:15]:[c:16]:[c:17]:[c:18]:[c;H0;D3;+0:19]:2-[CH3;D1;+0:20]):[c;H0;D3;+0:21](=[O;D1;H0:22]):[cH;D2;+0:... | 175.4 | [{"value": 89.0, "product": "COC(C1=C(C(=CC(=C1)C1=CC(C(C(=C1)C)CC1=NC=CC=C1)=O)[N+](=O)[O-])N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 175.4, "product": "COC(C1=C(C(=CC(=C1)C1=CC(C(C(=C1)C)CC1=NC=CC=C1)=O)[N+](=O)[O-])N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-amino-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.163 g, 0.51 mmol) in ethylene glycol dimethylether (5 mL) was added N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridone (0.136 g, 0.41 mmol), bis(triphenylphoshine)palladium (II) dichloride... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic ester | Ketone | B1OCCO1.c1ccccc1.c1ccncc1.c1ccncc1 | c1ccccc1.C1=CCCC=C1.c1ccncc1 | c1ccccc1.C1=CCCC=C1.c1ccncc1 | TfOH.HO-.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC | null | null | COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc([N+](=O)[O-])c1N.Cc1cccnc1-n1c(C)cc(OS(=O)(=O)C(F)(F)F)cc1=O>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.COCCOC>COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7f08f46a32ed4e2799df6df233f19d76 | COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N>>COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc(N)c1N | COC(C1=C(C(=CC(=C1)C1=CC(C(C(=C1)C)CC1=NC=CC=C1)=O)[N+](=O)[O-])N)=O>>COC(C1=C(C(=CC(=C1)C1=CC(C(C(=C1)C)CC1=NC=CC=C1)=O)N)N)=O | O=[N+:25]([O-])[c:24]1[cH:23][c:7]([C:8]2=[CH:9][C:10](=[O:11])[CH:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][n:19]3)[C:20]([CH3:21])=[CH:22]2)[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:26]1[NH2:27]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]2=[CH:9][C:10](=[O:11])[CH:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][c... | COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N | COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc(N)c1N | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1C=C(c2ccccc2)C=CC1Cc1ccccn1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 24 | HOUR | To a slurry of 10% palladium on carbon (0.045 g) in ethyl acetate (20 mL) was added 2-amino-5-(5-methyl-3-oxo-4-pyridin-2-ylmethyl-cyclohexa-1,5-dienyl)-3-nitro-benzoic acid methyl ester (0.176 g, 0.44 mmol). The resulting mixture was hydrogenated at 30 psi for 24 hours. The reaction was filtered, concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1=CCCC=C1.c1ccncc1 | Other | [Pd].C(C)(=O)OCC | null | 24 | COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc([N+](=O)[O-])c1N>[Pd].C(C)(=O)OCC>COC(=O)c1cc(C2=CC(=O)C(Cc3ccccn3)C(C)=C2)cc(N)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-81533076c8b148cfa53adb9113171694 | Cc1cc(O)cc(=O)o1.NCc1ccccn1>>Cc1cc(O)cc(=O)n1Cc1ccccn1 | OC1=CC(OC(=C1)C)=O.NCC1=NC=CC=C1>>OC1=CC(N(C(=C1)C)CC1=NC=CC=C1)=O | o1[c:2]([CH3:1])[cH:3][c:4]([OH:5])[cH:6][c:7]1=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7](=[O:8])[n:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1 | Cc1cc(O)cc(=O)o1.NCc1ccccn1 | Cc1cc(O)cc(=O)n1Cc1ccccn1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccccn1Cc1ccccn1 | [#7;a:1]:[c:2]-[C:3]-[NH2;D1;+0:4].[C;D1;H3:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10](=[O;D1;H0:11]):o:1>>[#7;a:1]:[c:2]-[C:3]-[n;H0;D3;+0:4]1:[c;H0;D3;+0:6](-[C;D1;H3:5]):[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1=[O;D1;H0:11] | 92 | [{"value": 92.0, "product": "OC1=CC(N(C(=C1)C)CC1=NC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "OC1=CC(N(C(=C1)C)CC1=NC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 12.6 g (0.1 mol) of 4-hydroxy-6-methyl-2-pyrone in 50 ml water was added 2-(aminomethyl)pyridine (10.3 ml, 0.1 mol) and the mixture heated to reflux for 2.5 hours. The resulting light yellow compound was filtered from the cooled mixture. Concentration of the filtrate and trituration of the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HO- | O | null | null | Cc1cc(O)cc(=O)o1.NCc1ccccn1>O>Cc1cc(O)cc(=O)n1Cc1ccccn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7c5490cbc6894f5eace522a61c214842 | CCC(=O)c1cc(-c2cccnc2)cc(N)c1N.CCOC(=O)Cl.CSC(=N)N>>CCOC(=O)Nc1nc2cc(-c3cccnc3)cc(C(=O)CC)c2[nH]1 | [OH-].[Na+].CSC(N)=N.ClC(=O)OCC.NC1=C(C=C(C=C1N)C=1C=NC=CC1)C(CC)=O>>C(C)OC(NC1=NC2=C(N1)C(=CC(=C2)C=2C=NC=CC2)C(CC)=O)=O | N[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[cH:18][c:19]([C:20](=[O:21])[CH2:22][CH3:23])[c:24]1[NH2:25].Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].CS[C:7](=[NH:6])[NH2:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[cH:18][c:19]([C:20]... | CCC(=O)c1cc(-c2cccnc2)cc(N)c1N.CCOC(=O)Cl.CSC(=N)N | CCOC(=O)Nc1nc2cc(-c3cccnc3)cc(C(=O)CC)c2[nH]1 | null | null | CCOC(=O)C.O.CC(=O)O | Aromatic Heterocycle Formation | OtherReaction | 4f29f3a8af52fec42d5fedbc355b03722bbdaeb3b09af1107ebe5468967a34c5 | 805e227b2c6755047f43a4a1a2e9d66e7cbb3ddfe7dff9346d36caf7629b7b5a | c1cncc(-c2ccc3[nH]cnc3c2)c1 | C-S-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[NH;D1;+0:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[#8:6]-[C:7].N-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]-[C:14]=[O;D1;H0:15]>>[C:7]-[#8:6]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](:[c:13]-[C:14]=[O;D1... | null | [] | 90 | CELSIUS | null | null | To a mixture of 2-methyl-2-thiopseudourea (109 mg, 0.39 mmol) and ethyl chloroformate (75 μL, 0.78 mmol) in water (2 mL) at 5° C. was added over 40 minutes a 6N aqueous NaOH solution until pH stabilized to 8. The pH was then adjusted to 5 with glacial AcOH. A suspension of 1-(2,3-diamino-5-pyridin-3-yl-phenyl)-propan-1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Primary amine.Primary amine.Monosulfide | Carbamic ester.Ether | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccncc1 | HCl | CCOC(=O)C.O.CC(=O)O | 90 | null | CCC(=O)c1cc(-c2cccnc2)cc(N)c1N.CCOC(=O)Cl.CSC(=N)N>CCOC(=O)C.O.CC(=O)O>CCOC(=O)Nc1nc2cc(-c3cccnc3)cc(C(=O)CC)c2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2a5afcdb095849ddb861073e42e5abbe | CN(CCCN)CCCNC(=O)OC(C)(C)C.O=C1OC(=O)c2cccc3cccc1c23>>CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 | C=1C=C2C=CC=C3C2=C(C1)C(=O)OC3=O.C(C)(C)(C)OC(NCCCN(C)CCCN)=O>>C(C)(C)(C)OC(NCCCN(C)CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)=O | [CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][CH2:16][NH2:17].O1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][c:28]([c:31]23)[C:29]1=[O:30]>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:... | CN(CCCN)CCCNC(=O)OC(C)(C)C.O=C1OC(=O)c2cccc3cccc1c23 | CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 | null | null | C(C)O | Acylation | OtherReaction | 22f1b70036b326cbdeda8645a1baab3f0ee3c30ace9b39f67ef3491a99d192d0 | bb5fdd7481898ce385823b84bf0948a8494704a7a4bb697222c9736fb995b96a | O=C1NC(=O)C2C=CC=C3C=CC=C1C32 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12]3:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16]-1:[c;H0;D3;+0:17]:3:2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[C;H0;D3;+0:16]2=[CH;D2... | 90 | [{"value": 90.0, "product": "C(C)(C)(C)OC(NCCCN(C)CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,8-naphthalic anhydride (0.18 g, 0.9 mmol) was added to a solution of [3-[(3-aminopropyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (0.2 g, 0.8 mmol) in absolute ethanol (20 ml). The reaction mixture was heated at reflux overnight. Rem... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide.Conjugated diene.Conjugated diene | c1cc2c3c(cccc3c1)COC2 | C1=CC2=CC=CC3C[NH]CC(=C1)C23 | C1=CC2=CC=CC3C[NH]CC(=C1)C23 | Other | C(C)O | null | null | CN(CCCN)CCCNC(=O)OC(C)(C)C.O=C1OC(=O)c2cccc3cccc1c23>C(C)O>CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-146cb0dd04144bee85c6a1e7e2520d6e | CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32>>CN(CCCN)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 | C(C)(C)(C)OC(NCCCN(C)CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)=O.FC(C(=O)O)(F)F>>NCCCN(CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)C | CC(C)(C)OC(=O)[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:8][CH2:9][N:10]1[C:11](=[O:12])[C:13]2=[CH:14][CH:15]=[CH:16][C:17]3=[CH:18][CH:19]=[CH:20][CH:21]([C:22]1=[O:23])[CH:24]23>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH2:6])[CH2:7][CH2:8][CH2:9][N:10]1[C:11](=[O:12])[C:13]2=[CH:14][CH:15]=[CH:16][C:17]3=[CH:1... | CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 | CN(CCCN)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1NC(=O)C2C=CC=C3C=CC=C1C32 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 92 | [{"value": 92.0, "product": "NCCCN(CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "NCCCN(CCCN1C(C2=CC=CC=3C2C(C1=O)C=CC3)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester (0.34 g, 0.81 mmol) in CH2Cl2 (24 ml) was added trifluoroacetic acid (6 ml). The reaction mixture was stirred at room temperature for 16 h at which point the reaction was completed b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1=CC2=CC=CC3C[NH]CC(=C1)C23 | HO- | C(Cl)Cl | null | 16 | CN(CCCNC(=O)OC(C)(C)C)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32>C(Cl)Cl>CN(CCCN)CCCN1C(=O)C2=CC=CC3=CC=CC(C1=O)C32 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2f3f5155806b4c4baa1dd17e76b333bc | CN(CCCN)CCCNC(=O)OC(C)(C)C.Cn1c2c3ccccc3nc-2c(Cl)c2ccccc21>>CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 | ClC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2.C(C)(C)(C)OC(NCCCN(C)CCCN)=O>>C(C)(C)(C)OC(NCCCN(CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2)C)=O | [CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][CH2:16][NH2:17].Cl[c:18]1[c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[c:27]-2[n:28]([CH3:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]12>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][C:... | CN(CCCN)CCCNC(=O)OC(C)(C)C.Cn1c2c3ccccc3nc-2c(Cl)c2ccccc21 | CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 | null | null | C(C)OCCO | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 69609c4e4cf9899b9e03307454546bc48609f2b76dae99c49aa2731f943f6380 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2[nH]c3c4ccccc4nc-3cc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4])-[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8](:[c:9]):[c:10]:1:[c:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3]:[c:4])-[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8](:[c:9]):[c:10]:1:[c:11] | 490 | [{"value": 490.0, "product": "C(C)(C)(C)OC(NCCCN(CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 11-chloro-5-methyl-5H-indolo[3,2-b]quinoline (cf. Bierer et al., J. Med. Chem. 1998, vol. 41, pp. 2754) (61 mg, 0.23 mmol) and [[3-[(3-amino-propyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (84_l, 0.34 mmol) in 2-ethoxyet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1c2ccccc2nc2c1[nH]c1ccccc12 | c1c2ccccc2nc2c1[nH]c1ccccc12 | c1c2ccccc2nc2c1[nH]c1ccccc12 | HCl | C(C)OCCO | 120 | null | CN(CCCN)CCCNC(=O)OC(C)(C)C.Cn1c2c3ccccc3nc-2c(Cl)c2ccccc21>C(C)OCCO>CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f3e9c5fcd68140c49a2971d0f6558957 | CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12>>CN(CCCN)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 | C(C)(C)(C)OC(NCCCN(CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2)C)=O.FC(C(=O)O)(F)F>>CN(CCCN)CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2 | CC(C)(C)OC(=O)[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[c:20]-2[n:21]([CH3:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH2:6])[CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]2[n:13][c:14]3[cH:15][c... | CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 | CN(CCCN)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2[nH]c3c4ccccc4nc-3cc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 101.2 | [{"value": 92.0, "product": "CN(CCCN)CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.2, "product": "CN(CCCN)CCCNC1=C2C(N(C3=CC=CC=C13)C)=C1C=CC=CC1=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of [3-[methyl-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-ylamino)-propyl]amino]propyl)-carbamic acid tert-butyl ester (49 mg, 0.1 mmol) in CH2Cl2 (10 ml), was added trifluoroacetic acid (12_l). This mixture was stirred at room temperature for 16 h, at which point the reaction was completed by TLC. All solve... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1c2ccccc2nc2c1[nH]c1ccccc12 | HO- | C(Cl)Cl | null | 16 | CN(CCCNC(=O)OC(C)(C)C)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12>C(Cl)Cl>CN(CCCN)CCCNc1c2nc3ccccc3c-2n(C)c2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5ef6c1c4b096459d8233747f623d138d | CN(C)CCN.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12>>CN(C)CCNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12 | CN(CCN)C.C(C)N(CC)CC.C1=C2C(=C3C(=NC2=CC=C1)C1=CC=CC=C1N3)C(=O)O>>CN(CCNC(=O)C1=C2C(=NC3=CC=CC=C13)C1=CC=CC=C1N2)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6].O[C:7](=[O:8])[c:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[n:16][c:17]2[c:18]1[nH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[n:16][c:17]2[c:18]1[nH:19][c:20]1[cH:21]... | CN(C)CCN.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12 | CN(C)CCNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12 | null | null | O=S(Cl)Cl.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2nc3c(cc2c1)[nH]c1ccccc13 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1:[#7;a:9]:[c:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1:[#7;a:9]:[c:10] | 61 | [{"value": 61.0, "product": "CN(CCNC(=O)C1=C2C(=NC3=CC=CC=C13)C1=CC=CC=C1N2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "CN(CCNC(=O)C1=C2C(=NC3=CC=CC=C13)C1=CC=CC=C1N2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 10H-indolo[3,2-b]quinoline-11-carboxylic acid (0.5 g, 1.9 mmol) was dissolved in 20 ml of refluxing SOCl2, After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylethylendiamine (0.2 mL, 2.26 mmol) and trie... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2nc3c(cc2c1)[nH]c1ccccc13 | HO- | O=S(Cl)Cl.C(Cl)Cl | null | 14 | CN(C)CCN.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12>O=S(Cl)Cl.C(Cl)Cl>CN(C)CCNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-35de871dc825411f82857dabd9c55ffb | CC(N)CN(C)C.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12>>CC(CNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12)N(C)C | CN(CC(C)N)C.C(C)N(CC)CC.C1=C2C(=C3C(=NC2=CC=C1)C1=CC=CC=C1N3)C(=O)O>>CN(C(CNC(=O)C1=C2C(=NC3=CC=CC=C13)C1=CC=CC=C1N2)C)C | [CH3:1][CH:2]([CH2:3][N:24]([CH3:25])[CH3:26])[NH2:4].O[C:5](=[O:6])[c:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[c:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][cH:20]... | CC(N)CN(C)C.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12 | CC(CNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12)N(C)C | null | null | O=S(Cl)Cl.C(Cl)Cl | Acylation | OtherReaction | c996ad5dbf7289e706e061ab1b9f479c4034ccc7d44d3c472cdd0f07dfb90f02 | bf57ff0584568f6455b9e238ebd2c49e1ed2227f45884308bd5a02d975532948 | c1ccc2nc3c(cc2c1)[nH]c1ccccc13 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1:[#7;a:9]:[c:10].[C;D1;H3:11]-[CH;D3;+0:12](-[NH2;D1;+0:13])-[CH2;D2;+0:14]-[N;H0;D3;+0:15](-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:11]-[CH;D3;+0:12](-[CH2;D2;+0:14]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1... | 31 | [{"value": 31.0, "product": "CN(C(CNC(=O)C1=C2C(=NC3=CC=CC=C13)C1=CC=CC=C1N2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 10H-Indolo[3,2-b]quinoline-11-carboxylic acid (0.2 g, 0.76 mmol) was dissolved in 8 ml of refluxing SOCl2. After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylproylendiamine (0.1 mL, 0.97 mmol) and trie... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine | Secondary amide.Tertiary amine | null | null | c1ccc2nc3c(cc2c1)[nH]c1ccccc13 | HO- | O=S(Cl)Cl.C(Cl)Cl | null | 14 | CC(N)CN(C)C.O=C(O)c1c2ccccc2nc2c1[nH]c1ccccc12>O=S(Cl)Cl.C(Cl)Cl>CC(CNC(=O)c1c2ccccc2nc2c1[nH]c1ccccc12)N(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-50c8a89c96a84c2d904d41d6dcbe2b7b | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1>>COC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | NC1=C(C=C(C(=O)OC)C=C1)NC(=O)C=1C(NN=C(C1)C1=CC=NC=C1)=O>>O=C1NN=C(C=C1C1=NC2=C(N1)C=CC(=C2)C(=O)OC)C2=CC=NC=C2 | O=[C:10]([c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[n:20][nH:21][c:22]1=[O:23])[NH:24][c:25]1[c:8]([NH2:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10](-[c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][n:17][cH:18][cH:19]4)[n:20][n... | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1 | COC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 76e10ab81a93773d04ca0e55f8fb55bcd635323b5b4a9b9acd135658778da8ae | a079090652d9d6c0e17c70eeab94f6d7afea064f52cf5fa9036d5feedd14143a | O=c1[nH]nc(-c2ccncc2)cc1-c1nc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10](-[c:11]):[#7;a:12]:[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[O;D1;H0:15]=[c:14]1:[#7;a:13]:[#7;a:12]:[c:10](-[c:11]):[c:9]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:7]):[nH;D2;+0:6]:1 | null | [] | 100 | CELSIUS | 10 | HOUR | A mixture of 1.3 g of methyl 4-amino-3-[(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazine-4-carbonyl)amino]benzoate and 20 ml of glacial acetic acid is heated with stirring at 100° C. for 10 hours. The precipitate which has formed is filtered off with suction, washed with water and dried in vacuo at 50° C.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1cnncc1.c1ccncc1 | HO- | C(C)(=O)O | 100 | 10 | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1>C(C)(=O)O>COC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c0220b86ef074eb9b947f35d3d72c66d | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1>>O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | Cl.NC1=C(C=C(C(=O)OC)C=C1)NC(=O)C=1C(NN=C(C1)C1=CC=NC=C1)=O.O1CCCC1.[OH-].[Li+]>>O=C1NN=C(C=C1C1=NC2=C(N1)C=CC(=C2)C(=O)O)C2=CC=NC=C2 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:24]([NH:23][C:9](=O)[c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][n:16][cH:17][cH:18]3)[n:19][nH:20][c:21]2=[O:22])[cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9](-[c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][n:16][cH:17][cH:18]4)[n:19][nH:20][c:21]3=[... | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1 | O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 48aa9b5dad0229f6283247a10f81eecd28630344f9188cdec5da8e2b5d867970 | 58ce411da13c66f484c8e30f72657c28f494944e68bff64e897497550b25cb23 | O=c1[nH]nc(-c2ccncc2)cc1-c1nc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[NH;D2;+0:7]-[C;H0;D3;+0:8](=O)-[c;H0;D3;+0:9]1:[c:10]:[c:11](-[c:12]):[#7;a:13]:[#7;a:14]:[c:15]:1=[O;D1;H0:16]):[c:17](-[NH2;D1;+0:18]):[c:19]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]:[c:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:9]2:[c:10]:[c:11](-[c:1... | null | [] | 50 | CELSIUS | 5 | HOUR | A mixture consisting of 500 mg of methyl 4-amino-3-[(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carbonyl)amino]benzoate, 6 ml of tetrahydrofuran (THF), 6 ml of methanol, 6 ml of water and 173 mg of lithium hydroxide is stirred at 50° C. for 5 hours. After cooling to room temperature, the pH is adjusted to 4-5 with 1N... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1cnncc1.c1ccncc1 | HO- | CO.O | 50 | 5 | COC(=O)c1ccc(N)c(NC(=O)c2cc(-c3ccncc3)n[nH]c2=O)c1>CO.O>O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e1a5216f3afb44469e559d9e36406dd2 | CCN(CC)CCN.O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1>>CCN(CC)CCNC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | C(C)N(CC)CCN.O=C1NN=C(C=C1C1=NC2=C(N1)C=CC(=C2)C(=O)O)C2=CC=NC=C2.C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C>>C(C)N(CCNC(=O)C1=CC2=C(NC(=N2)C=2C(NN=C(C2)C2=CC=NC=C2)=O)C=C1)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8].O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]2[nH:15][c:16](-[c:17]3[cH:18][c:19](-[c:20]4[cH:21][cH:22][n:23][cH:24][cH:25]4)[n:26][nH:27][c:28]3=[O:29])[n:30][c:31]2[cH:32]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13... | CCN(CC)CCN.O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | CCN(CC)CCNC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1[nH]nc(-c2ccncc2)cc1-c1nc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8]):[c:4] | null | [] | null | null | 10 | MINUTE | A mixture consisting of 50 mg of 2-(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazin-4-yl)-1H-benzoimidazole-5-carboxylic acid, 0.065 ml of triethylamine and 1.5 ml of dimethylformamide (DMF) is stirred at room temperature for 10 minutes, mixed with 68.4 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cnncc1.c1ccncc1 | HO- | O.CN(C=O)C | null | 0.166667 | CCN(CC)CCN.O=C(O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1>O.CN(C=O)C>CCN(CC)CCNC(=O)c1ccc2[nH]c(-c3cc(-c4ccncc4)n[nH]c3=O)nc2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-51cce0ef0913412cbbe7e442c680ab1a | CCNC(=N)N.COC(C)(OC)C(=O)C=CN(C)C>>CCNc1nccc(C(C)=O)n1 | CN(C=CC(C(C)(OC)OC)=O)C.Cl.C(C)NC(=N)N.[O-]CC.[Na+]>>C(C)NC1=NC=CC(=N1)C(C)=O | [CH3:1][CH2:2][NH:3][C:4](=[NH:5])[NH2:12].CO[C:9]([C:8](=O)[CH:7]=[CH:6]N(C)C)([CH3:10])[O:11]C>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8]([C:9]([CH3:10])=[O:11])[n:12]1 | CCNC(=N)N.COC(C)(OC)C(=O)C=CN(C)C | CCNc1nccc(C(C)=O)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1afa3d3b2993e219b919f6c309f76cb12069a08b72248b10b8c5223892bde6ae | cd3e3aec4550e62a12c260fe4030270c82d1dfd512053f92544190b939fd4229 | c1cncnc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[O;H0;D2;+0:3]-C)-[C;H0;D3;+0:4](=O)-[CH;D2;+0:5]=[CH;D2;+0:6]-N(-C)-C.[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C:7]-[#7:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:4](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:3]):[cH;D2;+0:5]:[cH;D2;+0:6]:[n;H0;D2;+0:11]:1 | null | [] | null | null | 8 | HOUR | A mixture of 6 g of 1-dimethylamino-4,4-dimethoxypent-1-en-3-one, 3.96 g of N-ethylguanidine hydrochloride and 26 ml of 20% strength ethanolic sodium ethoxide solution is heated under reflux for 2 hours. After cooling, the solid is filtered off with suction, and the filtrate is concentrated in vacuo and mixed with 20 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ether.Ether.Primary amine | Ketone | null | c1cncnc1 | c1cncnc1 | HO- | null | null | 8 | CCNC(=N)N.COC(C)(OC)C(=O)C=CN(C)C>>CCNc1nccc(C(C)=O)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0d9dbd0ceb884aa9952e31fab8bb9478 | CCNc1nccc(C(C)=O)n1.CCOC(=O)C(=O)C(=O)OCC>>CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1 | C(C)NC1=NC=CC(=N1)C(C)=O.O=C(C(=O)OCC)C(=O)OCC>>C(C)NC1=NC=CC(=N1)C(CC(C(=O)OCC)(C(=O)OCC)O)=O | [CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8]([C:9](=[O:10])[CH3:11])[n:24]1.[C:12](=[O:13])([C:14](=[O:15])[O:16][CH2:17][CH3:18])[C:19](=[O:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][C:12]([OH:13])([C:14](=[O:15])[O:16][CH2:17][CH3:18])[C:19](=[O:20])[O:21][... | CCNc1nccc(C(C)=O)n1.CCOC(=O)C(=O)C(=O)OCC | CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1 | null | null | null | C-C Coupling | OtherReaction | e88a4a7d8d6b5dee5ec6739bba985b00a792654307585b505d721a6c4424a1e7 | 622d9e177646f51219fadf1ea3ee007cb7d9c42cff173da68f5fdf3c13916e74 | c1cncnc1 | [#7;a:1]:[c:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[#7;a:1]:[c:2]-[C:3](=[O;D1;H0:5])-[CH2;D2;+0:4]-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[C:8](=[O;D1;H0:9])-[#8:7]-[C:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | null | [] | 110 | CELSIUS | null | null | A mixture consisting of 1.9 g of 1-(2-ethylaminopyrimidin-4-yl)ethanone and 1.86 ml of diethyl ketomalonate is heated at 110° C. for 18 hours. The mixture is purified by column chromatography (silica gel, mobile phase:methylene chloride:methanol=98:2).
Conditions: See reaction.notes.procedure_details.
Workup: The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone.Ester.Ester.Tertiary alcohol | null | null | c1cncnc1 | null | null | 110 | null | CCNc1nccc(C(C)=O)n1.CCOC(=O)C(=O)C(=O)OCC>>CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d8366a1b2fef4b479476f79a57cde650 | CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1.NN>>CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1 | C(C)NC1=NC=CC(=N1)C(CC(C(=O)OCC)(C(=O)OCC)O)=O.Cl.NN>>C(C)NC1=NC=CC(=N1)C=1C=C(C(NN1)=O)C(=O)OCC | CCO[C:17]([C:11](O)([CH2:10][C:9](=O)[c:8]1[cH:7][cH:6][n:5][c:4]([NH:3][CH2:2][CH3:1])[n:21]1)[C:12](=[O:13])[O:14][CH2:15][CH3:16])=[O:18].[NH2:19][NH2:20]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([C:12](=[O:13])[O:14][CH2:15][CH3:16])[c:17](=[O:18])[nH:19][n:20]2)[n:21]1 | CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1.NN | CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 54634d418c8596de45ab35c5695b00785263669907ca8fff6518a837f0632bdf | aa93ed92552ed79af2c3e55f1caa04b7f5a7360562e21df7516ddca07861385e | O=c1ccc(-c2ccncn2)n[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-O)(-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8](-[#7:9]):[#7;a:10]:[c:11]:[c:12]:1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16].[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[#7:9]-[c:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]2:[cH;D2;+0:4]:[c;H0;D3;+0:3](-[C:13](=[O;D1... | null | [] | 130 | CELSIUS | null | null | A mixture of 2 g of diethyl 2-[2-(2-ethylaminopyrimidin-4-yl)-2-oxo-ethyl]-2-hydroxy-malonate, 485 mg of hydrazine hydrochloride and 20 ml of ethanol is stirred under reflux for 24 hours. After cooling while stirring, the precipitate is filtered off with suction, heated in 4 ml of N-methylpyrrolidinone (NMP) at 130° C.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Ester.Tertiary alcohol | Ester | null | c1cnncc1 | c1cncnc1.c1cnncc1 | HO- | C(C)O | 130 | null | CCNc1nccc(C(=O)CC(O)(C(=O)OCC)C(=O)OCC)n1.NN>C(C)O>CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-01b279a3c593478bb244d5db8ca3aad0 | CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1>>CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1 | C(C)NC1=NC=CC(=N1)C=1C=C(C(NN1)=O)C(=O)OCC.C1CCOC1.O.[OH-].[Li+]>>C(C)NC1=NC=CC(=N1)C=1C=C(C(NN1)=O)C(=O)O | CC[O:14][C:12]([c:11]1[cH:10][c:9](-[c:8]2[cH:7][cH:6][n:5][c:4]([NH:3][CH2:2][CH3:1])[n:19]2)[n:18][nH:17][c:15]1=[O:16])=[O:13]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([C:12](=[O:13])[OH:14])[c:15](=[O:16])[nH:17][n:18]2)[n:19]1 | CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1 | CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccncn2)n[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | A mixture of 400 mg of ethyl 6-(2-ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydro-pyridazine-4-carboxylate, 2 ml of THF, 2 ml of water, 2 ml of methanol and 100 mg of lithium hydroxide is stirred at room temperature for 1 hour, and the volatile constituents are removed in vacuo. A pH of 4 is adjusted by dropwise addition o... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1cnncc1 | Other | CO | null | 1 | CCNc1nccc(-c2cc(C(=O)OCC)c(=O)[nH]n2)n1>CO>CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c6db62493a0541ae9904ac2a0c41fb10 | CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1.Nc1ccc(Cl)cc1N>>CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1 | ClC1=CC(=C(C=C1)N)N.C(C)NC1=NC=CC(=N1)C=1C=C(C(NN1)=O)C(=O)O.CN(C)C=O.C(C)N(CC)CC>>NC1=C(C=CC(=C1)Cl)NC(=O)C=1C(NN=C(C1)C1=NC(=NC=C1)NCC)=O | O[C:12]([c:11]1[cH:10][c:9](-[c:8]2[cH:7][cH:6][n:5][c:4]([NH:3][CH2:2][CH3:1])[n:27]2)[n:26][nH:25][c:23]1=[O:24])=[O:13].[NH2:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[NH2:22]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([C:12](=[O:13])[NH:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[... | CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1.Nc1ccc(Cl)cc1N | CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1 | null | null | O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cc(-c2ccncn2)n[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9].[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:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9] | null | [] | null | null | 30 | MINUTE | A solution of 110 mg of 6-(2-ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid, 2 ml of DMF and 0.17 ml of triethylamine is mixed with 192 mg of Hatu and stirred at room temperature for 30 minutes. Then 66 mg of 4-chloro-phenylenediamine are added, and the mixture is stirred at room temperature ov... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.c1cnncc1.c1ccccc1 | HO- | O | null | 0.5 | CCNc1nccc(-c2cc(C(=O)O)c(=O)[nH]n2)n1.Nc1ccc(Cl)cc1N>O>CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-72c1b37601314bc3b8dc57e3b5fa4dc1 | CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1>>CCNc1nccc(-c2cc(-c3nc4cc(Cl)ccc4[nH]3)c(=O)[nH]n2)n1 | NC1=C(C=CC(=C1)Cl)NC(=O)C=1C(NN=C(C1)C1=NC(=NC=C1)NCC)=O>>ClC1=CC2=C(NC(=N2)C=2C(NN=C(C2)C2=NC(=NC=C2)NCC)=O)C=C1 | O=[C:12]([c:11]1[cH:10][c:9](-[c:8]2[cH:7][cH:6][n:5][c:4]([NH:3][CH2:2][CH3:1])[n:26]2)[n:25][nH:24][c:22]1=[O:23])[NH:21][c:20]1[c:14]([NH2:13])[cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11](-[c:12]3[n:13][c:14]4[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]4[... | CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1 | CCNc1nccc(-c2cc(-c3nc4cc(Cl)ccc4[nH]3)c(=O)[nH]n2)n1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 76e10ab81a93773d04ca0e55f8fb55bcd635323b5b4a9b9acd135658778da8ae | a079090652d9d6c0e17c70eeab94f6d7afea064f52cf5fa9036d5feedd14143a | O=c1[nH]nc(-c2ccncn2)cc1-c1nc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10](-[c:11]:[#7;a:12]):[#7;a:13]:[#7;a:14]:[c:15]:1=[O;D1;H0:16]>>[#7;a:12]:[c:11]-[c:10]1:[#7;a:13]:[#7;a:14]:[c:15](=[O;D1;H0:16]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[nH;D2;+0:2]:... | null | [] | null | null | null | null | 6-(2-Ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-amino-4-chlorophenyl)amide (50 mg) are stirred in 1 ml of glacial acetic acid at 100° C. for 3 hours. After cooling, the precipitate is filtered off with suction, stirred with aqueous sodium bicarbonate solution and again filtered off with ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1cncnc1.c1cnncc1.c1ccc2[nH]cnc2c1 | HO- | C(C)(=O)O | null | null | CCNc1nccc(-c2cc(C(=O)Nc3ccc(Cl)cc3N)c(=O)[nH]n2)n1>C(C)(=O)O>CCNc1nccc(-c2cc(-c3nc4cc(Cl)ccc4[nH]3)c(=O)[nH]n2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-669cdacc1e58420e9b6082d0b7ac8879 | Nc1ccc(Cl)cc1NC(=O)c1cc(Cl)n[nH]c1=O>>O=c1[nH]nc(Cl)cc1-c1nc2ccc(Cl)cc2[nH]1 | NC1=C(C=C(C=C1)Cl)NC(=O)C=1C(NN=C(C1)Cl)=O.NC1=C(C=CC(=C1)Cl)NC(=O)C=1C(NN=C(C1)Cl)=O>>ClC=1C=C(C(NN1)=O)C1=NC2=C(N1)C=C(C=C2)Cl | O=[C:9]([c:8]1[c:2](=[O:1])[nH:3][n:4][c:5]([Cl:6])[cH:7]1)[NH:10][c:11]1[cH:12][c:13]([Cl:15])[cH:14][cH:16][c:17]1[NH2:18]>>[O:1]=[c:2]1[nH:3][n:4][c:5]([Cl:6])[cH:7][c:8]1-[c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[nH:18]1 | Nc1ccc(Cl)cc1NC(=O)c1cc(Cl)n[nH]c1=O | O=c1[nH]nc(Cl)cc1-c1nc2ccc(Cl)cc2[nH]1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | b8a14eed92d407c7877eafdd1aae168755826fc260dd09432d2786866f0a8b75 | 13a243a4a3d01197eb229b4226a0ab42e57cf7cc6968477100676d27a1f5f0f3 | O=c1[nH]nccc1-c1nc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3]1:[c:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:6]):[cH;D2;+0:7]:[c:8]:[c:9]:1-[NH2;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[c:13](-[Cl;D1;H0:14]):[#7;a:15]:[#7;a:16]:[c:17]:1=[O;D1;H0:18]>>[Cl;D1;H0:14]-[c:13]1:[#7;a:15]:[#7;a:16]:[c:17](=[O;D1;H0:18]):[c;H0;D3;+0:11](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2... | null | [] | 120 | CELSIUS | null | null | A mixture of 6-chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-amino-5-chlorophenyl)amide and 6-chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-amino-4-chlorophenyl)amide (1.0 g; 1.67 mmol) is dissolved in 100 ml of glacial acetic acid and heated at 120° C. for 90 min. A precipitate separates out on coo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide.Primary amine | Aromatic halide | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1cnncc1.c1ccc2[nH]cnc2c1 | HO- | C(C)(=O)O | 120 | null | Nc1ccc(Cl)cc1NC(=O)c1cc(Cl)n[nH]c1=O>C(C)(=O)O>O=c1[nH]nc(Cl)cc1-c1nc2ccc(Cl)cc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2239869004564afb8a547ed16cac6743 | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(Cl)cc3n2COCC[Si](C)(C)C)c1=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>>Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C)c1O | CC1=C(C(=CC(=C1)B1OC(C(O1)(C)C)(C)C)C)O.C([O-])([O-])=O.[Na+].[Na+].ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)Cl>>ClC=1C=CC2=C(N(C(=N2)C=2C(N(N=C(C2)C2=CC(=C(C(=C2)C)O)C)COCC[Si](C)(C)C)=O)COCC[Si](C)(C)C)C1 | Cl[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]3[n:17]2[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:24])[CH3:25])[c:26](=[O:27])[n:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:35])[CH3:36])[n:37]1.CC1(C)OB([c:4]2[cH:3][c:2]([CH3:1])[c:41]([OH:42])[c:39]([CH3:40])[cH... | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(Cl)cc3n2COCC[Si](C)(C)C)c1=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O | Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C)c1O | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | COCCOC | C-C Coupling | Suzuki coupling with boronic esters | 7d3abbda54e933df9ff9dc39c70f4c4ada1c268870f29590395c2cc6bed1dda1 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=c1[nH]nc(-c2ccccc2)cc1-c1nc2ccccc2[nH]1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:[c:11]:[c:12]:1>>[C:9]-[#7;a:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c:11]:[c:10]:1 | null | [] | 95 | CELSIUS | null | null | 6-Chloro-4-[6-chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (100 mg; 0.185 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.15 equivalents) are dissolved in DME, and argon is passed in for 10 min. 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccnnc1.B1OCCO1.c1ccccc1 | c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1.c1ccc2[nH]cnc2c1 | HCl.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC | 95 | null | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(Cl)cc3n2COCC[Si](C)(C)C)c1=O.Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1O>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC>Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n... |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-515db933f0c14a0293ea111721cec9cc | Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C)c1O>>Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4[nH]3)c(=O)[nH]n2)cc(C)c1O | Cl.FC(C(=O)O)(F)F.ClC=1C=CC2=C(N(C(=N2)C=2C(N(N=C(C2)C2=CC(=C(C(=C2)C)O)C)COCC[Si](C)(C)C)=O)COCC[Si](C)(C)C)C1.[OH-].[Na+]>>ClC=1C=CC2=C(NC(=N2)C=2C(NN=C(C2)C2=CC(=C(C(=C2)C)O)C)=O)C1 | C[Si](C)(C)CCOC[n:17]1[c:8](-[c:7]2[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:25]([OH:26])[c:23]([CH3:24])[cH:22]3)[n:21][n:20](COCC[Si](C)(C)C)[c:18]2=[O:19])[n:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]21>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7](-[c:8]3[n:9][c:10]4[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16... | Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C)c1O | Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4[nH]3)c(=O)[nH]n2)cc(C)c1O | null | null | ClCCl.CO.O | Reduction | OtherReaction | c1f0b959e3270c73ea431d54a86cf99be394391b1aeed84bffc9169fd737a4fd | 4c2ed0f567254ea4c771872583c9a3c5a0aabe43ba2b8e508678a1ced83aca48 | O=c1[nH]nc(-c2ccccc2)cc1-c1nc2ccccc2[nH]1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:1-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-C-O-C-C-[Si](-C)(-C)-C):[#7;a:12]:[c:13]>>[O;D1;H0:10]=[c:9](:[c:8]-[c:7]1:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[nH;D2;+0:1]:1):[nH;D2;+0:11]:[#7;a:12]:[c:13] | null | [] | null | null | 30 | MINUTE | 4-[6-Chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(4-hydroxy-3,5-dimethylphenyl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one is stirred in dichloromethane:trifluoroacetic acid/1:1 at RT for 30 min. The solvent is stripped off in vacuo, and the residue is dissolved in methanol, and 2M sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group.Silyl protective group | null | c1ccnnc1.c1ccc2nc[nH]c2c1 | c1cnncc1.c1ccc2[nH]cnc2c1 | c1ccccc1.c1cnncc1.c1ccc2[nH]cnc2c1 | HO- | ClCCl.CO.O | null | 0.5 | Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C)c1O>ClCCl.CO.O>Cc1cc(-c2cc(-c3nc4ccc(Cl)cc4[nH]3)c(=O)[nH]n2)cc(C)c1O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bb9f641574f3407fbcc52c5df3b9224e | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O>>C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O | ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C(F)(F)F.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+]>>O=C1C(=CC(=NN1COCC[Si](C)(C)C)B(O)O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C(F)(F)F | CC1(C)OB([B:12]2[O:13]C(C)(C)C(C)(C)[O:14]2)OC1(C)C.Cl[c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:38](=[O:39])[c:16](-[c:17]2[n:18][c:19]3[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][c:28]3[n:29]2[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[cH:15]1>... | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O | null | null | CS(=O)C | Miscellaneous | OtherReaction | 0f862682a552a117cbdb4251701683c41ea8d7c93834f0609621794a8532f1bb | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | O=c1[nH]nccc1-c1nc2ccccc2[nH]1 | C-C1(-C)-O-B(-[B;H0;D3;+0:1]2-[O;H0;D2;+0:2]-C(-C)(-C)-C(-C)(-C)-[O;H0;D2;+0:3]-2)-O-C-1(-C)-C.Cl-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:[c:9]:[c:10]:1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c;H0;D3;+0:4](-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3]):[c:10]:[c:9]:[c:8]:1 | null | [] | 95 | CELSIUS | null | null | 6-Chloro-4-[6-trifluormethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (prepared in analogy to example 15b), bis(pinacolato)diboron, (1,1′-bis(diphenylphosphine)ferrocene)-palladium(II) chloride-dichloromethane complex and potassium acetate are dissol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | B1OCCO1.[B]1OCCO1.c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccc2[nH]cnc2c1 | HCl.B | CS(=O)C | 95 | null | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O>CS(=O)C>C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-de6193c7d6a84e4199662d280a686708 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1>>C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O | O=C1C(=CC(=NN1COCC[Si](C)(C)C)B(O)O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C(F)(F)F.ClC1=NC=CC(=N1)Cl.[F-].[K+]>>ClC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C(F)(F)F | OB(O)[c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:42](=[O:43])[c:20](-[c:21]2[n:22][c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]3[n:33]2[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:39])([CH3:40])[CH3:41])[cH:19]1.Cl[c:12]1[cH:13][cH:14][n:15][c:16]([Cl:17])[n:18... | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1 | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | f8f5c061fa0766cf8bf2b56a909373cb6775dd68fbe7d26541aa38df8e9d5b4c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1[nH]nc(-c2ccncn2)cc1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8]1:[#7;a:9]:[#7;a:10](-[C:11]):[c:12]:[c:13]:[c:14]:1>>[C:11]-[#7;a:10]1:[#7;a:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:2):[c:14]:[c:13]:[c:12]:1 | null | [] | null | null | 16 | HOUR | 6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid, 2,4-di-chloropyrimidine, potassium fluoride and tris(dibenzylideneacetone)dipalladium(0) are dissolved in dry THF and degassed with argon for 10 minutes. Tri-tert... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccnnc1.c1cncnc1 | c1ccnnc1.c1cncnc1 | c1ccnnc1.c1cncnc1.c1ccc2[nH]cnc2c1 | HCl.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | null | 16 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1>C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-54dfd9217eb84573b049cba999822dc4 | COc1ccc(Cl)nn1>>COc1nnc(Cl)cc1C=O | C(CCC)[Li].CC1(NC(CCC1)(C)C)C.ClC=1N=NC(=CC1)OC.Cl.C(=O)(O)[O-].[Na+]>>ClC1=CC(=C(N=N1)OC)C=O | [CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][cH:9]1>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1[CH:10]=[O:11] | COc1ccc(Cl)nn1 | COc1nnc(Cl)cc1C=O | null | null | C1CCOC1.CN(C)C=O.C(C)O | Miscellaneous | OtherReaction | be7ff8b1310c070d854f9ef41f58f5c15ed6d3196fad23a27fa694b91ad9ce8f | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccnnc1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[cH;D2;+0:8]:1>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[c;H0;D3;+0:8]:1-[C:9]=[O;D1;H0:10] | null | [] | 0 | CELSIUS | 30 | MINUTE | n-Butyllithium is added dropwise at −75° C. to a solution of 2,2,6,6-tetramethyl-piperidine in THF. The solution is stirred at 0° C. for 30 minutes. After cooling to −75° C., a solution, precooled to −75° C., of 3-chloro-6-methoxypyridazine in THF is added dropwise. The reaction is stirred at −75° C. for 30 minutes. Su... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | Other | C1CCOC1.CN(C)C=O.C(C)O | 0 | 0.5 | COc1ccc(Cl)nn1>C1CCOC1.CN(C)C=O.C(C)O>COc1nnc(Cl)cc1C=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e986e39eba024f0d9b164fdcba6d54bc | COc1nnc(Cl)cc1C=O.Cc1cccc(N)c1N>>COc1nnc(Cl)cc1-c1nc2cccc(C)c2[nH]1 | ClC1=CC(=C(N=N1)OC)C=O.NC1=C(C=CC=C1N)C>>ClC1=CC(=C(N=N1)OC)C1=NC2=C(N1)C(=CC=C2)C | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][n:5][c:6]([Cl:7])[cH:8]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]1[NH2:19]>>[CH3:1][O:2][c:3]1[n:4][n:5][c:6]([Cl:7])[cH:8][c:9]1-[c:10]1[n:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]2[nH:19]1 | COc1nnc(Cl)cc1C=O.Cc1cccc(N)c1N | COc1nnc(Cl)cc1-c1nc2cccc(C)c2[nH]1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc2[nH]c(-c3ccnnc3)nc2c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[#7;a:7]:[c:8]:1-[#8:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:9]-[c:8]1:[#7;a:7]:[#7;a:6]:[c:4](-[Cl;D1;H0:5]):[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | null | [] | 120 | CELSIUS | null | null | 6-Chloro-3-methoxypyridazine-4-carbaldehyde is dissolved in DMF, und 2,3-diaminotoluene is added. The reaction solution is heated at 120° C. in a microwave for 30 minutes. The crude product is purified on silica gel (eluent ethyl acetate in heptane). MS (ES+) m/z 275 (M+H).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccnnc1.c1ccc2[nH]cnc2c1 | HO- | CN(C)C=O | 120 | null | COc1nnc(Cl)cc1C=O.Cc1cccc(N)c1N>CN(C)C=O>COc1nnc(Cl)cc1-c1nc2cccc(C)c2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2bb6dd6c1f964b519f78e8c155863158 | COC(=O)c1ccc2nc(-c3cc(Cl)nn(COCC[Si](C)(C)C)c3=O)n(COCC[Si](C)(C)C)c2c1>>C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O | ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C(=O)OC>>ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C=O | CO[C:21]([c:20]1[cH:19][cH:18][c:17]2[n:16][c:15](-[c:14]3[cH:13][c:11]([Cl:12])[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:34]3=[O:35])[n:25]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])[c:24]2[cH:23]1)=[O:22]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8]... | COC(=O)c1ccc2nc(-c3cc(Cl)nn(COCC[Si](C)(C)C)c3=O)n(COCC[Si](C)(C)C)c2c1 | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O | null | [O-2].[Mn+2].[O-2].[Mn+4].[O-2] | ClCCl.C1(=CC=CC=C1)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | O=c1[nH]nccc1-c1nc2ccccc2[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:4] | null | [] | 0 | CELSIUS | 1 | HOUR | 6-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (3.0 g, 5.3 mmol) is dissolved in dichloromethane, and the solution is cooled to 0° C. 15% DIBA1H in toluene is added dropwise, and the reaction mixture is stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccnnc1.c1ccc2[nH]cnc2c1 | HO- | [O-2].[Mn+2].[O-2].[Mn+4].[O-2].ClCCl.C1(=CC=CC=C1)C | 0 | 1 | COC(=O)c1ccc2nc(-c3cc(Cl)nn(COCC[Si](C)(C)C)c3=O)n(COCC[Si](C)(C)C)c2c1>[O-2].[Mn+2].[O-2].[Mn+4].[O-2].ClCCl.C1(=CC=CC=C1)C>C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e36806988f24499e97201003b5c7807a | CN1CCNCC1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O>>CN1CCN(Cc2ccc3nc(-c4cc(Cl)nn(COCC[Si](C)(C)C)c4=O)n(COCC[Si](C)(C)C)c3c2)CC1 | C(=O)(O)[O-].[Na+].ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)C=O.CN1CCNCC1.C(=O)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=C(C=C2)CN2CCN(CC2)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:40][CH2:41]1.O=[CH:6][c:7]1[cH:8][cH:9][c:10]2[n:11][c:12](-[c:13]3[cH:14][c:15]([Cl:16])[n:17][n:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[c:27]3=[O:28])[n:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[c:38]2[cH:39]1>>[CH3:1][N... | CN1CCNCC1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O | CN1CCN(Cc2ccc3nc(-c4cc(Cl)nn(COCC[Si](C)(C)C)c4=O)n(COCC[Si](C)(C)C)c3c2)CC1 | null | null | ClCCl.C(C)(=O)O | Heteroatom Alkylation and Arylation | reductive amination | 66e6667395903ee1c54d8aecc784ece1bccbdcbc9661ebcae0e6a980f9380640 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=c1[nH]nccc1-c1nc2ccc(CN3CCNCC3)cc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[c:3] | null | [] | null | null | 15 | MINUTE | 6-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one is dissolved in dichloro-methane. 4-Methylpiperazine and acetic acid are added. After 15 minutes, sodium triacetoxyborohydride is added in several portions over the course of 3 hours. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1.c1ccnnc1 | Other | ClCCl.C(C)(=O)O | null | 0.25 | CN1CCNCC1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccc(C=O)cc3n2COCC[Si](C)(C)C)c1=O>ClCCl.C(C)(=O)O>CN1CCN(Cc2ccc3nc(-c4cc(Cl)nn(COCC[Si](C)(C)C)c4=O)n(COCC[Si](C)(C)C)c3c2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9feb74f319eb4940b9784589c395aa8d | Nc1ccccc1N.O=C(O)c1cc(Cl)n[nH]c1=O>>Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O | ClC=1C=C(C(NN1)=O)C(=O)O.C1(=C(C=CC=C1)N)N.Cl.C(C)N=C=NCCCN(C)C>>NC1=C(C=CC=C1)NC(=O)C=1C(NN=C(C1)Cl)=O | [NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8].O[C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[n:15][nH:16][c:17]1=[O:18]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[n:15][nH:16][c:17]1=[O:18] | Nc1ccccc1N.O=C(O)c1cc(Cl)n[nH]c1=O | Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccn[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9].[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:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9] | null | [] | null | null | 4 | HOUR | 30.5 g of 6-chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid, 18 g of ortho-phenylenediamine and 2 g of DMAP are dissolved in 800 ml of DMF, at room temperature 32.2 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride are added, and the resulting solution is stirred at room temperature for 4 hours. For... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnncc1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 4 | Nc1ccccc1N.O=C(O)c1cc(Cl)n[nH]c1=O>CN(C)C=1C=CN=CC1.CN(C)C=O>Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0a5a35357a4242119c12cf0fec91f87f | Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O>>O=c1[nH]nc(Cl)cc1-c1nc2ccccc2[nH]1 | NC1=C(C=CC=C1)NC(=O)C=1C(NN=C(C1)Cl)=O>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)Cl)=O | O=[C:9]([c:8]1[c:2](=[O:1])[nH:3][n:4][c:5]([Cl:6])[cH:7]1)[NH:17][c:16]1[c:11]([NH2:10])[cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[c:2]1[nH:3][n:4][c:5]([Cl:6])[cH:7][c:8]1-[c:9]1[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[nH:17]1 | Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O | O=c1[nH]nc(Cl)cc1-c1nc2ccccc2[nH]1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 76e10ab81a93773d04ca0e55f8fb55bcd635323b5b4a9b9acd135658778da8ae | a079090652d9d6c0e17c70eeab94f6d7afea064f52cf5fa9036d5feedd14143a | O=c1[nH]nccc1-c1nc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10](-[Cl;D1;H0:11]):[#7;a:12]:[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[Cl;D1;H0:11]-[c:10]1:[#7;a:12]:[#7;a:13]:[c:14](=[O;D1;H0:15]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[nH;D2;+0:2]:2):[c:... | null | [] | null | null | null | null | A solution of 26.4 g of 6-chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-aminophenyl)amide in 500 ml of acetic acid is stirred at 110° C. for 2.5 hours and then the solvent is distilled off. The crude product obtained in this way is employed without further purification.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1cnncc1.c1ccc2[nH]cnc2c1 | HO- | C(C)(=O)O | null | null | Nc1ccccc1NC(=O)c1cc(Cl)n[nH]c1=O>C(C)(=O)O>O=c1[nH]nc(Cl)cc1-c1nc2ccccc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-89db74143efc4aeca5ac7a1cab291567 | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)c1ccsc1>>C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.S1C=C(C=C1)B(O)O.C([O-])([O-])=O.[K+].[K+].O>>S1C=C(C=C1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | Cl[c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:36](=[O:37])[c:18](-[c:19]2[n:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[n:27]2[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:34])[CH3:35])[cH:17]1.OB(O)[c:12]1[cH:13][cH:14][s:15][cH:16]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][... | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)c1ccsc1 | C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | null | null | C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 8a8f836bc650bf77052c587b6c83ef7234124a1e9a8c8578cf10835ba68ae5f7 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1[nH]nc(-c2ccsc2)cc1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[C:4]):[c:5]:[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#16;a:11]:[c:12]:1>>[C:4]-[#7;a:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[#16;a:11]:[c:12]:2):[c:7]:[c:6]:[c:5]:1 | null | [] | 85 | CELSIUS | 4 | HOUR | 44 mg of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 14 mg of thiophene-3-boronic acid and 36 mg of potassium carbonate are dissolved 1.5 ml of a 1:2 mixture of water and dimethoxyethane, and argon is passed through the solution for degass... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccnnc1.c1ccsc1 | c1ccnnc1.c1ccsc1 | c1ccnnc1.c1ccsc1.c1nc2ccccc2[nH]1 | HCl.B | C(OC)COC | 85 | 4 | C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)c1ccsc1>C(OC)COC>C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a0bb0e36af1c4605afc2d9a01c94eb29 | C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>>O=c1[nH]nc(-c2ccsc2)cc1-c1nc2ccccc2[nH]1 | S1C=C(C=C1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)C2=CSC=C2)=O | C[Si](C)(C)CCOC[n:3]1[c:2](=[O:1])[c:12](-[c:13]2[n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[n:21]2COCC[Si](C)(C)C)[cH:11][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[n:4]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[cH:11][c:12]1-[c:13]1[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[nH:21]1 | C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | O=c1[nH]nc(-c2ccsc2)cc1-c1nc2ccccc2[nH]1 | null | null | ClCCl.FC(C(=O)O)(F)F.C(C)(S)S | Reduction | OtherReaction | 7d1cf985bab34d788925de517a3955cc09e2a5635cb594c2eed22bd60af4aaef | 4c2ed0f567254ea4c771872583c9a3c5a0aabe43ba2b8e508678a1ced83aca48 | O=c1[nH]nc(-c2ccsc2)cc1-c1nc2ccccc2[nH]1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4](=[O;D1;H0:5]):[n;H0;D3;+0:6](-C-O-C-C-[Si](-C)(-C)-C):[#7;a:7]:[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[O;D1;H0:5]=[c:4](:[c:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1):[nH;D2;+0:6]:[#7;a:7]:[c:8] | null | [] | null | null | 18 | HOUR | 30 mg of 6-thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl -ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one is dissolved in a mixture of dichloromethane (1 ml) and trifluoroacetic acid (1 ml), 18 μl of ethanedithiol are added, and the resulting solution is stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group.Silyl protective group | null | c1ccnnc1.c1nc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]cnc2c1 | c1cnncc1.c1ccsc1.c1ccc2[nH]cnc2c1 | HO- | ClCCl.FC(C(=O)O)(F)F.C(C)(S)S | null | 18 | C[Si](C)(C)CCOCn1nc(-c2ccsc2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>ClCCl.FC(C(=O)O)(F)F.C(C)(S)S>O=c1[nH]nc(-c2ccsc2)cc1-c1nc2ccccc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ae34da666d0c49ec9f96cd03cabe9afb | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>>C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+]>>O=C1C(=CC(=NN1COCC[Si](C)(C)C)B(O)O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | CC1(C)OB([B:12]2[O:13]C(C)(C)C(C)(C)[O:14]2)OC1(C)C.Cl[c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:34](=[O:35])[c:16](-[c:17]2[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[n:25]2[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])[cH:15]1>>[CH3:1][Si:2]([CH3:3])([CH3:... | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | null | null | CS(=O)C | Miscellaneous | OtherReaction | 0f862682a552a117cbdb4251701683c41ea8d7c93834f0609621794a8532f1bb | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | O=c1[nH]nccc1-c1nc2ccccc2[nH]1 | C-C1(-C)-O-B(-[B;H0;D3;+0:1]2-[O;H0;D2;+0:2]-C(-C)(-C)-C(-C)(-C)-[O;H0;D2;+0:3]-2)-O-C-1(-C)-C.Cl-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:[c:9]:[c:10]:1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c;H0;D3;+0:4](-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3]):[c:10]:[c:9]:[c:8]:1 | null | [] | 95 | CELSIUS | null | null | 4 g of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxy-methyl) -1H-benzimidazol-2-yl]-2H-pyridazin-3-one (example 46), 4.1 g of bis(pinacolato)diboron, 0.19 g of (1,1 ′-bis(diphenylphosphine)-ferrocene)palladium(II) chloride-dichloromethane complex and 2.3 g of potassium acetate are dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | B1OCCO1.[B]1OCCO1.c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1nc2ccccc2[nH]1 | HCl.B | CS(=O)C | 95 | null | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>CS(=O)C>C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4020a0a57845445b83289a2bc3d60e68 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1>>C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | O=C1C(=CC(=NN1COCC[Si](C)(C)C)B(O)O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.ClC1=NC=CC(=N1)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | OB(O)[c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:38](=[O:39])[c:20](-[c:21]2[n:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3[n:29]2[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[cH:19]1.Cl[c:12]1[cH:13][cH:14][n:15][c:16]([Cl:17])[n:18]1>>[CH3:1][Si:2]([CH3:3])([C... | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1 | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | null | null | O.O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | f8f5c061fa0766cf8bf2b56a909373cb6775dd68fbe7d26541aa38df8e9d5b4c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1[nH]nc(-c2ccncn2)cc1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8]1:[#7;a:9]:[#7;a:10](-[C:11]):[c:12]:[c:13]:[c:14]:1>>[C:11]-[#7;a:10]1:[#7;a:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:2):[c:14]:[c:13]:[c:12]:1 | null | [] | 97 | CELSIUS | 3 | HOUR | 1.32 g of 6-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanylethoxy-methyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid, 583 mg of 2,4-dichlorpyrimidine and 3,3 g of cesium carbonate are dissolved in 17 ml of a 1:4 mixture of water and dioxane, and argon is passed through the solution for d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccnnc1.c1cncnc1 | c1ccnnc1.c1cncnc1 | c1ccnnc1.c1cncnc1.c1nc2ccccc2[nH]1 | HCl.B | O.O1CCOCC1 | 97 | 3 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.Clc1ccnc(Cl)n1>O.O1CCOCC1>C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-da03c4138f9d41ce88d2d0a3dba761c6 | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.NCCN1CCOCC1>>C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | ClC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.NCCN1CCOCC1>>N1(CCOCC1)CCNC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | Cl[c:16]1[n:15][cH:14][cH:13][c:12](-[c:11]2[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:46](=[O:47])[c:28](-[c:29]3[n:30][c:31]4[cH:32][cH:33][cH:34][cH:35][c:36]4[n:37]3[CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])[cH:27]2)[n:26]1.[NH2:17][CH2:18][CH2:19][N:20]1[CH2:21... | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.NCCN1CCOCC1 | C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]nc(-c2ccnc(NCCN3CCOCC3)n2)cc1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | 100 mg of 6-(2-chloropyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one are suspended in 0.5 ml of N-(2-aminoethyl)morpholine, and the reaction mixture is heated at 100° C. in a microwave for 20 minutes. The product is purified by preparativ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccnnc1.c1cncnc1.C1COCC[NH]1.c1nc2ccccc2[nH]1 | HCl | null | 100 | null | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.NCCN1CCOCC1>>C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1ed32532581c41498e6c601434eb109f | C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>>O=c1[nH]nc(-c2ccnc(NCCN3CCOCC3)n2)cc1-c1nc2ccccc2[nH]1 | N1(CCOCC1)CCNC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)C2=NC(=NC=C2)NCCN2CCOCC2)=O | C[Si](C)(C)CCOC[n:3]1[c:2](=[O:1])[c:22](-[c:23]2[n:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[n:31]2COCC[Si](C)(C)C)[cH:21][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[n:20]2)[n:4]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][CH... | C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | O=c1[nH]nc(-c2ccnc(NCCN3CCOCC3)n2)cc1-c1nc2ccccc2[nH]1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | OtherReaction | 7d1cf985bab34d788925de517a3955cc09e2a5635cb594c2eed22bd60af4aaef | 4c2ed0f567254ea4c771872583c9a3c5a0aabe43ba2b8e508678a1ced83aca48 | O=c1[nH]nc(-c2ccnc(NCCN3CCOCC3)n2)cc1-c1nc2ccccc2[nH]1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4](=[O;D1;H0:5]):[n;H0;D3;+0:6](-C-O-C-C-[Si](-C)(-C)-C):[#7;a:7]:[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[O;D1;H0:5]=[c:4](:[c:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1):[nH;D2;+0:6]:[#7;a:7]:[c:8] | null | [] | null | null | 2 | HOUR | 88 mg of 6-[2-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]-2-(2-trimethylsilanyl-ethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one are dissolved in 2 ml of a 1:1 mixture of dichloromethane and trifluoroacetic acid, and the mixture is stirred at room temperature for 2 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group.Silyl protective group | null | c1ccnnc1.c1nc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]cnc2c1 | c1cnncc1.c1cncnc1.C1COCC[NH]1.c1ccc2[nH]cnc2c1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 2 | C[Si](C)(C)CCOCn1nc(-c2ccnc(NCCN3CCOCC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>ClCCl.FC(C(=O)O)(F)F>O=c1[nH]nc(-c2ccnc(NCCN3CCOCC3)n2)cc1-c1nc2ccccc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2c8b3ade3271450f9aea1bf3410a9b3b | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccnc(SC)n1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>>CSc1nccc(-c2cc(-c3nc4ccccc4[nH]3)c(=O)[nH]n2)n1 | ClC=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.CSC1=NC=CC(=N1)[Sn](CCCC)(CCCC)CCCC.[F-].[K+]>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)C2=NC(=NC=C2)SC)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:24]1.C[Si](C)(C)CCOC[n:19]1[c:11](-[c:10]2[cH:9][c:8](Cl)[n:23][n:22](COCC[Si](C)(C)C)[c:20]2=[O:21])[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][c... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccnc(SC)n1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | CSc1nccc(-c2cc(-c3nc4ccccc4[nH]3)c(=O)[nH]n2)n1 | null | [Cl-].C(C)[N+](CC)(CC)CC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | OtherReaction | a8e5eb9fcb21c11b951297cb6cb6786be2ba17b443b370247ca2ac2ddeceecab | ac334791059cb918059e3bc1de4d0b64599a26cda3fbc8254e9a0dd486c2ef69 | O=c1[nH]nc(-c2ccncn2)cc1-c1nc2ccccc2[nH]1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:8]1:[c:9](-[c:10]2:[c:11]:[c;H0;D3;+0:12](-Cl):[#7;a:13]:[n;H0;D3;+0:14](-C-O-C-C-[Si](-C)(-C)-C):[c:15]:2=[O;D1;H0:16]):[#7;a:17]:[c:18](:[c:19]):[c:20]:1:[c:21]>>[#16:4]-[c:3... | null | [] | 80 | CELSIUS | 30 | MINUTE | The compound is prepared in analogy to example 15. A Stille coupling is carried out instead of the Suzuki coupling. This entails dissolving 6-chloro-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxy-methyl)-2H-pyridazin-3-one, 2-methylsulfanyl-4-tributylstannylpyrimidine, tetra-eth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Silyl protective group.Silyl protective group.Tin | null | c1cncnc1.c1ccnnc1.c1nc2ccccc2[nH]1 | c1cncnc1.c1cnncc1.c1ccc2[nH]cnc2c1 | c1cncnc1.c1cnncc1.c1ccc2[nH]cnc2c1 | HCl.Sn | [Cl-].C(C)[N+](CC)(CC)CC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | 80 | 0.5 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccnc(SC)n1.C[Si](C)(C)CCOCn1nc(Cl)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>[Cl-].C(C)[N+](CC)(CC)CC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CSc1nccc(-c2cc(-c3nc4ccccc4[nH]3)c(=O)[nH]n2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0b1e3bb90b464aa88133a65f8742aa21 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.c1c[nH]cn1>>C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21 | O=C1C(=CC(=NN1COCC[Si](C)(C)C)B(O)O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.N1C=NC=C1>>C[SiH](CCOCN1C(=NC2=C1C=CC=C2)C=2C(N(N=C(C2)N2C=NC=C2)COCC[Si](C)(C)C)=O)C | C[Si:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][O:6][CH2:7][n:8]1[c:9](-[c:10]2[cH:11][c:12](B(O)O)[n:18][n:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27])[c:28]2=[O:29])[n:30][c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]12.[nH:13]1[cH:14][cH:15][n:16][cH:17]1>>[CH3:1][SiH:2]([CH3:3])[CH2:4][CH2:5][O:6][CH2:... | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.c1c[nH]cn1 | C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | O.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 6467f9b8cfd58f6a53283597ffd368b9d3ea804dc7d6a518754aab70540629a5 | fa6d8644f910d21bb1c1692e112b1c812d7af5afcda733004f9d45091a0873f3 | O=c1[nH]nc(-n2ccnc2)cc1-c1nc2ccccc2[nH]1 | C-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5].O-B(-O)-[c;H0;D3;+0:6]1:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:[c:11]:[c:12]:1.[#7;a:13]1:[c:14]:[c:15]:[nH;D2;+0:16]:[c:17]:1>>[C:9]-[#7;a:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:16]2:[c:15]:[c:14]:[#7;a:13]:[c:17]:2):[c:12]:[c:11]:[c:10]:1.[C:5]-[C:4]-[SiH;D3;+0:1]... | null | [] | 80 | CELSIUS | 3 | HOUR | 100 mg of 6-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid (example 55), 35.5 mg of copper(II) acetate and 20 mg of imidazole are dissolved in dry pyridine, and the solution is stirred at 80° C. for 3 hours. For workup, it is dilu... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid.Silyl protective group | null | c1ccnnc1.c1c[nH]cn1 | c1ccnnc1.c1c[nH]cn1 | c1ccnnc1.c1c[nH]cn1.c1nc2ccccc2[nH]1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O.N1=CC=CC=C1 | 80 | 3 | C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.c1c[nH]cn1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O.N1=CC=CC=C1>C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-afba9e13ab974bc092140c0feb185cb3 | C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21>>O=c1[nH]nc(-n2ccnc2)cc1-c1nc2ccccc2[nH]1 | C[SiH](CCOCN1C(=NC2=C1C=CC=C2)C=2C(N(N=C(C2)N2C=NC=C2)COCC[Si](C)(C)C)=O)C>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)N2C=NC=C2)=O | C[SiH](C)CCOC[n:21]1[c:13](-[c:12]2[c:2](=[O:1])[n:3](COCC[Si](C)(C)C)[n:4][c:5](-[n:6]3[cH:7][cH:8][n:9][cH:10]3)[cH:11]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[n:6]2[cH:7][cH:8][n:9][cH:10]2)[cH:11][c:12]1-[c:13]1[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[nH:21]1 | C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21 | O=c1[nH]nc(-n2ccnc2)cc1-c1nc2ccccc2[nH]1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | OtherReaction | 69c0abd1a33ee5635ff31db131553721d00e2fdb697abe991abc87f32e437d8e | 0ba73238bad7c29e9afad223c6a4c9bb32fde37408eb7a5e7c67288f0e8d8816 | O=c1[nH]nc(-n2ccnc2)cc1-c1nc2ccccc2[nH]1 | C-[SiH](-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4](=[O;D1;H0:5]):[n;H0;D3;+0:6](-C-O-C-C-[Si](-C)(-C)-C):[#7;a:7]:[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[O;D1;H0:5]=[c:4](:[c:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1):[nH;D2;+0:6]:[#7;a:7]:[c:8] | null | [] | null | null | 2 | HOUR | 40 mg of 4-[1-(2-dimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-imidazol-1-yl-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one are dissolved in 2 ml of a 1:1 mixture of dichloromethane and trifluoroacetic acid, and the mixture is stirred at room temperature for 2 hours. The volatile components are then disti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | null | c1ccnnc1.c1nc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]cnc2c1 | c1cnncc1.c1c[nH]cn1.c1ccc2[nH]cnc2c1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 2 | C[SiH](C)CCOCn1c(-c2cc(-n3ccnc3)nn(COCC[Si](C)(C)C)c2=O)nc2ccccc21>ClCCl.FC(C(=O)O)(F)F>O=c1[nH]nc(-n2ccnc2)cc1-c1nc2ccccc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ec95a085efed4ea4bd8fe4a25e73c26c | COc1cc(Br)cc(C=O)c1O.C[Si](C)(C)CCOCCl>>COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C | BrC=1C=C(C(=C(C=O)C1)O)OC.C([O-])([O-])=O.[K+].[K+].ClCOCC[Si](C)(C)C>>BrC=1C=C(C(=C(C=O)C1)OCOCC[Si](C)(C)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH:9]=[O:10])[c:11]1[OH:12].Cl[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH:9]=[O:10])[c:11]1[O:12][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20] | COc1cc(Br)cc(C=O)c1O.C[Si](C)(C)CCOCCl | COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | null | [] | null | null | 48 | HOUR | 10 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 23.9 g of potassium carbonate and 12.2 g of (2-chloromethoxyethyl)trimethylsilane is suspended in 500 ml of DMF and stirred at room temperature for 48 hours. The DMF is distilled off in vacuo, the residue is dissolved in ethyl acetate, and the resulting solution is extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 48 | COc1cc(Br)cc(C=O)c1O.C[Si](C)(C)CCOCCl>CN(C)C=O>COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3838062fb5794b499372a71d6efce843 | CN.COc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C=O)c1OCOCC[Si](C)(C)C>>CNCc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(OC)c1OCOCC[Si](C)(C)C | COC=1C(=C(C=O)C=C(C1)C1=NN(C(C(=C1)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2)=O)COCC[Si](C)(C)C)OCOCC[Si](C)(C)C.CN.C1CCOC1.C(#N)[BH3-].[Na+]>>COC=1C=C(C=C(C1OCOCC[Si](C)(C)C)CNC)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9](-[c:10]3[n:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[n:18]3[CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[c:27](=[O:28])[n:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[n:38]2)[cH:39][c:40]([O:41][CH3:42])[c:43]... | CN.COc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C=O)c1OCOCC[Si](C)(C)C | CNCc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(OC)c1OCOCC[Si](C)(C)C | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=c1[nH]nc(-c2ccccc2)cc1-c1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | 200 mg of methoxy-5-{6-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazin-3-yl}-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde are dissolved in 4.5 ml of methanol and methylamine (0.146 ml of a THF solution), and 18.4 mg of sodium cyanoborohydride ar... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccnnc1.c1nc2ccccc2[nH]1 | Other | CO.C(C)(=O)O | null | 16 | CN.COc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(C=O)c1OCOCC[Si](C)(C)C>CO.C(C)(=O)O>CNCc1cc(-c2cc(-c3nc4ccccc4n3COCC[Si](C)(C)C)c(=O)n(COCC[Si](C)(C)C)n2)cc(OC)c1OCOCC[Si](C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-552dac4e3cd44625bf490bacd309abfc | COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>COc1cc(Br)cc(-c2cnco2)c1OCOCC[Si](C)(C)C | BrC=1C=C(C(=C(C=O)C1)OCOCC[Si](C)(C)C)OC.C1(=CC=C(C=C1)S(=O)(=O)C[N+]#[C-])C>>BrC=1C=C(C(=C(C1)C1=CN=CO1)OCOCC[Si](C)(C)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH:9]=[O:13])[c:14]1[O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23].Cc1ccc(S(=O)(=O)[CH2:10][N+:11]#[C-:12])cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][o:13]2)[c:14]1[O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20... | COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | COc1cc(Br)cc(-c2cnco2)c1OCOCC[Si](C)(C)C | null | null | CO | Functional Group Interconversion | OtherReaction | 350ec210554942a1358fcbd88dfbddb6e2b23a43f1c83725aa708598a14ee7ab | c716b04888bf3cb683ec79e24be07b585e1dc289053b42331c058bc5f98fd4eb | c1ccc(-c2cnco2)cc1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D2;+0:8]=[O;H0;D1;+0:9]):[c:10]:[c:11]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[c;H0;D3;+0:8]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[o;H0;D2;+0:9]:1):[c:10]:[c:11] | null | [] | null | null | null | null | 1 g of 5-bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde and 0.54 g of p-toluenesulfonylmethyl isocyanide are dissolved in 40 ml of methanol, 0.38 g of o-potassiumcarbonate is added in portions, and the reaction mixture is heated to reflux for 18 h. The solvent is then distilled off, and the crude produ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Isocyanide | null | c1ccccc1 | c1cocn1 | c1ccccc1.c1cocn1 | TsOH.HO- | CO | null | null | COc1cc(Br)cc(C=O)c1OCOCC[Si](C)(C)C.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>CO>COc1cc(Br)cc(-c2cnco2)c1OCOCC[Si](C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-75bad0bdb18843a0926daf2d162608bf | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)C1CC1>>C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | ClC1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.C1(CC1)B(O)O.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>C1(CC1)C1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | Cl[c:16]1[n:15][cH:14][cH:13][c:12](-[c:11]2[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:40](=[O:41])[c:22](-[c:23]3[n:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[n:31]3[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:38])[CH3:39])[cH:21]2)[n:20]1.OB(O)[CH:17]1[CH2:18][CH2:19]1>>[CH3:1... | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)C1CC1 | C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 412d14d936f2fe74271076c2d85cda822694d627c10e4da821198f343e0c85d8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1[nH]nc(-c2ccnc(C3CC3)n2)cc1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-1>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[CH;D3;+0:6]1-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | null | [] | 100 | CELSIUS | 9 | HOUR | 100 mg of 6-(2-chloropyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 29.2 mg of cyclopropylboronic acid and 138 mg of potassium phosphate are dissolved in 1 ml of toluene and 0.05 ml of water and, under an argon atmosphere, 17 mg of 1,1′... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.C1CC1 | c1cncnc1.C1CC1 | c1ccnnc1.c1cncnc1.C1CC1.c1nc2ccccc2[nH]1 | HCl.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.C1(=CC=CC=C1)C | 100 | 9 | C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O.OB(O)C1CC1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.C1(=CC=CC=C1)C>C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-836e08e052fe43058a58ca664df681f1 | C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>>O=c1[nH]nc(-c2ccnc(C3CC3)n2)cc1-c1nc2ccccc2[nH]1 | C1(CC1)C1=NC=CC(=N1)C=1C=C(C(N(N1)COCC[Si](C)(C)C)=O)C1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.C(C)O>>N1C(=NC2=C1C=CC=C2)C=2C(NN=C(C2)C2=NC(=NC=C2)C2CC2)=O | C[Si](C)(C)CCOC[n:3]1[c:2](=[O:1])[c:16](-[c:17]2[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[n:25]2COCC[Si](C)(C)C)[cH:15][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[n:14]2)[n:4]1>>[O:1]=[c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[n:14]2)[cH:15][c:16]1-[c:17... | C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O | O=c1[nH]nc(-c2ccnc(C3CC3)n2)cc1-c1nc2ccccc2[nH]1 | null | null | O1CCOCC1.Cl | Reduction | OtherReaction | 7d1cf985bab34d788925de517a3955cc09e2a5635cb594c2eed22bd60af4aaef | 4c2ed0f567254ea4c771872583c9a3c5a0aabe43ba2b8e508678a1ced83aca48 | O=c1[nH]nc(-c2ccnc(C3CC3)n2)cc1-c1nc2ccccc2[nH]1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]:[c:4](=[O;D1;H0:5]):[n;H0;D3;+0:6](-C-O-C-C-[Si](-C)(-C)-C):[#7;a:7]:[c:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[O;D1;H0:5]=[c:4](:[c:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1):[nH;D2;+0:6]:[#7;a:7]:[c:8] | null | [] | null | null | 3 | HOUR | 27 mg of 6-(2-cyclopropylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one are dissolved in 2.5 ml of 4M hydrochloric acid solution in dioxane and 1 ml of ethanol and stirred at room temperature for 2 days. The solvent is then distilled off... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group.Silyl protective group | null | c1ccnnc1.c1nc2ccccc2[nH]1 | c1cnncc1.c1ccc2[nH]cnc2c1 | c1cnncc1.c1cncnc1.C1CC1.c1ccc2[nH]cnc2c1 | HO- | O1CCOCC1.Cl | null | 3 | C[Si](C)(C)CCOCn1nc(-c2ccnc(C3CC3)n2)cc(-c2nc3ccccc3n2COCC[Si](C)(C)C)c1=O>O1CCOCC1.Cl>O=c1[nH]nc(-c2ccnc(C3CC3)n2)cc1-c1nc2ccccc2[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0989b2748d704d2894e860d20aea4ea4 | CO.O=C(O)Cc1ccc(Cl)cc1>>COC(=O)Cc1ccc(Cl)cc1 | ClC1=CC=C(C=C1)CC(=O)O.Cl.CO>>ClC1=CC=C(C=C1)CC(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | CO.O=C(O)Cc1ccc(Cl)cc1 | COC(=O)Cc1ccc(Cl)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | null | null | 4-Chlorophenylacetic acid (5.0 g) was dissolved in 10% hydrogen chloride-methanol solution (50 ml) and heated under reflex for 14 hours. The solvent then was removed under reduced pressure and saturated sodium hydrogencarbonate solution was added to the residue, followed by extraction with ethyl acetate. The organic la... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)Cc1ccc(Cl)cc1>>COC(=O)Cc1ccc(Cl)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-605b849843804862a90b8e36f41a45f4 | CI.COC(=O)C(c1ccc(Cl)cc1)C1CCCC1>>COC(=O)C(C)(c1ccc(Cl)cc1)C1CCCC1 | C(C)(C)NC(C)C.ClC1=CC=C(C=C1)C(C(=O)OC)C1CCCC1.CI>>ClC1=CC=C(C=C1)C(C(=O)OC)(C)C1CCCC1 | I[CH3:6].[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | CI.COC(=O)C(c1ccc(Cl)cc1)C1CCCC1 | COC(=O)C(C)(c1ccc(Cl)cc1)C1CCCC1 | null | null | C1CCOC1.C(CCC)[Li].[Cl-].[NH4+] | C-C Coupling | Methylation with MeI_tertiary | 4a52ebe9ffae5bdd307b0b4ac6a7069bc533ab8d42293ed2712c32b846010273 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | c1ccc(CC2CCCC2)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[CH;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[c:9](:[c:10]):[c:11])-[C:12]>>[C:2]-[C:3](-[C;H0;D4;+0:4](-[CH3;D1;+0:1])(-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[c:9](:[c:10]):[c:11])-[C:12] | null | [] | -35 | CELSIUS | 10 | MINUTE | To a solution of diisopropylamine (0.15 ml) in THF (2 ml), n-butyl lithium (1.5 M hexane solution, 0.6 ml) was added at −78° C., stirred for 10 minutes and another solution of methyl 2-(4-chlorophenyl)-2-cyclopentylacetate (200 mg) in THF (1.5 ml) was added dropwise. After 15 minutes' stirring, the system temperature w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.C1CCCC1 | HI | C1CCOC1.C(CCC)[Li].[Cl-].[NH4+] | -35 | 0.166667 | CI.COC(=O)C(c1ccc(Cl)cc1)C1CCCC1>C1CCOC1.C(CCC)[Li].[Cl-].[NH4+]>COC(=O)C(C)(c1ccc(Cl)cc1)C1CCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b6e31047605947038cdd2e34c6fc6eb3 | Brc1cccnc1.CCOC(=O)C(=O)c1ccc(Cl)cc1>>CCOC(=O)C(O)(c1ccc(Cl)cc1)c1cccnc1 | BrC=1C=NC=CC1.ClC1=CC=C(C=C1)C(C(=O)OCC)=O.[Cl-].[NH4+]>>ClC1=CC=C(C=C1)C(C(=O)OCC)(C=1C=NC=CC1)O | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([OH:7])([c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1 | Brc1cccnc1.CCOC(=O)C(=O)c1ccc(Cl)cc1 | CCOC(=O)C(O)(c1ccc(Cl)cc1)c1cccnc1 | null | null | C(CCC)[Li].C(C)OCC | C-C Coupling | Grignard_alcohol | 72d307076f6defa0943f87bbc847fe67f35fbaa78203fa718ec66467f1588bf4 | 9ad4a4524e70e857006264b5570f9463fa55d41dbe0be303433eb1b99baa979d | c1ccc(Cc2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:11](-[OH;D1;+0:12])(-[c:13](:[c:14]):[c:15])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 48.3 | [{"value": 48.3, "product": "ClC1=CC=C(C=C1)C(C(=O)OCC)(C=1C=NC=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 3-bromopyridine (640 mg) in diethyl ether (10 ml), n-butyl lithium (2.5M-hexane solution, 1.80 ml) was added at −74° C. After 15 minutes' stirring at the same temperature, a solution of ethyl 2-(4-chlorophenyl)-2-oxoacetate (960 mg) in diethyl ether (100 ml) was added. The temperature of the system was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Ester.Tertiary alcohol | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Br- | C(CCC)[Li].C(C)OCC | null | 0.25 | Brc1cccnc1.CCOC(=O)C(=O)c1ccc(Cl)cc1>C(CCC)[Li].C(C)OCC>CCOC(=O)C(O)(c1ccc(Cl)cc1)c1cccnc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c5bb6ebc07cd49ad9ab13e25aeb3b07a | COC(=O)C(Br)c1ccc(Cl)cc1.c1c[nH]cn1>>COC(=O)C(c1ccc(Cl)cc1)n1ccnc1 | O.N1C=NC=C1.C(C)N(CC)CC.BrC(C(=O)OC)C1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)C(C(=O)OC)N1C=NC=C1 | Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[nH:13]1[cH:14][cH:15][n:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[n:13]1[cH:14][cH:15][n:16][cH:17]1 | COC(=O)C(Br)c1ccc(Cl)cc1.c1c[nH]cn1 | COC(=O)C(c1ccc(Cl)cc1)n1ccnc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6e796d385604f3d786cae1d46df3d343d7680e137c2fb51f458a62eeb83d5c95 | 88c92d2671864e93a5b5578ca874d1de41e4f02ddd75a3966019ee10f35d4923 | c1ccc(Cn2ccnc2)cc1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:6](:[c:7]):[c:8].[#7;a:9]1:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[c:6](:[c:7]):[c:8])-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[#7;a:9]:[c:13]:1 | 64 | [{"value": 64.0, "product": "ClC1=CC=C(C=C1)C(C(=O)OC)N1C=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of imidazole (170 mg) and triethylamine (350 ml) in DMF (1 ml), a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (657 mg) in DMF (3 ml) was added. After stirring for an overnight, water was added to the reaction liquid, followed by extraction with ethyl acetate, washing with saturated brine and dry... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | null | 8 | COC(=O)C(Br)c1ccc(Cl)cc1.c1c[nH]cn1>CN(C)C=O>COC(=O)C(c1ccc(Cl)cc1)n1ccnc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d993797223ee4d3ca68c621030b8b789 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Fc1ccc(Br)cn1>>Fc1ccc(C2CCNCC2)cn1 | O.C(CCC)[Li].FC1=NC=C(C=C1)Br.O=C1CCN(CC1)C(=O)OC(C)(C)C>>FC1=CC=C(C=N1)C1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][C:6](=O)[CH2:11][CH2:10]1.Br[c:5]1[cH:4][cH:3][c:2]([F:1])[n:13][cH:12]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][n:13]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Fc1ccc(Br)cn1 | Fc1ccc(C2CCNCC2)cn1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 17baea866cb419c2d98bbfc24c0f6d4c3b0290618dd26f428f7bc9c349f7a7a8 | f252626502c0f696a1ffbbbaa2d43e4011a92af8563197ce7c691972462c5955 | c1cncc(C2CCNCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10](=O)-[C:11]-[C:12]-1>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[CH;D3;+0:10]2-[C:9]-[C:8]-[NH;D2;+0:7]-[C:12]-[C:11]-2):[c:6]:[c:5]:[c:4]:1 | 52.7 | [{"value": 52.7, "product": "FC1=CC=C(C=N1)C1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -35 | CELSIUS | 15 | MINUTE | A solution of 2-fluoro-5-bromopyridine (7.69 g) in diethyl ether (160 ml) was cooled to −78° C., and into which n-butyl lithium (1,56M-hexane solution, 30 ml) was added dropwise at a temperature not higher than −70° C. After 15 minutes' stirring, tert-butyl 4-oxo-1-piperidinecarboxylate (8.7 g) was added. Temperature o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ketone.Ether.Boc | Secondary amine | C1CC[NH]CC1.c1ccncc1 | c1ccncc1.C1CCNCC1 | c1ccncc1.C1CCNCC1 | HBr | C(C)OCC | -35 | 0.25 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Fc1ccc(Br)cn1>C(C)OCC>Fc1ccc(C2CCNCC2)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2c44211d2794451a9309e1c184ab987a | CN(CCCO)C(=O)OC(C)(C)C.CS(=O)(=O)Cl>>CN(CCCOS(C)(=O)=O)C(=O)OC(C)(C)C | OCCCN(C(OC(C)(C)C)=O)C.C(C)N(CC)CC.CS(=O)(=O)Cl.C(O)([O-])=O.[Na+]>>CS(=O)(=O)OCCCN(C)C(=O)OC(C)(C)C | [CH3:1][N:2]([CH2:3][CH2:4][CH2:5][OH:6])[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].Cl[S:7]([CH3:8])(=[O:9])=[O:10]>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][O:6][S:7]([CH3:8])(=[O:9])=[O:10])[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CN(CCCO)C(=O)OC(C)(C)C.CS(=O)(=O)Cl | CN(CCCOS(C)(=O)=O)C(=O)OC(C)(C)C | null | null | C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 2 | HOUR | To a solution of tert-butyl N-(3-hydroxypropyl)-N-methylcarbamate (12.0 g) and triethylamine (11.5 ml) in ethyl acetate (300 ml), methanesulfonyl chloride (5.4 ml) was added under cooling with ice. After 2 hours' stirring, saturated aqueous sodium hydrogencarbonate solution was added to the reaction liquid and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(C)(=O)OCC | null | 2 | CN(CCCO)C(=O)OC(C)(C)C.CS(=O)(=O)Cl>C(C)(=O)OCC>CN(CCCOS(C)(=O)=O)C(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2755bc43f82549f695ad2387daaac869 | Fc1ccc(C2CCNCC2)cn1.O=C(O)C(c1ccc(F)c(F)c1)N1CCCC1=O.O=C(O)C(c1ccc(F)cc1)c1ccc(F)cc1>>CN(CCCN1CCC(c2ccc(F)nc2)CC1)C(=O)C(c1ccc(F)cc1)c1ccc(F)cc1 | FC1=CC=C(C=C1)C(C(=O)O)C1=CC=C(C=C1)F.Cl.N1CCC2(CC1)OCC1=CC=CC=C12.FC1=CC=C(C=N1)C1CCNCC1.FC=1C=C(C=CC1F)C(C(=O)O)N1C(CCC1)=O>>FC1=CC=C(C=C1)C(C(=O)N(CCCN1CCC(CC1)C=1C=NC(=CC1)F)C)C1=CC=C(C=C1)F | [NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([F:14])[n:15][cH:16]2)[CH2:17][CH2:18]1.O=C(O)C(c1ccc(F)c(F)c1)[N:2]1[C:1](=O)[CH2:5][CH2:4][CH2:3]1.O[C:19](=[O:20])[CH:21]([c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1)[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][N... | Fc1ccc(C2CCNCC2)cn1.O=C(O)C(c1ccc(F)c(F)c1)N1CCCC1=O.O=C(O)C(c1ccc(F)cc1)c1ccc(F)cc1 | CN(CCCN1CCC(c2ccc(F)nc2)CC1)C(=O)C(c1ccc(F)cc1)c1ccc(F)cc1 | null | null | null | Acylation | OtherReaction | 6dc8ce944f8ef99676c344b9de2ea6b6a36d7d67e160d1bf4cc9aa1906ebb522 | da1c8aee4e3057b85d770db5d4db0174050a94cbaf55234256b22869faf4b463 | O=C(NCCCN1CCC(c2cccnc2)CC1)C(c1ccccc1)c1ccccc1 | F-c1:c:c:c(-C(-C(-O)=O)-[N;H0;D3;+0:1]2-[C:2]-[C:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5]-2=O):c:c:1-F.O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[c:9])-[c:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[CH2;D2;+0:4]-[C:3]-[C:2]-[N;H0;D3;+0:1](-[CH3;D1;+0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[c:9])-... | null | [] | null | null | null | null | Example 9 was repeated except that spiro[isobenzofuran-1(3H), 4′-piperidine] hydrochloride which was used in Example 9-(2) was replaced with 4-(6-fluoro-3-pyridinyl)piperidine, and 2-(3,4-difluorophenyl)-2-(2-oxo-1-pyrrolidinyl)acetic acid which was used in Example 9-(4), with 2,2-bis(4-fluorophenyl)acetic acid, to pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid.Tertiary amide.Secondary amine | Tertiary amide.Tertiary amine | C1CCNCC1.c1ccccc1.C1CC[NH]C1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1.c1ccccc1.c1ccccc1 | HF | null | null | null | Fc1ccc(C2CCNCC2)cn1.O=C(O)C(c1ccc(F)c(F)c1)N1CCCC1=O.O=C(O)C(c1ccc(F)cc1)c1ccc(F)cc1>>CN(CCCN1CCC(c2ccc(F)nc2)CC1)C(=O)C(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c64554637d384b8ca3dde17f86b2075e | Nc1ccc(Cl)nc1>>Nc1ccc(Cl)nc1I | C([O-])([O-])=O.[Ca+2].I(=O)(=O)Cl.I(=O)(=O)Cl.C(C1=CC=CC=C1)[N+](C)(C)C.NC=1C=CC(=NC1)Cl>>NC=1C(=NC(=CC1)Cl)I | [NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[n:7][cH:8]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[n:7][c:8]1[I:9] | Nc1ccc(Cl)nc1 | Nc1ccc(Cl)nc1I | null | null | ClCCl.CO | Functional Group Addition | Aromatic iodination | 7c108e53aa6849672ac0ea1998cfd24df7835b0d1bc5738d16f4d561a472c88e | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccncc1 | [N;D1;H2:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[#7;a:5]:[c:6]>>[I;D1;H0:7]-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]):[c:2](-[N;D1;H2:1]):[c:3] | 39.1 | [{"value": 39.1, "product": "NC=1C(=NC(=CC1)Cl)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 30.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 23.2 g (180.5 mM) of 5-amino-2-chloropyridine are mixed in 70 ml of dichloro-methane (DCM) and 180 ml of methanol, and 21.6 g (216 mM) of calcium carbonate and 75.3 g (226 mM) of benzyltrimethylammonium dichloroiodate are added. The reaction mixture is stirred at room temperature for 16 hours, and then filtered to remo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | ClCCl.CO | null | 16 | Nc1ccc(Cl)nc1>ClCCl.CO>Nc1ccc(Cl)nc1I |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d8ab2f2da6704ce983b0aa772fa77a07 | II.Nc1ccc(C(F)(F)F)nc1>>Nc1ccc(C(F)(F)F)nc1I | NC=1C=CC(=NC1)C(F)(F)F.II>>NC=1C(=NC(=CC1)C(F)(F)F)I | I[I:12].[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([F:7])([F:8])[F:9])[n:10][cH:11]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([F:7])([F:8])[F:9])[n:10][c:11]1[I:12] | II.Nc1ccc(C(F)(F)F)nc1 | Nc1ccc(C(F)(F)F)nc1I | null | S(=O)(=O)([O-])[O-].[Ag+2] | C(C)O | Functional Group Interconversion | OtherReaction | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | I-[I;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[#7;a:6]:[c:7]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 96 | [{"value": 96.0, "product": "NC=1C(=NC(=CC1)C(F)(F)F)I", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 3.85 g (12.3 mM) of silver sulfate are added, with stirring and at room temperature, to a solution of 2 g (12.3 mM) of 5-amino-2-(trifluoromethyl)pyridine in 100 ml of ethanol. 3.13 g of iodine are then added and the reaction mixture is stirred at room temperature for 24 hours. The solid in suspension in the medium is ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | S(=O)(=O)([O-])[O-].[Ag+2].C(C)O | null | 24 | II.Nc1ccc(C(F)(F)F)nc1>S(=O)(=O)([O-])[O-].[Ag+2].C(C)O>Nc1ccc(C(F)(F)F)nc1I |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-27352282c0af4dfbb16addeee00b36b0 | BrBr.COc1ccc(N)cn1>>COc1ccc(N)c(Br)n1 | BrBr.NC=1C=CC(=NC1)OC.C(C)(=O)[O-].[Na+].S(=S)(=O)([O-])[O-].[Na+].[Na+]>>NC=1C(=NC(=CC1)OC)Br | Br[Br:9].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:8][n:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([Br:9])[n:10]1 | BrBr.COc1ccc(N)cn1 | COc1ccc(N)c(Br)n1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[#7;a:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | null | [] | null | null | null | null | A mixture of 1.83 g (14.7 mM) of 5-amino-2-methoxypyridine and 1.21 g (14.7 mM) of sodium acetate in 12 ml of acetic acid is prepared and 0.75 ml (14.7 mM) of bromine is added gently, with stirring and while maintaining at room temperature. The reaction mixture is kept stirring for 30 minutes, at room temperature, and ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)(=O)O | null | null | BrBr.COc1ccc(N)cn1>C(C)(=O)O>COc1ccc(N)c(Br)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-547db05fcb5b4d15ad1859b271b0aa20 | Cc1ccc(N)c(Br)n1.O=S(=O)(Cl)c1ccc2ncsc2c1>>Cc1ccc(NS(=O)(=O)c2ccc3ncsc3c2)c(Br)n1 | NC=1C(=NC(=CC1)C)Br.S1C=NC2=C1C=C(C=C2)S(=O)(=O)Cl>>BrC1=NC(=CC=C1NS(=O)(=O)C1=CC2=C(N=CS2)C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:19]([Br:20])[n:21]1.Cl[S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][s:16][c:17]2[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][c:13]3[n:14][cH:15][s:16][c:17]3[cH:18]2)[c:19]([Br:20])[n:21]1 | Cc1ccc(N)c(Br)n1.O=S(=O)(Cl)c1ccc2ncsc2c1 | Cc1ccc(NS(=O)(=O)c2ccc3ncsc3c2)c(Br)n1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1cccnc1)c1ccc2ncsc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[c:7]:[#16;a:8].[Br;D1;H0:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#16;a:8]:[c:7]:[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[Br;D1;H0:9]):[#7;a:11]:[c:12]):[c:5] | 35 | [{"value": 35.0, "product": "BrC1=NC(=CC=C1NS(=O)(=O)C1=CC2=C(N=CS2)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By working in a manner similar to that of Preparation VII, starting with 3-amino-2-bromo-6-methylpyridine and 6-benzothiazolesulfonyl chloride, the expected product is obtained in the form of a beige-colored paste (yield=35%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccncc1.c1ccc2scnc2c1 | HCl | null | null | null | Cc1ccc(N)c(Br)n1.O=S(=O)(Cl)c1ccc2ncsc2c1>>Cc1ccc(NS(=O)(=O)c2ccc3ncsc3c2)c(Br)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-45295142de3d4273a02e51470b6ed47e | Nc1ccc(Cl)nc1I.O=S(=O)(Cl)c1ccc2ncsc2c1>>O=S(=O)(Nc1ccc(Cl)nc1I)c1ccc2ncsc2c1 | NC=1C(=NC(=CC1)Cl)I.S1C=NC2=C1C=C(C=C2)S(=O)(=O)Cl>>IC1=NC(=CC=C1NS(=O)(=O)C1=CC2=C(N=CS2)C=C1)Cl | [NH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[I:12].Cl[S:2](=[O:1])(=[O:3])[c:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][s:19][c:20]2[cH:21]1>>[O:1]=[S:2](=[O:3])([NH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][c:11]1[I:12])[c:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][s:19][c:20]2[cH:21]1 | Nc1ccc(Cl)nc1I.O=S(=O)(Cl)c1ccc2ncsc2c1 | O=S(=O)(Nc1ccc(Cl)nc1I)c1ccc2ncsc2c1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1cccnc1)c1ccc2ncsc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[c:7]:[#16;a:8].[I;D1;H0:9]-[c:10](:[#7;a:11]:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#16;a:8]:[c:7]:[c:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[c:13](:[c:15]):[c:10](-[I;D1;H0:9]):[#7;a:11]:[c:12]):[c:5] | 33 | [{"value": 33.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By working in a manner similar to that of Example 50, starting with 3-amino-2-iodo-6-chloropyridine and 6-benzothiazolesulfonyl chloride, the expected product is obtained in the form of an orange-colored solid (yield=33%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccncc1.c1ccc2scnc2c1 | HCl | null | null | null | Nc1ccc(Cl)nc1I.O=S(=O)(Cl)c1ccc2ncsc2c1>>O=S(=O)(Nc1ccc(Cl)nc1I)c1ccc2ncsc2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cdfec3e05fd34f118eb29ce450fe758e | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO | CC1(OC2=C(CN1)C=CC=C2)C.C1CCOC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1>>C(C)(C)NC1=C(C=CC=C1)CO | [CH3:1][C:2]1([CH3:3])[NH:4][CH2:11][c:10]2[c:5]([cH:6][cH:7][cH:8][cH:9]2)[O:12]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12] | CC1(C)NCc2ccccc2O1 | CC(C)Nc1ccccc1CO | null | null | null | Miscellaneous | OtherReaction | bf0fd08faea41f249ad245c627ae5eaa44305b733aa8f021166c9982d83d6e4c | 6731e713966699a550554bf52935dfe7a2b2eb2cafc83e524d2ff6fcc59af15d | c1ccccc1 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10])-[O;H0;D2;+0:11]-1>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[CH2;D2;+0:5]-[OH;D1;+0:11]):[c:7] | 95 | [{"value": 95.0, "product": "C(C)(C)NC1=C(C=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2,2-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine (125 g, 0.77 mol) in THF (1 L) was filtered through a scintillation funnel and then added dropwise via an addition funnel, over a period of 2.5 h, to a stirred solution of 1.0 M LiAlH4 in THF (800 mL) at 0° C. The reaction was quenched by slow portionwise addi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary alcohol.Secondary amine | c1ccc2c(c1)CNCO2 | c1ccccc1 | c1ccccc1 | null | null | null | 8 | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cf4a38b7d8274eeea2920ed5a8e9106a | CC(C)Nc1ccccc1CO>>CC(C)Nc1ccccc1C=O | C(C)(C)NC1=C(C=CC=C1)CO>>C(C)(C)NC1=C(C=O)C=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:12] | CC(C)Nc1ccccc1CO | CC(C)Nc1ccccc1C=O | null | [O-2].[O-2].[Mn+4] | C1(=CC=CC=C1)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.6 | [{"value": 90.0, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 117 | CELSIUS | null | null | Manganese dioxide (85% 182.6 g, 1.79 mol) was added to a stirred solution of 2-isopropylaminophenylmethanol (118 g, 0.71 mol) in toluene (800 mL) and the reaction mixture was heated to 117° C. for 4 h. The reaction mixture was allowed to cool to room temperature overnight and then filtered through a pad of Celite which... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | [O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C | 117 | null | CC(C)Nc1ccccc1CO>[O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C>CC(C)Nc1ccccc1C=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9b73b2020f5846258bd4e50f40a5b179 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | CC1(OC(CC(O1)=O)=O)C.CC1(OC(=O)CC(=O)O1)C.C(C)(C)NC1=C(C=O)C=CC=C1.C(C)(=O)O.C(CN)N>>C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O | O=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH:4][CH:2]([CH3:1])[CH3:3].CC1(C)O[C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1 | CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | null | null | CO | Miscellaneous | OtherReaction | 7da7c8932064b44b257d05fda8b8362a79f28b679166e64d691318db6946232e | ddbf93ce274a07b125aec0b5e9bfc602f13d41e2bbc449e0d8b2eac033b184d0 | O=c1ccc2ccccc2[nH]1 | C-C1(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.O=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])-[C;D1;H3:14]):[c:15]>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])-[n;H0;D3;+0:11]1:[c:10](:[c:15]):[c:8](:[c:9]):[cH;D2;+0:7]:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[OH... | 98 | [{"value": 98.0, "product": "C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 2,2-Dimethyl-[1,3]dioxane-4,6-dione, commonly Meldrum's acid, (166.9 g, 1.16 mol) was added to a stirred solution of 2-isopropylaminobenzaldehyde (105 g, 0.64 mol), acetic acid (73.6 mL, 1.29 mol) and ethylenediamine (43.0 mL, 0.64 mol) in methanol (1 L) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester.Secondary amine | Carboxylic acid | c1ccccc1.C1COCOC1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CO | 0 | 1 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>CO>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-520e1e20a5b74d83883664866993db0e | COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>>COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | CC(=O)O[C@H]1C[C@H]([C@@]2(CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]2C1=O)C)C=4C=COC4)C)C(=O)OC.C(=O)([O-])[O-].[Na+].[Na+]>>COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C | CC(=O)[O:8][C@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@:27]2([CH3:28])[C@H:11]([C:9]1=[O:10])[C@@:12]1([CH3:13])[CH2:14][C@@H:15]([c:16]3[cH:17][cH:18][o:19][cH:20]3)[O:21][C:22](=[O:23])[C@@H:24]1[CH2:25][CH2:26]2>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:9](=[O:10])[C@@H:11]2[C@@:12]3([CH3... | COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | O=C1CCCC2CC[C@@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]>>[C:6]-[C:4](=[O;D1;H0:5])-[C:2](-[OH;D1;+0:1])-[C:3] | 77 | [{"value": 77.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | null | null | A mixture of 1 (3.5 g, 8.0 mmol) and Na2CO3 (3.4 g, 32.2 mmol) in absolute MeOH (150 mL) was stirred at room temperature for 4 b. The solvent was removed under reduced pressure and CH2Cl2 (500 mL) was added to the crude residue. The organic extract was washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccoc1.C1CC[C@H]2[C@H](C1)CC[C@@H]1COCC[C@@H]12 | HO- | CO | null | null | COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>CO>COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8cf51e6dc1724239bb5526d1cc06716b | CC(C)C(=O)Cl.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>>COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | C(C(C)C)(=O)Cl.C(CC)(=O)OC(CC)=O.COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(C)C)=O)=O)C)C1=COC=C1)=O)C | Cl[C:9](=[O:10])[CH:11]([CH3:12])[CH3:13].[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:14](=[O:15])[C@H:16]2[C@@:17]1([CH3:18])[CH2:19][CH2:20][C@@H:21]1[C:22](=[O:23])[O:24][C@H:25]([c:26]3[cH:27][cH:28][o:29][cH:30]3)[CH2:31][C@:32]21[CH3:33]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8][C:9](... | CC(C)C(=O)Cl.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | null | Protection | Schotten-Baumann to ester | 0ff6f452f545c5714d297592668645b2f1aab4c7ba249a3331b014e41dc6881c | 96f6d8bed38830913bc384a75a5a9e04ad1b99b6be7c7e9d85b6ecc9049f5127 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5])-[C:11] | 62 | [{"value": 62.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(C)C)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that described in Example 4 except replacing the propionic anhydride used therein with the requisite anhydride, the title compound 10 (0.04 g, 62%) was prepared as a white solid, mp 209-211° C.; 10 was synthesized as described for 9 from 8a using isobutyryl chloride to afford 0.04 g (62%) o... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | null | null | null | CC(C)C(=O)Cl.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>>COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9700a765425b427197d058b4d8da3fd1 | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(Cl)c1ccccc1>>COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.C(C1=CC=CC=C1)(=O)Cl.CO>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:17](=[O:18])[C@H:19]2[C@@:20]1([CH3:21])[CH2:22][CH2:23][C@@H:24]1[C:25](=[O:26])[O:27][C@H:28]([c:29]3[cH:30][cH:31][o:32][cH:33]3)[CH2:34][C@:35]21[CH3:36].Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(Cl)c1ccccc1 | COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@H]1CCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@H]2C1=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11] | 98 | [{"value": 98.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C", "details... | null | null | null | null | A solution of 8a (0.05 g, 0.13 mmol), benzoyl chloride (0.09 g, 0.92 mmol) and a catalytic amount of DMAP in CH2Cl2 (20 mL) was stirred at room temperature for 2 h. Absolute MeOH (15 mL) was added and the solvent was removed under reduced pressure. CH2Cl2 (25 mL) was added to the residue and the solution was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(Cl)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d9a5df717c8f4c4e9915b036f94d0c9a | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.CS(=O)(=O)Cl>>COC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.CS(=O)(=O)Cl.CCN(CC)CC>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OS(=O)(=O)C)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:13](=[O:14])[C@H:15]2[C@@:16]1([CH3:17])[CH2:18][CH2:19][C@@H:20]1[C:21](=[O:22])[O:23][C@H:24]([c:25]3[cH:26][cH:27][o:28][cH:29]3)[CH2:30][C@:31]21[CH3:32].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8][S:9]([CH3:10]... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.CS(=O)(=O)Cl | COC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:10] | 32 | [{"value": 32.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OS(=O)(=O)C)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8a (0.05 g, 0.13 mmol), methanesulfonyl chloride (1 mL) and NEt3 (2 mL) in CH2Cl2 (30 mL) was stirred at room temperature overnight and then the mixture was washed with saturated NaHCO3 (20 mL) and saturated NaCl (2×15 mL) and dried (Na2SO4). The solvent was removed under reduced pressure. The resulting c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.CS(=O)(=O)Cl>C(Cl)Cl>COC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7caa50fd5b074b9d813eca73504ee6f7 | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.C[Si](C)(C)Cl>>COC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.CCN(CC)CC.Cl[Si](C)(C)C>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O[Si](C)(C)C)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:13](=[O:14])[C@H:15]2[C@@:16]1([CH3:17])[CH2:18][CH2:19][C@@H:20]1[C:21](=[O:22])[O:23][C@H:24]([c:25]3[cH:26][cH:27][o:28][cH:29]3)[CH2:30][C@:31]21[CH3:32].Cl[Si:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8][Si:9]([CH3... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.C[Si](C)(C)Cl | COC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[O;H0;D2;+0:9]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4])-[C:10] | 68 | [{"value": 68.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O[Si](C)(C)C)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.8, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O[Si](C)(C)C)=O)C)C1=COC=C1)=O)C", "details": "CALCUL... | null | null | null | null | A solution of 8a (0.08 g, 0.20 mmol), NEt3 (0.1 mL, 0.72 mmol) and chlorotrimethylsilane (0.1 mL, 0.79 mmol) in CH2Cl2 (30 mL) was stirred at room temperature overnight. The mixture was washed with saturated NaHCO3 (2×10 mL) and H20 (50 mL), dried (Na2SO4), and the solvent was removed under reduced pressure. The result... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.C[Si](C)(C)Cl>C(Cl)Cl>COC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aa8df4840fe94da7921b80707f1ba252 | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.N#CC(Cl)(Cl)Cl>>COC(=O)[C@@H]1C[C@H](OC(=N)C(Cl)(Cl)Cl)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.ClC(C#N)(Cl)Cl>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(Cl)(Cl)Cl)=N)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:15](=[O:16])[C@H:17]2[C@@:18]1([CH3:19])[CH2:20][CH2:21][C@@H:22]1[C:23](=[O:24])[O:25][C@H:26]([c:27]3[cH:28][cH:29][o:30][cH:31]3)[CH2:32][C@:33]21[CH3:34].[C:9](#[N:10])[C:11]([Cl:12])([Cl:13])[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8][C... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.N#CC(Cl)(Cl)Cl | COC(=O)[C@@H]1C[C@H](OC(=N)C(Cl)(Cl)Cl)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | ClC(C)Cl | Acylation | OtherReaction | 8045d30783d505e653fcb6064f74ac59e775d4240e5a26759512143eefde6598 | 2554d984b82cd13e50d59270df17cf414095f213aef52eb5729ce2a3821b08e4 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | [C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[OH;D1;+0:5])-[C:6].[Cl;D1;H0:7]-[C:8](-[Cl;D1;H0:9])(-[Cl;D1;H0:10])-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]>>[C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[O;H0;D2;+0:5]-[C;H0;D3;+0:11](=[NH;D1;+0:12])-[C:8](-[Cl;D1;H0:7])(-[Cl;D1;H0:9])-[Cl;D1;H0:10])-[C:6] | 37 | [{"value": 37.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(Cl)(Cl)Cl)=N)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.8, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(Cl)(Cl)Cl)=N)=O)C)C1=COC=C1)=O)C", "details... | null | null | null | null | A solution of 8a (0.05 g, 0.13 mmol), trichloroacetonitrile (0.1 mL, 1.0 mmol), 1,8-Diazobicylo[5.4.0]undec-7-ene (0.05 mL, 0.3 mmol) in dichloroethane (20 mL) was stirred at 0° C. for 24 h. The reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL) and dried (Na2SO4). The solvent was removed un... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol | Ether | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | null | ClC(C)Cl | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.N#CC(Cl)(Cl)Cl>ClC(C)Cl>COC(=O)[C@@H]1C[C@H](OC(=N)C(Cl)(Cl)Cl)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9edfd93c7b884bb8a336fb912c356863 | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C=Nc1ccccc1>>COC(=O)[C@@H]1C[C@H](OC(=O)Nc2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.C[Si](C)(C)Cl.C1(=CC=CC=C1)N=C=O>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(NC1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:18](=[O:19])[C@H:20]2[C@@:21]1([CH3:22])[CH2:23][CH2:24][C@@H:25]1[C:26](=[O:27])[O:28][C@H:29]([c:30]3[cH:31][cH:32][o:33][cH:34]3)[CH2:35][C@:36]21[CH3:37].[C:9](=[O:10])=[N:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C=Nc1ccccc1 | COC(=O)[C@@H]1C[C@H](OC(=O)Nc2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | C(Cl)Cl | Protection | OtherReaction | c9b35f80646c04bc8fccaa97f413140cb97715d748dadcda1fae2c6d3c1b477c | cbb53c7ae1c600f566fbe6a1a5d75bfb802798fe2863db2e91856277c64ee7ca | O=C(Nc1ccccc1)O[C@H]1CCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@H]2C1=O | [C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[OH;D1;+0:5])-[C:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[O;H0;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:6] | 14 | [{"value": 14.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(NC1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(NC1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C", "detai... | null | null | null | null | A solution of 8a (0.06 g, 0.14 mmol), trimethylsilyl chloride (0.01 mL, 0.08 mmol) and phenylisocyanate (0.1 mL, 0.92 mmol) in CH2Cl2 was stirred at room temperature for 5 days. The reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL) and dried (Na2SO4). The solvent was removed under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary alcohol | Carbamic ester | null | null | c1ccccc1.C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | null | C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C=Nc1ccccc1>C(Cl)Cl>COC(=O)[C@@H]1C[C@H](OC(=O)Nc2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f9598e26fdd74eaabb3e1d58e0618d41 | CC(=O)O.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>>COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C.COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.C1(=CC=CC=C1)P(C1=NC=CC=C1)C1=CC=CC=C1.C(C)(=O)O>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C)=O)=O)C)C1=COC=C1)=O)C | O[C:9]([CH3:10])=[O:11].[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:12](=[O:13])[C@H:14]2[C@@:15]1([CH3:16])[CH2:17][CH2:18][C@@H:19]1[C:20](=[O:21])[O:22][C@H:23]([c:24]3[cH:25][cH:26][o:27][cH:28]3)[CH2:29][C@:30]21[CH3:31]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8][C:9]([CH3:10])=[O:11])[... | CC(=O)O.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | ClCCl.C1CCOC1 | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:9] | 81.6 | [{"value": 80.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C)=O)=O)C)C1=COC=C1)=O)C", "details": "CALCULATEDPERCEN... | 60 | CELSIUS | 18 | HOUR | A mixture of 8a (0.20 g, 0.51 mmol), diphenyl-2-pyridylphosphine (0.20 g, 0.77 mmol) and acetic acid (0.12 mL, 2.05 mmol) was dissolved in anhydrous THF (15 mL) under an argon atmosphere. To this solution was added di-tert-butylazodicarboxylate (DBAD) (0.18 g, 0.77 mmol) in one portion and the mixture was stirred for 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HO- | ClCCl.C1CCOC1 | 60 | 18 | CC(=O)O.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>ClCCl.C1CCOC1>COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7c61a93160c64737938cc31ec6c2a77d | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(O)c1ccccc1>>COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.C(C1=CC=CC=C1)(=O)O>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([OH:8])[C:17](=[O:18])[C@H:19]2[C@@:20]1([CH3:21])[CH2:22][CH2:23][C@@H:24]1[C:25](=[O:26])[O:27][C@H:28]([c:29]3[cH:30][cH:31][o:32][cH:33]3)[CH2:34][C@:35]21[CH3:36].O[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C... | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(O)c1ccccc1 | COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | null | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(O[C@H]1CCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@H]2C1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:6]-[C:7](=[O;D1;H0:8])-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11] | 75 | [{"value": 75.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C1=CC=CC=C1)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 35 was synthesized using a procedure similar to that described in Example 29 from 8a using benzoic acid to afford 0.19 g (75%) of 35 as a white crystalline solid, mp 223-225° C.; 1H NMR (CDCl3): δ 1.13 (3H, s); 1.40 (1H, dd, J=11.6, 13.1); 1.50 (3H, s); 1.64 (2H, m); 1.84 (1H, dd, J=2.9, 11.3); 2.10 (2H, m); 2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HO- | null | null | null | COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.O=C(O)c1ccccc1>>COC(=O)[C@@H]1C[C@H](OC(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f9487c4143a64edc9e1870c4f003f434 | BrC(Br)Br.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>>COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)O)=O)C)C1=COC=C1)=O)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)Br>>COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@@H](C1)Br)=O)C)C1=COC=C1)=O)C | BrC(Br)[Br:8].O[C@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@:27]2([CH3:28])[C@H:11]([C:9]1=[O:10])[C@@:12]1([CH3:13])[CH2:14][C@@H:15]([c:16]3[cH:17][cH:18][o:19][cH:20]3)[O:21][C:22](=[O:23])[C@H:24]1[CH2:25][CH2:26]2>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([Br:8])[C:9](=[O:10])[C@@H:11]2[C@@:12]3(... | BrC(Br)Br.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | faceb3c80d4ce343366ddb6496c95727c0909c094053a92f52456100c2b3c591 | 565bfd67b81973146f8f155d2d66b870454c4c44b79e27e96b8183d7d581cec0 | O=C1CCCC2CC[C@@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Br-C(-Br)-[Br;H0;D1;+0:1].O-[C@@H;D3;+0:2](-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[C:10]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C@@H;D3;+0:2](-[Br;H0;D1;+0:1])-[C:8](=[O;D1;H0:9])-[C:10] | 59 | [{"value": 59.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@@H](C1)Br)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@@H](C1)Br)=O)C)C1=COC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD... | null | null | 8 | HOUR | A mixture of salvinorin B (8a) (0.15 g, 0.38 mmol), triphenylphosphine (0.21 g, 0.80 mmol), and bromoform (0.15 g, 0.45 mmol) in CH2Cl2 (30 mL) was stirred at room temperature overnight. TLC indicated that starting material was still present after 16 h, thus additional triphenylphosphine (0.11 g, 0.42 mmol) and bromofo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Ketone.Secondary alcohol | Secondary halide | C1CC[C@H]2[C@H](C1)CC[C@@H]1COCC[C@@H]12 | C1CC[C@H]2[C@H](C1)CC[C@@H]1COCC[C@@H]12 | c1ccoc1.C1CC[C@H]2[C@H](C1)CC[C@@H]1COCC[C@@H]12 | HBr | C(Cl)Cl | null | 8 | BrC(Br)Br.COC(=O)[C@@H]1C[C@H](O)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C>C(Cl)Cl>COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1fe8c4491a6241759a422c3930951f7d | COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.[N-]=[N+]=[N-]>>COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | O.COC(=O)[C@H]1[C@@]2(CC[C@@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@@H](C1)Br)=O)C)C1=COC=C1)=O)C.[N-]=[N+]=[N-].[Na+].C(C)(=O)O>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N=[N+]=[N-])=O)C)C1=COC=C1)=O)C | Br[C@@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@:14]2([CH3:15])[C@H:13]([C:11]1=[O:12])[C@:29]1([CH3:30])[C@H:18]([CH2:17][CH2:16]2)[C:19](=[O:20])[O:21][C@H:22]([c:23]2[cH:24][cH:25][o:26][cH:27]2)[CH2:28]1.[N-:8]=[N+:9]=[N-:10]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([N:8]=[N+:9]=[N-:10])[C:11](=[O... | COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.[N-]=[N+]=[N-] | COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 5c7109810c945939d2c8c3302f0b4dcb4495586c0a1c6b415a157c3d514ead82 | 06e32b8fc344f03e708f534c933054eeeb8596bf07b6161997913435e8cd3859 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Br-[C@H;D3;+0:1](-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[C:9].[N-;H0;D1:10]=[#7;+:11]=[N;-;D1;H0:12]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[C@H;D3;+0:1](-[N;H0;D2;+0:10]=[#7;+:11]=[N;-;D1;H0:12])-[C:7](=[O;D1;H0:8])-[C:9] | 87.5 | [{"value": 86.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N=[N+]=[N-])=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N=[N+]=[N-])=O)C)C1=COC=C1)=O)C", "details": "CALCULAT... | null | null | null | null | A solution of 36 (0.10 g, 0.22 mmol), sodium azide (0.05 g, 0.77 mmol) and glacial acetic acid in DMF (3 mL) was stirred at room temperature for 4 h. H2O (30 mL) was added and the mixture was extracted with EtOAc (20 mL). The EtOAc solution was washed with H2O (2×20 mL) and saturated NaCl (20 mL) and dried (Na2SO4). Re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone | Ketone.Azide | C1CC[C@H]2[C@H](C1)CC[C@@H]1COCC[C@@H]12 | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12 | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | Br- | CN(C)C=O | null | null | COC(=O)[C@@H]1C[C@@H](Br)C(=O)[C@@H]2[C@@]3(C)C[C@@H](c4ccoc4)OC(=O)[C@H]3CC[C@]21C.[N-]=[N+]=[N-]>CN(C)C=O>COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c717980336e8416f8ee2af5881c025b5 | COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>>COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N=[N+]=[N-])=O)C)C1=COC=C1)=O)C.[NH4+].[Cl-]>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C | [N-]=[N+]=[N:8][C@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@:12]2([CH3:13])[C@H:11]([C:9]1=[O:10])[C@:27]1([CH3:28])[C@@H:16]([CH2:15][CH2:14]2)[C:17](=[O:18])[O:19][C@H:20]([c:21]2[cH:22][cH:23][o:24][cH:25]2)[CH2:26]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH2:8])[C:9](=[O:10])[C@H:11]2[C@@:12]1(... | COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | [Zn] | C(Cl)Cl.CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | [C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[N;H0;D2;+0:5]=[N+]=[N-])-[C:6]>>[C:1]-[C:2](=[O;D1;H0:3])-[C:4](-[NH2;D1;+0:5])-[C:6] | 84 | [{"value": 84.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 3 | HOUR | A mixture of 38 (0.08 g, 0.19 mmol), Zn dust (0.16 g, 2.45 mmol) and NH4Cl (g, mmol) in a mixture of CH2Cl2/MeOH (1:4, 20 mL) was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. 2N NaOH (30 mL) was added to the residue and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | Other | [Zn].C(Cl)Cl.CO | null | 3 | COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>[Zn].C(Cl)Cl.CO>COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0a37b151aa0046209d46305b4b391f88 | CC(=O)OC(C)=O.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>>COC(=O)[C@@H]1C[C@H](NC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C.C(C)(=O)OC(C)=O>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NC(C)=O)=O)C)C1=COC=C1)=O)C | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH2:8])[C:12](=[O:13])[C@H:14]2[C@@:15]1([CH3:16])[CH2:17][CH2:18][C@H:19]1[C:20](=[O:21])[O:22][C@H:23]([c:24]3[cH:25][cH:26][o:27][cH:28]3)[CH2:29][C@:30]21[CH3:31]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH:8][C:9]([CH3:10])=[... | CC(=O)OC(C)=O.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@@H]1C[C@H](NC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:9] | 58 | [{"value": 58.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NC(C)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.9, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NC(C)=O)=O)C)C1=COC=C1)=O)C", "details": "CALCULATEDPERCEN... | null | null | null | null | A solution of 39 (0.06 g, 0.16 mmol), acetic anhydride (0.4 mL, 4.23 mmol) and a catalytic amount of DMAP in CH2Cl2 (30 mL) was stirred at room temperature for 2 h. The mixture was washed with 2N HCl (30 mL), 2N NaOH (30 mL), and H2O (30 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure afforded a c... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | null | CC(=O)OC(C)=O.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1C[C@H](NC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c3231ec3b7b04f169d839bf51b685ede | CO.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=C(Cl)c1ccccc1>>COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C.C(C1=CC=CC=C1)(=O)Cl.CO>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(C)C)=O)=O)C)C1=COC=C1)=O)C | C[OH:8].N[C@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@@:17]2([CH3:18])[C@H:16]([C:14]1=[O:15])[C@:32]1([CH3:33])[C@@H:21]([CH2:20][CH2:19]2)[C:22](=[O:23])[O:24][C@H:25]([c:26]2[cH:27][cH:28][o:29][cH:30]2)[CH2:31]1.Cl[C:9](=[O:10])[c:11]1[cH:12]ccc[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([O:8... | CO.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=C(Cl)c1ccccc1 | COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Protection | OtherReaction | 862476cb7bfa0b299b6bda8446b35088b6733227f3ff9b95ad63933419707f60 | 5528e9c46f2221c5ba9db86fcdf8258cf91882ed3b43678d1e0ae747a17c947b | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | C-[OH;D1;+0:1].Cl-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:c:c:c:[cH;D2;+0:6]:1.N-[C@@H;D3;+0:7](-[C:8]-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12])-[C:13](=[O;D1;H0:14])-[C:15]>>[#8:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:8]-[C@H;D3;+0:7](-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH;D3;+0:4](-[CH3;D1;+0:5])-[C... | 67 | [{"value": 67.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)OC(C(C)C)=O)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 39 (0.10 g, 0.26 mmol), benzoyl chloride (0.11 g, 0.78 mmol) and DMAP (0.08 g, 0.78 mmol) in CH2Cl2 (20 mL) was stirred at room temperature for 2 h. Absolute MeOH (15 mL) was added and the solvent was removed under reduced pressure. CH2Cl2 (25 mL) was added to the residue and the solution was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Primary amine.Methanol | Ketone.Ester | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccccc1 | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12 | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | null | CO.COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=C(Cl)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1C[C@H](OC(=O)C(C)C)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c8cbe8556e3840b9b3958908f0a60857 | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.CS(=O)(=O)Cl>>COC(=O)[C@@H]1C[C@H](NS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C.CS(=O)(=O)Cl.CCN(CC)CC>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH2:8])[C:13](=[O:14])[C@H:15]2[C@@:16]1([CH3:17])[CH2:18][CH2:19][C@H:20]1[C:21](=[O:22])[O:23][C@H:24]([c:25]3[cH:26][cH:27][o:28][cH:29]3)[CH2:30][C@:31]21[CH3:32].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH:8][S:9]([CH3:10... | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.CS(=O)(=O)Cl | COC(=O)[C@@H]1C[C@H](NS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1CCCC2CC[C@H]3C(=O)O[C@H](c4ccoc4)CC3[C@@H]12 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:5]-[C:6](=[O;D1;H0:7])-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:10] | 575.9 | [{"value": 56.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 575.9, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C)=O)C)C1=COC=C1)=O)C", "details": "CALCULA... | null | null | null | null | A solution of 39 (0.10 g, 0.26 mmol), methanesulfonyl chloride (0.08 mL, 1.03 mmol), NEt3 (0.04 mL, 0.28 mmol) and a catalytic amount of DMAP in CH2Cl2 (50 mL) was stirred at room temperature for 2 h. The mixture was washed with 2N HCl (30 mL), 2N NaOH (30 mL), and H2O (30 mL) and dried (Na2SO4). Removal of the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.CS(=O)(=O)Cl>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1C[C@H](NS(C)(=O)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f09243616f4044a5a3266a405d02034e | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=S(=O)(Cl)c1ccccc1>>COC(=O)[C@@H]1C[C@H](NS(=O)(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)N)=O)C)C1=COC=C1)=O)C.C1(=CC=CC=C1)S(=O)(=O)Cl.C(C)N(CC)CC.CO>>COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C1=CC=CC=C1)=O)C)C1=COC=C1)=O)C | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH2:8])[C:18](=[O:19])[C@H:20]2[C@@:21]1([CH3:22])[CH2:23][CH2:24][C@H:25]1[C:26](=[O:27])[O:28][C@H:29]([c:30]3[cH:31][cH:32][o:33][cH:34]3)[CH2:35][C@:36]21[CH3:37].Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]... | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=S(=O)(Cl)c1ccccc1 | COC(=O)[C@@H]1C[C@H](NS(=O)(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@H]2C(CC[C@@H]1NS(=O)(=O)c1ccccc1)CC[C@H]1C(=O)O[C@H](c3ccoc3)CC21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](=[O;D1;H0:9])-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:7]-[C:8](=[O;D1;H0:9])-[C:10](-[NH;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:12] | 98.9 | [{"value": 97.0, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C1=CC=CC=C1)=O)C)C1=COC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "COC(=O)[C@H]1[C@@]2(CC[C@H]3C(O[C@@H](C[C@@]3([C@H]2C([C@H](C1)NS(=O)(=O)C1=CC=CC=C1)=O)C)C1=COC=C1)=O)C", ... | null | null | null | null | A solution of 39 (0.08 g, 0.21 mmol), benzenesulfonyl chloride (0.07 g, 0.42 mmol), triethylamine (0.06 g, 0.63 mmol), and a catalytic amount of DMAP in CH2Cl2 (40 mL) was stirred at room temperature for 18 h. Absolute MeOH was then added and the solution was washed with 10% HCl (3×25 mL) and saturated NaCl (2×25 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[C@H]2[C@H](C1)CC[C@H]1COCC[C@@H]12.c1ccoc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | null | COC(=O)[C@@H]1C[C@H](N)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C.O=S(=O)(Cl)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1C[C@H](NS(=O)(=O)c2ccccc2)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-48ec6b01a3864024ac16587c981afead | CCOC(=O)CCCl.Nc1ccc2c(c1)CCC2>>CCOC(=O)CCNc1ccc2c(c1)CCC2 | NC=1C=C2CCCC2=CC1.ClCCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CCNC=1C=C2CCCC2=CC1)=O | Cl[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][CH2:17]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][CH2:17]2 | CCOC(=O)CCCl.Nc1ccc2c(c1)CCC2 | CCOC(=O)CCNc1ccc2c(c1)CCC2 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2c(c1)CCC2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 71 | [{"value": 71.0, "product": "C(C)OC(CCNC=1C=C2CCCC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "C(C)OC(CCNC=1C=C2CCCC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 16 | HOUR | To a mixture of 5-aminoindane (5 g, 37.6 mmol), ethyl 3-chloropropionate (4.7 mL, 37.6 mmol) and potassium carbonate (5.2 g, 37.6 mmol) was added tetrabutylammonium bromide (200 mg). The mixture was stirred at 100° C. for 16 hours. After cooling to room temperature (rt), the mixture was extracted into ethyl acetate (Et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2c(c1)CCC2 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | 100 | 16 | CCOC(=O)CCCl.Nc1ccc2c(c1)CCC2>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>CCOC(=O)CCNc1ccc2c(c1)CCC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-388c20312aad4c688e3949a8286aa8af | CCOC(=O)CCNc1ccc2c(c1)CCC2.CCOC(=O)c1cnc(SC)nc1Cl>>CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC | C(C)OC(CCNC=1C=C2CCCC2=CC1)=O.ClC1=NC(=NC=C1C(=O)OCC)SC.C(C)N(CC)CC>>C(C)OC(=O)C=1C(=NC(=NC1)SC)N(C=1C=C2CCCC2=CC1)CCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][CH2:17]2.Cl[c:18]1[n:19][c:20]([S:21][CH3:22])[n:23][cH:24][c:25]1[C:26](=[O:27])[O:28][CH2:29][CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]([c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15]... | CCOC(=O)CCNc1ccc2c(c1)CCC2.CCOC(=O)c1cnc(SC)nc1Cl | CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(Nc2ccc3c(c2)CCC3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]-[C:15]-[NH;D2;+0:16]-[c:17](:[c:18]):[c:19]>>[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]-[C:15]-[N;H0;D3;+0:16](-[c:17](:[c:18]):[c:19])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7](=[... | 90 | [{"value": 90.0, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)N(C=1C=C2CCCC2=CC1)CCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)N(C=1C=C2CCCC2=CC1)CCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of 3-(indan-5-ylamino)-propionic acid ethyl ester (5 g, 21.4 mmol) and ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (5 g, 21.4 mmol) in 40 mL of n-butanol was added triethylamine (3 mL, 21.4 mmol). The solution was stirred at rt for 2 days. The solvent was removed under vacuum. The residue was extr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCC2.c1cncnc1 | HCl | C(CCC)O | null | 48 | CCOC(=O)CCNc1ccc2c(c1)CCC2.CCOC(=O)c1cnc(SC)nc1Cl>C(CCC)O>CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-97b2d45e987f4f5581a86c3d7fc3bcd7 | CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC>>CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O | C(C)OC(=O)C=1C(=NC(=NC1)SC)N(C=1C=C2CCCC2=CC1)CCC(=O)OCC.CC(C)([O-])C.[Na+].N#N.Cl.[Na]>>C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O | CCO[C:26]([c:25]1[c:18]([N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[n:19][c:20]([S:21][CH3:22])[n:23][cH:24]1)=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[... | CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC | CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O | null | null | C(C)(C)(C)O.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 30bc859f342e7454d65786ffc9dd9e1f370c7689a335282691882093ec0ad590 | 6f130a746a78d10ca37f94948711de2b0c76f45052ca887b0e681c66276a7764 | O=C1CCN(c2ccc3c(c2)CCC3)c2ncncc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9]-[C:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[CH;D3;+0:11]1-[C:10]-[#7:9]-[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:2-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | 90 | CELSIUS | 10 | MINUTE | To sodium (25 wt % dispersion in paraffin wax, 1.6 g, 16.9 mmol) was added t-butanol (30 mL) under stirring and N2. After 10 minutes, a solution of 4-[(2-ethoxycarbonyl-ethyl)-indan-5-yl-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (6.6 g, 15.4 mmol) in 40 mL of toluene was added to the sodium t-but... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | c1ncc2c(n1)[NH]CCC2 | c1ccc2c(c1)CCC2.c1ncc2c(n1)[NH]CCC2 | HO- | C(C)(C)(C)O.C1(=CC=CC=C1)C | 90 | 0.166667 | CCOC(=O)CCN(c1ccc2c(c1)CCC2)c1nc(SC)ncc1C(=O)OCC>C(C)(C)(C)O.C1(=CC=CC=C1)C>CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2321ae9f98384267a85d98e9a630843a | CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O | C(C)N(CC)CC.C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O.BrBr.N#N>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[c:18]2[n:19][c:20]([S:21][CH3:22])[n:23][cH:24][c:25]2[C:26]1=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[c:18]2[... | CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O | null | null | C(Cl)Cl | Oxidation | OtherReaction | e6fdfa5ad0e8b814bf3d3d5cf077356d203a162eff2c4a4b9336450468009711 | 90d664ba841914112433e4101d37ffefd1e45e7dce983b85577c7f1d5a635093 | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[N;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[c:13]2:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:2-[C;H0;D3;+0:19]-1=[O;D1;H0:20]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[n;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:... | 94 | [{"value": 94.0, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.32 g, 0.84 mmol) in 5 mL of methylene chloride (CH2Cl2) was added bromine (43 μL, 0.84 mmol) slowly under N2. The solution was stirred at room temperature for 2 hours (or to completion). The ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Tertiary amine | Ester | c1ncc2c(n1)[NH]CCC2 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | null | C(Cl)Cl | null | 2 | CCOC(=O)C1CN(c2ccc3c(c2)CCC3)c2nc(SC)ncc2C1=O>C(Cl)Cl>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5e2c409cf06f4d6b8bfbb2bddbc35dab | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O | C([O-])(O)=O.[Na+].S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C=1C=C2CCCC2=CC1)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[c:18]2[n:19][c:20]([S:21][CH3:22])[n:25][cH:26][c:27]2[c:28]1=[O:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[c:18]2[n... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O | null | null | C(Cl)Cl | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[S;H0;D2;+0:5]-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:9])=[O;D1;H0:10]):[#7;a:7]:[c:8] | 67 | [{"value": 67.0, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.3 g, 0.79 mmol) in 5 mL of CH2Cl2, was added 3-chloroperoxybenzoic acid (m-CPBA, 69.5%, 431 mg, 1.73 mmol) portionwise. The solution was stirred at room temperature for 3 hours. An aqueous solution ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | null | C(Cl)Cl | null | 3 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(SC)ncc2c1=O>C(Cl)Cl>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2e80798a5f184cd09efdc0cbdbcb7c58 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCCCC3)ncc2c1=O | N1(CCCCC1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCN2CCCCC2)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33](=[O:34])[c:32]2[cH:31][n:30]1.[NH2:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCCCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCCCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1(Step F) the title compound was prepared from 2-piperidin-1-yl-ethylamine (5.2 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 15 mg, 0.036 mmol). 6.6 mg of 8-indan-5-yl-5-oxo-2-(... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.C1CC[NH]CC1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCCCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-09ed7dd69e214258a42cde07500db0dc | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O | N1(C=NC=C1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33](=[O:34])[c:32]2[cH:31][n:30]1.[NH2:21][CH2:22][CH2:23][CH2:24][n:25]1[cH:26][cH:27][n:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1(Step F) the title compound was prepared from 3-imidazol-1-yl-propylamine (4.4 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 15 mg, 0.036 mmol). 19.2 mg of 2-(3-imidazol-1-yl-pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c631ee24ba914cb3bfcfa098644fb64f | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCOCC3)ncc2c1=O | N1(CCOCC1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCN2CCOCC2)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33](=[O:34])[c:32]2[cH:31][n:30]1.[NH2:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCOCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCOCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1(Step F) the title compound was prepared from 2-morpholin-4-yl-ethylamine (4.8 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 15 mg, 0.036 mmol). 15.5 mg of 8-indan-5-yl-2-(2-mor... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.C1COCC[NH]1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCOCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-221d7370a8be4b47a16e7531e653c480 | CC(CN)N1CCOCC1.CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCC(C)N3CCOCC3)ncc2c1=O | N1(CCOCC1)C(CN)C.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCC(C)N2CCOCC2)N(C1)C=1C=C2CCCC2=CC1)=O | [NH2:21][CH2:22][CH:23]([CH3:24])[N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1.CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:34](=[O:35])[c:33]2[cH:32][n:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-... | CC(CN)N1CCOCC1.CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCC(C)N3CCOCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCN3CCOCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1(Step F) the title compound was prepared from 2-morpholin-4-yl-propylamine (5.3 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 15 mg, 0.036 mmol). 17.2 mg of 8-indan-5-yl-2-(2-mo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.C1COCC[NH]1 | HO- | null | null | null | CC(CN)N1CCOCC1.CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCC(C)N3CCOCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c76918262cac4fbda4c8bbbb28c023b4 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O | CN(CCCN)C.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN(C)C)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:31](=[O:32])[c:30]2[cH:29][n:28]1.[NH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1(Step F) the title compound was prepared from N1,N1-dimethyl-propane-1,3-diamine (4.6 μL, 0.036 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 15 mg, 0.036 mmol). 9.7 mg of 2-(3-dimethylam... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5416bb0874aa4c6b90233d86501eee42 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCOC)ncc2c1=O | COCCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCOC)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[c:29]2[cH:28][n:27]1.[NH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCOC)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared from 3-methoxy-propylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 20 mg, 0.040 mmol). 11 mg of 8-Indan-5-yl-2-(3-methoxy-propylamino)-5-oxo-5,8-d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCOC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7103322ccabc4c2ba5b9486553491181 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3=O)ncc2c1=O | NCCCN1C(CCC1)=O.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C(CCC2)=O)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:34](=[O:35])[c:33]2[cH:32][n:31]1.[NH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][CH2:28][C:29]1=[O:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1=O | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3=O)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1CCCN1CCCNc1ncc2c(=O)ccn(-c3ccc4c(c3)CCC4)c2n1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared from 1-(3-amino-propyl)-pyrrolidin-2-one and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E) 25 mg, 0.052 mmol). 17 mg of 8-Indan-5-yl-5-oxo-2-[3-(2-oxo-pyrrol... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.C1CC[NH]C1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1=O>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3=O)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1919b9c11bfd4ee3b0e8b1354be000fd | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3)ncc2c1=O | N1(CCCC1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2CCCC2)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33](=[O:34])[c:32]2[cH:31][n:30]1.[NH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure described in Example 1 Step F, the title compound was prepared from 3-pyrrolidin-1-yl-propylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(Step E), 10 mg, 0.022 mmol). 7 mg of 8-Indan-5-yl-5-oxo-2-(3-pyrrolidin-1-yl-pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.C1CC[NH]C1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN3CCCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b7ba26de978f4a50af0d8f824c40513a | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCOC)ncc2c1=O | COCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCOC)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:29](=[O:30])[c:28]2[cH:27][n:26]1.[NH2:21][CH2:22][CH2:23][O:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCOC)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared from 2-methoxy-ethylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 1, Step E, 10 mg, 0.022 mmol). 7 mg of 8-indan-5-yl-2-(2-methoxy-ethylamino)-5-oxo-5,8-dihydro-p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCOC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2c8622961eb94f9ca0d59f465c4d5070 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O | COC=1C=C(CN)C=C(C1)OC.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCC2=CC(=CC(=C2)OC)OC)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:36](=[O:37])[c:35]2[cH:34][n:33]1.[NH2:21][CH2:22][c:23]1[cH:24][c:25]([O:26][CH3:27])[cH:28][c:29]([O:30][CH3:31])[cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCc3ccccc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared from 3,5-dimethoxybenzylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (10 mg, 0.02 mmol). 10 mg of 2-(3,5-Dimethoxy-benzylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f01a3334192e489f87d7b57eca61d2a1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O.CN>>CNC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O | CN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN(C)C)N(C1)C=1C=C2CCCC2=CC1)=O>>CNC(=O)C=1C(C2=C(N=C(N=C2)NCCCN(C)C)N(C1)C=1C=C2CCCC2=CC1)=O | CCO[C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[CH2:14][CH2:15][CH2:16]3)[c:17]2[n:18][c:19]([NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[n:27][cH:28][c:29]2[c:30]1=[O:31].[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][n:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[CH... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O.CN | CNC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=c1ccn(-c2ccc3c(c2)CCC3)c2ncncc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6](-[c:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[#7;a:9]:[c:8]:[#7;a:6](-[c:7]):[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10]):[c:4] | 77 | [{"value": 77.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A solution of methylamine (1N, 1 mL in methanol) was added to 2-(3-dimethylamino-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 6 Step A, 6 mg, 0.015 mmol). The mixture was kept in a sealed tube at 110° C. with stirring for 2 days. The solution, after cooling ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1 | HO- | null | null | 48 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O.CN>>CNC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCN(C)C)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1b855d8e9b0c46178a8fa3663c80ab40 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | COC1=CC=C(C=C1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCC2=CC=C(C=C2)OC)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:35](=[O:36])[c:34]2[cH:33][n:32]1.[NH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccccc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared 2-(4-methoxyphenyl)-ethylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1 Step E, 20 mg, 0.04 mmol). 19 mg of 8-Indan-5-yl-2-[2-(4-methoxy-phenyl)-ethylamino]... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-586bc51c127c4e3c8344b2f9a0952509 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON>>CONC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O | C(C)N(CC)CC.Cl.CON.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C=1C=C2CCCC2=CC1)=O>>CONC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C=1C=C2CCCC2=CC1)=O | CCO[C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH2:15][CH2:16][CH2:17]3)[c:18]2[n:19][c:20]([NH:21][CH2:22][CH2:23][CH2:24][n:25]3[cH:26][cH:27][n:28][cH:29]3)[n:30][cH:31][c:32]2[c:33]1=[O:34].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON | CONC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | CO.O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6](-[c:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#7;a:9]:[c:8]:[#7;a:6](-[c:7]):[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[#8:11]-[C;D1;H3:10]):[c:4] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Triethylamine (0.5 mL) was added to a mixture of O-methylhydroxylamine hydrochloride (220 mg) and 2-(3-imidazol-1-yl-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 3 Step A, 3.0 mg, 0.006 mmol) in 0.5 mL of methanol. The reaction mixture was kept in a sealed t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | CO.O | null | 48 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON>CO.O>CONC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-919543a4f7864fcdaad14c824ac2a07e | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | COC1=CC=C(C=C1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C=1C=C2CCCC2=CC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCC2=CC=C(C=C2)OC)N(C1)C=1C=C2CCCC2=CC1)=O | CS(=O)(=O)[c:20]1[n:19][c:18]2[n:8](-[c:9]3[cH:10][cH:11][c:12]4[c:13]([cH:14]3)[CH2:15][CH2:16][CH2:17]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:35](=[O:36])[c:34]2[cH:33][n:32]1.[NH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccccc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Using the procedure outlined in Example 1 Step F, the title compound was prepared from 2-(4-methoxy-phenyl)-ethylamine and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 1 Step E, 20 mg, 0.040 mmol). 16 mg of 8-Indan-5-yl-2-(2-(4-methoxy-phenyl)-ethylamin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccc2c(c1)CCC2.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-66ca2717a0e24c2293f8cef297ade30e | CCOC(=O)CCCl.NC1CCCCC1>>CCOC(=O)CCNC1CCCCC1 | C1(CCCCC1)N.C(C)OC(CCCl)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(CCNC1CCCCC1)=O | Cl[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1 | CCOC(=O)CCCl.NC1CCCCC1 | CCOC(=O)CCNC1CCCCC1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C1CCCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:10] | 72.3 | [{"value": 72.0, "product": "C(C)OC(CCNC1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "C(C)OC(CCNC1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1CCCCC1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | 80 | null | CCOC(=O)CCCl.NC1CCCCC1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC>CCOC(=O)CCNC1CCCCC1 |
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