dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-62d2192aded34cdfa64452a6022fb411 | N#Cc1ccc(CCO)cc1.Oc1cc(O)cc(Cl)c1>>N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)/N=N/C(=O)OCC.ClC1=CC(=CC(=C1)O)O.C(#N)C1=CC=C(C=C1)CCO>>ClC=1C=C(C=C(C1)OCCC1=CC=C(C=C1)C#N)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:18][cH:19]1.O[c:10]1[cH:11][c:12]([OH:13])[cH:14][c:15]([Cl:16])[cH:17]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[cH:14][c:15]([Cl:16])[cH:17]2)[cH:18][cH:19]1 | N#Cc1ccc(CCO)cc1.Oc1cc(O)cc(Cl)c1 | N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1 | null | null | CCOCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 21.3 | [{"value": 21.0, "product": "ClC=1C=C(C=C(C1)OCCC1=CC=C(C=C1)C#N)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.3, "product": "ClC=1C=C(C=C(C1)OCCC1=CC=C(C=C1)C#N)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triphenylphoshine (32 g; 122 mmol) and diethylazodicarboxylate (19.2 mL; 122 mmol) were dissolved in CH2Cl2 (150 mL). Chloro-3,5-dihydroxybenzene (9.1 g; 63 mmol; from step (i) above) and 2-(4-cyanophenyl)ethanol (9.04 g; 61 mmol) were added and the solution was stirred at room temperature overnight. The mixture was di... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CCOCC.C(Cl)Cl | null | 8 | N#Cc1ccc(CCO)cc1.Oc1cc(O)cc(Cl)c1>CCOCC.C(Cl)Cl>N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc3a3854b6594410bd7d1f6b1836866b | N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1.O=S(=O)(Cl)c1ccc(F)cc1Cl>>N#Cc1ccc(CCOc2cc(Cl)cc(OS(=O)(=O)c3ccc(F)cc3Cl)c2)cc1 | ClC1=C(C=CC(=C1)F)S(=O)(=O)Cl.ClC=1C=C(C=C(C1)OCCC1=CC=C(C=C1)C#N)O.O>>ClC1=C(C=CC(=C1)F)S(=O)(=O)OC1=CC(=CC(=C1)Cl)OCCC1=CC=C(C=C1)C#N | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([OH:16])[cH:28]2)[cH:29][cH:30]1.Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]1[Cl:27]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([O:16][S:... | N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1.O=S(=O)(Cl)c1ccc(F)cc1Cl | N#Cc1ccc(CCOc2cc(Cl)cc(OS(=O)(=O)c3ccc(F)cc3Cl)c2)cc1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 9339e107bef60affc137d23d580808fc37a7625dc676ebb48fe8271cd9670535 | 7ef9cdb7b67e90f0e8b5d9f8fed73f04903b09cd9fd8ced1da4341e88385cae2 | O=S(=O)(Oc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 72.1 | [{"value": 72.0, "product": "ClC1=C(C=CC(=C1)F)S(=O)(=O)OC1=CC(=CC(=C1)Cl)OCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "ClC1=C(C=CC(=C1)F)S(=O)(=O)OC1=CC(=CC(=C1)Cl)OCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 2-Chloro-4-fluorobenzenesulfonyl chloride (1.16 g; 5.0 mmol) was added to a cold solution (ice:water temperature) of 3-chloro-5-[2-(4-cyanophenyl)ethoxy]phenol (0.689 g; 2.5 mmol; from step (ii) above) in pyridine (8 mL). The temperature was allowed to rise (slowly) to ambient overnight. The mixture was re-cooled (ice:... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonyl halide | Sulfonate | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 4 | N#Cc1ccc(CCOc2cc(O)cc(Cl)c2)cc1.O=S(=O)(Cl)c1ccc(F)cc1Cl>N1=CC=CC=C1>N#Cc1ccc(CCOc2cc(Cl)cc(OS(=O)(=O)c3ccc(F)cc3Cl)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aca5d9a5cf0247d095e0826dbde90a3e | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1ccccc1S>>N#Cc1ccc(CCSc2ccccc2N)cc1 | C1(=CC=C(C=C1)S(=O)(=O)OCCC1=CC=C(C=C1)C#N)C.C(=O)([O-])[O-].[K+].[K+].NC1=C(C=CC=C1)S>>NC1=C(C=CC=C1)SCCC1=CC=C(C=C1)C#N | Cc1ccc(S(=O)(=O)O[CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)cc1.[SH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[NH2:16]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][S:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[NH2:16])[cH:17][cH:18]1 | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1ccccc1S | N#Cc1ccc(CCSc2ccccc2N)cc1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | fa9f9600581ef05dca04b54e63c21080ab3037c0f706082a272f2da0c08c4f32 | 8d10c46c4c89029273335615fb077055d8239c352e37ee1740069c99de11581b | c1ccc(CCSc2ccccc2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3]):c:c:1.[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[S;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[c:3]):[c:7] | 82.4 | [{"value": 78.0, "product": "NC1=C(C=CC=C1)SCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "NC1=C(C=CC=C1)SCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Toluenesulfonic acid, 2-(4-cyanophenyl)ethyl ester (1.9 g; 6.3 mmol; from Example 18(i) above) and K2CO3 (2.0 g) were added to a solution of 2-aminothiophenol (0.875 g; 7.0 mmol) in EtOH (20 mL). The mixture was heated to reflux for 48 hours, cooled, filtered and concentrated in vacuo to an oil which was dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic thiol | Monosulfide | c1ccccc1 | null | c1ccccc1.c1ccccc1 | TsOH.HO- | CCO | null | null | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1ccccc1S>CCO>N#Cc1ccc(CCSc2ccccc2N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12133860a5c54d39883253623972c7f1 | CCC(=O)Nc1ccc(O)cc1C(=O)OC.O=[N+]([O-])c1ccccc1F>>CCC(=O)Nc1ccc(Oc2ccccc2[N+](=O)[O-])cc1C(=O)OC | O.COC(C1=C(C=CC(=C1)O)NC(CC)=O)=O.C([O-])([O-])=O.[K+].[K+].FC1=C(C=CC=C1)[N+](=O)[O-]>>COC(C1=C(C=CC(=C1)OC1=C(C=CC=C1)[N+](=O)[O-])NC(CC)=O)=O | [CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:20][c:21]1[C:22](=[O:23])[O:24][CH3:25].F[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])[cH:20][c:21]1... | CCC(=O)Nc1ccc(O)cc1C(=O)OC.O=[N+]([O-])c1ccccc1F | CCC(=O)Nc1ccc(Oc2ccccc2[N+](=O)[O-])cc1C(=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 75.6 | [{"value": 75.6, "product": "COC(C1=C(C=CC(=C1)OC1=C(C=CC=C1)[N+](=O)[O-])NC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 5-hydroxy-2-propionylamino-benzoic acid methyl ester (1.0 g, 4.5 mmol) and potassium carbonate (0.62 g, 4.5 mmol) was stirred in DMF (5 mL) for 10 minutes. 2-fluoronitrobenzene (0.63 g, 4.5 mmol) was then added and stirring was continued at room temperature overnight. Water (10 mL) was added and the result... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C)C=O | null | 8 | CCC(=O)Nc1ccc(O)cc1C(=O)OC.O=[N+]([O-])c1ccccc1F>CN(C)C=O>CCC(=O)Nc1ccc(Oc2ccccc2[N+](=O)[O-])cc1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f276a7881514110b2e1046b912dafe8 | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC>>CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1 | COC(C1=C(C=CC(=C1)OC1=C(C=CC=C1)N)NC(CC)=O)=O.COC(C1=C(C=CC(=C1)SC1=C(C=CC=C1)N)NC(CC)=O)=O>>C(CC)(=O)NC1=C(C(=O)O)C=C(C=C1)OC1=C(C=CC=C1)NCCC | C[O:24][C:22]([c:21]1[c:15]([NH:16][C:17](=[O:18])[CH2:19][CH3:20])[cH:14][cH:13][c:12]([O:11][c:10]2[c:5]([NH2:4])[cH:6][cH:7][cH:8][cH:9]2)[cH:25]1)=[O:23].COC(=O)c1cc(Sc2ccccc2N)ccc1N[C:3](=O)[CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:1... | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC | CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7c9959ece595136903671dbc43e3606173b1661c8592aabffd58c937be899619 | eb033e889bc3d0e0de4abfad1774a353af3583b793f1f6246ddd1bf7fd308c55 | c1ccc(Oc2ccccc2)cc1 | C-O-C(=O)-c1:c:c(-S-c2:c:c:c:c:c:2-N):c:c:c:1-N-[C;H0;D3;+0:1](=O)-[C:2]-[C;D1;H3:3].C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | null | [] | null | null | null | null | The following compounds were obtained by reacting the intermediate 2-propionylamino-5-(2-amino-phenoxy)-benzoic methyl ester or 5-(2-amino-phenylsulfanyl)-2-propionylamino-benzoic acid methyl ester (EXAMPLE 17) with boronic acids according to EXAMPLE 6 or with aldehydes as described above.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary amide.Primary amine.Primary amine.Monosulfide | Carboxylic acid.Secondary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC>>CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e623b6bc5f04c73904e0abc285f158f | CCCC(=O)Cl.CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1>>CCCC(=O)Nc1ccccc1Oc1ccc(NC(=O)C2CC2)c(C(=O)O)c1 | C(CC)(=O)NC1=C(C(=O)O)C=C(C=C1)OC1=C(C=CC=C1)NCCC.C(CCC)(=O)Cl.C(Cl)Cl>>C(CCC)(=O)NC1=C(OC=2C=CC(=C(C(=O)O)C2)NC(=O)C2CC2)C=CC=C1 | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].CCC[NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[CH2:21][CH3:23])[c:24]([C:25](=[O:26])[OH:27])[cH:28]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[O:13][c:14]1[cH:15][cH:16][c:17]([NH:18][C... | CCCC(=O)Cl.CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1 | CCCC(=O)Nc1ccccc1Oc1ccc(NC(=O)C2CC2)c(C(=O)O)c1 | null | null | null | Acylation | OtherReaction | dfdd11d82189d4bd6e02e360b3ad99b8bc852356d07ad161ee75447d35c43285 | 6eb461acad9b82d73f63ecd50ffcdfb948c52682e1fcc6482d20f4e00ad2aa6f | O=C(Nc1ccc(Oc2ccccc2)cc1)C1CC1 | C-C-C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10].Cl-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:13]-[C:14]>>[C:14]-[C:13]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:8]=[C:7](-[#7:9]-[c:10])-[CH;D3;+0:6]1-[C:15]-[CH2;D2;+0:5]-1 | 31 | [{"value": 31.0, "product": "C(CCC)(=O)NC1=C(OC=2C=CC(=C(C(=O)O)C2)NC(=O)C2CC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 5-(2-amino-phenoxy)-2-(cyclopropanecarbonyl-amino)-benzoic acid methyl ester (50.0 mg, 0.153 mmol, prepared according to EXAMPLE 2) and butyryl chloride (23.3 mg, 0.184 mmol) in CH2Cl2 (1.5 mL) was heated in a microwave oven at 110° C. for 10 minutes. The reaction mixture was allowed to reach room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Secondary amide | null | C1CC1 | c1ccccc1.c1ccccc1.C1CC1 | HCl | null | 110 | null | CCCC(=O)Cl.CCCNc1ccccc1Oc1ccc(NC(=O)CC)c(C(=O)O)c1>>CCCC(=O)Nc1ccccc1Oc1ccc(NC(=O)C2CC2)c(C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84e606289c9f4648b52ded2ff752b4ed | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.O=C=Nc1ccccc1>>CCC(=O)Nc1ccc(Oc2ccccc2NC(=O)Nc2ccccc2)cc1C(=O)O | COC(C1=C(C=CC(=C1)OC1=C(C=CC=C1)N)NC(CC)=O)=O.C1(=CC=CC=C1)N=C=O>>C1(=CC=CC=C1)NC(NC1=C(OC=2C=CC(=C(C(=O)O)C2)NC(CC)=O)C=CC=C1)=O | C[O:31][C:29]([c:28]1[c:6]([NH:5][C:3]([CH2:2][CH3:1])=[O:4])[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[cH:27]1)=[O:30].[C:18](=[O:19])=[N:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c... | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.O=C=Nc1ccccc1 | CCC(=O)Nc1ccc(Oc2ccccc2NC(=O)Nc2ccccc2)cc1C(=O)O | null | null | C(Cl)Cl | Acylation | OtherReaction | 1b1f5d27ed581b17dbaf13aca09e739af76059624bf9c2fd467f15f89c191ed7 | 836cd3195ff002b70ac993f14127c4a295ae76fd2cc94467565bdc7c17ea4e21 | O=C(Nc1ccccc1)Nc1ccccc1Oc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 80 | [{"value": 80.0, "product": "C1(=CC=CC=C1)NC(NC1=C(OC=2C=CC(=C(C(=O)O)C2)NC(CC)=O)C=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 2-propionylamino-5-(2-amino-phenoxy)-benzoic acid methyl ester (50.0 mg, 0.153 mmol, prepared as described in EXAMPLE 2) and phenyl isocyanate (21.0 mg, 0.175 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 2 hours. The solvent was removed by evaporation and the crude ester product was hydrolys... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Primary amine | Carboxylic acid.Urea | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 2 | CCC(=O)Nc1ccc(Oc2ccccc2N)cc1C(=O)OC.O=C=Nc1ccccc1>C(Cl)Cl>CCC(=O)Nc1ccc(Oc2ccccc2NC(=O)Nc2ccccc2)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b8091968c0248508f09ffdb2d46031b | FC(F)(F)c1ccccc1CBr.O=C(O)c1cc(O)ccc1NC(=O)C1CC1>>O=C(O)c1cc(OCc2ccccc2C(F)(F)F)ccc1NC(=O)C1CC1 | C1(CC1)C(=O)NC1=C(C(=O)O)C=C(C=C1)O.FC(C1=C(CBr)C=CC=C1)(F)F.[OH-].[K+]>>C1(CC1)C(=O)NC1=C(C(=O)O)C=C(C=C1)OCC1=C(C=CC=C1)C(F)(F)F | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([OH:7])[cH:19][cH:20][c:21]1[NH:22][C:23](=[O:24])[CH:25]1[CH2:26][CH2:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][... | FC(F)(F)c1ccccc1CBr.O=C(O)c1cc(O)ccc1NC(=O)C1CC1 | O=C(O)c1cc(OCc2ccccc2C(F)(F)F)ccc1NC(=O)C1CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(Nc1ccc(OCc2ccccc2)cc1)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 50 | [{"value": 50.0, "product": "C1(CC1)C(=O)NC1=C(C(=O)O)C=C(C=C1)OCC1=C(C=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.4, "product": "C1(CC1)C(=O)NC1=C(C(=O)O)C=C(C=C1)OCC1=C(C=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 2-(cyclopropanecarbonyl-amino)-5-hydroxy-benzoic acid (7.0 g, 32 mmol) and 2-(trifluoromethyl)-benzyl bromide (9.09 g, 38 mmol) in 0.5 M KOH (158 mL, 79 mmol) and acetone (200 mL) was heated to reflux. After 4 hours, acetone was evaporated and the resulting mixture was diluted with more water and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CC1 | HBr | CC(=O)C | null | 4 | FC(F)(F)c1ccccc1CBr.O=C(O)c1cc(O)ccc1NC(=O)C1CC1>CC(=O)C>O=C(O)c1cc(OCc2ccccc2C(F)(F)F)ccc1NC(=O)C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1a1e104cb264a8a82da99664cd0d420 | C=Cc1ccccc1F.CCC(=O)Nc1ccc(Br)cc1C(=O)OC>>CCC(=O)Nc1ccc(/C=C/c2ccccc2F)cc1C(=O)O | FC1=C(C=C)C=CC=C1.COC(C1=C(C=CC(=C1)Br)NC(CC)=O)=O.C([O-])([O-])=O.[K+].[K+].C(CCC)N(CCCC)CCCC.[OH-].[Na+]>>FC1=C(C=CC=C1)/C=C/C=1C=CC(=C(C(=O)O)C1)NC(CC)=O | [CH2:10]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18].C[O:23][C:21]([c:20]1[c:6]([NH:5][C:3]([CH2:2][CH3:1])=[O:4])[cH:7][cH:8][c:9](Br)[cH:19]1)=[O:22]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9](/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[F:18])[cH:19][c:20]1[C:21](=[O:22])[OH... | C=Cc1ccccc1F.CCC(=O)Nc1ccc(Br)cc1C(=O)OC | CCC(=O)Nc1ccc(/C=C/c2ccccc2F)cc1C(=O)O | 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 | O.CN(C)C=O | C-C Coupling | OtherReaction | baa255812d3085a2fbde11c9a3bb505607bb1e7be6585b006e36fbd19aacac44 | 25fe5b093fd8b2d72592e9621976dfa9f08f4d400c17b9b589c6f54a4710e331 | C(=C/c1ccccc1)\c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C):[c:7]:[c:8].[CH2;D1;+0:9]=[C:10]-[c:11]>>[O;D1;H0:5]=[C:4](-[OH;D1;+0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](/[CH;D2;+0:9]=[C:10]/[c:11]):[c:7]:[c:8] | null | [] | 150 | CELSIUS | 18 | HOUR | To a mixture of 5-bromo-2-propionylamino-benzoic acid methyl ester (1.0 g, 3.50 mmol), potassium carbonate (532 mg, 3.85 mmol), tri-n-butyl amine (0.917 mL, 3.85 mmol) and PdCl2(PPh3)2 (35 mg, 0.05 mmol) in DMF (20 mL) was added 2-fluoro-styrene (0.50 mL, 4.2 mmol). The reaction mixture was heated to 150° C. and left a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Vinyl | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | 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.O.CN(C)C=O | 150 | 18 | C=Cc1ccccc1F.CCC(=O)Nc1ccc(Br)cc1C(=O)OC>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.O.CN(C)C=O>CCC(=O)Nc1ccc(/C=C/c2ccccc2F)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c9f48fec2cb482d80d9f2140cec9bbb | COC(=O)c1ccccc1N.OCc1ccccc1>>COC(=O)c1cc(Cc2ccccc2)ccc1N | Cl.C(C=1C(N)=CC=CC1)(=O)OC.C(C1=CC=CC=C1)O.O>>C(C1=CC=CC=C1)C1=CC=C(C(C(=O)OC)=C1)N | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:15][cH:16][c:17]1[NH2:18].O[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:17]1[NH2:18] | COC(=O)c1ccccc1N.OCc1ccccc1 | COC(=O)c1cc(Cc2ccccc2)ccc1N | null | null | CC=1C=CC(=CC1)C | C-C Coupling | OtherReaction | af88eddf36fc242c9cce4a4d8506a2fbe58640bd518e16ac5d6bb59a1a9d9b61 | 5086858461038ad8c4c4a388cee61b6d9e9118227e969bc00fcc5a7517669191 | c1ccc(Cc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[c;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11]:[c:12] | 4.4 | [{"value": 4.4, "product": "C(C1=CC=CC=C1)C1=CC=C(C(C(=O)OC)=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.4, "product": "C(C1=CC=CC=C1)C1=CC=C(C(C(=O)OC)=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Methyl anthranilate (30.9 g; 205 mmols) and benzyl alcohol (4.43 g; 40,9 mmols) were dissolved in 50 mL of p-xylene. Montmorillonite (1.3 g), activated with hydrochloric acid, was added to the reaction mixture, which was then heated to boiling. The water produced during the reaction was collected using a Dean-Starck-ap... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CC=1C=CC(=CC1)C | null | 3 | COC(=O)c1ccccc1N.OCc1ccccc1>CC=1C=CC(=CC1)C>COC(=O)c1cc(Cc2ccccc2)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ad511abece24f04a183842d292cd7fa | CCC(=O)Cl.COC(=O)c1cc(Cc2ccccc2)ccc1N>>CCC(=O)Nc1ccc(Cc2ccccc2)cc1C(=O)O | C(C1=CC=CC=C1)C1=CC=C(C(C(=O)OC)=C1)N.C(CC)(=O)Cl.C([O-])(O)=O.[Na+]>>C(C1=CC=CC=C1)C=1C=CC(=C(C(=O)O)C1)NC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].C[O:21][C:19]([c:18]1[c:6]([NH2:5])[cH:7][cH:8][c:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1)=[O:20]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[C:19](=[O:20])[OH:21] | CCC(=O)Cl.COC(=O)c1cc(Cc2ccccc2)ccc1N | CCC(=O)Nc1ccc(Cc2ccccc2)cc1C(=O)O | null | null | C(Cl)(Cl)Cl | Protection | OtherReaction | 38d0ee372433fbbe336780b47adc73f08791f5521c108d354eaa542b2747a5b4 | 88f5d7ff84f4ba180aefa4ce7745e5509dd1a3deb0add33de7fca1d17a38ff92 | c1ccc(Cc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7].Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:10]-[C;D1;H3:11]>>[C;D1;H3:11]-[C:10]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:6]-[c:5](:[c:7]):[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 60 | CELSIUS | 18 | HOUR | Methyl 5-benzylanthranilate (300 mg; 1.24 mmols) was dissolved in 7 mL of chloroform and propionyl chloride (344 mg; 3.72 mmols) was added and the reaction mixture was left at room temperature for 18 hours. Aqueous saturated sodium bicarbonate (5 mL) was added to the reaction mixture whereafter the organic phase was se... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | 60 | 18 | CCC(=O)Cl.COC(=O)c1cc(Cc2ccccc2)ccc1N>C(Cl)(Cl)Cl>CCC(=O)Nc1ccc(Cc2ccccc2)cc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2087ff8c32ec4f379e147c94479483ad | CCC(=O)OC(=O)CC.O=c1[nH]c2ccc(O)cc2c(=O)o1>>CCC(=O)Nc1ccc(O)cc1C(=O)OC | OC1=CC=C2C(C(=O)OC(N2)=O)=C1.C[O-].[Na+].C(CC)(=O)OC(CC)=O>>COC(C1=C(C=CC(=C1)O)NC(CC)=O)=O | CCC(=O)OC(=O)[CH2:2][CH3:1].[c:3]1(=[O:4])[nH:5][c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]2[c:13](=[O:14])[o:15]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]1[C:13](=[O:14])[O:15][CH3:16] | CCC(=O)OC(=O)CC.O=c1[nH]c2ccc(O)cc2c(=O)o1 | CCC(=O)Nc1ccc(O)cc1C(=O)OC | null | null | CO | C-C Coupling | OtherReaction | 800c25e7540fa530b9df9e0d63d0c4f9b16f474a44597419e10a6e69aa6fa9c3 | 964ea8aadca46e00cac38224ca36d0cdd5b61a54c25f21006cd47ec67bc0b6e9 | c1ccccc1 | C-C-C(=O)-O-C(=O)-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[c;H0;D3;+0:4]1:[o;H0;D2;+0:5]:[c;H0;D3;+0:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[C;D1;H3:13]-[O;H0;D2;+0:5]-[C;H0;D3;+0:4](=[O;D1;H0:3])-[c:11](:[c:12]):[c:9](-[NH;D2;+0:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:10] | 680 | [{"value": 680.0, "product": "COC(C1=C(C=CC(=C1)O)NC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Hydroxy isatoic anhydride (17.9 g, 0.1 mol) was heated to reflux with sodium methoxide (0.5 g, 0.01 mol) in methanol (600 mL) for 1 h. The reaction mixture was cooled on icebath, propionic anhydride (15.0 g, 0.115 mol) was added and then the mixture was heated to reflux for 0.5 h The mixture was then concentrated und... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester.Secondary amide | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1 | HO- | CO | null | null | CCC(=O)OC(=O)CC.O=c1[nH]c2ccc(O)cc2c(=O)o1>CO>CCC(=O)Nc1ccc(O)cc1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-215d2c327f6d4a1a9bc8cd835e984599 | C[O-].O=C(Cl)C1CC1.O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)o1>>COC(=O)c1cc([N+](=O)[O-])ccc1NC(=O)C1CC1 | O.[N+](=O)([O-])C1=CC=C2C(C(=O)OC(N2)=O)=C1.C[O-].[Na+].C1(CC1)C(=O)Cl>>COC(C1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)C1CC1)=O | [CH3:1][O-:2].Cl[C:15](=[O:16])[CH:17]1[CH2:18][CH2:19]1.O=c1o[c:3](=[O:4])[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]2[nH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[NH:14][C:15](=[O:16])[CH:17]1[CH2:18][CH2:19]1 | C[O-].O=C(Cl)C1CC1.O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)o1 | COC(=O)c1cc([N+](=O)[O-])ccc1NC(=O)C1CC1 | null | null | CO | Acylation | OtherReaction | 32775032831a07f6993772d54860229989557a78c48f659e5f73ffbd052e4314 | bc4f51e695a72647be11534703474732542179306ee227d4cbe367095aebb2ca | O=C(Nc1ccccc1)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.O=c1:[nH;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11](=[O;D1;H0:12]):o:1.[C;D1;H3:13]-[O-;H0;D1:14]>>[C;D1;H3:13]-[O;H0;D2;+0:14]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:9](:[c:10]):[c:7](-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:8] | 0.1 | [{"value": 0.1, "product": "COC(C1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | 5-nitroisatoic anhydride (20.8 g, 0.1 mol) ) was heated to reflux with sodium methoxide (0.5 g, 0.01 mol) in methanol (600 mL). After 1 h, the solvent was evaporated under vacuum and the residue dissolved in 1,2-dichloroethane (400 mL), washed with cold water and dried over MgSO4. Cyclopropanecarbonyl chloride (20.9 g,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ester.Secondary amide | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1.C1CC1 | Other | CO | 80 | 1 | C[O-].O=C(Cl)C1CC1.O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)o1>CO>COC(=O)c1cc([N+](=O)[O-])ccc1NC(=O)C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4624dff17464e99b1a38f46df62301a | CCC(=O)Nc1ccc(Sc2ccccc2[N+](=O)[O-])cc1C(=O)OC>>CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC | COC(C1=C(C=CC(=C1)SC1=C(C=CC=C1)[N+](=O)[O-])NC(CC)=O)=O.[H][H]>>COC(C1=C(C=CC(=C1)SC1=C(C=CC=C1)N)NC(CC)=O)=O | O=[N+:17]([O-])[c:16]1[c:11]([S:10][c:9]2[cH:8][cH:7][c:6]([NH:5][C:3]([CH2:2][CH3:1])=[O:4])[c:19]([C:20](=[O:21])[O:22][CH3:23])[cH:18]2)[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([S:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[cH:18][c:19]1[C:20](=[O:21])[O:22][... | CCC(=O)Nc1ccc(Sc2ccccc2[N+](=O)[O-])cc1C(=O)OC | CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Sc2ccccc2)cc1 | 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 | null | null | A mixture of 5-(2-nitro-phenylsulfanyl)-2-propionylamino-benzoic acid methyl ester (110 mg, 0.31 mmol, prepared according to Sevbo et al. 1976) and palladium-on-charcoal (10%, 25 mg) in ethyl acetate (5 mL) was stirred in an atmosphere of hydrogen (1 atm) at room temperature for 2 hours. The catalyst was filtered off a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CCC(=O)Nc1ccc(Sc2ccccc2[N+](=O)[O-])cc1C(=O)OC>[Pd].C(C)(=O)OCC>CCC(=O)Nc1ccc(Sc2ccccc2N)cc1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-badfb920f6794f76916d9157a13ee71c | CC1(C)C(=O)N(Br)C(=O)N1Br.CCC(=O)Nc1ccc(C)cc1C(=O)OC>>CCC(=O)Nc1ccc(CBr)cc1C(=O)OC | COC(C1=C(C=CC(=C1)C)NC(CC)=O)=O.BrN1C(=O)N(C(=O)C1(C)C)Br>>COC(C1=C(C=CC(=C1)CBr)NC(CC)=O)=O | CC1(C)C(=O)N(Br)C(=O)N1[Br:11].[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH3:10])[cH:12][c:13]1[C:14](=[O:15])[O:16][CH3:17]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][Br:11])[cH:12][c:13]1[C:14](=[O:15])[O:16][CH3:17] | CC1(C)C(=O)N(Br)C(=O)N1Br.CCC(=O)Nc1ccc(C)cc1C(=O)OC | CCC(=O)Nc1ccc(CBr)cc1C(=O)OC | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | a91473c9fc7adf6b60e0ee6cf76d9fd57c945a06f854d599808c46e63bd1107a | ec61c5bd294ca43b589396f2ba98d7399502293434ea706d257f78fef795027a | c1ccccc1 | Br-N1-C(=O)-N(-[Br;H0;D1;+0:1])-C(-C)(-C)-C-1=O.[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 106.6 | [{"value": 53.0, "product": "COC(C1=C(C=CC(=C1)CBr)NC(CC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.6, "product": "COC(C1=C(C=CC(=C1)CBr)NC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The radical bromination was performed as described by Patil et al. 1989: 5-Methyl-2-propionylamino-benzoic acid methyl ester (8.85 g, 40 mmol) and 1,3-dibromo-5,5-dimethyl hydantoin (DDH) (5,72 g, 20 mmol) in a mixture of CHCl3 (500 mL) and CCl4 (500 mL) was heated to reflux. Every 60 minutes 50 mg of dibenzoyl peroxid... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Tertiary amide | Primary halide | C1CNCN1 | null | c1ccccc1 | HBr | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl | null | null | CC1(C)C(=O)N(Br)C(=O)N1Br.CCC(=O)Nc1ccc(C)cc1C(=O)OC>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>CCC(=O)Nc1ccc(CBr)cc1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8420a191fe64d6da39e948f3c6427f3 | CC(=O)OC(C)=O.C[C@]12C[C@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)[C@H](c3ccc(OC4CCCCO4)cc3)C[C@@H]1CC[C@@H]2O>>CC(=O)O[C@H]1CC[C@H]2C[C@@H](c3ccc(OC4CCCCO4)cc3)[C@@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)C[C@@]21C | O[C@H]1CC[C@H]2C[C@H]([C@H](C[C@]12C)C1=CC=C(C=C1)OCCCCCSCCCC(C(F)(F)F)(F)F)C1=CC=C(C=C1)OC1OCCCC1.C(C)(=O)OC(C)=O.C([O-])(O)=O.[Na+]>>C(C)(=O)O[C@H]1CC[C@H]2C[C@H]([C@H](C[C@]12C)C1=CC=C(C=C1)OCCCCCSCCCC(C(F)(F)F)(F)F)C1=CC=C(C=C1)OC1OCCCC1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][C@H:5]1[CH2:6][CH2:7][C@H:8]2[CH2:9][C@@H:10]([c:11]3[cH:12][cH:13][c:14]([O:15][CH:16]4[CH2:17][CH2:18][CH2:19][CH2:20][O:21]4)[cH:22][cH:23]3)[C@@H:24]([c:25]3[cH:26][cH:27][c:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][CH2:38][C:39]([F:40])([F:41])[C:42... | CC(=O)OC(C)=O.C[C@]12C[C@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)[C@H](c3ccc(OC4CCCCO4)cc3)C[C@@H]1CC[C@@H]2O | CC(=O)O[C@H]1CC[C@H]2C[C@@H](c3ccc(OC4CCCCO4)cc3)[C@@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)C[C@@]21C | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccc([C@H]2CC3CCC[C@H]3C[C@H]2c2ccc(OC3CCCCO3)cc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | 86 | [{"value": 86.0, "product": "C(C)(=O)O[C@H]1CC[C@H]2C[C@H]([C@H](C[C@]12C)C1=CC=C(C=C1)OCCCCCSCCCC(C(F)(F)F)(F)F)C1=CC=C(C=C1)OC1OCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The solution of 1.43 g (2.51 mmol) of the compound that is presented in Example 2c is reacted analogously to Example 1, and after working-up, a mixture that consists of the title compound is isolated, and (1S,3S,4R,6S,9S)-9-hydroxy-4-[4-(tetrahydropyran-2-yloxy)phenyl]-1-methyl-3-[4-(10,10,11,11,11-pentafluoro-6-thia-u... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1CC[C@@H]2CCC[C@H]2C1.c1ccccc1.C1CCOCC1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.C[C@]12C[C@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)[C@H](c3ccc(OC4CCCCO4)cc3)C[C@@H]1CC[C@@H]2O>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>CC(=O)O[C@H]1CC[C@H]2C[C@@H](c3ccc(OC4CCCCO4)cc3)[C@@H](c3ccc(OCCCCCSCCCC(F)(F)C(F)(F)F)cc3)C[C@@]21C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dcf2571f40d74e4fa4e40efe25cd9928 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCC[C@H]1C#N>>CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N | C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)N1[C@@H](CCC1)C#N.C(C)N(CC)CC>>N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1[C@@H](CCC1)C#N | O[C@H:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:13]([C:14](=[O:15])[N:16]2[CH2:17][CH2:18][CH2:19][C@H:20]2[C:21]#[N:22])[CH2:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([NH2:11])[CH2:12][C@H:13]1[C:14](=[O:15])[N:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[C:21]#... | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCC[C@H]1C#N | CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | e4cc4275430598cab66a42f9c2c21b8e5ceb97a0109cfc650cb16b8f9873032e | 608b51d94fe5549150a4eeda0c360f1a7d8cad8a20df73f53fb2f5a4d4581c18 | O=C([C@@H]1CCCN1)N1CCCC1 | O-[C@@H;D3;+0:1]1-[C:2]-[C:3](-[C:4](-[#7:5])=[O;D1;H0:6])-[#7:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[C:15]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]1-[C:2]-[C@H;D3;+0:1](-[N;D1;H2:16])-[C:15]-[#7:7]-1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14] | null | [] | null | null | null | null | (S)-1-((2S,4R)-1-tert-Butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl)-2-cyanopyrrolidine (title compound of Reference Example 2, 60.7 g) and triethylamine (30.1 mL) were dissolved in DMF (300 mL). Methanesulfonyl chloride (16 mL) was added thereto under ice-cooling. After stirring at room temperature for 3 hr, the rea... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary amine | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.C1CC[NH]C1 | null | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCC[C@H]1C#N>CN(C)C=O>CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12c1e64ab7074546a3d625ad998258d9 | COC(=O)[C@@H]1C[C@@H](N)CN1C(=O)OC(C)(C)C.Clc1nc2ccccc2o1>>COC(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1C(=O)OC(C)(C)C | O.N[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)OC.C(C)N(CC)CC.ClC=1OC2=C(N1)C=CC=C2>>O1C(=NC2=C1C=CC=C2)N[C@@H]2C[C@H](N(C2)C(=O)OC(C)(C)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([NH2:8])[CH2:18][N:19]1[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].Cl[c:9]1[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[o:17]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([NH:8][c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[o:17]2)[CH2:18]... | COC(=O)[C@@H]1C[C@@H](N)CN1C(=O)OC(C)(C)C.Clc1nc2ccccc2o1 | COC(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 56122dec6b9213d311e74462a865e17687f4178b6e2e5d6eb3cc0c5bc48da7a7 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2oc(N[C@@H]3CCNC3)nc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1)-[C:10] | null | [] | null | null | 48 | HOUR | Methyl (2S,4R)-4-amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate [product of Reference Example 4(2), 3.32 g] and triethylamine (1.4 mL) were dissolved in tetrahydrofuran (20 mL). 2-Chlorobenzoxazole (0.86 mL) was added thereto and the mixture was stirred at room temperature for 48 hr. The reaction mixture was adde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | C1CC[NH]C1.c1ccc2ocnc2c1 | HCl | O1CCCC1 | null | 48 | COC(=O)[C@@H]1C[C@@H](N)CN1C(=O)OC(C)(C)C.Clc1nc2ccccc2o1>O1CCCC1>COC(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93270218ce10478a89ccd5f0b8ad94c6 | COC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C.O=C(Cl)c1ccccc1>>COC(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1C(=O)OC(C)(C)C | O.N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)OC.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([NH2:8])[CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].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][C@H:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][N:18]1[C:... | COC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C.O=C(Cl)c1ccccc1 | COC(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(N[C@H]1CCNC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | null | [] | null | null | 1 | HOUR | Methyl (2S,4S)-4-amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate [product of Reference Example 5(3), 2.4 g] and triethylamine (2.0 mL) were dissolved in tetrahydrofuran (20 mL), and benzoyl chloride (1.1 mL) was added thereto. The mixture was stirred for 1 hr. The reaction mixture was added to water and extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccccc1 | HCl | O1CCCC1 | null | 1 | COC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C.O=C(Cl)c1ccccc1>O1CCCC1>COC(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fdb38059e574bf2a76b53793b763be8 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCSC1>>CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCSC1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)N1CSCC1.C(C)N(CC)CC>>N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1CSCC1 | O[C@H:10]1[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:13]([C:14](=[O:15])[N:16]2[CH2:17][CH2:18][S:19][CH2:20]2)[CH2:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([NH2:11])[CH2:12][C@H:13]1[C:14](=[O:15])[N:16]1[CH2:17][CH2:18][S:19][CH2:20]1 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCSC1 | CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCSC1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | e4cc4275430598cab66a42f9c2c21b8e5ceb97a0109cfc650cb16b8f9873032e | 608b51d94fe5549150a4eeda0c360f1a7d8cad8a20df73f53fb2f5a4d4581c18 | O=C([C@@H]1CCCN1)N1CCSC1 | O-[C@@H;D3;+0:1]1-[C:2]-[C:3](-[C:4](-[#7:5])=[O;D1;H0:6])-[#7:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[C:15]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]1-[C:2]-[C@H;D3;+0:1](-[N;D1;H2:16])-[C:15]-[#7:7]-1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14] | null | [] | null | null | null | null | 3-((2S,4R)-1-tert-Butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (title compound of Reference Example 9, 56.3 g) and triethylamine (28.5 mL) were dissolved in dichloromethane (1.0 l), and methanesulfonyl chloride (15.1 mL) was added thereto under ice-cooling. After stirring under ice-cooling for 1 hr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary amine | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.C1CSC[NH]1 | null | ClCCl | null | null | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)N1CCSC1>ClCCl>CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27ee47580eff4093893eb1a7d0d256ad | CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N>>Cl.N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](N)CN1 | N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1[C@@H](CCC1)C#N.Cl.O1CCOCC1>>Cl.Cl.N[C@H]1C[C@H](NC1)C(=O)N1[C@@H](CCC1)C#N | CC(C)(C)OC(=O)[N:17]1[C@H:12]([C:10]([N:9]2[C@H:5]([C:4]#[N:3])[CH2:6][CH2:7][CH2:8]2)=[O:11])[CH2:13][C@H:14]([NH2:15])[CH2:16]1>>[ClH:2].[N:3]#[C:4][C@@H:5]1[CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[C@@H:12]1[CH2:13][C@H:14]([NH2:15])[CH2:16][NH:17]1 | CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N | Cl.N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](N)CN1 | null | null | null | Miscellaneous | Boc amine deprotection | f8d276f6195a26b4ed25eb5f7dc89f1f5d8836bc1a35a891d3ddc666caa9552d | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=C([C@@H]1CCCN1)N1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C:9])-[C:10]>>[C:9]-[#7:8](-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1)-[C:10] | null | [] | null | null | null | null | (S)-1-((2S,4S)-4-Amino-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl)-2-cyanopyrrolidine (title compound of Reference Example 3, 308 mg) was dissolved in 4 mol/L hydrochloric acid-1,4-dioxane (1.25 mL), and the mixture was stirred at room temperature for 27 hr. The solvent was evaporated under reduced pressure and tetra... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CC[NH]C1.C1CCNC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1C[C@@H](N)C[C@H]1C(=O)N1CCC[C@H]1C#N>>Cl.N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](N)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4aa30a3e9374e00a8e16b40d26689e9 | CC(C)(C)OC(=O)N1C[C@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>>Cl.N#Cc1ccc(N[C@H]2CN[C@H](C(=O)N3CCC[C@H]3C#N)C2)nc1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)NC1=NC=C(C=C1)C#N)C(=O)O.Cl.C(#N)[C@H]1NCCC1>>Cl.Cl.C(#N)C=1C=CC(=NC1)N[C@@H]1C[C@H](NC1)C(=O)N1[C@@H](CCC1)C#N | CC(C)(C)OC(=O)[N:12]1[CH2:11][C@H:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:4]#[N:3])[cH:25][n:24]2)[CH2:23][C@H:13]1[C:14](O)=[O:15].[NH:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[C:21]#[N:22]>>[ClH:2].[N:3]#[C:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C@H:10]2[CH2:11][NH:12][C@H:13]([C:14](=[O:15])[N:16]3[CH2:17][CH2:18][CH2:19][C@H:20... | CC(C)(C)OC(=O)N1C[C@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1 | Cl.N#Cc1ccc(N[C@H]2CN[C@H](C(=O)N3CCC[C@H]3C#N)C2)nc1 | null | null | CN(C)C=O | Acylation | OtherReaction | 0f0e880dc075a48f825a869e028ef98e81f3b02c1beed442e7abdf308715a5a0 | 2970d4696d72ec70ee67b9ef1a98e9bece9c7164685fe99968569ccd95891147 | O=C([C@@H]1C[C@@H](Nc2ccccn2)CN1)N1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | (2S,4R)-1-tert-Butoxycarbonyl-4-(5-cyano-2-pyridyl)aminopyrrolidine-2-carboxylic acid (title compound of Reference Example 4, 0.73 g) and (S)-2-cyanopyrrolidine hydrochloride (0.29 g) were dissolved in DMF (10 mL), and triethylamine (0.62 mL), HOBT (0.34 g) and EDC hydrochloride (0.42 g) were successively added thereto... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Secondary amine | C1CC[NH]C1.C1CCNC1 | C1CCNC1.C1CC[NH]C1 | c1ccncc1.C1CCNC1.C1CC[NH]C1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>CN(C)C=O>Cl.N#Cc1ccc(N[C@H]2CN[C@H](C(=O)N3CCC[C@H]3C#N)C2)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1ab302cd5a3460dbc413e2d38f638e1 | CC(C)(C)OC(=O)N1C[C@@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](Nc2nc3ccccc3o2)CN1 | O1C(=NC2=C1C=CC=C2)N[C@H]2C[C@H](N(C2)C(=O)OC(C)(C)C)C(=O)O.Cl.C(#N)[C@H]1NCCC1>>Cl.O1C(=NC2=C1C=CC=C2)N[C@H]2C[C@H](NC2)C(=O)N2[C@@H](CCC2)C#N | CC(C)(C)OC(=O)[N:25]1[C@H:11]([C:9](O)=[O:10])[CH2:12][C@H:13]([NH:14][c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[o:23]2)[CH2:24]1.[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1>>[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[C@@H:11]1[CH2:12][C@H:13]([NH:14][c:15]2[n:16][c:17]3[cH:18][cH:1... | CC(C)(C)OC(=O)N1C[C@@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1 | N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](Nc2nc3ccccc3o2)CN1 | null | null | CN(C)C=O | Acylation | OtherReaction | 0f0e880dc075a48f825a869e028ef98e81f3b02c1beed442e7abdf308715a5a0 | 2970d4696d72ec70ee67b9ef1a98e9bece9c7164685fe99968569ccd95891147 | O=C([C@@H]1C[C@H](Nc2nc3ccccc3o2)CN1)N1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | (2S,4S)-4-(2-Benzoxazolyl)amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (title compound of Reference Example 5, 1.04 g) and (S)-2-cyanopyrrolidine hydrochloride (0.40 g) were dissolved in DMF (5 mL), and triethylamine (0.84 mL), HOBT (0.51 g) and EDC hydrochloride (0.63 g) were successively added thereto. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Secondary amine | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1.c1ccc2ocnc2c1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>CN(C)C=O>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](Nc2nc3ccccc3o2)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d03f60aa277241cba44e5f871f303d38 | CC(C)(C)OC(=O)N1C[C@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1 | O1C(=NC2=C1C=CC=C2)N[C@@H]2C[C@H](N(C2)C(=O)OC(C)(C)C)C(=O)O.Cl.C(#N)[C@H]1NCCC1>>Cl.O1C(=NC2=C1C=CC=C2)N[C@@H]2C[C@H](NC2)C(=O)N2[C@@H](CCC2)C#N | CC(C)(C)OC(=O)[N:25]1[C@H:11]([C:9](O)=[O:10])[CH2:12][C@@H:13]([NH:14][c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[o:23]2)[CH2:24]1.[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1>>[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[C@@H:11]1[CH2:12][C@@H:13]([NH:14][c:15]2[n:16][c:17]3[cH:18][cH... | CC(C)(C)OC(=O)N1C[C@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1 | N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1 | null | null | CN(C)C=O | Acylation | OtherReaction | 0f0e880dc075a48f825a869e028ef98e81f3b02c1beed442e7abdf308715a5a0 | 2970d4696d72ec70ee67b9ef1a98e9bece9c7164685fe99968569ccd95891147 | O=C([C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1)N1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | (2S,4R)-4-(2-Benzoxazolyl)amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (title compound of Reference Example 6, 1.0 g) and (S)-2-cyanopyrrolidine hydrochloride (0.38 g) were dissolved in DMF (10 mL), and triethylamine (0.81 mL), HOBT (0.49 g) and EDC hydrochloride (0.61 g) were successively added thereto. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Secondary amine | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1.c1ccc2ocnc2c1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@H](Nc2nc3ccccc3o2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>CN(C)C=O>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](Nc2nc3ccccc3o2)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6395491b54a6412db2d538169cebcf09 | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCC[C@H]1C#N>>CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCC[C@H]2C#N)N(C(=O)OC(C)(C)C)C1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)NCC1=CC=C(C=C1)C#N)C(=O)N1[C@@H](CCC1)C#N.Cl.Cl.C(#N)[C@H]1N(CCC1)C(=O)[C@H]1NC[C@H](C1)NCC1=CC=C(C=C1)C#N.C=O.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(C)CC1=CC=C(C=C1)C#N)C(=O)N1[C@@H](CCC1)C#N | O=[CH2:1].[NH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1)[C@H:12]1[CH2:13][C@@H:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][C@H:21]2[C:22]#[N:23])[N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1)[C... | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCC[C@H]1C#N | CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCC[C@H]2C#N)N(C(=O)OC(C)(C)C)C1 | null | null | C(C)#N.C(C)(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C([C@@H]1C[C@H](NCc2ccccc2)CN1)N1CCCC1 | O=[CH2;D1;+0:1].[#7:2]-[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[c:7])-[C:8]>>[#7:2]-[C:3]-[C:4](-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[C:6]-[c:7])-[C:8] | null | [] | null | null | 1 | HOUR | (S)-1-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-2-cyanopyrrolidine [product of Example 31 (1), 1.04 g] and 37% formaldehyde solution (0.7 mL) were dissolved in acetonitrile (15 mL), and the mixture was stirred at room temperature for 1 hr. Sodium cyanoborohydride (0.240 g) and ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CC[NH]C1.C1CC[NH]C1 | Other | C(C)#N.C(C)(=O)O | null | 1 | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCC[C@H]1C#N>C(C)#N.C(C)(=O)O>CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCC[C@H]2C#N)N(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4847b7bcabea4e71a27ae3755e210c13 | CC(C)(C)OC(=O)N1C[C@@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1 | C(C1=CC=CC=C1)(=O)N[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)O.Cl.C(#N)[C@H]1NCCC1>>Cl.C(C1=CC=CC=C1)(=O)N[C@H]1C[C@H](NC1)C(=O)N1[C@@H](CCC1)C#N | CC(C)(C)OC(=O)[N:24]1[C@H:11]([C:9](O)=[O:10])[CH2:12][C@H:13]([NH:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1.[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1>>[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[C@@H:11]1[CH2:12][C@H:13]([NH:14][C:15](=[O:16])[c:17]2[cH:18][cH:19]... | CC(C)(C)OC(=O)N1C[C@@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1 | N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1 | null | null | CN(C)C=O | Acylation | OtherReaction | 0f0e880dc075a48f825a869e028ef98e81f3b02c1beed442e7abdf308715a5a0 | 2970d4696d72ec70ee67b9ef1a98e9bece9c7164685fe99968569ccd95891147 | O=C(N[C@@H]1CN[C@H](C(=O)N2CCCC2)C1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | (2S,4S)-4-Benzoylamino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (title compound of Reference Example 7, 1.1 g) and (S)-2-cyanopyrrolidine hydrochloride (0.44 g) were dissolved in DMF (10 mL), and triethylamine (0.98 mL), HOBT (0.54 g) and EDC hydrochloride (0.67 g) were successively added. The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Secondary amine | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1.c1ccccc1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>CN(C)C=O>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@H](NC(=O)c2ccccc2)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-defa255eef994bfa94bf4e3fc64a8ca9 | CC(C)(C)OC(=O)N1C[C@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](NC(=O)c2ccccc2)CN1 | C(C1=CC=CC=C1)(=O)N[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)O.Cl.C(#N)[C@H]1NCCC1>>Cl.C(C1=CC=CC=C1)(=O)N[C@@H]1C[C@H](NC1)C(=O)N1[C@@H](CCC1)C#N | CC(C)(C)OC(=O)[N:24]1[C@H:11]([C:9](O)=[O:10])[CH2:12][C@@H:13]([NH:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1.[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1>>[N:2]#[C:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[C@@H:11]1[CH2:12][C@@H:13]([NH:14][C:15](=[O:16])[c:17]2[cH:18][cH:1... | CC(C)(C)OC(=O)N1C[C@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1 | N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](NC(=O)c2ccccc2)CN1 | null | null | CN(C)C=O | Acylation | OtherReaction | 0f0e880dc075a48f825a869e028ef98e81f3b02c1beed442e7abdf308715a5a0 | 2970d4696d72ec70ee67b9ef1a98e9bece9c7164685fe99968569ccd95891147 | O=C(N[C@H]1CN[C@H](C(=O)N2CCCC2)C1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[N;D1;H0:8]#[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | (2S,4R)-4-Benzoylamino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (title compound of Reference Example 8, 1.6 g) and (S)-2-cyanopyrrolidine hydrochloride (0.63 g) were dissolved in DMF (10 mL), and triethylamine (1.32 mL), HOBT (0.79 g) and EDC hydrochloride (0.99 g) were successively added. The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Secondary amine | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1 | C1CC[NH]C1.C1CCNC1.c1ccccc1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N1C[C@H](NC(=O)c2ccccc2)C[C@H]1C(=O)O.N#C[C@@H]1CCCN1>CN(C)C=O>N#C[C@@H]1CCCN1C(=O)[C@@H]1C[C@@H](NC(=O)c2ccccc2)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1a44d6bc3cc472b913ff26449bf5948 | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1>>CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)NCC1=CC=C(C=C1)C#N)C(=O)N1CSCC1.Cl.Cl.C(#N)C1=CC=C(C=C1)CN[C@H]1C[C@H](NC1)C(=O)N1CSCC1.C=O.C(#N)[BH3-].[Na+]>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(C)CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1 | O=[CH2:1].[NH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1)[C@H:12]1[CH2:13][C@@H:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][S:20][CH2:21]2)[N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1)[C@H:12]1[CH2:13]... | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 | CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | null | C(C)(=O)O | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C([C@@H]1C[C@H](NCc2ccccc2)CN1)N1CCSC1 | O=[CH2;D1;+0:1].[#7:2]-[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[c:7])-[C:8]>>[#7:2]-[C:3]-[C:4](-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[C:6]-[c:7])-[C:8] | null | [] | null | null | 30 | MINUTE | 3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 63 (1), 1.35 g] and 37% formaldehyde solution (0.788 mL) were dissolved in acetonitrile (20 mL), and the mixture was stirred at room temperature for 30 min. Sodium cyanoborohydride (0.305 g) and se... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CC[NH]C1.C1CSC[NH]1 | Other | C(C)(=O)O.C(C)#N | null | 0.5 | C=O.CC(C)(C)OC(=O)N1C[C@@H](NCc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1>C(C)(=O)O.C(C)#N>CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a12d8afff4e34429af22e1d224db33ae | O=C([C@@H]1C[C@H](Nc2ccc([N+](=O)[O-])cc2)CN1)N1CCSC1>>Nc1ccc(N[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1 | Cl.[N+](=O)([O-])C1=CC=C(C=C1)N[C@H]1C[C@H](NC1)C(=O)N1CSCC1.Cl.O1CCOCC1>>Cl.NC1=CC=C(C=C1)N[C@H]1C[C@H](NC1)C(=O)N1CSCC1 | O=[N+:2]([O-])[c:3]1[cH:4][cH:5][c:6]([NH:7][C@@H:8]2[CH2:9][NH:10][C@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][S:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1>>[NH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C@@H:8]2[CH2:9][NH:10][C@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][S:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1 | O=C([C@@H]1C[C@H](Nc2ccc([N+](=O)[O-])cc2)CN1)N1CCSC1 | Nc1ccc(N[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C([C@@H]1C[C@H](Nc2ccccc2)CN1)N1CCSC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 7.1 | [{"value": 7.1, "product": "Cl.NC1=CC=C(C=C1)N[C@H]1C[C@H](NC1)C(=O)N1CSCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | The title compound (200 mg) of Example 55 was dissolved in ethanol (10 mL), and 4 mol/L hydrochloric acid-1,4-dioxane (0.28 mL) and 10% palladium/carbon (100 mg) were added. The mixture was stirred under a hydrogen atomosphere (1 atm) at room temperature for 18 hr. The reaction mixture was filtrated and the filtrate wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCNC1.C1CSC[NH]1 | Other | [Pd].C(C)O | null | 18 | O=C([C@@H]1C[C@H](Nc2ccc([N+](=O)[O-])cc2)CN1)N1CCSC1>[Pd].C(C)O>Nc1ccc(N[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d420f37c18ae4fd8aae271345f20a892 | FC(F)(F)c1ccc(Cl)nc1>>[O-][n+]1cc(C(F)(F)F)ccc1Cl | ClC1=CC(=CC=C1)C(=O)OO.ClC1=NC=C(C=C1)C(F)(F)F.S(=S)(=O)([O-])[O-].[Na+].[Na+].C(O)([O-])=O.[Na+]>>ClC1=[N+](C=C(C=C1)C(F)(F)F)[O-] | [n:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[Cl:12]>>[O-:1][n+:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[Cl:12] | FC(F)(F)c1ccc(Cl)nc1 | [O-][n+]1cc(C(F)(F)F)ccc1Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc[nH+]cc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O;-;D1;H0:7]):[c:5]:[c:6] | 11.8 | [{"value": 11.8, "product": "ClC1=[N+](C=C(C=C1)C(F)(F)F)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | HOUR | 2-Chloro-5-trifluoromethylpyridine (5 g) was dissolved in chloroform (150 mL) and m-chloroperbenzoic acid (14.3 g) was added thereto. The mixture was stirred at 60° C. for 30 hr. Aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogencarbonate solution were added to the reaction mixture, and after sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(Cl)(Cl)Cl | 60 | 30 | FC(F)(F)c1ccc(Cl)nc1>C(Cl)(Cl)Cl>[O-][n+]1cc(C(F)(F)F)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-999a2d1f33744c50bceba70860d4b33a | N#Cc1ccc(Cl)nc1.OO>>N#Cc1ccc(Cl)[n+]([O-])c1 | FC(C(=O)OC(C(F)(F)F)=O)(F)F.OO.NC(=O)N.ClC1=NC=C(C=C1)C#N.S(=S)(=O)([O-])[O-].[Na+].[Na+]>>ClC1=[N+](C=C(C=C1)C#N)[O-] | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:10]1.O[OH:9]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n+:8]([O-:9])[cH:10]1 | N#Cc1ccc(Cl)nc1.OO | N#Cc1ccc(Cl)[n+]([O-])c1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | d7f3c84fb751fef5567bc0e84a2e7c0afb271257e8dfb17aa871e038ff1a84c7 | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1cc[nH+]cc1 | O-[OH;D1;+0:1].[Cl;D1;H0:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[Cl;D1;H0:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | null | [] | null | null | 18 | HOUR | 2-Chloropyridine-5-carbonitrile (7.01 g) was dissolved in acetonitrile (70 mL), and urea hydrogen peroxide addition compound (10 g) was added. Trifluoroacetic anhydride was added dropwise to the reaction mixture under ice-cooling and the mixture was stirred at room temperature for 18 hr. The reaction mixture was added ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | C(C)#N | null | 18 | N#Cc1ccc(Cl)nc1.OO>C(C)#N>N#Cc1ccc(Cl)[n+]([O-])c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7776923fa85494fafd076a7edc9fc9f | BrCc1ccccc1.CC(C)(C)OC(=O)N1C[C@@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1>>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccccc2)c2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1 | C(C1=CC=CC=C1)Br.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)NC1=NC=C(C=C1)C#N)C(=O)N1CSCC1.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)N(C1=NC=C(C=C1)C#N)[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1CSCC1 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([NH:11][c:19]2[cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25][n:26]2)[CH2:27][C@H:28]1[C:29](=[O:30])[N:31]1[CH2:32][CH2:33][S:34][CH2:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:... | BrCc1ccccc1.CC(C)(C)OC(=O)N1C[C@@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1 | CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccccc2)c2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C([C@@H]1C[C@H](N(Cc2ccccc2)c2ccccn2)CN1)N1CCSC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C:13]>>[#7:5]-[C:6]-[C:7](-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C:13] | null | [] | null | null | 10 | MINUTE | 3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(5-cyano-2-pyridyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 58(1)] (305 mg) was dissolved in DMF (10 mL), and potassium tert-butoxide (93 mg) was added under ice cooling. After stirring the mixture for 10 min, benzyl bromide (94 μl) was added, and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccncc1.C1CSC[NH]1 | HBr | CN(C)C=O | null | 0.166667 | BrCc1ccccc1.CC(C)(C)OC(=O)N1C[C@@H](Nc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1>CN(C)C=O>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccccc2)c2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf76bdab7fe6409e9a5ea4cc18b9883f | CCN(C(C)C)C(C)C.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.OCCBr>>CC(C)(C)OC(=O)N1C[C@@H](N(CCO)Cc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 | C(O)([O-])=O.[Na+].BrCCO.C(C)(C)N(CC)C(C)C.Cl.Cl.C(#N)C1=CC=C(C=C1)CN[C@H]1C[C@H](NC1)C(=O)N1CSCC1.CN1C(CCC1)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(CCO)CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1 | CCN(C(C)[CH3:4])[CH:2]([CH3:1])[CH3:3].[NH:8]1[CH2:9][C@@H:10]([NH:11][CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[CH2:24][C@H:25]1[C:26](=[O:27])[N:28]1[CH2:29][CH2:30][S:31][CH2:32]1.Br[CH2:12][CH2:13][OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([N:11]([CH2:12]... | CCN(C(C)C)C(C)C.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.OCCBr | CC(C)(C)OC(=O)N1C[C@@H](N(CCO)Cc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d8a307254dc3bc6e195371883ab2dcb9c63e02e01e71116906b5082e7b8a3200 | 23d66b49c456aba6d2ef193a6aa42c9f8b3e98a106c32c8e4e3d9ccc98c1a74b | O=C([C@@H]1C[C@H](NCc2ccccc2)CN1)N1CCSC1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].C-C-N(-C(-C)-[CH3;D1;+0:4])-[CH;D3;+0:5](-[C;D1;H3:6])-[C;D1;H3:7].[#16:8]-[C:9]-[#7:10](-[C:11](=[O;D1;H0:12])-[C:13]1-[C:14]-[C:15](-[NH;D2;+0:16]-[C:17]-[c:18])-[C:19]-[NH;D2;+0:20]-1)-[C:21]>>[#16:8]-[C:9]-[#7:10](-[C:11](=[O;D1;H0:12])-[C:13]1-[C:14]-[C:15](-[N;H0;D3;+0:16](-[C:1... | null | [] | 80 | CELSIUS | 2 | DAY | The product (1.67 g) of Example 63 (1) was dissolved in N-methyl-2-pyrrolidone (12 mL), and 2-bromoethanol (1.42 mL) and diisopropylethylamine (2.09 mL) were added thereto. The mixture was stirred at 80° C. for 2 days. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Secondary amine.Tertiary amine | Carbamic ester.Ether.Tertiary amine.Boc | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.C1CSC[NH]1 | HBr | null | 80 | 48 | CCN(C(C)C)C(C)C.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.OCCBr>>CC(C)(C)OC(=O)N1C[C@@H](N(CCO)Cc2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a2f1cb2330a4ca7b53b094e463eda13 | CCN(C(C)C)C(C)C.CCOC(=O)CBr.CN1CCCC1=O.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.O=C([O-])O>>CCOC(=O)CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | C(O)([O-])=O.[Na+].BrCC(=O)OCC.C(C)(C)N(CC)C(C)C.Cl.Cl.C(#N)C1=CC=C(C=C1)CN[C@H]1C[C@H](NC1)C(=O)N1CSCC1.CN1C(CCC1)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(CC(=O)OCC)CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1 | CC(C)N(C[CH3:32])C([CH3:33])[CH3:34].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=C1CCCN1[CH3:31].[NH:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1)[C@H:17]1[CH2:18][C@@H:19]([C:20](=[O:21])[N:22]2[CH2:23][CH2:24][S:25][CH2:26]2)[NH:27][CH2:35]1.[O-][C:28](=[O:29])[OH:30]>>[CH3:1][CH2:2][O:3][C:4](=... | CCN(C(C)C)C(C)C.CCOC(=O)CBr.CN1CCCC1=O.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.O=C([O-])O | CCOC(=O)CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | null | null | null | C-C Coupling | OtherReaction | c34b37c1c3456c4cc5767c06a849a038b92593613830dabf5bbb3d79137a5f76 | d0c137067a29add8cdf05b563209a5df4ae9b3038bbd325e8cf2afe78f23ca5a | O=C([C@@H]1C[C@H](NCc2ccccc2)CN1)N1CCSC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-C(-C)-N(-C-[CH3;D1;+0:6])-C(-[CH3;D1;+0:7])-[CH3;D1;+0:8].O=C1-C-C-C-N-1-[CH3;D1;+0:9].[#16:10]-[C:11]-[#7:12](-[C:13](=[O;D1;H0:14])-[C:15]1-[C:16]-[C:17](-[NH;D2;+0:18]-[C:19]-[c:20])-[C:21]-[NH;D2;+0:22]-1)-[C:23].[O-]-[C;H0;D3;+0:24](=[O;D1;H0:25])-[OH;D1;+0:26]>>... | null | [] | null | null | 18 | HOUR | The product (0.833 g) of Example 63 (1) was dissolved in N-methyl-2-pyrrolidone (6 mL), and ethyl bromoacetate (0.333 mL) and diisopropylethylamine (1.05 mL) were added thereto. The mixture was stirred at room temperature for 18 hr. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Acid.Ester.Tertiary amide.Secondary amine.Secondary amine.Tertiary amine | Carbamic ester.Ester.Ether.Tertiary amine.Boc | C1CCNC1.C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.C1CSC[NH]1 | HBr | null | null | 18 | CCN(C(C)C)C(C)C.CCOC(=O)CBr.CN1CCCC1=O.N#Cc1ccc(CN[C@@H]2CN[C@H](C(=O)N3CCSC3)C2)cc1.O=C([O-])O>>CCOC(=O)CN(Cc1ccc(C#N)cc1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d78402d1c48e463d8efe9e734f7ec81b | CC(C)(C)OC(=O)N1C[C@@H](NS(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1.N#Cc1ccc(CBr)cc1>>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)S(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)NS(=O)(=O)C1=CC=C(C=C1)C#N)C(=O)N1CSCC1.Cl.C(#N)C1=CC=C(C=C1)S(=O)(=O)N[C@H]1C[C@H](NC1)C(=O)N1CSCC1.C([O-])([O-])=O.[K+].[K+].C(#N)C1=CC=C(CBr)C=C1.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(S(=O)(=O)C1=CC=C(C=C1)C#N)CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([NH:11][S:21](=[O:22])(=[O:23])[c:24]2[cH:25][cH:26][c:27]([C:28]#[N:29])[cH:30][cH:31]2)[CH2:32][C@H:33]1[C:34](=[O:35])[N:36]1[CH2:37][CH2:38][S:39][CH2:40]1.Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3]... | CC(C)(C)OC(=O)N1C[C@@H](NS(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1.N#Cc1ccc(CBr)cc1 | CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)S(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C([C@@H]1C[C@H](N(Cc2ccccc2)S(=O)(=O)c2ccccc2)CN1)N1CCSC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13]>>[#7:5]-[C:6]-[C:7](-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13] | 84.3 | [{"value": 84.3, "product": "C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(S(=O)(=O)C1=CC=C(C=C1)C#N)CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylsulfonyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 123 (1), 856 mg] was dissolved in DMF (20 mL), and potassium carbonate (380 mg) and 4-cyanobenzyl bromide (400 mg) were added thereto at room temperature. The mixture was stirred for 4 hr. To the... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1.C1CSC[NH]1 | HBr | CN(C)C=O | null | 4 | CC(C)(C)OC(=O)N1C[C@@H](NS(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1.N#Cc1ccc(CBr)cc1>CN(C)C=O>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)S(=O)(=O)c2ccc(C#N)cc2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e85e41b6af834b57955dea0a08467d75 | CC(C)(C)OC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2>>CC(C)(C)OC(=O)N1CCC(N2CCc3ccccc32)CC1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)(C)(C)OC(=O)N1CCC(CC1)=O.N1CCC2=CC=CC=C12.C(C)(=O)O>>C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=CC=C12 | O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]1.[NH:12]1[CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[CH2:21][C... | CC(C)(C)OC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2 | CC(C)(C)OC(=O)N1CCC(N2CCc3ccccc32)CC1 | null | null | O.ClCCCl | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc2c(c1)CCN2C1CCNCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 74.3 | [{"value": 74.3, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 1-tert-Butoxycarbonylpiperidin-4-one (2.50 g), indoline (1.50 g) and acetic acid (0.73 mL) were dissolved in 1,2-dichloroethane (75 mL), and sodium triacetoxyborohydride (5.32 g) was added thereto. The mixture was stirred at room temperature for 12 hr. The reaction mixture was added to iced water and the mixture was ex... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CC[NH]CC1.c1ccc2c(c1)CCN2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O.ClCCCl | null | 12 | CC(C)(C)OC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2>O.ClCCCl>CC(C)(C)OC(=O)N1CCC(N2CCc3ccccc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdc8330fdabf4b8090f409cf85b62274 | CC(C)(C)OC(=O)N1CCN(N)CC1.O=[N+]([O-])c1ccc(F)cc1>>CC(C)(C)OC(=O)N1CCC(Nc2ccc([N+](=O)[O-])cc2)CC1 | O.NN1CCN(CC1)C(=O)OC(C)(C)C.FC1=CC=C(C=C1)[N+](=O)[O-].C(C)(C)N(C(C)C)CC>>C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=CC=C(C=C1)[N+](=O)[O-] | N1([NH2:12])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1.F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]... | CC(C)(C)OC(=O)N1CCN(N)CC1.O=[N+]([O-])c1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCC(Nc2ccc([N+](=O)[O-])cc2)CC1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | cc9b9901cf7bcaed21146ada6cf4db3f680b984a6f9db4384ca71eee47dcc6c5 | 955fdd0cb8b5627845dcae067e53d4eb8e2b1614a3423f9d92a540c8222ab38b | c1ccc(NC2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[CH2;D2;+0:15]-N(-[NH2;D1;+0:16])-[CH2;D2;+0:17]-[C:18]-1>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]1-[C:14]-[CH2;D2;+0:15]-[C:19](-[NH;D2;+0:1... | 53.2 | [{"value": 53.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | 4-Amino-1-tert-butoxycarbonylpiperazine (3.00 g), 4-fluoronitrobenzene (2.54 g) and N,N-diisopropylethylamine (8.82 g) were dissolved in N-methyl-2-pyrrolidone (30 mL), and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was added to water and the mixture was extracted with ethyl acetate. The extract ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Secondary amine | C1CNCC[NH]1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | Other | CN1C(CCC1)=O | 80 | 18 | CC(C)(C)OC(=O)N1CCN(N)CC1.O=[N+]([O-])c1ccc(F)cc1>CN1C(CCC1)=O>CC(C)(C)OC(=O)N1CCC(Nc2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7d395d8b4204e2f810e2e993877d9bd | C=O.CC(C)(C)OC(=O)N1C[C@@H](N2CCC(Nc3ccccc3)CC2)C[C@H]1C(=O)N1CCSC1>>CN(c1ccccc1)C1CCN([C@H]2C[C@@H](C(=O)N3CCSC3)N(C(=O)OC(C)(C)C)C2)CC1 | N(C1=CC=CC=C1)C1CCN(CC1)[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1CSCC1.Cl.Cl.Cl.N(C1=CC=CC=C1)C1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)N(C1=CC=CC=C1)C)C(=O)N1CSCC1 | O=[CH2:1].[NH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH:9]1[CH2:10][CH2:11][N:12]([C@H:13]2[CH2:14][C@@H:15]([C:16](=[O:17])[N:18]3[CH2:19][CH2:20][S:21][CH2:22]3)[N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]2)[CH2:32][CH2:33]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH:9]1[CH2... | C=O.CC(C)(C)OC(=O)N1C[C@@H](N2CCC(Nc3ccccc3)CC2)C[C@H]1C(=O)N1CCSC1 | CN(c1ccccc1)C1CCN([C@H]2C[C@@H](C(=O)N3CCSC3)N(C(=O)OC(C)(C)C)C2)CC1 | null | null | C(C)(=O)O.ClCCCl.O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C([C@@H]1C[C@H](N2CCC(Nc3ccccc3)CC2)CN1)N1CCSC1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]>>[C:2]-[C:3](-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5](:[c:6]):[c:7])-[C:8] | null | [] | null | null | 12 | HOUR | 3-[(2S,4S)-4-(4-Anilinopiperidino)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 148 (3), 1.18 g] was dissolved in 1,2-dichloroethane (75 mL), and sodium triacetoxyborohydride (5.32 g), acetic acid (0.73 mL) and 37% formaldehyde solution (5.0 mL) were added thereto. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CC[NH]CC1.C1CC[NH]C1.C1CSC[NH]1 | Other | C(C)(=O)O.ClCCCl.O | null | 12 | C=O.CC(C)(C)OC(=O)N1C[C@@H](N2CCC(Nc3ccccc3)CC2)C[C@H]1C(=O)N1CCSC1>C(C)(=O)O.ClCCCl.O>CN(c1ccccc1)C1CCN([C@H]2C[C@@H](C(=O)N3CCSC3)N(C(=O)OC(C)(C)C)C2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83132976d59148e8bea04b988527ffdb | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(F)cc1>>O=[N+]([O-])c1ccc(N2CCC3(CC2)OCCO3)cc1 | O1CCOC12CCNCC2.C(C)(C)N(CC)C(C)C.FC1=CC=C(C=C1)[N+](=O)[O-]>>C1COC2(CCN(CC2)C2=CC=C(C=C2)[N+](=O)[O-])O1 | [NH:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[O:14][CH2:15][CH2:16][O:17]2.F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][cH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][C:11]3([CH2:12][CH2:13]2)[O:14][CH2:15][CH2:16][O:17]3)[cH:18][cH:19]1 | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(F)cc1 | O=[N+]([O-])c1ccc(N2CCC3(CC2)OCCO3)cc1 | null | null | O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 163ff2ee5dd6c15769cf883428ba870eed9db794603d1900dd68b8b7dc727535 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC3(CC2)OCCO3)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 80.2 | [{"value": 80.2, "product": "C1COC2(CCN(CC2)C2=CC=C(C=C2)[N+](=O)[O-])O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1,4-Dioxa-8-azaspiro[4,5]decane (7.88 g) was dissolved in N-methyl-2-pyrrolidine (50 mL), and diisopropylethylamine (9.5.8 mL) and 4-fluoronitrobenzene (7.06 g) were successively added. The mixture was stirred at room temperature for 2 hr. The reaction mixture was added to iced water, and the precipitated solid was col... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CC2(CCN1)OCCO2.c1ccccc1 | c1ccccc1.C1CC2(CC[NH]1)OCCO2 | c1ccccc1.C1CC2(CC[NH]1)OCCO2 | HF | O | null | 2 | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(F)cc1>O>O=[N+]([O-])c1ccc(N2CCC3(CC2)OCCO3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ed59873ae734812b5b5a08a76fbb05e | CCN(C(C)C)C(C)C.N#Cc1ccc(CBr)cc1.O=C([C@@H]1C[C@H](NC2CCN(c3ccc([N+](=O)[O-])cc3)CC2)CN1)N1CCSC1>>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)C2CCN(c3ccc([N+](=O)[O-])cc3)CC2)C[C@H]1C(=O)N1CCSC1 | C(O)([O-])=O.[Na+].C(#N)C1=CC=C(CBr)C=C1.C(C)(C)N(CC)C(C)C.Cl.Cl.Cl.[N+](=O)([O-])C1=CC=C(C=C1)N1CCC(CC1)N[C@H]1C[C@H](NC1)C(=O)N1CSCC1.CN1C(CCC1)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N(C1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-])CC1=CC=C(C=C1)C#N)C(=O)N1CSCC1 | CCN(C(C)[CH3:4])[CH:2]([CH3:1])[CH3:3].Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1.[NH:8]1[CH2:9][C@@H:10]([NH:11][CH:21]2[CH2:22][CH2:23][N:24]([c:25]3[cH:26][cH:27][c:28]([N+:29](=[O:30])[O-:31])[cH:32][cH:33]3)[CH2:34][CH2:35]2)[CH2:36][C@H:37]1[C:38](=[O:39])[N:40]1[CH2:41][CH2:42][S:43][CH2... | CCN(C(C)C)C(C)C.N#Cc1ccc(CBr)cc1.O=C([C@@H]1C[C@H](NC2CCN(c3ccc([N+](=O)[O-])cc3)CC2)CN1)N1CCSC1 | CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)C2CCN(c3ccc([N+](=O)[O-])cc3)CC2)C[C@H]1C(=O)N1CCSC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d8a307254dc3bc6e195371883ab2dcb9c63e02e01e71116906b5082e7b8a3200 | 23d66b49c456aba6d2ef193a6aa42c9f8b3e98a106c32c8e4e3d9ccc98c1a74b | O=C([C@@H]1C[C@H](N(Cc2ccccc2)C2CCN(c3ccccc3)CC2)CN1)N1CCSC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-N(-C(-C)-[CH3;D1;+0:5])-[CH;D3;+0:6](-[C;D1;H3:7])-[C;D1;H3:8].[#16:9]-[C:10]-[#7:11](-[C:12](=[O;D1;H0:13])-[C:14]1-[C:15]-[C:16](-[NH;D2;+0:17]-[C:18](-[C:19])-[C:20])-[C:21]-[NH;D2;+0:22]-1)-[C:23]>>[#16:9]-[C:10]-[#7:11](-[C:12](=[O;D1;H0:13])-[C:14]1-[C:15]-[C:16](-[N;H0;D3... | null | [] | 80 | CELSIUS | 8 | HOUR | The product (1.01 g) of Example 156 (3) was dissolved in N-methyl-2-pyrrolidone (6 mL), and 4-cyanobenzyl bromide (0.392 g) and diisopropylethylamine (1.05 mL) were added thereto. The mixture was stirred at 80° C. for 8 hr with heating. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Secondary amine.Tertiary amine | Carbamic ester.Ether.Tertiary amine.Boc | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.C1CSC[NH]1 | HBr | null | 80 | 8 | CCN(C(C)C)C(C)C.N#Cc1ccc(CBr)cc1.O=C([C@@H]1C[C@H](NC2CCN(c3ccc([N+](=O)[O-])cc3)CC2)CN1)N1CCSC1>>CC(C)(C)OC(=O)N1C[C@@H](N(Cc2ccc(C#N)cc2)C2CCN(c3ccc([N+](=O)[O-])cc3)CC2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-204c7715386d4076acd8efd08ea4eaac | C1CNCCN1.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1N1CCNCC1 | N1CCNCC1.FC1=C(C=CC=C1)[N+](=O)[O-].O>>[N+](=O)([O-])C1=C(C=CC=C1)N1CCNCC1 | [NH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | C1CNCCN1.O=[N+]([O-])c1ccccc1F | O=[N+]([O-])c1ccccc1N1CCNCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 74.3 | [{"value": 74.3, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Piperazine (12.9 g) was dissolved in DMF (100 mL), and a solution of 2-fluoronitrobenzene (7.06 g) in DMF (30 mL) was added dropwise. The mixture was stirred at room temperature for 3 hr. The reaction mixture was added to water and the mixture was extracted with ethyl acetate. The extract was washed with water and drie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HF | CN(C)C=O | null | 3 | C1CNCCN1.O=[N+]([O-])c1ccccc1F>CN(C)C=O>O=[N+]([O-])c1ccccc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-330decb74c1641509158bc72bf2d1e53 | C1CNCCN1.FC(F)(F)c1ccc(Cl)nc1>>FC(F)(F)c1ccc(N2CCNCC2)nc1 | N1CCNCC1.ClC1=NC=C(C=C1)C(F)(F)F.O>>FC(C=1C=CC(=NC1)N1CCNCC1)(F)F | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:16][n:15]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[n:15][cH:16]1 | C1CNCCN1.FC(F)(F)c1ccc(Cl)nc1 | FC(F)(F)c1ccc(N2CCNCC2)nc1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 99.4 | [{"value": 99.4, "product": "FC(C=1C=CC(=NC1)N1CCNCC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Piperazine (12.9 g) was suspended in N-methyl-2-pyrrolidone (130 mL), and a solution of 2-chloro-5-trifluoromethylpyridine (9.08 g) in N-methyl-2-pyrrolidone (30 mL) was added dropwise. The mixture was stirred at room temperature for 18 hr. The reaction mixture was added to water and the mixture was extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | CN1C(CCC1)=O | null | 18 | C1CNCCN1.FC(F)(F)c1ccc(Cl)nc1>CN1C(CCC1)=O>FC(F)(F)c1ccc(N2CCNCC2)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ede453e32e24a7c87809f58521e105c | C1CNCCN1.Clc1ccnc2ccccc12>>c1ccc2c(N3CCNCC3)ccnc2c1 | N1CCNCC1.ClC1=CC=NC2=CC=CC=C12>>N1=CC=C(C2=CC=CC=C12)N1CCNCC1 | [NH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1.Cl[c:5]1[c:4]2[cH:3][cH:2][cH:1][cH:16][c:15]2[n:14][cH:13][cH:12]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([N:6]3[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[cH:12][cH:13][n:14][c:15]2[cH:16]1 | C1CNCCN1.Clc1ccnc2ccccc12 | c1ccc2c(N3CCNCC3)ccnc2c1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3fbb016f359467d4eec60eb9e91655d372a48980ac0112856b33886c38619450 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCNCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:7]:1:[c:8] | 105.9 | [{"value": 105.9, "product": "N1=CC=C(C2=CC=CC=C12)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 30 | MINUTE | Piperazine (13.2 g) was melted by heating at 140° C., and 4-chloroquinoline (2.5 g) was added thereto. The mixture was stirred at 140° C. for 30 min. The reaction mixture was added to iced water, and the mixture was extracted with chloroform to give 1-(4-quinolyl)piperazine (3.45 g) as a pale-yellow oil.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2ncccc2c1 | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CCN1.c1ccc2ncccc2c1 | HCl | O | 140 | 0.5 | C1CNCCN1.Clc1ccnc2ccccc12>O>c1ccc2c(N3CCNCC3)ccnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b054729c25147f6b59e545e209052b6 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1cccc2cccnc12>>O=S(=O)(c1cccc2cccnc12)N1CCNCC1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)(C)(C)OC(=O)N1CCNCC1.C(C)N(CC)CC.N1=CC=CC2=CC=CC(=C12)S(=O)(=O)Cl>>N1=CC=CC2=CC=CC(=C12)S(=O)(=O)N1CCNCC1 | CC(C)(C)OC(=O)[N:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]12>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]12)[N:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1cccc2cccnc12 | O=S(=O)(c1cccc2cccnc12)N1CCNCC1 | null | null | ClCCl | Acylation | OtherReaction | fe80f4ba0030540fe0dd5c07c99df28cb9dc1f06dbe0a7382338f606945d5f85 | 705725ff5b1b5bdebe12db390e8895152ae89941b9a07e00716e981f5b25c654 | O=S(=O)(c1cccc2cccnc12)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.Cl-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10](:[c:11]):[c:12](:[c:13]):[#7;a:14]:[c:15]>>[O;D1;H0:8]=[S;H0;D4;+0:7](=[O;D1;H0:9])(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-[c:10](:[c:11]):[c:12](:[c:13]):[#7;a:14]:[c:15] | 22.1 | [{"value": 22.1, "product": "N1=CC=CC2=CC=CC(=C12)S(=O)(=O)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 1-tert-Butoxycarbonylpiperazine (2.22 g) and triethylamine (2.0 mL) were dissolved in dichloromethane (100 mL), and 8-quinolinesulfonyl chloride (2.71 g) was added thereto. The mixture was stirred at room temperature for 14 hr. 10% citric acid solution was added to the reaction mixture and the mixture was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CCN1 | c1ccc2ncccc2c1.C1C[NH]CCN1 | HCl | ClCCl | null | 14 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1cccc2cccnc12>ClCCl>O=S(=O)(c1cccc2cccnc12)N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8bbdd2e30e644bb99b1cbacfcc867298 | C1CNCCN1.N#Cc1cccnc1Cl>>N#Cc1cccnc1N1CCNCC1 | N1CCNCC1.ClC1=NC=CC=C1C#N>>C(#N)C=1C(=NC=CC1)N1CCNCC1 | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[c:8]1[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][n:7]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | C1CNCCN1.N#Cc1cccnc1Cl | N#Cc1cccnc1N1CCNCC1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1):[#7;a:2]:[c:3] | 89.1 | [{"value": 89.1, "product": "C(#N)C=1C(=NC=CC1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 2 | HOUR | Piperazine (125 g) was melted by heating at 150° C. and 2-chloro-3-cyanopyridine (20.0 g) was added thereto. The mixture was stirred at 110° C. for 2 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | O | 150 | 2 | C1CNCCN1.N#Cc1cccnc1Cl>O>N#Cc1cccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e222f2b038a4783a0650a01c212fb9d | C1CNCCN1.Clc1cccnc1Cl>>Clc1cccnc1N1CCNCC1 | N1CCNCC1.ClC1=NC=CC=C1Cl>>ClC=1C(=NC=CC1)N1CCNCC1 | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Cl[c:7]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][n:6]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | C1CNCCN1.Clc1cccnc1Cl | Clc1cccnc1N1CCNCC1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 102.5 | [{"value": 102.5, "product": "ClC=1C(=NC=CC1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | Piperazine (20.0 g) was melted by heating at 140° C. and 2,3-dichloropyridine (3.42 g) was added thereto. The mixture was stirred at 120° C. for 2 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | O | 140 | 2 | C1CNCCN1.Clc1cccnc1Cl>O>Clc1cccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69c0cd41b4cf4561add0bc2143501f5e | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(N2CCNCC2)nc1 | O.C(C)(C)(C)OC(=O)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].ClC1=NC=C(C(=O)OCC)C=C1>>C(C)OC(=O)C=1C=CC(=NC1)N1CCNCC1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][NH:10][CH2:15][CH2:14]1.Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][n:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[n:16][cH:17]1 | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(N2CCNCC2)nc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f9ec877b49b3a228c02d63b268ec6a17dab199dccd6d2eaf006bf52df974c50d | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | c1ccc(N2CCNCC2)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.Cl-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[#7;a:8]:[c;H0;D3;+0:7](-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1):[c:10]:[c:11] | 82.4 | [{"value": 82.4, "product": "C(C)OC(=O)C=1C=CC(=NC1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | Ethyl 6-chloronicotinate (1.12 g) was dissolved in DMF (30 mL), and 1-tert-butoxycarbonylpiperazine (1.24 g) and potassium carbonate (1.00 g) were added thereto. The mixture was stirred at 80° C. for 18 hr. Water (100 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1C[NH]CCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | CN(C)C=O | 80 | 18 | CC(C)(C)OC(=O)N1CCNCC1.CCOC(=O)c1ccc(Cl)nc1>CN(C)C=O>CCOC(=O)c1ccc(N2CCNCC2)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-848321933638496791a905e67270be84 | CCOC(=O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1.Cl>>Cl.O=C(O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1 | Cl.Cl.Cl.Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1)C(=O)OCC)C(=O)N1CSCC1.Cl.Cl.Cl.C(C)OC(=O)C=1C=CC(=NC1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1>>Cl.Cl.Cl.C(=O)(O)C=1C=CC(=NC1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1 | CC[O:6][C:5](=[O:4])[c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([C@@H:15]3[CH2:16][NH:17][C@H:18]([C:19](=[O:20])[N:21]4[CH2:22][CH2:23][S:24][CH2:25]4)[CH2:26]3)[CH2:27][CH2:28]2)[n:29][cH:30]1.[ClH:3]>>[ClH:3].[O:4]=[C:5]([OH:6])[c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([C@@H:15]3[CH2:16][NH:1... | CCOC(=O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1.Cl | Cl.O=C(O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1 | null | null | null | Miscellaneous | OtherReaction | 16eb0e22715fadede32e44259800ac2375ae7dbc609f9ec677d59917bae07bec | b51da43dbb7140dac708518f8dbf83c5b067214819134afdb3f427285d08d6f8 | O=C([C@@H]1C[C@H](N2CCN(c3ccccn3)CC2)CN1)N1CCSC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 6 mol/L Hydrochloric acid was added to 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(5-ethoxycarbonyl-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine trihydrochloride [product of Example 211 (2), 1.00 g] and the mixture was refluxed for 2 hr. The solvent was evaporated under reduced pressure, and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.C1C[NH]CC[NH]1.C1CCNC1.C1CSC[NH]1 | Other | null | null | null | CCOC(=O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1.Cl>>Cl.O=C(O)c1ccc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d07e9a838ac401f84a0d0ffd1310bb7 | C1CNCCN1.NC(=O)c1ccc(Cl)nc1>>NC(=O)c1ccc(N2CCNCC2)nc1 | ClC1=NC=C(C(=O)N)C=C1.N1CCNCC1>>C(N)(=O)C=1C=CC(=NC1)N1CCNCC1 | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Cl[c:7]1[cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:15][n:14]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[n:14][cH:15]1 | C1CNCCN1.NC(=O)c1ccc(Cl)nc1 | NC(=O)c1ccc(N2CCNCC2)nc1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 6.2 | [{"value": 6.2, "product": "C(N)(=O)C=1C=CC(=NC1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 6-chloronicotinamide (5.00 g) and piperazine (27.6 g), and by reaction in the same manner as in Example 196 (1) at 100° C., 1-(5-carbamoyl-2-pyridyl)piperazine (0.41 g) was obtained as a yellow powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | null | null | null | C1CNCCN1.NC(=O)c1ccc(Cl)nc1>>NC(=O)c1ccc(N2CCNCC2)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-898e10ec32214655b9bc6942c0a9890c | C1CNCCN1.FC(F)(F)c1cnc(Cl)c(Cl)c1>>FC(F)(F)c1cnc(N2CCNCC2)c(Cl)c1 | N1CCNCC1.ClC1=NC=C(C=C1Cl)C(F)(F)F>>ClC=1C(=NC=C(C1)C(F)(F)F)N1CCNCC1 | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[c:8]1[n:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:17][c:15]1[Cl:16]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][n:7][c:8]([N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[c:15]([Cl:16])[cH:17]1 | C1CNCCN1.FC(F)(F)c1cnc(Cl)c(Cl)c1 | FC(F)(F)c1cnc(N2CCNCC2)c(Cl)c1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 104.1 | [{"value": 104.1, "product": "ClC=1C(=NC=C(C1)C(F)(F)F)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | Piperazine (40 g) was melted by heating at 140° C. and 2,3-dichloro-5-trifluoromethylpyridine (10 g) was added thereto. The mixture was stirred at 120° C. for 2 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried and concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | O | 140 | 2 | C1CNCCN1.FC(F)(F)c1cnc(Cl)c(Cl)c1>O>FC(F)(F)c1cnc(N2CCNCC2)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cca9370459ad44c084ce39b7dbc25385 | CCO.O=C(O)c1cnc(Cl)c(Cl)c1>>CCOC(=O)c1cnc(Cl)c(Cl)c1 | ClC=1C(=NC=C(C(=O)O)C1)Cl.C(C)O.S(=O)(Cl)Cl>>ClC=1C(=NC=C(C(=O)OCC)C1)Cl | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1 | CCO.O=C(O)c1cnc(Cl)c(Cl)c1 | CCOC(=O)c1cnc(Cl)c(Cl)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | 5,6-Dichloronicotinic acid (4.90 g) was dissolved in ethanol (40 mL), and thionyl chloride (2.0 mL) was added thereto under ice-cooling. The mixture was refluxed for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | null | null | null | CCO.O=C(O)c1cnc(Cl)c(Cl)c1>>CCOC(=O)c1cnc(Cl)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe7f0f39209c476a8500b303e5d04434 | CCOC(=O)c1cnc(N2CCN([C@H]3C[C@@H](C(=O)N4CCSC4)N(C(=O)OC(C)(C)C)C3)CC2)c(Cl)c1>>CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1Cl)C(=O)OCC)C(=O)N1CSCC1.Cl.Cl.Cl.ClC=1C(=NC=C(C1)C(=O)OCC)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1.[OH-].[Li+]>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1Cl)C(=O)O)C(=O)N1CSCC1 | CC[O:21][C:19]([c:18]1[cH:17][n:16][c:15]([N:14]2[CH2:13][CH2:12][N:11]([C@@H:10]3[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:28]([C:29](=[O:30])[N:31]4[CH2:32][CH2:33][S:34][CH2:35]4)[CH2:27]3)[CH2:26][CH2:25]2)[c:23]([Cl:24])[cH:22]1)=[O:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8... | CCOC(=O)c1cnc(N2CCN([C@H]3C[C@@H](C(=O)N4CCSC4)N(C(=O)OC(C)(C)C)C3)CC2)c(Cl)c1 | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C([C@@H]1C[C@H](N2CCN(c3ccccn3)CC2)CN1)N1CCSC1 | 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] | 42.8 | [{"value": 42.8, "product": "C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1Cl)C(=O)O)C(=O)N1CSCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 19 | HOUR | 3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(3-chloro-5-ethoxycarbonyl-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 216 (3), 6.49 g] was dissolved in ethanol (30 mL), and aqueous solution (30 mL) of lithium hydroxide (0.59 g) was added thereto. The mixture was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.C1C[NH]CC[NH]1.c1ccncc1.C1CSC[NH]1 | Other | C(C)O | null | 19 | CCOC(=O)c1cnc(N2CCN([C@H]3C[C@@H](C(=O)N4CCSC4)N(C(=O)OC(C)(C)C)C3)CC2)c(Cl)c1>C(C)O>CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6feafa42ea546d59bfe96bfbd63e1fb | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1.[NH4+]>>CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(N)=O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1Cl)C(=O)O)C(=O)N1CSCC1.Cl.Cl.Cl.C(=O)(O)C=1C=C(C(=NC1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1)Cl.[Cl-].[NH4+].CN1CCOCC1.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.Cl>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=NC=C(C=C1Cl)C(N)=O)C(=O)N1CSCC1 | O[C:19]([c:18]1[cH:17][n:16][c:15]([N:14]2[CH2:13][CH2:12][N:11]([C@@H:10]3[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:28]([C:29](=[O:30])[N:31]4[CH2:32][CH2:33][S:34][CH2:35]4)[CH2:27]3)[CH2:26][CH2:25]2)[c:23]([Cl:24])[cH:22]1)=[O:21].[NH4+:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[... | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1.[NH4+] | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(N)=O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C([C@@H]1C[C@H](N2CCN(c3ccccn3)CC2)CN1)N1CCSC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH4+;D0:8]>>[NH2;D1;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | 4 | HOUR | 3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-carboxy-3-chloro-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 217 (1), 2.63 g] and ammonium chloride (0.54 g) were dissolved in DMF (30 mL), and N-methylmorpholine (1.1 mL), HOBT (1.53 g) and EDC hydrochloride (1.15 g) were successively ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]C1.C1C[NH]CC[NH]1.c1ccncc1.C1CSC[NH]1 | HO- | CN(C)C=O | null | 4 | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(=O)O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1.[NH4+]>CN(C)C=O>CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3ncc(C(N)=O)cc3Cl)CC2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12a1736fbd544a5eb37ab329d42b0b4e | C1CNCCN1.Clc1cnc(Cl)c(Cl)c1>>Clc1cnc(N2CCNCC2)c(Cl)c1 | N1CCNCC1.ClC1=NC=C(C=C1Cl)Cl>>ClC=1C(=NC=C(C1)Cl)N1CCNCC1 | [NH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1.Cl[c:5]1[n:4][cH:3][c:2]([Cl:1])[cH:14][c:12]1[Cl:13]>>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]([Cl:13])[cH:14]1 | C1CNCCN1.Clc1cnc(Cl)c(Cl)c1 | Clc1cnc(N2CCNCC2)c(Cl)c1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2cfe79e260e5807469ed13cb0f911e98374b23b23e32c97becca8eb2afcb1c66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 101.1 | [{"value": 101.1, "product": "ClC=1C(=NC=C(C1)Cl)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | Piperazine (24.0 g) was melted by heating at 140° C. and 2,3,5-trichloropyridine (5.00 g) was added thereto. The mixture was stirred at 120° C. for 2 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccncc1.C1C[NH]CCN1 | HCl | O | 140 | 2 | C1CNCCN1.Clc1cnc(Cl)c(Cl)c1>O>Clc1cnc(N2CCNCC2)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-083e1cd12178472ea21d4ea0d900884f | C=C1CC(=O)O1.CC(C)(C)OC(=O)N1CCNCC1>>CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCNCC1.C=C1CC(=O)O1>>C(CC(=O)C)(=O)N1CCN(CC1)C(=O)OC(C)(C)C | [CH2:1]=[C:2]1[O:3][C:5](=[O:6])[CH2:4]1.[NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | C=C1CC(=O)O1.CC(C)(C)OC(=O)N1CCNCC1 | CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C)C=O | Acylation | OtherReaction | 4577f8e5153c38d78e55723b317d2862b784dfad0b721d4d59f15977da6300d6 | 9efa0c835be0aa9453aa895a9d5c6a73c10e08e695158204e8f0348795b4fe67 | C1CNCCN1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[CH2;D1;+0:7]=[C;H0;D3;+0:8]1-[C:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-1>>[CH3;D1;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:12])-[C:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | null | [] | null | null | 1.5 | HOUR | 1-tert-Butoxycarbonylpiperazine (5.02 g) was dissolved in DMF (90 mL), and diketene (2.50 mL) was added thereto at room temperature. The mixture was stirred for 1.5 hr and the solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ketone.Tertiary amide | C1COC1.C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | null | CN(C)C=O | null | 1.5 | C=C1CC(=O)O1.CC(C)(C)OC(=O)N1CCNCC1>CN(C)C=O>CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fff3605f9f014a9eafe9279be4b48ca9 | CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1.CC(C)(C)NN>>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)n(C(C)(C)C)n1 | C(CC(=O)C)(=O)N1CCN(CC1)C(=O)OC(C)(C)C.Cl.Cl.Cl.CC1=NN(C(=C1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1)C1=CC=CC=C1.Cl.C(C)(C)(C)NN>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=NN1C(C)(C)C)C | O=[C:2]([CH3:1])[CH2:3][C:4](=O)[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1.[NH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[NH2:23]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[n:18]([C:19... | CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1.CC(C)(C)NN | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)n(C(C)(C)C)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | Pyrazole formation | 98c29b40d20c526874877c5fbed4227dd1e6c8e39c4320f02dcfd98c265cd20f | 67d101f2f6bbc4d05f99152dec77d6bb3f9da60ddd000ebe4afa876d58cef3b4 | c1cc(N2CCNCC2)[nH]n1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[#7:5](-[C:6])-[C:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH;D2;+0:12]-[NH2;D1;+0:13]>>[C:6]-[#7:5](-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:13]:[n;H0;D3;+0:12]:1-[C:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C;D1;H3:11])-[C... | 18.9 | [{"value": 18.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=NN1C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 1-Acetoacetyl-4-tert-butoxycarbonylpiperazine [product of Example 222 (1), 3.92 g] was dissolved in ethanol (300 mL), and tert-butylhydrazine hydrochloride (1.81 g) and molecular sieves 3A (10 g) were added thereto at room temperature. The mixture was stirred for 15 hr. The reaction mixture was filtrated and the filtra... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Tertiary amide | null | null | c1cc[nH]n1 | c1cc[nH]n1.C1C[NH]CC[NH]1 | HO- | C(C)O | null | 15 | CC(=O)CC(=O)N1CCN(C(=O)OC(C)(C)C)CC1.CC(C)(C)NN>C(C)O>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)n(C(C)(C)C)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ed808e92b9946238c3435597a9880a9 | O=C(OCc1ccccc1)N1CCNCC1.S=C=Nc1ccccc1>>O=C(OCc1ccccc1)N1CCN(C(=S)Nc2ccccc2)CC1 | C(C1=CC=CC=C1)OC(=O)N1CCNCC1.C1(=CC=CC=C1)N=C=S>>N(C1=CC=CC=C1)C(=S)N1CCN(CC1)C(=O)OCC1=CC=CC=C1 | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][NH:14][CH2:24][CH2:25]1.[C:15](=[S:16])=[N:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([C:15](=[S:16])[NH:17][c:18]2[cH:19][cH:20][cH:21... | O=C(OCc1ccccc1)N1CCNCC1.S=C=Nc1ccccc1 | O=C(OCc1ccccc1)N1CCN(C(=S)Nc2ccccc2)CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | thiourea | beb066691ff40a37c26bc4234840e891c6843c6d14f49542e84576855b81b429 | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | O=C(OCc1ccccc1)N1CCN(C(=S)Nc2ccccc2)CC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[S;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[S;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | null | [] | null | null | 1 | HOUR | 1-Benzyloxycarbonylpiperazine (5.00 g) was dissolved in acetone (50 mL), and phenyl isothiocyanate (2.9 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration to give 1-(anilinocarbothioyl)-4-(benzyloxycarbonyl)piperazine (5.08 g... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | CC(=O)C | null | 1 | O=C(OCc1ccccc1)N1CCNCC1.S=C=Nc1ccccc1>CC(=O)C>O=C(OCc1ccccc1)N1CCN(C(=S)Nc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-042cd53d25eb4022aafcc06889b6859c | C#CCN.CSC(=Nc1ccccc1)N1CCN(C(=O)OCc2ccccc2)CC1>>Cc1cnc(N2CCN(C(=O)OCc3ccccc3)CC2)n1-c1ccccc1 | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C(=NC1=CC=CC=C1)SC.Cl.Cl.Cl.C1(=CC=CC=C1)N1C(=NC=C1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1.C(C#C)N>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1N(C(=CN1)C)C1=CC=CC=C1 | [CH:1]#[C:2][CH2:3][NH2:4].CS[C:5]([N:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1)=[N:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH... | C#CCN.CSC(=Nc1ccccc1)N1CCN(C(=O)OCc2ccccc2)CC1 | Cc1cnc(N2CCN(C(=O)OCc3ccccc3)CC2)n1-c1ccccc1 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 73ac30e747e4229428260662dbb12dd45b5d2176b6d4b63c7267db806047c81f | 4c8e418b01f6182030f1526ea2fcf5c0ebd529284eb47d16a13d089a87d05fd0 | O=C(OCc1ccccc1)N1CCN(c2nccn2-c2ccccc2)CC1 | C-S-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[#7:8](-[C:9])-[C:10].[CH;D1;+0:11]#[C;H0;D2;+0:12]-[CH2;D2;+0:13]-[NH2;D1;+0:14]>>[C:9]-[#7:8](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[cH;D2;+0:13]:[c;H0;D3;+0:12](-[CH3;D1;+0:11]):[n;H0;D3;+0:2]:1-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[C:10] | null | [] | null | null | null | null | 1-Benzyloxycarbonyl-4-[(methylthio)phenyliminomethyl]piperazine [product of Example 224 (2), 2.70 g] and propargylamine (2.3 mL) were dissolved in 1-butanol (25 mL), and p-toluenesulfonic acid monohydrate (156 mg) was added thereto. The mixture was refluxed for 20 hr. The reaction mixture was concentrated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Alkyne | null | null | c1c[nH]cn1 | c1c[nH]cn1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | C(CCC)O | null | null | C#CCN.CSC(=Nc1ccccc1)N1CCN(C(=O)OCc2ccccc2)CC1>C(CCC)O>Cc1cnc(N2CCN(C(=O)OCc3ccccc3)CC2)n1-c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a138f0e4d992421a948682e1f55043e6 | C1CNCCN1.Clc1nnnn1-c1ccccc1>>c1ccc(-n2nnnc2N2CCNCC2)cc1 | ClC1=NN=NN1C1=CC=CC=C1.N1CCNCC1>>C1(=CC=CC=C1)N1N=NN=C1N1CCNCC1 | [NH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1.Cl[c:9]1[n:5](-[c:4]2[cH:3][cH:2][cH:1][cH:17][cH:16]2)[n:6][n:7][n:8]1>>[cH:1]1[cH:2][cH:3][c:4](-[n:5]2[n:6][n:7][n:8][c:9]2[N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[cH:16][cH:17]1 | C1CNCCN1.Clc1nnnn1-c1ccccc1 | c1ccc(-n2nnnc2N2CCNCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 4370c4208f04c18549baf32cb111eed2207b9d9119be11b2c908568f35fda136 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-n2nnnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[#7;a:4]:[#7;a:5]:1-[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[c:6]-[#7;a:5]1:[#7;a:4]:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | 99.7 | [{"value": 99.7, "product": "C1(=CC=CC=C1)N1N=NN=C1N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 5-chloro-1-phenyl-1H-tetrazol (2.10 g) and piperazine (10.0 g), and reaction at 100° C. in the same manner as in Example 196 (1), 1-(1-phenyl-1H-tetrazol-5-yl)piperazine (2.67 g) was obtained as a pale-yellow powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1nnn[nH]1 | c1nnn[nH]1.C1C[NH]CCN1 | c1ccccc1.c1nnn[nH]1.C1C[NH]CCN1 | HCl | null | null | null | C1CNCCN1.Clc1nnnn1-c1ccccc1>>c1ccc(-n2nnnc2N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e62a5004f074b199fdeda059775825a | N#Cc1ccc(N)c([N+](=O)[O-])c1>>N#Cc1ccc(N)c(N)c1 | NC1=C(C=C(C#N)C=C1)[N+](=O)[O-]>>NC=1C=C(C#N)C=CC1N | O=[N+:9]([O-])[c:8]1[c:6]([NH2:7])[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:10]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([NH2:9])[cH:10]1 | N#Cc1ccc(N)c([N+](=O)[O-])c1 | N#Cc1ccc(N)c(N)c1 | null | [Pd] | O1CCCC1.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "NC=1C=C(C#N)C=CC1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-3-nitrobenzonitrile (25 g) was dissolved in methanol (200 mL) and tetrahydrofuran (200 mL). The mixture was stirred in the presence of 10% palladium/carbon (3.0 g) under a hydrogen atomosphere (1 atm) for 20 hr. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure to give ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].O1CCCC1.CO | null | null | N#Cc1ccc(N)c([N+](=O)[O-])c1>[Pd].O1CCCC1.CO>N#Cc1ccc(N)c(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26147d012fea46848867a779534fd71d | Clc1nc2ccccc2[nH]1.O=C1CCC(=O)N1Cl>>Clc1ccc2nc(Cl)[nH]c2c1 | ClC=1NC2=C(N1)C=CC=C2.ClN1C(CCC1=O)=O.O>>ClC=1NC2=C(N1)C=CC(=C2)Cl | [cH:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([Cl:8])[nH:9][c:10]2[cH:11]1.O=C1CCC(=O)N1[Cl:1]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([Cl:8])[nH:9][c:10]2[cH:11]1 | Clc1nc2ccccc2[nH]1.O=C1CCC(=O)N1Cl | Clc1ccc2nc(Cl)[nH]c2c1 | null | null | CN(C)C=O | Functional Group Interconversion | Chlorination | fbcb510fe012bb024cb5d3ac9e0bf4b976f46e215ed905e0c24c89cd8edf8077 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2[nH]cnc2c1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]:[c:10]:1:2>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c:10]:2:[c:9]:[c:8]:1 | 37.3 | [{"value": 37.3, "product": "ClC=1NC2=C(N1)C=CC(=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | 2-Chlorobenzimidazole (1.05 g) was dissolved in DMF (10 mL), and N-chlorosuccinimide (1.01 g) was added thereto. The mixture was stirred at 60° C. for 30 min and the reaction mixture was added to water. The precipitated solid was collected by filtration to give 2,5-dichlorobenzimidazole (0.480 g) as a white solid.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2[nH]cnc2c1.C1CCNC1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | CN(C)C=O | 60 | 0.5 | Clc1nc2ccccc2[nH]1.O=C1CCC(=O)N1Cl>CN(C)C=O>Clc1ccc2nc(Cl)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e9ba6ad0e98430d9baae746e4614fd4 | CI.Clc1nc2ccccc2[nH]1>>Cn1c(Cl)nc2ccccc21 | O.[H-].[Na+].ClC=1NC2=C(N1)C=CC=C2.CI>>ClC1=NC2=C(N1C)C=CC=C2 | I[CH3:1].[nH:2]1[c:3]([Cl:4])[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12>>[CH3:1][n:2]1[c:3]([Cl:4])[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | CI.Clc1nc2ccccc2[nH]1 | Cn1c(Cl)nc2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b959860a194ba554eb04b7d214c30055f34ef752b392c88b943b67fec007e3e6 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2[nH]cnc2c1 | I-[CH3;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:9]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:9]1:[c:7](:[c:8]):[c:5](:[c:6]):[#7;a:4]:[c:3]:1-[Cl;D1;H0:2] | null | [] | null | null | 30 | MINUTE | Sodium hydride (contained by 60%, 0.288 g) was suspended in DMF (10 mL), and 2-chlorobenzimidazole (1 g) was added thereto. The mixture was stirred at room temperature for 30 min and methyl iodide (0.61 mL) was added thereto. After stirring at room temperature for 1 hr, water was added to the reaction mixture. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1 | HI | CN(C)C=O | null | 0.5 | CI.Clc1nc2ccccc2[nH]1>CN(C)C=O>Cn1c(Cl)nc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3a335ea328f4a87b63664f41e90b9a5 | CN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1F>>CNc1ccc(C(F)(F)F)cc1[N+](=O)[O-] | FC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-].CN.C(C)O.O>>CNC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-] | [CH3:1][NH2:2].F[c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15] | CN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1F | CNc1ccc(C(F)(F)F)cc1[N+](=O)[O-] | null | null | C(C)O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C;D1;H3:7]):[c:2]:[c:3] | 96.9 | [{"value": 96.9, "product": "CNC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 4-Fluoro-3-nitrobenzotrifluoride (25 g) was dissolved in ethanol (50 mL), and 30% methylamine-ethanol solution (97.9 g) was gradually added dropwise under ice-cooling, and the mixture was stirred at room temperature for 40 min. The reaction mixture was added to water, and the precipitated solid was collected by filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)O | null | 0.666667 | CN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1F>C(C)O>CNc1ccc(C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ca9eb8ff3b4e49cd9faf6813ffe9e145 | CCOC(=S)[S-].Nc1cc([N+](=O)[O-])ccc1Br>>O=[N+]([O-])c1ccc2sc(S)nc2c1 | BrC1=C(N)C=C(C=C1)[N+](=O)[O-].C(C)OC(=S)[S-].[K+]>>SC=1SC2=C(N1)C=C(C=C2)[N+](=O)[O-] | CCO[C:9]([S-:8])=[S:10].Br[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:13][c:12]1[NH2:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[s:8][c:9]([SH:10])[n:11][c:12]2[cH:13]1 | CCOC(=S)[S-].Nc1cc([N+](=O)[O-])ccc1Br | O=[N+]([O-])c1ccc2sc(S)nc2c1 | null | null | CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | 02db7beb47c6da870010e245f6db10a58d2bc4b2e2c685b01f3605f7a3cf723b | f9c9e1616cbfafcf863bdd1e9fe84bb954b8f3b409b7bf896e5abd1affbe360c | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].C-C-O-[C;H0;D3;+0:7](-[S-;H0;D1:8])=[S;H0;D1;+0:9]>>[SH;D1;+0:9]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:5]:[c:4](:[c:6]):[c;H0;D3;+0:1](:[c:2]:[c:3]):[s;H0;D2;+0:8]:1 | 86.2 | [{"value": 86.2, "product": "SC=1SC2=C(N1)C=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 2-Bromo-5-nitroaniline (10 g) was dissolved in N-methyl-2-pyrrolidone (50 mL), and potassium ethylxanthate (14.8 g) was added thereto. The mixture was stirred at 140° C. with heating. The reaction mixture was concentrated under reduced pressure, and water (300 mL) and conc. hydrochloric acid (10 mL) were added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine.Thiocarbonyl | Aromatic thiol | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | CN1C(CCC1)=O | 140 | null | CCOC(=S)[S-].Nc1cc([N+](=O)[O-])ccc1Br>CN1C(CCC1)=O>O=[N+]([O-])c1ccc2sc(S)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4de3f2addb3c4a68bcd3fc84a411955c | CN(C)C=O.O=[N+]([O-])c1ccc2nc(S)sc2c1>>CSc1nc2ccc([N+](=O)[O-])cc2s1 | [H-].[Na+].SC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].CN(C)C=O>>CSC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-] | CN(C=O)[CH3:1].[SH:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[s:14]1>>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[s:14]1 | CN(C)C=O.O=[N+]([O-])c1ccc2nc(S)sc2c1 | CSc1nc2ccc([N+](=O)[O-])cc2s1 | null | null | null | Heteroatom Alkylation and Arylation | S-methylation | 931eb9954dd138479cd7340b2b0ff5ba38d3e11935f9dd9ea63aa3dfd63853ff | 52869605e231957850ab88e7d5013b32cc121894e7d0d1cc33e1915e04b9e0b9 | c1ccc2scnc2c1 | C-N(-[CH3;D1;+0:1])-C=O.[SH;D1;+0:2]-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 18 | HOUR | Sodium hydride (containing by 60%, 6.15 g) was suspended in DMF (120 mL) and 2-mercapto-6-nitrobenzothiazole (20 g) was added thereto under ice-cooling. After completion of bubbling, methyl iodide (26.4 mL) was added thereto. The mixture was stirred at room temperature for 18 hr. Water (800 mL) was added to the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aromatic thiol | Monosulfide | null | null | c1ccc2scnc2c1 | HO- | null | null | 18 | CN(C)C=O.O=[N+]([O-])c1ccc2nc(S)sc2c1>>CSc1nc2ccc([N+](=O)[O-])cc2s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75d7e96e81334e7c8e9c2b8f6a7049a2 | CCOC(=S)[S-].Nc1ccc(C(F)(F)F)cc1Br>>FC(F)(F)c1ccc2nc(S)sc2c1 | NC1=C(C=C(C=C1)C(F)(F)F)Br.C(C)OC(=S)[S-].[K+].O>>FC(C1=CC2=C(N=C(S2)S)C=C1)(F)F | CCO[C:10](=[S:11])[S-:12].Br[c:13]1[c:8]([NH2:9])[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([SH:11])[s:12][c:13]2[cH:14]1 | CCOC(=S)[S-].Nc1ccc(C(F)(F)F)cc1Br | FC(F)(F)c1ccc2nc(S)sc2c1 | null | null | CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | 02db7beb47c6da870010e245f6db10a58d2bc4b2e2c685b01f3605f7a3cf723b | f9c9e1616cbfafcf863bdd1e9fe84bb954b8f3b409b7bf896e5abd1affbe360c | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].C-C-O-[C;H0;D3;+0:7](-[S-;H0;D1:8])=[S;H0;D1;+0:9]>>[SH;D1;+0:9]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:5]:[c:4](:[c:6]):[c;H0;D3;+0:1](:[c:2]:[c:3]):[s;H0;D2;+0:8]:1 | 25.8 | [{"value": 25.8, "product": "FC(C1=CC2=C(N=C(S2)S)C=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 3 | HOUR | 4-Amino-3-bromobenzotrifluoride (2.40 g) was dissolved in N-methyl-2-pyrrolidone (10 mL), and potassium ethylxanthate (3.52 g) was added thereto. The mixture was stirred at 160° C. for 3 hr with heating. Water (300 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine.Thiocarbonyl | Aromatic thiol | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | CN1C(CCC1)=O | 160 | 3 | CCOC(=S)[S-].Nc1ccc(C(F)(F)F)cc1Br>CN1C(CCC1)=O>FC(F)(F)c1ccc2nc(S)sc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44cd83b575bd42f9936fd736835dfe85 | BrBr.CC(C)Oc1ccc(N)cc1>>CC(C)Oc1ccc(N)c(Br)c1 | C(C)(C)OC1=CC=C(N)C=C1.BrBr>>BrC1=C(N)C=CC(=C1)OC(C)C | Br[Br:11].[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][cH:12]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([Br:11])[cH:12]1 | BrBr.CC(C)Oc1ccc(N)cc1 | CC(C)Oc1ccc(N)c(Br)c1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | null | [] | null | null | 2 | HOUR | 4-Isopropoxyaniline (24.2 g) was dissolved in acetic acid (300 mL), and a mixture of bromine (8.25 mL) and acetic acid (80 mL) was added dropwise. After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. Water was added to residue, and the mixture was extracted with die... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 2 | BrBr.CC(C)Oc1ccc(N)cc1>C(C)(=O)O>CC(C)Oc1ccc(N)c(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-219e30c1dca24637845e5b3d4c9459db | Clc1nc2ccccc2s1.O=[N+]([O-])O>>O=[N+]([O-])c1ccc2nc(Cl)sc2c1 | S(O)(O)(=O)=O.ClC=1SC2=C(N1)C=CC=C2.[N+](=O)(O)[O-]>>ClC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-] | [cH:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([Cl:10])[s:11][c:12]2[cH:13]1.O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([Cl:10])[s:11][c:12]2[cH:13]1 | Clc1nc2ccccc2s1.O=[N+]([O-])O | O=[N+]([O-])c1ccc2nc(Cl)sc2c1 | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | 668b9c8f526506609a3c1bae67dc3186759376057ca0511251a32d7865e504f8 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2scnc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#16;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:1:2>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[c:11]:[c:12]2:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | null | [] | null | null | null | null | Conc. sulfuric acid (50 mL) was added to 2-chlorobenzothiazole (10 g) under ice-cooling, and conc. nitric acid (5 mL) was added dropwise under ice-cooling. The mixture was stirred under ice-cooling for 1 hr, and iced water (600 mL) was added to the reaction mixture. The precipitated solid was collected by filtration, w... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HO- | O | null | null | Clc1nc2ccccc2s1.O=[N+]([O-])O>O>O=[N+]([O-])c1ccc2nc(Cl)sc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f3cc27de9b54598aeb7b5073ac9d63b | CCOC(=O)c1ccccc1O.[NH3+]O>>O=C(NO)c1ccccc1O | Cl.O[NH3+].C(C=1C(O)=CC=CC1)(=O)OCC>>C(C=1C(O)=CC=CC1)(=O)NO | CCO[C:2](=[O:1])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11].[NH3+:3][OH:4]>>[O:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11] | CCOC(=O)c1ccccc1O.[NH3+]O | O=C(NO)c1ccccc1O | null | null | O1CCOCC1.[OH-].[Na+] | Acylation | OtherReaction | 2d87d4ce8b797d207a4d720ddca5314a71ae21452d103320c99ec97070478dba | 00b364fcf2d2396af24ca4500c386e4a8a422045f0a912c21eff7cf619606bb9 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3+;D1:6]-[O;D1;H1:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 54.3 | [{"value": 54.3, "product": "C(C=1C(O)=CC=CC1)(=O)NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Hydroxylammonium hydrochloride (15 g) was dissolved in 10% aqueous sodium hydroxide solution (220 mL), and a solution of ethyl salicylate (24 g) in 1,4-dioxane (70 mL) was gradually added, and the mixture was stirred at room temperature for 5 hr. The reaction mixture was concentrated until the amount thereof became alm... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary amide | null | null | c1ccccc1 | HO- | O1CCOCC1.[OH-].[Na+] | null | 5 | CCOC(=O)c1ccccc1O.[NH3+]O>O1CCOCC1.[OH-].[Na+]>O=C(NO)c1ccccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ef8d76b7e7c40c7ab4635c843fc3db3 | BrBr.COC(=O)c1ccccc1O>>COC(=O)c1cc(Br)ccc1O | C(C=1C(O)=CC=CC1)(=O)OC.BrBr.O>>BrC1=CC=C(C(C(=O)OC)=C1)O | Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12] | BrBr.COC(=O)c1ccccc1O | COC(=O)c1cc(Br)ccc1O | 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] | null | [] | null | null | 21 | HOUR | Methyl salicylate (149 g) was dissolved in acetic acid (900 mL), and bromine (50 mL) was added thereto. The mixture was stirred at room temperature for 21 hr. Water (10 L) was added to the reaction mixture, and the precipitated solid was collected by filtration, which was then recrystallized from methanol to give methy... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 21 | BrBr.COC(=O)c1ccccc1O>C(C)(=O)O>COC(=O)c1cc(Br)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-60dd5431afaf477babfb87ec33d04de8 | Nc1ncccc1O>>Sc1nc2ncccc2o1 | C(C)OC(=S)[S-].[K+].NC1=NC=CC=C1O.O.Cl>>O1C(=NC2=NC=CC=C21)S | [NH2:3][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[OH:10]>>[SH:1][c:2]1[n:3][c:4]2[n:5][cH:6][cH:7][cH:8][c:9]2[o:10]1 | Nc1ncccc1O | Sc1nc2ncccc2o1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 41e8a4c852be5f8941b1a63345cbe497a313afe0c537ae18d00f7d68d3792051 | 43a68e502bebb4894b205d94c44e8d052be6ce3d241cfadf7f1d04b13c7f9ab7 | c1cnc2ncoc2c1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7]>>[S;D1;H1:8]-[c:9]1:[n;H0;D2;+0:1]:[c:2](:[#7;a:3]:[c:4]):[c:5](:[c:7]):[o;H0;D2;+0:6]:1 | 67.4 | [{"value": 67.4, "product": "O1C(=NC2=NC=CC=C21)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino-3-hydroxypyridine (5.51 g) was dissolved in pyridine (100 mL), and potassium ethylxanthate (8.82 g) was added thereto. The mixture was refluxed for 2 hr. Iced water (400 mL) was added to the reaction mixture, and concentrated hydrochloric acid (40 mL) was added thereto. The mixture was extracted with chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Aromatic thiol | c1ccncc1 | c1cnc2ncoc2c1 | c1cnc2ncoc2c1 | Other | N1=CC=CC=C1 | null | null | Nc1ncccc1O>N1=CC=CC=C1>Sc1nc2ncccc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4b4c6110f8743b0a1fd6fdb3c424c09 | C1CNCCN1.CCOC(=O)C(C)(C)c1cn2nc(Cl)ccc2n1>>CCOC(=O)C(C)(C)c1cn2nc(N3CCNCC3)ccc2n1 | ClC=1C=CC=2N(N1)C=C(N2)C(C(=O)OCC)(C)C.N1CCNCC1>>C(C)OC(=O)C(C)(C)C=1N=C2N(N=C(C=C2)N2CCNCC2)C1 | [NH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1.Cl[c:13]1[n:12][n:11]2[cH:10][c:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[n:23][c:22]2[cH:21][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][n:11]2[n:12][c:13]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[cH:20][cH:21]... | C1CNCCN1.CCOC(=O)C(C)(C)c1cn2nc(Cl)ccc2n1 | CCOC(=O)C(C)(C)c1cn2nc(N3CCNCC3)ccc2n1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6f8fbd59e8065cb5d16a4ee70ca3b28d0ef327664784d16ab1e6dc53fb9f46d3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cn2nc(N3CCNCC3)ccc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7:10]1-[C:11]-[C:12]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3]3:[c:4]:[c:5]:[#7;a:6]:[c:7]:3:[c:8]:[c:9]:2)-[C:14]-[C:15]-1 | 100 | [{"value": 100.0, "product": "C(C)OC(=O)C(C)(C)C=1N=C2N(N=C(C=C2)N2CCNCC2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate (2.00 g) and piperazine (19.7 g), and by a reaction at 100° C. in the same manner as in Example 196 (1), 1-[2-(1-ethoxycarbonyl-1-methylethyl)-6-imidazo[1,2-b]pyridazinyl]piperazine (2.37 g) was obtained as an oil.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnn2ccnc2c1 | c1cnn2ccnc2c1.C1C[NH]CCN1 | c1cnn2ccnc2c1.C1C[NH]CCN1 | HCl | null | null | null | C1CNCCN1.CCOC(=O)C(C)(C)c1cn2nc(Cl)ccc2n1>>CCOC(=O)C(C)(C)c1cn2nc(N3CCNCC3)ccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e2bf5b0eeed4dbba026aa20889124f7 | Cc1cc(O)c2ccccc2n1.O=P(Cl)(Cl)Cl>>Cc1cc(Cl)c2ccccc2n1 | OC1=CC(=NC2=CC=CC=C12)C.P(=O)(Cl)(Cl)Cl>>ClC1=CC(=NC2=CC=CC=C12)C | O[c:4]1[cH:3][c:2]([CH3:1])[n:12][c:11]2[c:6]1[cH:7][cH:8][cH:9][cH:10]2.O=P(Cl)(Cl)[Cl:5]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1 | Cc1cc(O)c2ccccc2n1.O=P(Cl)(Cl)Cl | Cc1cc(Cl)c2ccccc2n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[C;D1;H3:5]-[c:4]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3]:1 | null | [] | null | null | 30 | MINUTE | Phosphorus oxychloride (30 mL) was added to 4-hydroxy-2-methylquinoline (10 g), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate solution was added to the residue under ice-cooling. The mixture was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | 0.5 | Cc1cc(O)c2ccccc2n1.O=P(Cl)(Cl)Cl>>Cc1cc(Cl)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ef913eea72040918018fad2ac95998a | FC(F)(F)c1cc(Cl)c2ccccc2n1.OCCNCCO>>OCCN(CCO)c1cc(C(F)(F)F)nc2ccccc12 | N(CCO)CCO.ClC1=CC(=NC2=CC=CC=C12)C(F)(F)F>>OCCN(CCO)C1=CC(=NC2=CC=CC=C12)C(F)(F)F | Cl[c:8]1[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7]>>[OH:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][OH:7])[c:8]1[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | FC(F)(F)c1cc(Cl)c2ccccc2n1.OCCNCCO | OCCN(CCO)c1cc(C(F)(F)F)nc2ccccc12 | null | null | [Cl-].[Na+].O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 58b519bcefc8b0884f30564d454d0bf8e19d1792705c71f74402c97f0a6633f3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[C:16]-[C:17])-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:... | null | [] | 80 | CELSIUS | 19 | HOUR | Diethanolamine (20 mL) was added to 4-chloro-2-trifluoromethylquinoline (5.04 g), and the mixture was stirred at 80° C. for 19 hr. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure. The residue was purified by silica ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | [Cl-].[Na+].O | 80 | 19 | FC(F)(F)c1cc(Cl)c2ccccc2n1.OCCNCCO>[Cl-].[Na+].O>OCCN(CCO)c1cc(C(F)(F)F)nc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e74ad20a28894c1bbbb6389949431e49 | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3cc(C(N)=O)nc4ccccc34)CC2)C[C@H]1C(=O)N1CCSC1.Cl>>Cl.NC(=O)c1cc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)c2ccccc2n1 | C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCN(CC1)C1=CC(=NC2=CC=CC=C12)C(N)=O)C(=O)N1CSCC1.Cl.Cl.Cl.COC(=O)C1=NC2=CC=CC=C2C(=C1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1>>Cl.Cl.Cl.C(N)(=O)C1=NC2=CC=CC=C2C(=C1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][C@@H:14]([N:13]2[CH2:12][CH2:11][N:10]([c:9]3[cH:8][c:7]([C:5]([NH2:4])=[O:6])[n:34][c:33]4[c:28]3[cH:29][cH:30][cH:31][cH:32]4)[CH2:27][CH2:26]2)[CH2:25][C@H:17]1[C:18](=[O:19])[N:20]1[CH2:21][CH2:22][S:23][CH2:24]1.[ClH:3]>>[ClH:3].[NH2:4][C:5](=[O:6])[c:7]1[cH:8][c:9]([N:10]2[CH2:11][CH... | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3cc(C(N)=O)nc4ccccc34)CC2)C[C@H]1C(=O)N1CCSC1.Cl | Cl.NC(=O)c1cc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)c2ccccc2n1 | null | null | null | Miscellaneous | OtherReaction | f8d276f6195a26b4ed25eb5f7dc89f1f5d8836bc1a35a891d3ddc666caa9552d | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=C([C@@H]1C[C@H](N2CCN(c3ccnc4ccccc34)CC2)CN1)N1CCSC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C:9])-[C:10]-[#16:11]>>[#16:11]-[C:10]-[#7:8](-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1)-[C:9] | null | [] | null | null | null | null | Using 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(2-carbamoyl-4-quinolyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 262 (3), 1.05 g], and in the same manner as in Example 186 (2), the title compound (696 mg) was obtained as a brown powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1C[NH]CC[NH]1.C1CCNC1.C1CSC[NH]1.c1ccc2ncccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1C[C@@H](N2CCN(c3cc(C(N)=O)nc4ccccc34)CC2)C[C@H]1C(=O)N1CCSC1.Cl>>Cl.NC(=O)c1cc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb5a3fd241214b508b2809001144e82b | CCOC=C(C(=O)OCC)C(=O)OCC.Nc1ccccc1>>CCOC(=O)c1cnc2ccccc2c1O | C(C)OC=C(C(=O)OCC)C(=O)OCC.NC1=CC=CC=C1>>OC1=C(C=NC2=CC=CC=C12)C(=O)OCC | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:15](OCC)=[O:16].[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15]1[OH:16] | CCOC=C(C(=O)OCC)C(=O)OCC.Nc1ccccc1 | CCOC(=O)c1cnc2ccccc2c1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e04d5084bd6bde4efb79456fdff70fdac6e2cf2829400707e635c879cfe5d271 | 4a985e8b872e7ba2e4af89799e804f05fef7f2382ed6af4bf801b35cf0e038a9 | c1ccc2ncccc2c1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[c;H0;D3;+0:7]:1-[OH;D1;+0:8] | 44.1 | [{"value": 44.1, "product": "OC1=C(C=NC2=CC=CC=C12)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 2 | HOUR | Diethyl ethoxymethylenemalonate (115 g) was dropwise added to aniline (50 g), and the mixture was refluxed for 1 hr. The resulting ethanol was evaporated under atmospheric pressure, and the residue was heated at 200° C. and poured into diphenyl ether (750 mL). The mixture was stirred at 220-250° C. for 2 hr with heatin... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine | Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | null | 200 | 2 | CCOC=C(C(=O)OCC)C(=O)OCC.Nc1ccccc1>>CCOC(=O)c1cnc2ccccc2c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce7bfe590e3a4a64a00c07b68f3053f5 | NC(=O)c1cc(Cl)c2ccccc2n1>>Nc1cc(Cl)c2ccccc2n1 | ClC1=CC(=NC2=CC=CC=C12)C(=O)N.Cl.Cl.Cl.COC(=O)C1=NC2=CC=CC=C2C(=C1)N1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1.BrBr>>NC1=NC2=CC=CC=C2C(=C1)Cl | O=[C:2](c1[cH:3][c:4]([Cl:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1)[NH2:1]>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1 | NC(=O)c1cc(Cl)c2ccccc2n1 | Nc1cc(Cl)c2ccccc2n1 | null | null | O1CCCC1.[OH-].[K+] | Miscellaneous | OtherReaction | db13421ac872302695d3ef4c6aa1985fa1af435b90dfc9e11f331be76489d7d2 | 49d40a8831465b2291100ac78f3ed653b3694eee3493e3566de3b9018d8cc734 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-c1:[cH;D2;+0:3]:[c:4](-[Cl;D1;H0:5]):[c:6]:[c:7](:[c:8]):[n;H0;D2;+0:9]:1>>[Cl;D1;H0:5]-[c:4]1:[c:6]:[c:7](:[c:8]):[n;H0;D2;+0:9]:[c;H0;D3;+0:1](-[N;D1;H2:2]):[cH;D2;+0:3]:1 | null | [] | null | null | 30 | MINUTE | Bromine (2.32 mL) was dissolved in 5% aqueous potassium hydroxide solution (190 mL), and a solution of 4-chloroquinoline-2-carboxamide [product of Example 262 (1), 9.80 g] in tetrahydrofuran (190 mL) was dropwise added thereto. The mixture was stirred at room temperature for 30 min, and the mixture was stirred at 80° C... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | O1CCCC1.[OH-].[K+] | null | 0.5 | NC(=O)c1cc(Cl)c2ccccc2n1>O1CCCC1.[OH-].[K+]>Nc1cc(Cl)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-816c337a791d4fc79493c67e92e65e50 | C1CNCCN1.Clc1ccc2c(Cl)ccnc2c1>>Clc1ccc2c(N3CCNCC3)ccnc2c1 | N1CCNCC1.ClC1=CC=NC2=CC(=CC=C12)Cl>>ClC1=CC=C2C(=CC=NC2=C1)N1CCNCC1 | [NH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1.Cl[c:6]1[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:17][c:16]2[n:15][cH:14][cH:13]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[cH:13][cH:14][n:15][c:16]2[cH:17]1 | C1CNCCN1.Clc1ccc2c(Cl)ccnc2c1 | Clc1ccc2c(N3CCNCC3)ccnc2c1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3fbb016f359467d4eec60eb9e91655d372a48980ac0112856b33886c38619450 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCNCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:7]:1:[c:8] | 41.1 | [{"value": 41.1, "product": "ClC1=CC=C2C(=CC=NC2=C1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2.5 | HOUR | Piperazine (65.2 g) was melted by heating at 120° C., and 4,7-dichloroquinoline (15.0 g) was added thereto. The mixture was stirred at 120° C. for 2.5 hr and the reaction mixture was added to water. The mixture was extracted with chloroform and concentrated under reduced pressure to give 1-(7-chloro-4-quinolyl)piperazi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2ncccc2c1 | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CCN1.c1ccc2ncccc2c1 | HCl | O | 120 | 2.5 | C1CNCCN1.Clc1ccc2c(Cl)ccnc2c1>O>Clc1ccc2c(N3CCNCC3)ccnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a786ded399443c7afc06d6e8649e3ce | CCOC(=O)CC(=O)C(F)(F)F.Cc1ccccc1N>>Cc1cccc2c(O)cc(C(F)(F)F)nc12 | CC1=C(N)C=CC=C1.FC(C(CC(=O)OCC)=O)(F)F.O>>FC(C1=NC2=C(C=CC=C2C(=C1)O)C)(F)F | CCO[C:7](=[O:8])[CH2:9][C:10](=O)[C:11]([F:12])([F:13])[F:14].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:16]1[NH2:15]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([OH:8])[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[n:15][c:16]12 | CCOC(=O)CC(=O)C(F)(F)F.Cc1ccccc1N | Cc1cccc2c(O)cc(C(F)(F)F)nc12 | null | null | P(O)(O)(O)=O | Aromatic Heterocycle Formation | OtherReaction | 03fb309d467457208d11accffba771ac71177021179459bf0cc1e729b7f7524b | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc2ncccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](... | 17.4 | [{"value": 17.4, "product": "FC(C1=NC2=C(C=CC=C2C(=C1)O)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 5.5 | HOUR | 2-Methylaniline (5.00 g) was dissolved in 75% phosphoric acid (20 mL), and ethyl trifluoroacetoacetate (8.60 g) was dropwise added thereto at 105° C. The mixture was stirred at 105° C. for 5.5 hr. After allowing to cool, the reaction mixture was added to water. The precipitated solid was collected by filtration to give... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | P(O)(O)(O)=O | 105 | 5.5 | CCOC(=O)CC(=O)C(F)(F)F.Cc1ccccc1N>P(O)(O)(O)=O>Cc1cccc2c(O)cc(C(F)(F)F)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aaeb23c7d47e4c37afe76145535b2e03 | O=P(Cl)(Cl)Cl.Oc1cc(C(F)(F)F)nc2ccc(C(F)(F)F)cc12>>FC(F)(F)c1ccc2nc(C(F)(F)F)cc(Cl)c2c1 | OC1=CC(=NC2=CC=C(C=C12)C(F)(F)F)C(F)(F)F.P(=O)(Cl)(Cl)Cl>>ClC1=CC(=NC2=CC=C(C=C12)C(F)(F)F)C(F)(F)F | O=P(Cl)(Cl)[Cl:17].O[c:16]1[cH:15][c:10]([C:11]([F:12])([F:13])[F:14])[n:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:19][c:18]21>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([Cl:17])[c:18]2[cH:19]1 | O=P(Cl)(Cl)Cl.Oc1cc(C(F)(F)F)nc2ccc(C(F)(F)F)cc12 | FC(F)(F)c1ccc2nc(C(F)(F)F)cc(Cl)c2c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13] | null | [] | null | null | 17 | HOUR | 4-Hydroxy-2,6-bis(trifluoromethyl)quinoline (1.28 g) was dissolved in phosphorus oxychloride (5.0 mL), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | 17 | O=P(Cl)(Cl)Cl.Oc1cc(C(F)(F)F)nc2ccc(C(F)(F)F)cc12>>FC(F)(F)c1ccc2nc(C(F)(F)F)cc(Cl)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8809f565982e48bd9ed66429e37203cc | CCOC(=O)CC(=O)C(F)(F)F.COc1ccc(N)cc1>>COc1ccc2nc(C(F)(F)F)cc(O)c2c1 | COC1=CC=C(N)C=C1.FC(C(CC(=O)OCC)=O)(F)F.C(O)([O-])=O.[Na+]>>FC(C1=NC2=CC=C(C=C2C(=C1)O)OC)(F)F | CCO[C:14]([CH2:13][C:8](=O)[C:9]([F:10])([F:11])[F:12])=[O:15].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]([OH:15])[c:16]2[cH:17]1 | CCOC(=O)CC(=O)C(F)(F)F.COc1ccc(N)cc1 | COc1ccc2nc(C(F)(F)F)cc(O)c2c1 | null | null | P(O)(O)(O)=O | Aromatic Heterocycle Formation | OtherReaction | 03fb309d467457208d11accffba771ac71177021179459bf0cc1e729b7f7524b | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc2ncccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](... | 4.6 | [{"value": 4.6, "product": "FC(C1=NC2=CC=C(C=C2C(=C1)O)OC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 4 | HOUR | 4-Methoxyaniline (5.00 g) was dissolved in 75% phosphoric acid (20 mL) and ethyl trifluoroacetoacetate (7.48 g) was dropwise added thereto at 110° C. The mixture was stirred at 110° C. for 4 hr with heating. After allowing to cool, the reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | P(O)(O)(O)=O | 110 | 4 | CCOC(=O)CC(=O)C(F)(F)F.COc1ccc(N)cc1>P(O)(O)(O)=O>COc1ccc2nc(C(F)(F)F)cc(O)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-536255495e2a44b2857c9407963d2f6a | CCOC(=O)CC(=O)C(F)(F)F.Nc1ccccc1F>>Oc1cc(C(F)(F)F)nc2c(F)cccc12 | FC1=C(N)C=CC=C1.FC(C(CC(=O)OCC)=O)(F)F.Cl>>FC=1C=CC=C2C(=CC(=NC12)C(F)(F)F)O | CCO[C:2](=[O:1])[CH2:3][C:4](=O)[C:5]([F:6])([F:7])[F:8].[NH2:9][c:10]1[c:11]([F:12])[cH:13][cH:14][cH:15][cH:16]1>>[OH:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[n:9][c:10]2[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]12 | CCOC(=O)CC(=O)C(F)(F)F.Nc1ccccc1F | Oc1cc(C(F)(F)F)nc2c(F)cccc12 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 03fb309d467457208d11accffba771ac71177021179459bf0cc1e729b7f7524b | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc2ncccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](... | 8.5 | [{"value": 8.5, "product": "FC=1C=CC=C2C(=CC(=NC12)C(F)(F)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 5 | HOUR | 2-Fluoroaniline (10.0 g), ethyl trifluoroacetoacetate (16.6 g) and concentrated hydrochloric acid (0.1 mL) were dissolved in benzene (40 mL), and the mixture was refluxed in a reaction vessel equipped with Dean-Stark trap for 7 hr. The reaction mixture was concentrated under reduced pressure and 75% phosphoric acid (40... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C1=CC=CC=C1 | 110 | 5 | CCOC(=O)CC(=O)C(F)(F)F.Nc1ccccc1F>C1=CC=CC=C1>Oc1cc(C(F)(F)F)nc2c(F)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e297209212a341e9b02c2b927f4d1f4b | Oc1ncc(Br)c2ccccc12.[C-]#N>>N#Cc1cnc(O)c2ccccc12 | BrC1=CN=C(C2=CC=CC=C12)O.[Cu](C#N)C#N.[C-]#N.[Na+]>>C(#N)C1=CN=C(C2=CC=CC=C12)O | Br[c:3]1[cH:4][n:5][c:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.[N:1]#[C-:2]>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | Oc1ncc(Br)c2ccccc12.[C-]#N | N#Cc1cnc(O)c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 92707350c198f3a27d317e8fa64c689eac735ee51a37176521f223f0bfcebd15 | 2549b026e730aedabd9d1c88337e10b7987bb7b86597cabf3fd7fef1a79c8a9a | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[C-;H0;D1:8]#[N;D1;H0:9]>>[N;D1;H0:9]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | 52.3 | [{"value": 52.3, "product": "C(#N)C1=CN=C(C2=CC=CC=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 4 | HOUR | 4-Bromo-1-hydroxyisoquinoline (1.56 g) was dissolved in N-methyl-2-pyrrolidine (25 mL), and copper cyanide (1.56 g) was added thereto. The mixture was stirred at 180° C. for 4 hr with heating. The reaction mixture was added to cool to 100° C. and added to an aqueous solution (125 mL) of sodium cyanide (31.25 g). The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Br- | null | 180 | 4 | Oc1ncc(Br)c2ccccc12.[C-]#N>>N#Cc1cnc(O)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-892bf58bc5f249259d29bc6954817092 | C1CNCCN1.Clc1nc(-c2ccccc2)nc2ccccc12>>c1ccc(-c2nc(N3CCNCC3)c3ccccc3n2)cc1 | N1CCNCC1.ClC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)N1CCNCC1 | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Cl[c:7]1[n:6][c:5](-[c:4]2[cH:3][cH:2][cH:1][cH:22][cH:21]2)[n:20][c:19]2[c:14]1[cH:15][cH:16][cH:17][cH:18]2>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[n:20]2)[cH:21][cH:22]1 | C1CNCCN1.Clc1nc(-c2ccccc2)nc2ccccc12 | c1ccc(-c2nc(N3CCNCC3)c3ccccc3n2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | f13699ff5146e0568096477cb3cce45c70a67b236ed45674e8779117004a8dcf | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2nc(N3CCNCC3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:8]:[c:7]1:[c:5](:[c:6]):[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[#7:9]-[C:10]-[C:11]-1 | 62.7 | [{"value": 62.7, "product": "C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Piperazine (3.22 g) was dissolved in DMF (830 mL), and 4-chloro-2-phenylquinazoline (3 g) was added thereto. The mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, water and chloroform were added to the residue and an insoluble material was filtered off. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2ncncc2c1 | C1C[NH]CCN1.c1ccc2ncncc2c1 | c1ccccc1.C1C[NH]CCN1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | null | 6 | C1CNCCN1.Clc1nc(-c2ccccc2)nc2ccccc12>CN(C)C=O>c1ccc(-c2nc(N3CCNCC3)c3ccccc3n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b0f1f72213e420485430ea327cd8215 | N#Cc1ccncc1.[Cl-].[NH4+]>>Cl.N=C(N)c1ccncc1 | CC(=O)C.C(#N)C1=CC=NC=C1.C[O-].[Na+].CO.[Cl-].[NH4+]>>Cl.C(N)(=N)C1=CC=NC=C1 | [N:2]#[C:3][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1 | N#Cc1ccncc1.[Cl-].[NH4+] | Cl.N=C(N)c1ccncc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccncc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[NH4+;D0:10]>>[ClH;D0;+0:1].[NH2;D1;+0:10]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 83 | [{"value": 83.0, "product": "Cl.C(N)(=N)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 4-Cyanopyridine (50.0 g) was suspended in methanol (50 mL), and 28% sodium methoxide-methanol solution (4.14 mL) was added thereto. After stirring at room temperature for 15 min, ammonium chloride (25.7 g) was added to the mixture. The mixture was stirred at room temperature for 24 hr. Acetone (200 mL) was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | CO | null | 0.25 | N#Cc1ccncc1.[Cl-].[NH4+]>CO>Cl.N=C(N)c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d863b73c392e4aa7ab2a5db34021dbe8 | NC(=O)C1CCNCC1.O=C(Cl)OOCc1ccccc1>>NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1 | C(O)([O-])=O.[Na+].N1CCC(C(=O)N)CC1.C(C)N(CC)CC.C(OOCC1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)C(N)=O | [NH2:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][NH:7][CH2:18][CH2:19]1.Cl[C:8](O[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:9]>>[NH2:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | NC(=O)C1CCNCC1.O=C(Cl)OOCc1ccccc1 | NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | ClCCl | Protection | OtherReaction | 9b3e16e3365fc2aab67381996da7bc0ea1118efbb735841432d91d1d6fbc92af | 6bd83aa074f5ddfdc0cbd04384f2ba85b7424fcae0840640aecc60fd7897d28c | O=C(OCc1ccccc1)N1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-[O;H0;D2;+0:3]-[C:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:3]-[C:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | 18 | HOUR | Isonipecotamide (19.4 g) and triethylamine (42 mL) were dissolved in dichloromethane (500 mL), and benzyloxy chlorocarbonate (24 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 18 hr. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine.Peroxide | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HCl | ClCCl | null | 18 | NC(=O)C1CCNCC1.O=C(Cl)OOCc1ccccc1>ClCCl>NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-14f11ccce1a74aa28b695244722b3993 | CCO.N#CC1CCN(C(=O)OCc2ccccc2)CC1>>CCOC(=N)C1CCN(C(=O)OCc2ccccc2)CC1 | C(C)(=O)Cl.C(C)O.C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)C#N.Cl.Cl.C(C)(C)(C)N1N=C(N=N1)C1CCN(CC1)[C@H]1C[C@H](NC1)C(=O)N1CSCC1>>Cl.C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)C(=N)OCC | [CH3:1][CH2:2][OH:3].[C:4](#[N:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[CH3:1][CH2:2][O:3][C:4](=[NH:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | CCO.N#CC1CCN(C(=O)OCc2ccccc2)CC1 | CCOC(=N)C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | e564e96d7d2f965b49edf364feccacb527e51024ce8a97adfccc27d77cbffea1 | 515b5097d48e8822f99e612a636ab28d5c6d3dcc515412839570278fb17e2efd | O=C(OCc1ccccc1)N1CCCCC1 | [C;D1;H3:1]-[C:2]-[OH;D1;+0:3].[C:4]-[C:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7])-[C:8]>>[C:4]-[C:5](-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[O;H0;D2;+0:3]-[C:2]-[C;D1;H3:1])-[C:8] | null | [] | null | null | 30 | MINUTE | Acetyl chloride (180 mL) was dropwise added to a mixture of ethanol (160 mL) and chloroform (180 mL) under ice-cooling. After the mixture was stirred for 30 min, a solution of 1-benzyloxycarbonyl-4-cyanopiperidine [product of Example 298 (2), 20.6 g] in chloroform (180 mL) was added thereto under ice-cooling. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Ether | null | null | C1CC[NH]CC1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | 0.5 | CCO.N#CC1CCN(C(=O)OCc2ccccc2)CC1>C(Cl)(Cl)Cl>CCOC(=N)C1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-139a19a6f6bb445a83961b53fe14abaf | CCOC(=O)c1ccc2oc(C3CCN([C@H]4C[C@@H](C(=O)N5CCSC5)N(C(=O)OC(C)(C)C)C4)CC3)nc2c1>>CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 | O.[OH-].[Li+].C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)C=1OC2=C(N1)C=C(C=C2)C(=O)OCC)C(=O)N2CSCC2.C(C)OC(=O)C=1C=CC2=C(N=C(O2)C2CCN(CC2)[C@H]2C[C@H](NC2)C(=O)N2CSCC2)C1>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)C=1OC2=C(N1)C=C(C=C2)C(=O)O)C(=O)N2CSCC2 | CC[O:22][C:20]([c:19]1[cH:18][c:17]2[n:16][c:15]([CH:14]3[CH2:13][CH2:12][N:11]([C@@H:10]4[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:30]([C:31](=[O:32])[N:33]5[CH2:34][CH2:35][S:36][CH2:37]5)[CH2:29]4)[CH2:28][CH2:27]3)[o:26][c:25]2[cH:24][cH:23]1)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6... | CCOC(=O)c1ccc2oc(C3CCN([C@H]4C[C@@H](C(=O)N5CCSC5)N(C(=O)OC(C)(C)C)C4)CC3)nc2c1 | CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 | null | null | Cl.O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C([C@@H]1C[C@H](N2CCC(c3nc4ccccc4o3)CC2)CN1)N1CCSC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 80.5 | [{"value": 80.5, "product": "C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)C=1OC2=C(N1)C=C(C=C2)C(=O)O)C(=O)N2CSCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | 3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-ethoxycarbonyl-2 -benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 309 (3), 4.51 g] was dissolved in ethanol (16 mL) and water (8 mL), and lithium hydroxide monohydrate (678 mg) was added. The mixture was stirred at room temperature for 3.5 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.C1CC[NH]CC1.c1ccc2ocnc2c1.C1CSC[NH]1 | Other | Cl.O.C(C)O | null | 3.5 | CCOC(=O)c1ccc2oc(C3CCN([C@H]4C[C@@H](C(=O)N5CCSC5)N(C(=O)OC(C)(C)C)C4)CC3)nc2c1>Cl.O.C(C)O>CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e5f8a227751f4bb0aad3aad7cf9cb409 | CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1.N>>CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(N)=O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 | N.CO.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)C=1OC2=C(N1)C=C(C=C2)C(=O)O)C(=O)N2CSCC2.Cl.Cl.C(=O)(O)C=1C=CC2=C(N=C(O2)C2CCN(CC2)[C@H]2C[C@H](NC2)C(=O)N2CSCC2)C1.C(OCC(C)C)(=O)Cl>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1CCC(CC1)C=1OC2=C(N1)C=C(C=C2)C(N)=O)C(=O)N2CSCC2 | O[C:20]([c:19]1[cH:18][c:17]2[n:16][c:15]([CH:14]3[CH2:13][CH2:12][N:11]([C@@H:10]4[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:30]([C:31](=[O:32])[N:33]5[CH2:34][CH2:35][S:36][CH2:37]5)[CH2:29]4)[CH2:28][CH2:27]3)[o:26][c:25]2[cH:24][cH:23]1)=[O:22].[NH3:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1.N | CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(N)=O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 | null | null | O1CCCC1.O.C(C)N(CC)CC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C([C@@H]1C[C@H](N2CCC(c3nc4ccccc4o3)CC2)CN1)N1CCSC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[NH3;D0;+0:8]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2]):[c:4] | null | [] | null | null | 30 | MINUTE | 3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-carboxy-2-benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 310 (1), 1.06 g] was dissolved in tetrahydrofuran (5 mL), and triethylamine (0.279 mL) and isobutyl chlorocarbonate (0.263 mL) were added thereto under ice-cooling. The mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]C1.C1CC[NH]CC1.c1ccc2ocnc2c1.C1CSC[NH]1 | HO- | O1CCCC1.O.C(C)N(CC)CC | null | 0.5 | CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(=O)O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1.N>O1CCCC1.O.C(C)N(CC)CC>CC(C)(C)OC(=O)N1C[C@@H](N2CCC(c3nc4cc(C(N)=O)ccc4o3)CC2)C[C@H]1C(=O)N1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9aa6435213864e11a89093531e131a22 | CC(=O)Cl.CC(C)(C)OC(=O)N1C[C@@H](NCCNc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1>>CC(=O)N(CCNc1ccc(C#N)cn1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | C(O)([O-])=O.[Na+].C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)NCCNC1=NC=C(C=C1)C#N)C(=O)N1CSCC1.Cl.Cl.Cl.C(#N)C=1C=CC(=NC1)NCCN[C@H]1C[C@H](NC1)C(=O)N1CSCC1.C(C)(=O)Cl>>C(C)(=O)N(CCNC1=NC=C(C=C1)C#N)[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)N1CSCC1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]([CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][n:15]1)[C@H:16]1[CH2:17][C@@H:18]([C:19](=[O:20])[N:21]2[CH2:22][CH2:23][S:24][CH2:25]2)[N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34]1>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][CH2:6][NH:7][c:8]1[cH:9][c... | CC(=O)Cl.CC(C)(C)OC(=O)N1C[C@@H](NCCNc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1 | CC(=O)N(CCNc1ccc(C#N)cn1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 | null | null | ClCCl.C(C)N(CC)CC | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C([C@@H]1C[C@H](NCCNc2ccccn2)CN1)N1CCSC1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5]-[C:6](-[NH;D2;+0:7]-[C:8]-[C:9])-[C:10]>>[#7:4]-[C:5]-[C:6](-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:10] | null | [] | null | null | 5 | HOUR | 3-{(2S,4S)-1-tert-Butoxycarbonyl-4-{2-[(5-cyano-2-pyridyl)amino]ethyl}amino-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 319 (1), 800 mg] and triethylamine (0.42 mL) were dissolved in dichloromethane (20 mL), and acetyl chloride (0.18 mL) was added thereto under ice-cooling. The mixture was stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.C1CC[NH]C1.C1CSC[NH]1 | HCl | ClCCl.C(C)N(CC)CC | null | 5 | CC(=O)Cl.CC(C)(C)OC(=O)N1C[C@@H](NCCNc2ccc(C#N)cn2)C[C@H]1C(=O)N1CCSC1>ClCCl.C(C)N(CC)CC>CC(=O)N(CCNc1ccc(C#N)cn1)[C@H]1C[C@@H](C(=O)N2CCSC2)N(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61df165efc81456c875f291a49f95b22 | C=CC=C.C=Cc1ccccc1>>C=CC=C.C=Cc1ccccc1 | CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1.C(C)(CC)[Li].C=CC(C)=C.C=CC=C.CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1>>C=CC(C)=C.C=CC=C.CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1 | [CH2:6]=[CH:7][CH:8]=[CH2:9].[CH2:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH2:6]=[CH:7][CH:8]=[CH2:9].[CH2:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | C=CC=C.C=Cc1ccccc1 | C=CC=C.C=Cc1ccccc1 | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | In a pressure-tight case equipped with a stirrer, 2700 g of cyclohexane, 70 g of a 40:60 monomer mixture of p-methylstyrene and styrene, and 2.52 ml of 1.3 mol cyclohexane solution of sec-butyllithium were placed and polymerized at 50° C. for 120 minutes. The resulting mixture was further polymerized with 326.6 g of a ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C1CCCCC1 | null | null | C=CC=C.C=Cc1ccccc1>C1CCCCC1>C=CC=C.C=Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70d5ddae6d1947cb96eb4ce682854070 | C=CC=C.C=Cc1ccccc1>>C=CC=C.C=Cc1ccccc1 | CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1.C(C)(CC)[Li].C=CC(C)=C.C=CC=C.CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1>>C=CC(C)=C.C=CC=C.CC1=CC=C(C=C)C=C1.C=CC1=CC=CC=C1 | [CH2:6]=[CH:7][CH:8]=[CH2:9].[CH2:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH2:6]=[CH:7][CH:8]=[CH2:9].[CH2:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | C=CC=C.C=Cc1ccccc1 | C=CC=C.C=Cc1ccccc1 | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | In a pressure-tight case equipped with a stirrer, 2700 g of cyclohexane, 70 g of a 20:80 monomer mixture of p-methylstyrene and styrene, and 2.52 ml of 1.3 mol cyclohexane solution of sec-butyllithium were placed and polymerized at 50° C. for 120 minutes. The resulting mixture was further polymerized with 326.6 g of a ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C1CCCCC1 | null | null | C=CC=C.C=Cc1ccccc1>C1CCCCC1>C=CC=C.C=Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2b5b169b18742f7ae8ae0fa569d6ef7 | O=C(O)CCCc1c[nH]c2ccccc12>>O=C(O)CCCc1c[nH]c2ccccc12 | C1=CC2=C(C=C1)NC=C2CCCC(=O)O.CC(=C)C(=O)OCCO.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C1=CC2=C(C=C1)NC=C2CCCC(=O)O.CC(=C)C(=O)OCCO | [O:10]=[C:11]([OH:12])[CH2:13][CH2:14][CH2:15][c:16]1[cH:17][nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[O:10]=[C:11]([OH:12])[CH2:13][CH2:14][CH2:15][c:16]1[cH:17][nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12 | O=C(O)CCCc1c[nH]c2ccccc12 | O=C(O)CCCc1c[nH]c2ccccc12 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2[nH]ccc2c1 | null | null | [] | 60 | CELSIUS | null | null | In a glass polymerization bottle were charged 80 g I0A, 18 g IBA, 2 g HEMA, 100 g ethyl acetate, and 0.5 g dibenzoyl peroxide. The bottle was purged with nitrogen, sealed, and tumbled in a water bath maintained at 60° C. for 14 hrs. The resulting terpolymer, IOA/IBA/HEMA, was isolated by precipitation in petroleum ethe... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2[nH]ccc2c1 | null | C(C)(=O)OCC | 60 | null | O=C(O)CCCc1c[nH]c2ccccc12>C(C)(=O)OCC>O=C(O)CCCc1c[nH]c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef7d24618e704333a9b3102d27a16042 | C=CC(=O)OCCCCCCCCCCCCCCCCCC>>C=CC(=O)OCCCCCCCCCCCCCCCCCC | C(C=C)(=O)OCCCCCCCCCCCCCCCCCC.CC(=C)C(=O)OCCO.CCC(C)(C#N)N=NC(C)(CC)C#N>>C(C=C)(=O)OCCCCCCCCCCCCCCCCCC.CC(=C)C(=O)OCCO | [CH2:10]=[CH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH2:10]=[CH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2... | C=CC(=O)OCCCCCCCCCCCCCCCCCC | C=CC(=O)OCCCCCCCCCCCCCCCCCC | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 60 | CELSIUS | null | null | Crosslinked compositions with low tack can be of use in particular applications. Compositions with these properties are described in the following three examples. In a glass polymerization bottle were charged 72 g IOA, 18 g octadecyl acrylate (ODA), 10 g HEMA, 150 g ethyl acetate, and 0.4 g VAZO-67 (Wako). The bottle w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | 60 | null | C=CC(=O)OCCCCCCCCCCCCCCCCCC>C(C)(=O)OCC>C=CC(=O)OCCCCCCCCCCCCCCCCCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0cb5f17bb55a4411a16162629ce0c187 | O=C1CCc2ccccc21>>C1=Cc2ccccc2C1 | C1(CCC2=CC=CC=C12)=O.[BH4-].[Na+].O1CCCC1>>C1C=CC2=CC=CC=C12 | O=[C:2]1[CH2:1][CH2:9][c:8]2[c:3]1[cH:4][cH:5][cH:6][cH:7]2>>[CH:1]1=[CH:2][c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9]1 | O=C1CCc2ccccc21 | C1=Cc2ccccc2C1 | null | null | CO | Miscellaneous | OtherReaction | 0be32836af524a7021c2943c6ba4a10e46073e2d9ec6e948809ecba5e7cb2f0e | 9db0f73aed071f5fa7238b261fc87a241efa69e871d2f239452605149d0c954e | C1=Cc2ccccc2C1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[c:4]:[c:5]-1:[c:6]>>[c:6]:[c:5]1:[c:4]-[C:3]-[CH;D2;+0:2]=[CH;D2;+0:1]-1 | null | [] | null | null | null | null | Alternatively, the keto group in the indanone may simply be reduced under standard conditions (e.g. sodium borohydride in methanol and/or tetrahydrofuran (THF)) followed by dehydration to form the desired indene or indene skeleton-containing compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | Other | CO | null | null | O=C1CCc2ccccc21>CO>C1=Cc2ccccc2C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c27413ba3f90416cbba4e2a1548bf543 | O=C1CCc2c(O)cccc21>>O=C1CCc2ccccc21 | O.OC1=C2CCC(C2=CC=C1)=O.N1C=NC=C1.C(C)(C)(C)[Si](Cl)(C)C>>C1CC(=O)C2=CC=CC=C21 | O[c:6]1[c:5]2[c:10]([cH:9][cH:8][cH:7]1)[C:2](=[O:1])[CH2:3][CH2:4]2>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | O=C1CCc2c(O)cccc21 | O=C1CCc2ccccc21 | null | null | CN(C)C=O | Reduction | OtherReaction | afd9e864364ae0cef12a16dde11813ff9301e0c6d3277e777bf47b8b23d70231 | 27ebe27a5e17883303ac9a42d30f2cb918c0044de7ff3c79776e1ddb80cc53d9 | O=C1CCc2ccccc21 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]-[C:6]=[O;D1;H0:7])-[C:8]>>[C:8]-[c:4](:[c:5]-[C:6]=[O;D1;H0:7]):[cH;D2;+0:1]:[c:2]:[c:3] | 79.9 | [{"value": 79.9, "product": "C1CC(=O)C2=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C1CC(=O)C2=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-hydroxy-1-indanone (25.0 g, 169 mmol) and imidazole (28.7 g, 422 mmol) in DMF (500 ml) was added tert-butyldimethylchiorosilane. The reaction mixture was stirred overnight at room temperature and treated with water (500 ml) and extracted with diethyl ether (500 ml). The organic phase was collected an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | CN(C)C=O | null | 8 | O=C1CCc2c(O)cccc21>CN(C)C=O>O=C1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-954144c60d7e4434824a463f16a0b3ac | CC(C)(C)[Si](C)(C)Cl.CC1Cc2cccc(O)c2C1=O>>CC1Cc2cccc(O[Si](C)(C)C(C)(C)C)c2C1=O | O.OC=1C=CC=C2CC(C(C12)=O)C.N1C=NC=C1.C(C)(C)(C)[Si](Cl)(C)C>>O([Si](C)(C)C(C)(C)C)C=1C=CC=C2CC(C(C12)=O)C | Cl[Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16].[CH3:1][CH:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][c:8]([OH:9])[c:17]2[C:18]1=[O:19]>>[CH3:1][CH:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][c:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]2[C:18]1=[O:19] | CC(C)(C)[Si](C)(C)Cl.CC1Cc2cccc(O)c2C1=O | CC1Cc2cccc(O[Si](C)(C)C(C)(C)C)c2C1=O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1CCc2ccccc21 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[O;D1;H0:8]=[C:9]-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:9]=[O;D1;H0:8])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | 8 | HOUR | To a solution of 7-hydroxy-2-methyl-1-indanone (6) (10.2 g, 37 mmol) and imidazole (3.02 g, 44 mmol) dissolved in DMF (200 ml) was added tert-butyldimethylchlorosilane (6.11 g, 41 mmol) in DMF (50 ml). The reaction mixture was stirred overnight at room temperature and treated with water (200 ml) and extracted with diet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)CCC2 | HCl | CN(C)C=O | null | 8 | CC(C)(C)[Si](C)(C)Cl.CC1Cc2cccc(O)c2C1=O>CN(C)C=O>CC1Cc2cccc(O[Si](C)(C)C(C)(C)C)c2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3f367f672ce48239ecf93d61c972ddf | CC(C)(C)[Si](C)(C)Cl.O=C1CCc2c(O)cccc21>>CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O | O.OC1=C2CCC(C2=CC=C1)=O.C(C)N(CC)CC.C(C)(C)(C)[Si](Cl)(C)C>>O([Si](C)(C)C(C)(C)C)C1=C2CCC(C2=CC=C1)=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[CH2:15][CH2:16][C:17]2=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[CH2:15][CH2:16][C:17]2=[O:18] | CC(C)(C)[Si](C)(C)Cl.O=C1CCc2c(O)cccc21 | CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1CCc2ccccc21 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 82.8 | [{"value": 82.7, "product": "O([Si](C)(C)C(C)(C)C)C1=C2CCC(C2=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "O([Si](C)(C)C(C)(C)C)C1=C2CCC(C2=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-hydroxy-1-indanone (25.0 g, 169 mmol) in DMF (500 ml) was triethylamine (22.2 g, 220 mmol) added, to the resulting solution was tert-butyldimethylchlorosilane (28.0 g, 186 mmol) added. The reaction mixture was stirred overnight at room temperature and treated with water (500 ml) and extracted with di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)CCC2 | HCl | CN(C)C=O | null | 8 | CC(C)(C)[Si](C)(C)Cl.O=C1CCc2c(O)cccc21>CN(C)C=O>CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2eff2f10331b4e68bad3123965ac0956 | CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O>>Oc1cccc2c1C=CC2 | O([Si](C)(C)C(C)(C)C)C1=C2CCC(C2=CC=C1)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl.C(C(=O)O)(=O)O.[NH4+].[Cl-].[BH4-].[Na+]>>OC1=C2C=CCC2=CC=C1 | CC(C)(C)[Si](C)(C)[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][CH2:9][C:10]2=O>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]=[CH:9][CH2:10]2 | CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O | Oc1cccc2c1C=CC2 | null | null | CO.C1CCOC1 | Functional Group Interconversion | OtherReaction | be130c8a5e55734cd2b2af0b79058d40d1fec3efc3bf58d687e6527259482781 | 46a40dcb0b03cb539403c87f5504d123d46819138b107daa53759e3da1668131 | C1=Cc2ccccc2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5](:[c:6])-[C;H0;D3;+0:7](=O)-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5](:[c:6])-[CH2;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-1 | 65.1 | [{"value": 65.1, "product": "OC1=C2C=CCC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.1, "product": "OC1=C2C=CCC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-(tert-butyldimethylsiloxy)-1-indanone (35.0 g, 133 mmol) in methanol/THF (100 ml:200 ml) was NaBH4 (7.57 g, 200 mmol) added in portions at 0° C. The reaction mixture is stirred overnight. The resulting solution is poured on ice, acidified with concentrated hydrochloric acid to pH=1 and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.TMS ether protective group | Aromatic alcohol | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | HO- | CO.C1CCOC1 | null | 8 | CC(C)(C)[Si](C)(C)Oc1cccc2c1CCC2=O>CO.C1CCOC1>Oc1cccc2c1C=CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eda8294c306d46c180abf6eac9bf154e | CCN1CC=CB1c1ccccc1>>CCN1C=C[CH-]B1c1ccccc1 | C(C)N1B(C=CC1)C1=CC=CC=C1.C(C)(C)[N-]C(C)C.[Li+]>>C(C)N1B([CH-]C=C1)C1=CC=CC=C1.[Li+] | [CH3:1][CH2:2][N:3]1[CH2:4][CH:5]=[CH:6][B:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH2:2][N:3]1[CH:4]=[CH:5][CH-:6][B:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCN1CC=CB1c1ccccc1 | CCN1C=C[CH-]B1c1ccccc1 | null | null | CCOCC | Functional Group Addition | OtherReaction | d558737e1105e7bd7b5be3615d72379bceb9091db9732de9d593410fdadd3e04 | fc933fdd7baf3b8acf9bd94a15b8568b76358dfcf07000fc6c83b12a47ed99ee | C1=CNB(c2ccccc2)[CH-]1 | [C:1]-[#7:2]1-[CH2;D2;+0:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-[#5:6]-1-[c:7]>>[C:1]-[#7:2]1-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH-;D2:5]-[#5:6]-1-[c:7] | 77 | [{"value": 77.0, "product": "C(C)N1B([CH-]C=C1)C1=CC=CC=C1.[Li+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "C(C)N1B([CH-]C=C1)C1=CC=CC=C1.[Li+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 10 | HOUR | 1,5-Dihydro-1-ethyl-2-phenyl-1,2-azaborole (5.0 g, 29.2 mmol) was dissolved in 15 mL of ether at −78° C. To this was added a solution of lithiumdiisopropylamide (3.13 g, 29.2 mmol) in 15 mL of ether. The mixture was stirred at −78° C. for 2 hours and at 25° C. for 10 hours. After removal of the solvent the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine | [B]1C=CC[NH]1 | [B]1[CH-]C=C[NH]1 | [B]1[CH-]C=C[NH]1.c1ccccc1 | null | CCOCC | 25 | 10 | CCN1CC=CB1c1ccccc1>CCOCC>CCN1C=C[CH-]B1c1ccccc1 |
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