dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-281e0b038bcd402b86969e2545e33af4 | CC(=O)CS(=O)(=O)N1CCCC1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>>CC1=C(S(=O)(=O)N2CCCC2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 | N1(CCCC1)S(=O)(=O)CC(C)=O.ClC=1C=C(C=O)C=CC1Cl.CC1=NNC(=C1)N>>ClC=1C=C(C=CC1Cl)C1C(=C(NC=2N1N=C(C2)C)C)S(=O)(=O)N2CCCC2 | O=[C:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.[nH:21]1[n:22][c:23]([CH3:24])[cH:25][c:26]1[NH2:27].O=[CH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[c:18]([Cl:19])[cH:20]1>>[CH3:1][C:2]1=[C:3]([S:4](=[O:5])(=[O:6])[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[CH:12]([c:13]2[cH:14][cH:15][c:16](... | CC(=O)CS(=O)(=O)N1CCCC1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1 | CC1=C(S(=O)(=O)N2CCCC2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 | null | N1CCCCC1 | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c621ba864f656a559eb5849cd46ef70261d98951ba565d11bf39f9f8fcdc5da5 | bd2570d285dcbb89a92430e1ca5da930fc4b87af1197036ccf7a83f622f8a245 | O=S(=O)(C1=CNc2ccnn2C1c1ccccc1)N1CCCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[#16:4](-[#7:5])(=[O;D1;H0:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[NH2;D1;+0:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[nH;D2;+0:17]:1>>[#7:5]-[#16:4](=[O;D1;H0:6])(=[O;D1;H0:7])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:12]-[c:13]2:[c:14]:[c:15]:[#7;a:1... | null | [] | 80 | CELSIUS | 24 | HOUR | A mixture of 1-(pyrrolidin-1-ylsulfonyl)propan-2-one (191 mg, 1.0 mmol), 3,4-dichlorobenzaldehyde (175 mg, 1.0 mmol), 3-methyl-1H-pyrazol-5-amine (97 mg, 1.0 mmol), piperidine (2 drops) and Ti(OPr-i)4 (2 drops) in 1,4-dioxane (4.0 mL) in a sealed tube was stirred at 80° C. for 24 hrs. Solvent was removed and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine | Enamine | c1cn[nH]c1 | C1=CNc2ccnn2C1 | C1CC[NH]C1.c1ccccc1.C1=CNc2ccnn2C1 | HO- | N1CCCCC1.O1CCOCC1 | 80 | 24 | CC(=O)CS(=O)(=O)N1CCCC1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>N1CCCCC1.O1CCOCC1>CC1=C(S(=O)(=O)N2CCCC2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c2886ef1d6d4ad683a8640399023baa | CC(=O)CS(=O)(=O)N1CCCC1.O=Cc1ccc(Cl)c(Cl)c1>>CC(=O)C(=Cc1ccc(Cl)c(Cl)c1)S(=O)(=O)N1CCCC1 | N1(CCCC1)S(=O)(=O)CC(C)=O.ClC=1C=C(C=O)C=CC1Cl>>ClC=1C=C(C=CC1Cl)C=C(C(C)=O)S(=O)(=O)N1CCCC1 | [CH3:1][C:2](=[O:3])[CH2:4][S:14](=[O:15])(=[O:16])[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1.O=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1)[S:14](=[O:15])(=[O:16])[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1 | CC(=O)CS(=O)(=O)N1CCCC1.O=Cc1ccc(Cl)c(Cl)c1 | CC(=O)C(=Cc1ccc(Cl)c(Cl)c1)S(=O)(=O)N1CCCC1 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | C1CCOC1 | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=S(=O)(C=Cc1ccccc1)N1CCCC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[#7:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | null | [] | 80 | CELSIUS | 8 | HOUR | Alternatively, the Bignelli reaction was carried out in two steps with higher yields. To 1-(pyrrolidin-1-ylsulfonyl)propan-2-one in THF was added an equivalent amount of 3,4-dichlorobenzaldehyde and a catalytic amount of titanium tetraisopropoxide. The reaction was stirred at 80° C. overnight. Solvent was removed and t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1CC[NH]C1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].C1CCOC1 | 80 | 8 | CC(=O)CS(=O)(=O)N1CCCC1.O=Cc1ccc(Cl)c(Cl)c1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].C1CCOC1>CC(=O)C(=Cc1ccc(Cl)c(Cl)c1)S(=O)(=O)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f309522928541618f1c407bb431030d | CI.COc1ccc(S(=O)(=O)NC(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1>>COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | ClC=1C=C(C=CC1Cl)C1C(=C(N(C=2N1N=CC2)C(=O)OC(C)(C)C)C)C(NS(=O)(=O)C2=CC=C(C=C2)OC)=O.IC.C(=O)([O-])[O-].[K+].[K+]>>ClC=1C=C(C=CC1Cl)C1C(=C(N(C=2N1N=CC2)C(=O)OC(C)(C)C)C)C(N(C)S(=O)(=O)C2=CC=C(C=C2)OC)=O | I[CH3:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][C:12](=[O:13])[C:14]2=[C:15]([CH3:16])[N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]3[cH:26][cH:27][n:28][n:29]3[CH:30]2[c:31]2[cH:32][cH:33][c:34]([Cl:35])[c:36]([Cl:37])[cH:38]2)[cH:39][cH:40]1>>[CH3:1][O:2][c:3]1[cH:4][... | CI.COc1ccc(S(=O)(=O)NC(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | af7afb2f9573ffe613dbf948d5df1eacb27ad38b14d3c191bbea322501901cb6 | b48c6a9d806f5b76b29b35b38aa518ee07570dc9bf82077a5f8da64f84d8d7d7 | O=C(NS(=O)(=O)c1ccccc1)C1=CNc2ccnn2C1c1ccccc1 | I-[CH3;D1;+0:1].[#7;a:2]-[C:3]-[C:4](-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])=[C:12](-[C;D1;H3:13])-[#7:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21]>>[#7;a:2]-[C:3]-[C:4](-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[#16:8](=[O;D1;H0:9]... | null | [] | null | null | 4 | HOUR | To a mixture of the product obtained from Step B (59.3 mg, 0.1 mmol) and iodomethane (excess) in DMF was added solid K2CO3 (excess). The mixture was stirred at room temperature under N2 for 4 h. LC-MS indicated the completion of reaction. Most of the solvent was evaporated, and mixture was diluted with ethyl acetate, w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Secondary amide | Tertiary amide | null | null | c1ccccc1.C1=C[NH]c2ccnn2C1.c1ccccc1 | HI | CN(C)C=O | null | 4 | CI.COc1ccc(S(=O)(=O)NC(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1>CN(C)C=O>COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89f7734614894818964308a5f87de7e4 | COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1>>COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)Nc3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | ClC=1C=C(C=CC1Cl)C1C(=C(N(C=2N1N=CC2)C(=O)OC(C)(C)C)C)C(N(C)S(=O)(=O)C2=CC=C(C=C2)OC)=O.C(=O)(C(F)(F)F)O>>ClC=1C=C(C=CC1Cl)C1C(=C(NC=2N1N=CC2)C)C(=O)N(C)S(=O)(=O)C2=CC=C(C=C2)OC | CC(C)(C)OC(=O)[N:17]1[C:15]([CH3:16])=[C:14]([C:12]([N:10]([S:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]2)(=[O:8])=[O:9])[CH3:11])=[O:13])[CH:23]([c:24]2[cH:25][cH:26][c:27]([Cl:28])[c:29]([Cl:30])[cH:31]2)[n:22]2[c:18]1[cH:19][cH:20][n:21]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]([... | COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)Nc3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | c1fb10b8e97a2d0ffbb2d633806bd11c9787b1977887dcec24de7023266387c3 | 1f86b549cdf11842d40da7dad1f281ce065a914480da1675879f61d92c5c12e8 | O=C(NS(=O)(=O)c1ccccc1)C1=CNc2ccnn2C1c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2](-[C;D1;H3:3])=[C:4](-[C:5](-[#7:6])=[O;D1;H0:7])-[C:8]-[#7;a:9]2:[#7;a:10]:[c:11]:[c:12]:[c:13]:2-1>>[#7:6]-[C:5](=[O;D1;H0:7])-[C:4]1=[C:2](-[C;D1;H3:3])-[NH;D2;+0:1]-[c:13]2:[c:12]:[c:11]:[#7;a:10]:[#7;a:9]:2-[C:8]-1 | null | [] | null | null | 1.5 | HOUR | To a mixture of the product obtained from Step C (60 mg, 0.1 mmol) in CH2Cl2 (5.0 mL) at room temperature under N2 was added TFA (5.0 mL). The mixture was stirred for 1.5 h. LC-MS indicated the completion of reaction. Solvent was evaporated, and the mixture was purified by reverse phase HPLC (acetonitrile/water). The d... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carbamic ester.Ether.Boc | Enamine | C1=C[NH]c2ccnn2C1 | C1=CNc2ccnn2C1 | c1ccccc1.C1=CNc2ccnn2C1.c1ccccc1 | HO- | C(Cl)Cl | null | 1.5 | COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)N(C(=O)OC(C)(C)C)c3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1>C(Cl)Cl>COc1ccc(S(=O)(=O)N(C)C(=O)C2=C(C)Nc3ccnn3C2c2ccc(Cl)c(Cl)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-842a3aa7bb76466793cc67e65e645878 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1>>COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 | Cl.COC(N)=N.C[O-].[Na+].COC(CNC(=O)OCC1=CC=CC=C1)=O.C(C)(C)(C)OC(N(C)C)N(C)C>>COC=1NC(C(=CN1)NC(=O)OCC1=CC=CC=C1)=O | CN(C)[CH:5](OC(C)(C)C)N(C)C.[CH3:1][O:2][C:3](=[NH:4])[NH2:20].CO[C:18]([CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:19]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18](=[O:19])[nH:20]1 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1 | COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 | null | null | C(C)#N.C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | 548d76e34acf7e86ba84bdb6a47012358c70ab5395e90e11851c473204b086b1 | 58b79cf011b6f077916b63354b5123590ae7adbae1159a4c2e0d562a7f8d1bee | O=C(Nc1cnc[nH]c1=O)OCc1ccccc1 | C-N(-C)-[CH;D3;+0:1](-O-C(-C)(-C)-C)-N(-C)-C.C-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[#7:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:1]:[n;H0;D2;+0:13]:[c;H0;D3;+0:11](-[#8:10]-[C;D1;H3:9]):[nH;D2;+0... | 77.3 | [{"value": 77.3, "product": "COC=1NC(C(=CN1)NC(=O)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | Toluene (10 ml) was added to N-benzyloxycarbonyl-glycine methyl ester (1.50 g, 6.73 mmol) and tert-butoxybisdimethylaminomethane (1.83 ml, 8.91 mmol) and the mixture was stirred overnight at 70° C. The mixture was washed with saturated brine and concentrated under reduced pressure. MTBE (20 ml) and 1N hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Primary amine.Tertiary amine.Tertiary amine | Ether | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)#N.C1(=CC=CC=C1)C.CO | 70 | 8 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1>C(C)#N.C1(=CC=CC=C1)C.CO>COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6aa613286fb646b9aef176ff3d7009b6 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1>>COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 | Cl.COC(N)=N.C[O-].[Na+].COC(CNC(=O)OCC1=CC=CC=C1)=O.C(C)(C)(C)OC(N(C)C)N(C)C>>COC=1NC(C(=CN1)NC(=O)OCC1=CC=CC=C1)=O | CN(C)[CH:5](OC(C)(C)C)N(C)C.[CH3:1][O:2][C:3](=[NH:4])[NH2:20].CO[C:18]([CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:19]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18](=[O:19])[nH:20]1 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1 | COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 | null | null | C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | 548d76e34acf7e86ba84bdb6a47012358c70ab5395e90e11851c473204b086b1 | 58b79cf011b6f077916b63354b5123590ae7adbae1159a4c2e0d562a7f8d1bee | O=C(Nc1cnc[nH]c1=O)OCc1ccccc1 | C-N(-C)-[CH;D3;+0:1](-O-C(-C)(-C)-C)-N(-C)-C.C-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[#7:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:1]:[n;H0;D2;+0:13]:[c;H0;D3;+0:11](-[#8:10]-[C;D1;H3:9]):[nH;D2;+0... | 77.3 | [{"value": 77.3, "product": "COC=1NC(C(=CN1)NC(=O)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | Toluene (10 ml) was added to methyl-N-benzyloxycarbonyl-glycinate (1.50 g, 6.73 mmol) and tert-butoxybisdimethylaminomethane (1.83 ml, 8.91 mmol) and the mixture was stirred overnight at 70° C. The mixture was then washed with saturated brine and concentrated under reduced pressure. MTBE (20 ml) and 1N hydrochloric aci... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Primary amine.Tertiary amine.Tertiary amine | Ether | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CO | 70 | 8 | CN(C)C(OC(C)(C)C)N(C)C.COC(=N)N.COC(=O)CNC(=O)OCc1ccccc1>C1(=CC=CC=C1)C.CO>COc1ncc(NC(=O)OCc2ccccc2)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68a311cfdda04b29ba6b15d97ba6f2e8 | COC(=N)N.COC(=O)CNC(=O)OC(C)(C)C>>COc1ncc(NC(=O)OC(C)(C)C)c(=O)[nH]1 | COC(CNC(=O)OC(C)(C)C)=O.C(=O)OC.[H-].[Na+].Cl.COC(N)=N>>COC=1NC(C(=CN1)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[NH:4])[NH2:17].CO[C:15]([CH2:6][NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:16]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15](=[O:16])[nH:17]1 | COC(=N)N.COC(=O)CNC(=O)OC(C)(C)C | COc1ncc(NC(=O)OC(C)(C)C)c(=O)[nH]1 | null | null | CO.CC(C)(C)OC | Aromatic Heterocycle Formation | OtherReaction | 7f91aad39c6351572c32115ec2b1c20c3e669b32ba9e57dd85292a7d17d7d6d4 | f55be847ecc76ef10f697e8277b41d25919009271eb54c10c31f40f5ae4974e1 | O=c1ccnc[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C;D1;H3:12]-[#8:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[NH;D1;+0:16]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[c;H0;D3;+0:3]1:[c:17]:[n;H0;D2;+0:16]:[... | 43 | [{"value": 43.0, "product": "COC=1NC(C(=CN1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.9, "product": "COC=1NC(C(=CN1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under a nitrogen atmosphere, MTBE (3 ml) was added to 60% sodium hydride (0.10 g). Methyl-N-tert-butoxycarbonyl-glycinate (0.39 g, 2.05 mmol) and methyl formate (0.31 g, 5.13 mmol) were dissolved in MTBE (2 ml) in an ice bath and the solution was added dropwise over 1 hr. After overnight stirring at normal temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Ether | null | c1cncnc1 | c1cncnc1 | HO- | CO.CC(C)(C)OC | null | 8 | COC(=N)N.COC(=O)CNC(=O)OC(C)(C)C>CO.CC(C)(C)OC>COc1ncc(NC(=O)OC(C)(C)C)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe48ac5603824a4ea55b70df8080cb50 | CCOC(=O)CC(=O)[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F>>CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)Cl)C=C(C(=C1F)F)F.C(CC(=O)[O-])(=O)OCC.[K+].[Mg+2].[Cl-].[Cl-]>>C(C)OC(CC(C1=C(C(=C(C(=C1)F)F)F)F)=O)=O | O=C([O-])[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].Cl[C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]1[F:18] | CCOC(=O)CC(=O)[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F | null | null | C(C)#N | C-C Coupling | OtherReaction | 9c255438d8e6adeba9ee52582b8e97af5f85bef382cd416953270ac55bd10486 | 4c7bc8856483317e0c04a17d8cd6aba13cdf5ed9f64b61fe01f230a819039f82 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=C(-[O-])-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | Potassium ethyl malonate (3.66 g, 21.5 mmol), MgCl2 (2.44 g, 25.7 mmol) and TEA (2.05 g, 20.3 mmol) were mixed in acetonitrile (70 ml) at 10-15° C. for 2.5 hr. 2,3,4,5-tetrafluorobenzoyl chloride (2.00 g, 10.3 mmol) in acetonitrile (10 ml) was added at 0° C. over 15 min followed by a second addition of TEA (0.23 g, 2.3... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | Ketone | null | null | c1ccccc1 | Other | C(C)#N | null | 16 | CCOC(=O)CC(=O)[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F>C(C)#N>CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86153f91d107428ca217001288ddeecd | COc1cc2c(=O)[nH]cnc2cc1[N+](=O)[O-]>>O=[N+]([O-])c1cc2ncnc(O)c2cc1O | Br.COC=1C=C2C(NC=NC2=CC1[N+](=O)[O-])=O>>[N+](=O)([O-])C1=C(C=C2C(=NC=NC2=C1)O)O | C[O:15][c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]2[n:7][cH:8][nH:9][c:10](=[O:11])[c:12]2[cH:13]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[n:7][cH:8][n:9][c:10]([OH:11])[c:12]2[cH:13][c:14]1[OH:15] | COc1cc2c(=O)[nH]cnc2cc1[N+](=O)[O-] | O=[N+]([O-])c1cc2ncnc(O)c2cc1O | null | null | CC(=O)O | Deprotection | OtherReaction | d02ad6873b139984ebef9eb23f015d204c5593defccf141ba8494ff8ee09de95 | ecc1e7b4e77460851eb3f2289eb4f1036d8c8c9d3f9d3dfb0f10124e32cf7746 | c1ccc2ncncc2c1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]2:[c:5](:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c;H0;D3;+0:9]:2=[O;H0;D1;+0:10]):[c:11]:[c:12]:1>>[OH;D1;+0:10]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:8]:[c:7]:[#7;a:6]:[c:5]2:[c:11]:[c:12]:[c:2](-[OH;D1;+0:1]):[c:3]:[c:4]:2:1 | null | [] | null | null | null | null | To a solution containing 20 ml of 48% aqueous HBr and 20 ml of AcOH was added 6-methoxy-7-nitro-3,4-dihydroquinazolin-4-one (1.4 g, 6.3 mmol) and the mixture was refluxed overnight. The resulting solution was evaporated to afford the crude phenol as a residue and was used without further purification (1.2 g, 5.8 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol.Aromatic alcohol | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | CC(=O)O | null | null | COc1cc2c(=O)[nH]cnc2cc1[N+](=O)[O-]>CC(=O)O>O=[N+]([O-])c1cc2ncnc(O)c2cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72e79b4176b448e884eb9dbeeaa83cc5 | O=C1C2=Cc3ccccc3C2=CC([N+](=O)[O-])=C1O>>NC1=C(O)C(=O)C2=Cc3ccccc3C2=C1 | [OH-].[NH4+].[N+](=O)([O-])C1=C(C(C2=CC3=CC=CC=C3C2=C1)=O)O.Cl[Sn]Cl.Cl>>NC1=C(C(C2=CC3=CC=CC=C3C2=C1)=O)O | O=[N+:1]([O-])[C:2]1=[C:3]([OH:4])[C:5](=[O:6])[C:7]2=[CH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[C:15]2=[CH:16]1>>[NH2:1][C:2]1=[C:3]([OH:4])[C:5](=[O:6])[C:7]2=[CH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[C:15]2=[CH:16]1 | O=C1C2=Cc3ccccc3C2=CC([N+](=O)[O-])=C1O | NC1=C(O)C(=O)C2=Cc3ccccc3C2=C1 | null | null | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | af6c5b301491be261a262616a03eb9b7e8465cf4d54efa20d6e4ba026dae1843 | 932aeb69032745ef767518b2869fbe1b80680a98af29f5f41fa577be193d71ee | O=C1C=CC=C2C1=Cc1ccccc12 | O=[N+;H0;D3:1](-[O-])-[C:2]1=[C:3](-[O;D1;H1:4])-[C:5](=[O;D1;H0:6])-[C:7](=[C:8])-[C:9](=[C:10]-1)-[c:11]>>[C:8]=[C:7]1-[C:9](=[C:10]-[C:2](-[NH2;D1;+0:1])=[C:3](-[O;D1;H1:4])-[C:5]-1=[O;D1;H0:6])-[c:11] | 65 | [{"value": 65.0, "product": "NC1=C(C(C2=CC3=CC=CC=C3C2=C1)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-nitro-2-hydroxyfluorenone (1.6 g, 6.6 mmol) and SnCl2 (3 g, 6.6 mmol) was refluxed in 100 ml acetic acid:conc. HCl (1:1) for 1 hour. The mixture was allowed to cool to room temperature and neutralized with ammonium hydroxide. After extracting with EtOAc (3×100 ml), combined organic fractions were dried o... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Enamine | null | null | C1=CCC2=Cc3ccccc3C2=C1 | Other | C(C)(=O)O | null | null | O=C1C2=Cc3ccccc3C2=CC([N+](=O)[O-])=C1O>C(C)(=O)O>NC1=C(O)C(=O)C2=Cc3ccccc3C2=C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-543a2ceb0ca843d9ab6b33ebfcafa686 | N#CC1CCCN1N.c1cnc2c(n1)CCN2>>CN1CCCC1CCN | C(#N)C1N(CCC1)N.N1=CC=NC2=C1CCN2.N1[C@H](C(=O)O)CCC1>>NCCC1N(CCC1)C | N#[C:7][CH:6]1[N:2](N)[CH2:3][CH2:4][CH2:5]1.c1cnc2c(n1)C[CH2:8][NH:9]2>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH2:9] | N#CC1CCCN1N.c1cnc2c(n1)CCN2 | CN1CCCC1CCN | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e121b6cecdf75c8a34ea0a39cc6856f961707d56917557fb64fd73886b4a5f75 | b1db5b2535767c32a84ef4d5573e9d95f1ecfc90659e9baae8229df2007eac41 | C1CCNC1 | C1-[CH2;D2;+0:1]-[NH;D2;+0:2]-c2:n:c:c:n:c:2-1.N-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1-[C;H0;D2;+0:8]#N>>[C;D1;H3:9]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[NH2;D1;+0:2] | null | [] | null | null | null | null | In more detail, pyrazinopyrrolidine 1A is synthesized via a [3+2] cycloaddition chemistry. Conversion of L-proline 7 to cyano-1-aminopyrrolidine 8 without loss of stereochemistry, followed by reduction provides the chiral 2-aminoethyl-1-methylpyrrolidine 2A in high yield. CX-3543 was found to have a formulated solubili... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Nitrile.Secondary amine | Primary amine.Tertiary amine | C1CC[NH]C1.c1cnc2c(n1)CCN2 | C1CC[NH]C1 | C1CC[NH]C1 | Other | null | null | null | N#CC1CCCN1N.c1cnc2c(n1)CCN2>>CN1CCCC1CCN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d021555713be4ce78de4cd74f87a0d5a | CCOC(=O)c1cnc(S(=O)(=O)CC)nc1C.CN1CCC(CCCN)CC1>>CCOC(=O)c1cnc(NCCCC2CCN(C)CC2)nc1C | C(C)OC(=O)C=1C(=NC(=NC1)S(=O)(=O)CC)C.CN1CCC(CC1)CCCN>>C(C)OC(=O)C=1C(=NC(=NC1)NCCCC1CCN(CC1)C)C | CCS(=O)(=O)[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:22]([CH3:23])[n:21]1.[NH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2... | CCOC(=O)c1cnc(S(=O)(=O)CC)nc1C.CN1CCC(CCCN)CC1 | CCOC(=O)c1cnc(NCCCC2CCN(C)CC2)nc1C | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | c1cnc(NCCCC2CCNCC2)nc1 | C-C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A mixture of 2-ethanesulfonyl-4-methyl-pyrimidine-5-carboxylic acid ethyl ester (0.30 g, 1.18 mmol) and 3-(1-methyl-piperidin-4-yl)-propylamine (0.18 mg, 1.10 mmol) in EtOH (3 mL) was heated in a sealed tube at 100° C. for 6 h. The mixture was concentrated and purified by FCC to give 200 mg (53%). 1H NMR (CDCl3): 8.88-... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CC[NH]CC1 | HO- | CCO | 100 | null | CCOC(=O)c1cnc(S(=O)(=O)CC)nc1C.CN1CCC(CCCN)CC1>CCO>CCOC(=O)c1cnc(NCCCC2CCN(C)CC2)nc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0171e5355ca43d981eefa0aa3929cc1 | Cc1c(F)ccc(N)c1N.Cc1nc(NCCCC2CCN(C)CC2)ncc1C=O>>Cc1nc(NCCCC2CCN(C)CC2)ncc1-c1nc2c(C)c(F)ccc2[nH]1 | CC1=NC(=NC=C1C=O)NCCCC1CCN(CC1)C.FC=1C(=C(C(=CC1)N)N)C.CO>>FC1=C(C2=C(NC(=N2)C=2C(=NC(=NC2)NCCCC2CCN(CC2)C)C)C=C1)C | [NH2:20][c:21]1[c:22]([CH3:23])[c:24]([F:25])[cH:26][cH:27][c:28]1[NH2:29].O=[CH:19][c:18]1[c:2]([CH3:1])[n:3][c:4]([NH:5][CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]2)[n:16][cH:17]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:1... | Cc1c(F)ccc(N)c1N.Cc1nc(NCCCC2CCN(C)CC2)ncc1C=O | Cc1nc(NCCCC2CCN(C)CC2)ncc1-c1nc2c(C)c(F)ccc2[nH]1 | null | O=[Mn]=O | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc2[nH]c(-c3cnc(NCCCC4CCNCC4)nc3)nc2c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c:12](:[c:14]):[nH;D2;+0:13]:1 | null | [] | null | null | 30 | MINUTE | [5-(5-Fluoro-4-methyl-1 H-benzoimidazol-2-yl)-pyrimidin-2-yl]-3-(1-methyl-piperidin-4-yl)-propyl]-amine. A mixture of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidin-5-yl}-methanol (0.14 g, 0.49 mmol) in toluene (3 mL) was added MnO2 (0.22 g, 2.48 mmol). After 30 min at 70° C., the mixture was filtered t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1cncnc1.C1CC[NH]CC1.c1ccc2[nH]cnc2c1 | HO- | O=[Mn]=O.C1(=CC=CC=C1)C | null | 0.5 | Cc1c(F)ccc(N)c1N.Cc1nc(NCCCC2CCN(C)CC2)ncc1C=O>O=[Mn]=O.C1(=CC=CC=C1)C>Cc1nc(NCCCC2CCN(C)CC2)ncc1-c1nc2c(C)c(F)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c65d9bf616fe48dc8db25c65061ec97e | Clc1ccc2c(n1)CCC2>>[O-][n+]1c(Cl)ccc2c1CCC2 | ClC1=CC(=CC=C1)C(=O)OO.ClC1=CC=C2C(=N1)CCC2>>ClC1=CC=C2C(=[N+]1[O-])CCC2 | [n:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]2[c:8]1[CH2:9][CH2:10][CH2:11]2>>[O-:1][n+:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]2[c:8]1[CH2:9][CH2:10][CH2:11]2 | Clc1ccc2c(n1)CCC2 | [O-][n+]1c(Cl)ccc2c1CCC2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 170d79cd02249a36195e4d00f11d060de9d6afe4011384f55ab4e8738e4e43dc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1c[nH+]c2c(c1)CCC2 | [C:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5](-[Cl;D1;H0:6]):[c:7]>>[C:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O;-;D1;H0:8]):[c:5](-[Cl;D1;H0:6]):[c:7] | null | [] | null | null | 8 | HOUR | A solution of m-chloroperbenzoic acid 70% (520.9 mg, 2.113 mmol) in 5 mL of CH2Cl2 was added drop wise to a stirring solution of 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (295 mg, 1.921 mmol) in 3 mL of CH2Cl2 and the resulting solution was allowed to stir at room temperature overnight. The reaction mixture was que... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cnc2c(c1)CCC2 | C1=CC2=C(CCC2)[NH+]=C1 | C1=CC2=C(CCC2)[NH+]=C1 | null | C(Cl)Cl | null | 8 | Clc1ccc2c(n1)CCC2>C(Cl)Cl>[O-][n+]1c(Cl)ccc2c1CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afd79f390d3c498cba101c73f1e022a6 | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OCc1ccc(F)c([N+](=O)[O-])c1>>CC(C)(C)OC(=O)N1CCN(Cc2ccc(F)c([N+](=O)[O-])c2)CC1 | N1(CCNCC1)C(=O)OC(C)(C)C.FC1=C(C=C(COS(=O)(=O)C)C=C1)[N+](=O)[O-].FC1=C(C=C(COS(=O)(=O)C)C=C1)[N+](=O)[O-]>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=C(C=C1)F)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]1.CS(=O)(=O)O[CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]([F:17])[c:18]([N+:1... | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OCc1ccc(F)c([N+](=O)[O-])c1 | CC(C)(C)OC(=O)N1CCN(Cc2ccc(F)c([N+](=O)[O-])c2)CC1 | null | null | CCOC(=O)C | Functional Group Addition | Alkylation of amines | 08f9737e136e098a34473d5f90b95956d5ff635b2b870052b44cde793e2afecc | ba457d59727bfe139ad507f1fe09c6cb84d4876103102e4229920ebed8a57f1b | c1ccc(CN2CCNCC2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1):[c:4] | null | [] | null | null | 30 | MINUTE | To 1.0 eq of methanesulfonic acid 4-fluoro-3-nitro-benzyl ester (2B) in DMF (about 0.6 M 2B in DMF) was added about 1.05 eq of TEA and about 1.0 eq of t-butyl piperazine-1-carboxylate. The mixture was stirred for 30 min at room temperature, diluted with EtOAc, washed with NH4Cl solution, dried (Na2SO4) and evaporated. ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | CCOC(=O)C | null | 0.5 | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OCc1ccc(F)c([N+](=O)[O-])c1>CCOC(=O)C>CC(C)(C)OC(=O)N1CCN(Cc2ccc(F)c([N+](=O)[O-])c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7d986fb81254f74ab7771b870846ec3 | Cc1ccc(NC(=O)Nc2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)ccc2F)cn1>>COC(=O)N1CCN(Cc2ccc(F)c(NC(=O)Nc3ccc(C)nc3)c2)CC1 | Cl.C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=C(C=C1)F)NC(=O)NC=1C=NC(=CC1)C.C(C)(C)(C)OC(=O)N1CCN(CC1)CC1=CC(=C(C=C1)F)NC(=O)NC=1C=NC(=CC1)C.CC(=O)Cl>>COC(=O)N1CCN(CC1)CC1=CC(=C(C=C1)F)NC(=O)NC=1C=NC(=CC1)C | C[C:1](C)(C)[O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([NH:16][C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][c:23]([CH3:24])[n:25][cH:26]3)[cH:27]2)[CH2:28][CH2:29]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([NH:16... | Cc1ccc(NC(=O)Nc2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)ccc2F)cn1 | COC(=O)N1CCN(Cc2ccc(F)c(NC(=O)Nc3ccc(C)nc3)c2)CC1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 47ee087222cc986f9fb1ced28c92ac84f92f81e26297f2d960a13936e28e91e9 | 1b4ed01a2f690ab7de22ff29ffe33634aafc80d6e4fc163123671460c5372d70 | O=C(Nc1cccnc1)Nc1cccc(CN2CCNCC2)c1 | C-[C;H0;D4;+0:1](-C)(-C)-[#8:2]-[C:3](-[#7:4])=[O;D1;H0:5]>>[#7:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH3;D1;+0:1] | null | [] | 50 | CELSIUS | 15 | MINUTE | To 1.0 eq of 4-{4-fluoro-3-[3-(6-methyl-pyridin-3-yl)-ureido]-benzyl}-piperazine-1-carboxylic acid tert-butyl ester (2D) in MeOH (about 0.1 M 2D in MeOH) was added 2 volumes of HCl in dioxane (4 N) and the reaction mixture stirred at 50° C. for 15 min and evaporated to a solid. The solid was combined with DCM and treat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | Ether | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccncc1 | Other | O1CCOCC1 | 50 | 0.25 | Cc1ccc(NC(=O)Nc2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)ccc2F)cn1>O1CCOCC1>COC(=O)N1CCN(Cc2ccc(F)c(NC(=O)Nc3ccc(C)nc3)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fbbf6e7d6ca46a0a192e2b6af06de2f | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)Cc1cccc([N+](=O)[O-])c1>>CC(C)(C)OC(=O)N1CCN(C(=O)Cc2cccc([N+](=O)[O-])c2)CC1 | [N+](=O)([O-])C=1C=C(C=CC1)CC(=O)O.C(C)N(CC)CC.N1(CCNCC1)C(=O)OC(C)(C)C.[N+](=O)([O-])C=1C=C(C=CC1)CC(=O)O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O>>[N+](=O)([O-])C=1C=C(C=CC1)CC(=O)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:24][CH2:25]1.O[C:12](=[O:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]... | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)Cc1cccc([N+](=O)[O-])c1 | CC(C)(C)OC(=O)N1CCN(C(=O)Cc2cccc([N+](=O)[O-])c2)CC1 | null | null | CCOC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1 | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | An oven-dried, round-bottom flask was charged with tert-butyl piperazine-1-carboxylate (1.1 eq), 3-nitrophenylacetic acid (7A, 1.0 eq), EDC (1.2 eq), and HOBT (1.2 eq). The flask was flushed with nitrogen, and N,N-dimethylformamide (about 0.5 M 7A in DMF) and triethylamine (2.0 eq) were added by syringe. The resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HO- | CCOC(=O)C | null | 8 | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)Cc1cccc([N+](=O)[O-])c1>CCOC(=O)C>CC(C)(C)OC(=O)N1CCN(C(=O)Cc2cccc([N+](=O)[O-])c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e47decf88fb94e42a9708e14355edcdf | CC(C)(C)OC(=O)N1CCN(CCc2cccc([N+](=O)[O-])c2)CC1>>CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1 | [H][H].[N+](=O)([O-])C=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1.[N+](=O)([O-])C=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1>>NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1 | O=[N+:19]([O-])[c:18]1[cH:17][cH:16][cH:15][c:14]([CH2:13][CH2:12][N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]2)[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][c:18]([NH2:19])[cH:20]2)[CH2... | CC(C)(C)OC(=O)N1CCN(CCc2cccc([N+](=O)[O-])c2)CC1 | CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1 | null | [OH-].[OH-].[Pd+2].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCN2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 63 | [{"value": 63.0, "product": "NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/ven... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].[Pd].CO | null | 2.5 | CC(C)(C)OC(=O)N1CCN(CCc2cccc([N+](=O)[O-])c2)CC1>[OH-].[OH-].[Pd+2].[Pd].CO>CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9e783dd23b640daaf1c96a3a3eab1d2 | CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1.Cc1ccc(N=C=O)cn1>>Cc1ccc(NC(=O)Nc2cccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)c2)cn1 | C(=O)(O)[O-].[Na+].N(=C=O)C=1C=CC(=NC1)C.NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1.NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1>>CC1=CC=C(C=N1)NC(NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1)=O | [NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:30]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:31][n:32]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13]... | CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1.Cc1ccc(N=C=O)cn1 | Cc1ccc(NC(=O)Nc2cccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)c2)cn1 | null | null | CCOC(=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1cccnc1)Nc1cccc(CCN2CCNCC2)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 63 | [{"value": 63.0, "product": "CC1=CC=C(C=N1)NC(NC=1C=C(CCN2CCN(CC2)C(=O)OC(C)(C)C)C=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccncc1.c1ccccc1.C1C[NH]CC[NH]1 | null | CCOC(=O)C | null | 2 | CC(C)(C)OC(=O)N1CCN(CCc2cccc(N)c2)CC1.Cc1ccc(N=C=O)cn1>CCOC(=O)C>Cc1ccc(NC(=O)Nc2cccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0187f9bd4d8442db85d80f59adc4af0b | CC(C)(C)OC(=O)NC1(CCO)CC1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1 | S(=O)(=O)(C)Cl.OCCC1(CC1)NC(OC(C)(C)C)=O.C(C)N(CC)CC>>CS(=O)(=O)OCCC1(CC1)NC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][CH2:11][OH:12])[CH2:17][CH2:18]1.Cl[S:13]([CH3:14])(=[O:15])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][CH2:11][O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17][CH2:18]1 | CC(C)(C)OC(=O)NC1(CCO)CC1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 87 | [{"value": 87.0, "product": "CS(=O)(=O)OCCC1(CC1)NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2 | HOUR | To a solution of 6.472 g (32.16 mmol) of tert-butyl 1-(2-hydroxyethyl)cyclopropylcarbamate in 61 ml of anhydrous dichloromethane was added 12.79 ml (91 mmol) of anhydrous triethylamine. The resulting mixture is cooled at −20° C. Then 3.54 ml (45.66 mmol) of mesyl chloride in 11 ml of anhydrous dichloromethane was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC1 | HCl | ClCCl | -20 | 2 | CC(C)(C)OC(=O)NC1(CCO)CC1.CS(=O)(=O)Cl>ClCCl>CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b11e0e4e9fa49aabf72bc36725928b3 | CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1.O=C1NC(=O)c2ccccc21>>CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1 | CS(=O)(=O)OCCC1(CC1)NC(=O)OC(C)(C)C.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>O=C1N(C(C2=CC=CC=C12)=O)CCC1(CC1)NC(OC(C)(C)C)=O | CS(=O)(=O)O[CH2:11][CH2:10][C:9]1([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:24]1.[NH:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][CH2:11][N:12]2[C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:1... | CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1.O=C1NC(=O)c2ccccc21 | CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Alkylation of amines | 8c55c1be63954a68557ba4cda7025bc5216a4a18e41dee3e27297e05487159d8 | 3761faea2e60c075e79428329c94e300333bad052ba97daeccc915afb3519a77 | O=C1c2ccccc2C(=O)N1CCC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5](=[O;D1;H0:4])-[c:10]:[c:9]-[C:7]-1=[O;D1;H0:8] | 50.1 | [{"value": 50.1, "product": "O=C1N(C(C2=CC=CC=C12)=O)CCC1(CC1)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 18 | HOUR | To a solution of 7.82 g (28 mmol) of 2-{1-[(tert-butoxycarbonyl)amino]-cyclopropyl}ethyl methanesulfonate in 35 ml of anhydrous dimethylformamide was added 5.45 g (29.4 mmol) of potassium phthalimide. The resulting mixture was stirred at 150° C. for 18 h. The mixture was then filtered and washed with diethyl ether. The... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC1 | MsOH.HO- | CN(C=O)C | 150 | 18 | CC(C)(C)OC(=O)NC1(CCOS(C)(=O)=O)CC1.O=C1NC(=O)c2ccccc21>CN(C=O)C>CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-176c32185fd343709c7037315fa0835c | CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1>>CC(C)(C)OC(=O)NC1(CCN)CC1 | O=C1N(C(C2=CC=CC=C12)=O)CCC1(CC1)NC(OC(C)(C)C)=O.O.NN>>NCCC1(CC1)NC(OC(C)(C)C)=O | O=C1c2ccccc2C(=O)[N:12]1[CH2:11][CH2:10][C:9]1([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][CH2:11][NH2:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1 | CC(C)(C)OC(=O)NC1(CCN)CC1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | C1CC1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 83 | [{"value": 83.0, "product": "NCCC1(CC1)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4.57 g (13.83 mmol) of tert-butyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]cyclopropylcarbamate in 80 ml of ethanol was added 3.36 ml (69.16 mmol) of hydrazine hydrate and the resulting mixture was heated under reflux for 16 h. The mixture was filtered and washed with diethyl ether. The filtr... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC1 | HO- | C(C)O | null | null | CC(C)(C)OC(=O)NC1(CCN2C(=O)c3ccccc3C2=O)CC1>C(C)O>CC(C)(C)OC(=O)NC1(CCN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9905b422f43f4231929ff61b45876211 | N#CBr.NCCC1(N)CC1>>NC1=NCCC2(CC2)N1 | N#CBr.Br.NCCC1(CC1)N.C[O-].[Na+]>>Br.C1CC12NC(=NCC2)N | Br[C:3]#[N:2].[NH2:4][CH2:5][CH2:6][C:7]1([NH2:10])[CH2:8][CH2:9]1>>[NH2:2][C:3]1=[N:4][CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]2)[NH:10]1 | N#CBr.NCCC1(N)CC1 | NC1=NCCC2(CC2)N1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 42ed30e58c9665e1a8a34dacf1ada35ff15b064eeb3c64ae7f5bbdeb3d7bf919 | 69ad61c86291c403233abc757a0516bd3889966adc07bd67c5e23ba55bb742c0 | C1=NCCC2(CC2)N1 | Br-[C;H0;D2;+0:1]#[N;H0;D1;+0:2].[NH2;D1;+0:3]-[C:4]1(-[C:5]-[C:6]-[NH2;D1;+0:7])-[C:8]-[C:9]-1>>[NH2;D1;+0:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:7]-[C:6]-[C:5]-[C:4]2(-[C:8]-[C:9]-2)-[NH;D2;+0:3]-1 | 99.8 | [{"value": 99.8, "product": "Br.C1CC12NC(=NCC2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2.65 g (10.11 mmol) of 1-(2-aminoethyl)cyclopropanamine hydrobromide in 21 ml of methanol was added 3.83 ml (21.24 mmol) of a solution of sodium methoxide in methanol (5.55 N). The mixture was stirred at room temperature for 2 h. The precipitate was filtered and the filtrate was evaporated. The crude w... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine.Primary amine | Primary amine.Secondary amine | null | C1=NCCC2(CC2)N1 | C1=NCCC2(CC2)N1 | HBr | CO | null | 2 | N#CBr.NCCC1(N)CC1>CO>NC1=NCCC2(CC2)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bcd291d62cbb4cc4bfa2c1d100e42272 | O=c1cc(-c2ccncc2)nc2n1CCC1(CC1)N2C[C@@H](O)c1ccccc1>>O=C(CN1c2nc(-c3ccncc3)cc(=O)n2CCC12CC2)c1ccccc1 | C[N+]1(CCOCC1)[O-].O[C@H](CN1C=2N(CCC13CC3)C(C=C(N2)C2=CC=NC=C2)=O)C2=CC=CC=C2>>O=C(CN1C=2N(CCC13CC3)C(C=C(N2)C2=CC=NC=C2)=O)C2=CC=CC=C2 | [OH:1][C@H:2]([CH2:3][N:4]1[c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[cH:14][c:15](=[O:16])[n:17]2[CH2:18][CH2:19][C:20]12[CH2:21][CH2:22]2)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[C:2]([CH2:3][N:4]1[c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][n:11][cH:12][cH:13]3)[cH:14][c:15](=[O:16])[n:17]2[CH2:... | O=c1cc(-c2ccncc2)nc2n1CCC1(CC1)N2C[C@@H](O)c1ccccc1 | O=C(CN1c2nc(-c3ccncc3)cc(=O)n2CCC12CC2)c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CN1c2nc(-c3ccncc3)cc(=O)n2CCC12CC2)c1ccccc1 | [#7:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[#7:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7] | 25.2 | [{"value": 25.2, "product": "O=C(CN1C=2N(CCC13CC3)C(C=C(N2)C2=CC=NC=C2)=O)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 12 | HOUR | 0.31 g (0.83 mmol) of 1′-[(2S)-2-hydroxy-2-phenylethyl]-8′-pyridin-4-yl-3′,4′-dihydrospiro[cyclopropane-1,2′-pyrimido[1,2-a]pyrimidin]-6′(1′H)-one was dissolved in 8 ml of anhydrous dichloromethane and mixed with 0.145 g (1.24 mmol) of N-methylmorpholine N-oxide, 0.003 g (0.0083 mmol) of tetra-n-propylammonium perruthe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccncc1.c1ccn2c(n1)NC1(CC2)CC1.c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl | 20 | 12 | O=c1cc(-c2ccncc2)nc2n1CCC1(CC1)N2C[C@@H](O)c1ccccc1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl>O=C(CN1c2nc(-c3ccncc3)cc(=O)n2CCC12CC2)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ba81659adf441e4a9a62d5919b20e8d | N.N#CC=C1CCCC1>>N#CCC1(N)CCCC1 | C1(CCCC1)=CC#N.N>>NC1(CCCC1)CC#N | [NH3:5].[N:1]#[C:2][CH:3]=[C:4]1[CH2:6][CH2:7][CH2:8][CH2:9]1>>[N:1]#[C:2][CH2:3][C:4]1([NH2:5])[CH2:6][CH2:7][CH2:8][CH2:9]1 | N.N#CC=C1CCCC1 | N#CCC1(N)CCCC1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 75bd03265b7ec40301307e27ea49a48a9d2e18deaa444c86a611dbf4f43e5db0 | c11dd83c068740ca20b16d565f91433dd074d28859845a6bf059dbf425b3ed05 | C1CCCC1 | [N;D1;H0:1]#[C:2]-[CH;D2;+0:3]=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1.[NH3;D0;+0:9]>>[N;D1;H0:1]#[C:2]-[CH2;D2;+0:3]-[C;H0;D4;+0:4]1(-[NH2;D1;+0:9])-[C:5]-[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | A solution of 15.91 g (0.15 mol) of cyclopentylideneacetonitrile in 170 ml of an aqueous ammonia solution (29%) and 57 ml of methanol was heated at 100° C. in a sealed tube for 24 h. The reaction mixture was concentrated, and the residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methan... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | CO | null | null | N.N#CC=C1CCCC1>CO>N#CCC1(N)CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a66a4fb583f5418db97171546addd0fa | CC(C)(C)OC(=O)NC1(CC#N)CCCC1>>CC(C)(C)OC(=O)NC1(CCN)CCCC1 | S(=O)(=O)([O-])[O-].[Na+].[Na+].C(#N)CC1(CCCC1)NC(OC(C)(C)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)([O-])[O-].[Na+].[Na+]>>NCCC1(CCCC1)NC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][C:11]#[N:12])[CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([CH2:10][CH2:11][NH2:12])[CH2:13][CH2:14][CH2:15][CH2:16]1 | CC(C)(C)OC(=O)NC1(CC#N)CCCC1 | CC(C)(C)OC(=O)NC1(CCN)CCCC1 | null | null | C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1CCCC1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 81.3 | [{"value": 81.3, "product": "NCCC1(CCCC1)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a suspension of 8.48 g (223.63 mmol) of lithium aluminum hydride in 687 ml of diethyl ether at 0° C. was added dropwise 16.7 g (74.54 mmol) of tert-butyl 1-(cyanomethyl)cyclopentylcarbamate dissolved in 344 ml of diethyl ether. The resulting mixture was stirred at 0° C. under nitrogen atmosphere for 1 h. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CCCC1 | null | C(C)OCC | 0 | 1 | CC(C)(C)OC(=O)NC1(CC#N)CCCC1>C(C)OCC>CC(C)(C)OC(=O)NC1(CCN)CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b4abc04cd214ce2aeb75a4d102e3819 | O=c1[nH]c2ccc(Cl)cc2c2nc(C3CC3)nn12>>Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1 | C(C)(=O)O.[OH-].[Na+].ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C3CC3.O>>ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1CC1 | O=c1[nH:1][c:2]2[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]2[c:9]2[n:10][c:11]([CH:12]3[CH2:13][CH2:14]3)[n:15][n:16]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1-[c:9]1[n:10][c:11]([CH:12]2[CH2:13][CH2:14]2)[n:15][nH:16]1 | O=c1[nH]c2ccc(Cl)cc2c2nc(C3CC3)nn12 | Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1 | null | null | C(CO)O | Reduction | OtherReaction | b8c88d2efcc054802d36031bc2f34013d2ef407151431abc6468f52811024052 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2nc(C3CC3)n[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[C:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[C:10]-[c:9]1:[#7;a:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[NH2;D1;+0:1]):[c:3]):[nH;D2;+0:12]:[#7;a:11]:1 | 86.7 | [{"value": 86.0, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a well stirred slurry of 9-chloro-2-cyclopropyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (5.20 g, 19.9 mmol) in ethylene glycol (40 mL) which was heated to 100° C. was added aqueous sodium hydroxide (10 N, 4 mL, 39.9 mmol). The slurry was heated at reflux for 18 h. After cooling, water (25 mL) was added to the resu... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1ccccc1.c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1.C1CC1 | Other | C(CO)O | null | 0.5 | O=c1[nH]c2ccc(Cl)cc2c2nc(C3CC3)nn12>C(CO)O>Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3fb94c1777df47b18fb32b5778c33b28 | Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1>>O=C1Cn2nc(C3CC3)nc2-c2cc(Cl)ccc2N1 | Cl.ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1CC1.ClCC(=O)Cl.[OH-].[Na+]>>ClC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)C2CC2)C1 | [nH:4]1[n:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[n:10][c:11]1-[c:12]1[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]1[NH2:19]>>[O:1]=[C:2]1[CH2:3][n:4]2[n:5][c:6]([CH:7]3[CH2:8][CH2:9]3)[n:10][c:11]2-[c:12]2[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]2[NH:19]1 | Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1 | O=C1Cn2nc(C3CC3)nc2-c2cc(Cl)ccc2N1 | null | null | O1CCOCC1.N1=CC=CC=C1.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 3061731bbe7c4d65edb84f79cdb21c7724c1444461c7a74c6cb4109501b58fee | afdc35c0b9bc6721279627216295916722564d5171b6640e3413043af9d3c810 | O=C1Cn2nc(C3CC3)nc2-c2ccccc2N1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[O;D1;H0:10]=[C:11]1-[C:12]-[n;H0;D3;+0:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 65.4 | [{"value": 65.0, "product": "ClC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)C2CC2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "ClC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)C2CC2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 30 | MINUTE | A suspension of 4-chloro-2-(5-cyclopropyl-2H-[1,2,4]triazol-3-yl)-phenylamine (3.95 g, 16.8 mmol) in dioxane (120 mL) and pyridine (1.5 mL) was cooled to 10° C. A solution of chloroacetyl chloride (1.54 mL, 19.3 mmol) in diethylether (5 mL) was then added dropwise over 15 min. The reaction mixture was stirred at this t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | c1nc[nH]n1 | c1ccc2c(c1)NCCn1ncnc21 | C1CC1.c1ccc2c(c1)NCCn1ncnc21 | Other | O1CCOCC1.N1=CC=CC=C1.C(C)OCC | 10 | 0.5 | Nc1ccc(Cl)cc1-c1nc(C2CC2)n[nH]1>O1CCOCC1.N1=CC=CC=C1.C(C)OCC>O=C1Cn2nc(C3CC3)nc2-c2cc(Cl)ccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-966f88043c0a4b97b0f02e8322057c1f | CCOC(=O)Nc1ccc(Cl)cc1C#N.COCC(=O)NN>>COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1 | C(C)OC(NC1=C(C=C(C=C1)Cl)C#N)=O.COCC(=O)NN>>ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC | CCO[C:15]([NH:14][c:13]1[c:7]([C:6]#[N:5])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1)=[O:16].O=[C:4]([CH2:3][O:2][CH3:1])[NH:18][NH2:17]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[c:7]3[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]3[nH:14][c:15](=[O:16])[n:17]2[n:18]1 | CCOC(=O)Nc1ccc(Cl)cc1C#N.COCC(=O)NN | COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d2308f602e6dc11b4ba0f40919f5bd5c726c02babdc9c30ca500a3550bcd8e7b | 5614a0a0aead52e65295238e6475465c8f3e5bdda31aa14a8bf980584483e473 | O=c1[nH]c2ccccc2c2ncnn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9].O=[C;H0;D3;+0:10](-[C:11]-[#8:12])-[NH;D2;+0:13]-[NH2;D1;+0:14]>>[#8:12]-[C:11]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:13]:[n;H0;D3;+0:14]2:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:9]):[c;H0;D3;+0:7]... | 88 | [{"value": 88.0, "product": "ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 1a) (4-chloro-2-cyano-phenyl)-carbamic acid ethyl ester (71.0 g, 316 mmol) using methoxymethyl-carboxylic acid hydrazide instead of cyclopropane-carboxylic acid hydrazide, was converted to the title compound (73.9 g, 88%) which was obtained as a yellow solid. MS: m/e=264.9 [M+H]+.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Ether.Nitrile | null | c1ccccc1 | c1ccc2ncn3ncnc3c2c1 | c1ccc2ncn3ncnc3c2c1 | HO- | null | null | null | CCOC(=O)Nc1ccc(Cl)cc1C#N.COCC(=O)NN>>COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-572e832a6c0e4cea9e047c688cfc995b | COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1>>COCc1n[nH]c(-c2cc(Cl)ccc2N)n1 | ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC.ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C3CC3>>ClC1=CC(=C(C=C1)N)C=1NN=C(N1)COC | O=c1[n:6]2[n:5][c:4]([CH2:3][O:2][CH3:1])[n:16][c:7]2[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[nH:15]1>>[CH3:1][O:2][CH2:3][c:4]1[n:5][nH:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[NH2:15])[n:16]1 | COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1 | COCc1n[nH]c(-c2cc(Cl)ccc2N)n1 | null | null | null | Reduction | OtherReaction | ddc0e92aa6f3d6549b695733411e0176a0a7729e91b959e11a5e5d4eca230934 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2ncn[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[C:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[C:10]-[c:9]1:[#7;a:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[NH2;D1;+0:1]):[c:3]):[nH;D2;+0:12]:[#7;a:11]:1 | 92.3 | [{"value": 92.0, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)COC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 1b) 9-chloro-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (73.4 g, 277 mmol), instead of 9-chloro-2-cyclopropyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one, was converted to the title compound (61.0 g, 92%) which was obtained as a brown solid. MS: m/e=238.9 [M+H]+.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1nc[nH]n1.c1ccccc1 | c1nc[nH]n1.c1ccccc1 | Other | null | null | null | COCc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1>>COCc1n[nH]c(-c2cc(Cl)ccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ca5778a5a764a9084eaaad0dc9355fc | COCc1n[nH]c(-c2cc(Cl)ccc2N)n1.O=C(Cl)CCl>>COCc1n[nH]c(-c2cc(Cl)ccc2NC(=O)CCl)n1 | ClC1=CC(=C(C=C1)N)C=1NN=C(N1)COC.ClCC(=O)Cl.O>>ClCC(=O)NC1=C(C=C(C=C1)Cl)C=1NN=C(N1)COC | [CH3:1][O:2][CH2:3][c:4]1[n:5][nH:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[NH2:15])[n:20]1.Cl[C:16](=[O:17])[CH2:18][Cl:19]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][nH:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[NH:15][C:16](=[O:17])[CH2:18][Cl:19])[n:20]1 | COCc1n[nH]c(-c2cc(Cl)ccc2N)n1.O=C(Cl)CCl | COCc1n[nH]c(-c2cc(Cl)ccc2NC(=O)CCl)n1 | null | null | C(C)(=O)O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2ncn[nH]2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 87.9 | [{"value": 83.0, "product": "ClCC(=O)NC1=C(C=C(C=C1)Cl)C=1NN=C(N1)COC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "ClCC(=O)NC1=C(C=C(C=C1)Cl)C=1NN=C(N1)COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | 4-Chloro-2-(5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-phenylamine (60.6 g, 239 mmol) was dissolved in acetic acid (1.2 L) and chloroacetic chloride (40.4 mL, 508 mmol) was added dropwise at 14-16° C. over a period of 30 min. The resulting reaction mixture was stirred for 22 h at ambient temperature. After addition of wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1nc[nH]n1.c1ccccc1 | HCl | C(C)(=O)O | null | 22 | COCc1n[nH]c(-c2cc(Cl)ccc2N)n1.O=C(Cl)CCl>C(C)(=O)O>COCc1n[nH]c(-c2cc(Cl)ccc2NC(=O)CCl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a4940bf20274760a754394e86f2677e | COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2.c1nc[nH]n1>>COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Cl)cc1-2 | ClC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1.C(C)(C)N(C(C)C)CC.N1N=CN=C1.P(=O)(Cl)(Cl)Cl>>ClC1=CC2=C(N=C(CN3N=C(N=C23)COC)N2N=CN=C2)C=C1 | O=[C:10]1[CH2:9][n:7]2[c:6]([n:5][c:4]([CH2:3][O:2][CH3:1])[n:8]2)-[c:23]2[c:17]([cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[NH:16]1.[nH:11]1[cH:12][n:13][cH:14][n:15]1>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[n:7]([n:8]1)[CH2:9][C:10]([n:11]1[cH:12][n:13][cH:14][n:15]1)=[N:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]1... | COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2.c1nc[nH]n1 | COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Cl)cc1-2 | null | null | O.C(C)#N | Protection | OtherReaction | 47af92e4446adbb2406957215222f9575bfc6f47ac731f2cd44d23ec1272e5de | e3b229d46a65e45080a1da2050d2d40258c0ddc5128ae54c4fcfdda02a9b00a6 | c1ccc2c(c1)N=C(n1cncn1)Cn1ncnc1-2 | O=[C;H0;D3;+0:1]1-[C:2]-[#7;a:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-1.[#7;a:12]1:[c:13]:[nH;D2;+0:14]:[#7;a:15]:[c:16]:1>>[c:10]:[c:9]1:[c:8]-[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[#7;a:3]:2-[C:2]-[C;H0;D3;+0:1](-[n;H0;D3;+0:14]2:[#7;a:15]:[c:16]:[#7;a:12]:[c:13]:2)=[N;H0;D2;+0:11]-1 | 63 | [{"value": 63.0, "product": "ClC1=CC2=C(N=C(CN3N=C(N=C23)COC)N2N=CN=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "ClC1=CC2=C(N=C(CN3N=C(N=C23)COC)N2N=CN=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 2 | HOUR | 1,2,4-Triazole (74.3 g, 1.08 mol) was dissolved in acetonitrile (850 mL) and N,N-diisopropylethylamine (195 mL, 1.14 mol) was added. After cooling to 0° C. phosphorous oxychloride (29.8 mL, 326 mmol) was added dropwise and the reaction mixture was stirred at 0-5° C. for 2 h. 9-Chloro-2-methoxymethyl-6H-1,3,3a,6-tetraaz... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)NCCn1ncnc21.c1nc[nH]n1 | c1nc[nH]n1.C1=Nc2ccccc2c2ncnn2C1 | c1nc[nH]n1.C1=Nc2ccccc2c2ncnn2C1 | HO- | O.C(C)#N | 2.5 | 2 | COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2.c1nc[nH]n1>O.C(C)#N>COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Cl)cc1-2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10b35571eb37418eb7d2de4465667b0c | CCOC(=O)Nc1ccc(Br)cc1C#N.COCC(=O)NN>>COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1 | C(C)OC(NC1=C(C=C(C=C1)Br)C#N)=O.COCC(=O)NN>>BrC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC | CCO[C:15]([NH:14][c:13]1[c:7]([C:6]#[N:5])[cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:16].O=[C:4]([CH2:3][O:2][CH3:1])[NH:18][NH2:17]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[c:7]3[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]3[nH:14][c:15](=[O:16])[n:17]2[n:18]1 | CCOC(=O)Nc1ccc(Br)cc1C#N.COCC(=O)NN | COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d2308f602e6dc11b4ba0f40919f5bd5c726c02babdc9c30ca500a3550bcd8e7b | 5614a0a0aead52e65295238e6475465c8f3e5bdda31aa14a8bf980584483e473 | O=c1[nH]c2ccccc2c2ncnn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9].O=[C;H0;D3;+0:10](-[C:11]-[#8:12])-[NH;D2;+0:13]-[NH2;D1;+0:14]>>[#8:12]-[C:11]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:13]:[n;H0;D3;+0:14]2:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:9]):[c;H0;D3;+0:7]... | 92 | [{"value": 92.0, "product": "BrC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 1a) (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (19.9 g, 74.2 mmol) instead of (4-chloro-2-cyano-phenyl)-carbamic acid ethyl ester using methoxymethyl-carboxylic acid hydrazide instead of cyclopropane-carboxylic acid hydrazide, was converted to the title compound (21.1 g, 92%) which was ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Ether.Nitrile | null | c1ccccc1 | c1ccc2ncn3ncnc3c2c1 | c1ccc2ncn3ncnc3c2c1 | HO- | null | null | null | CCOC(=O)Nc1ccc(Br)cc1C#N.COCC(=O)NN>>COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a04a2da259b64d18a20cf3563a9b9544 | COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1>>COCc1n[nH]c(-c2cc(Br)ccc2N)n1 | BrC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)COC.ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C3CC3>>BrC1=CC(=C(C=C1)N)C=1NN=C(N1)COC | O=c1[n:6]2[n:5][c:4]([CH2:3][O:2][CH3:1])[n:16][c:7]2[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[nH:15]1>>[CH3:1][O:2][CH2:3][c:4]1[n:5][nH:6][c:7](-[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[NH2:15])[n:16]1 | COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1 | COCc1n[nH]c(-c2cc(Br)ccc2N)n1 | null | null | null | Reduction | OtherReaction | ddc0e92aa6f3d6549b695733411e0176a0a7729e91b959e11a5e5d4eca230934 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2ncn[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[C:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[C:10]-[c:9]1:[#7;a:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[NH2;D1;+0:1]):[c:3]):[nH;D2;+0:12]:[#7;a:11]:1 | 99.8 | [{"value": 99.0, "product": "BrC1=CC(=C(C=C1)N)C=1NN=C(N1)COC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "BrC1=CC(=C(C=C1)N)C=1NN=C(N1)COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 1b) 9-bromo-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (20.9 g, 67.6 mmol), instead of 9-chloro-2-cyclopropyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one, was converted to the title compound (19.1 g, 99%) which was obtained as an off-white solid. MS: m/e=282.7/284.7 [M+H]+.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1nc[nH]n1.c1ccccc1 | c1nc[nH]n1.c1ccccc1 | Other | null | null | null | COCc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1>>COCc1n[nH]c(-c2cc(Br)ccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-927f268940ee4dfcabfc932e7e0c3b97 | COCc1n[nH]c(-c2cc(Br)ccc2NC(=O)CCl)n1>>COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2 | ClCC(=O)NC1=C(C=C(C=C1)Br)C=1NN=C(N1)COC.ClCC(=O)NC1=C(C=C(C=C1)Cl)C=1NN=C(N1)COC>>BrC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1 | Cl[CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]1-[c:6]1[n:5][c:4]([CH2:3][O:2][CH3:1])[n:8][nH:7]1>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[n:7]([n:8]1)[CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]1-2 | COCc1n[nH]c(-c2cc(Br)ccc2NC(=O)CCl)n1 | COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c0ff723938761d7064aaa132212d46041be0f781d682d859d75854b82583bc8c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1Cn2ncnc2-c2ccccc2N1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[c:6]-[c:7]1:[#7;a:8]:[c:9](-[C:10]):[#7;a:11]:[nH;D2;+0:12]:1>>[C:10]-[c:9]1:[#7;a:8]:[c:7]2:[n;H0;D3;+0:12](:[#7;a:11]:1)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[c:6]-2 | 68 | [{"value": 68.0, "product": "BrC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "BrC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 4d) 2-chloro-N-[4-bromo-2-(5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-phenyl]-acetamide (20.6 g, 57.3 mmol), instead of 2-chloro-N-[4-chloro-2-(5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-phenyl]-acetamide, was converted to the title compound (12.6 g, 68%) which was obtained as an off-white solid. MS:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1ccc2c(c1)NCCn1ncnc21 | c1ccc2c(c1)NCCn1ncnc21 | HCl | null | null | null | COCc1n[nH]c(-c2cc(Br)ccc2NC(=O)CCl)n1>>COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96938691ce02453eaba8ea601fa48333 | COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2.COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2>>COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Br)cc1-2 | BrC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1.ClC=1C=CC2=C(C3=NC(=NN3CC(N2)=O)COC)C1>>BrC1=CC2=C(N=C(CN3N=C(N=C23)COC)N2N=CN=C2)C=C1 | O=[C:10]1[CH2:9][n:7]2[c:6]([n:5][c:4]([CH2:3][O:2][CH3:1])[n:8]2)-[c:23]2[c:17]([cH:18][cH:19][c:20]([Br:21])[cH:22]2)[NH:16]1.O=C1C[n:15]2[n:11]c(CO[CH3:12])[n:13][c:14]2-c2cc(Cl)ccc2N1>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[n:7]([n:8]1)[CH2:9][C:10]([n:11]1[cH:12][n:13][cH:14][n:15]1)=[N:16][c:17]1[cH:18][cH:19][c:20... | COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2.COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2 | COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Br)cc1-2 | null | null | null | Protection | OtherReaction | f4b19abe4b89abc164448d1cc528c28258a5bd5fbeba1c4b5257f8fc10968380 | 05c2a10734e86cbeedb550a9596aa666850ba7b3fef95e8a5d6d6383dec88c76 | c1ccc2c(c1)N=C(n1cncn1)Cn1ncnc1-2 | Cl-c1:c:c:c2:c(:c:1)-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:c(-C-O-[CH3;D1;+0:3]):[n;H0;D2;+0:4]:[n;H0;D3;+0:5]:1-C-C(=O)-N-2.O=[C;H0;D3;+0:6]1-[C:7]-[#7;a:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2-[c:13]:[c:14](:[c:15])-[NH;D2;+0:16]-1>>[c:15]:[c:14]1:[c:13]-[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[#7;a:8]:2-[C:7]-[C;H0;D3;+0:6](-[n;H... | 79 | [{"value": 79.0, "product": "BrC1=CC2=C(N=C(CN3N=C(N=C23)COC)N2N=CN=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 4e) 9-bromo-2-methoxymethyl-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one (12.5 g, 38.7 mmol), instead of 9-chloro-2-methoxymethyl-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one, was converted to the title compound (11.4 g, 79%) which was obtained as a light yellow solid. MS: m/e=373.0/375.1 [M+H]+.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amide.Secondary amide | null | c1ccc2c(c1)NCCn1ncnc21.c1ccc2c(c1)NCCn1ncnc21 | c1nc[nH]n1.C1=Nc2ccccc2c2ncnn2C1 | c1nc[nH]n1.C1=Nc2ccccc2c2ncnn2C1 | HCl | null | null | null | COCc1nc2n(n1)CC(=O)Nc1ccc(Br)cc1-2.COCc1nc2n(n1)CC(=O)Nc1ccc(Cl)cc1-2>>COCc1nc2n(n1)CC(n1cncn1)=Nc1ccc(Br)cc1-2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-def137155da94eccaf1fd18f4c149956 | Cc1c[nH]cn1.N#Cc1cc(Br)ccc1F>>Cc1cn(-c2ccc(Br)cc2C#N)cn1 | O.BrC=1C=CC(=C(C#N)C1)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>BrC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1cc(Br)ccc1F | Cc1cn(-c2ccc(Br)cc2C#N)cn1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 59.1 | [{"value": 59.0, "product": "BrC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.1, "product": "BrC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 16 | HOUR | A mixture of 5-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol), 4-methylimidazole (12.5 g, 152 mmol), potassium carbonate (34.55 g, 250 mmol) in DMSO (500 mL) was stirred at 90° C. for 16 h. Water (1.5 L) was added and the resulting suspension was stirred with ice-bath cooling for 1 h. The precipitate was then filtered o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | CS(=O)C | 90 | 16 | Cc1c[nH]cn1.N#Cc1cc(Br)ccc1F>CS(=O)C>Cc1cn(-c2ccc(Br)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa0ad0d8c8554b1ea3911e7b64043a1e | Cc1cn(-c2ccc(Br)cc2C#N)cn1>>Cc1ncn(-c2ccc(Br)cc2C#N)c1CN(C)C | BrC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C>>BrC=1C=CC(=C(C#N)C1)N1C=NC(=C1CN(C)C)C | [CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | Cc1cn(-c2ccc(Br)cc2C#N)cn1 | Cc1ncn(-c2ccc(Br)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | Functional Group Addition | OtherReaction | 24cb39cd08c389cd49a7ea6089f707b8bf11505b657f868e94c539938a1c060c | a5ecc0f9f40a26873e3f25b9146fa7daf7ef454ae1fed653ab37babf6624d21a | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5](-[c:6]):[cH;D2;+0:7]:1>>[#7:8]-[C:9]-[c;H0;D3;+0:7]1:[#7;a:5](-[c:6]):[c:4]:[#7;a:3]:[c:2]:1-[C;D1;H3:1] | null | [] | null | null | null | null | A solution of 5-bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile (11.0 g, 42.0 mmol) and N,N-dimethylmethyleneiminium chloride (5.0 g, 53.4 mmol) in DMF (75 mL) was stirred at 90° C. for 16 h. The solvent was evaporated and the oily residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | CN(C)C=O | null | null | Cc1cn(-c2ccc(Br)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(Br)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eee3ae66b2de48798d85d450d673db46 | COC(=O)CC(F)(F)F.NN>>NNC(=O)CC(F)(F)F | COC(CC(F)(F)F)=O.O.NN>>FC(CC(=O)NN)(F)F | CO[C:3](=[O:4])[CH2:5][C:6]([F:7])([F:8])[F:9].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][C:6]([F:7])([F:8])[F:9] | COC(=O)CC(F)(F)F.NN | NNC(=O)CC(F)(F)F | null | null | CO | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[N;D1;H2:8] | 58 | [{"value": 58.0, "product": "FC(CC(=O)NN)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.8, "product": "FC(CC(=O)NN)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,3,3-trifluoro-propionic acid methyl ester (24.6 g, 173 mmol) in methanol (173 mL) was treated with hydrazine hydrate (8.4 mL, 173 mmol). The resulting mixture was then heated under reflux for 16 h and filtered. The filtrate was adsorbed on silica, evaporated and chromatographed (SiO2, dichloromethane:me... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | null | HO- | CO | null | null | COC(=O)CC(F)(F)F.NN>CO>NNC(=O)CC(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbd11b3c07694e559b5256fd8bf9638c | CCOC(=O)CC1CCCO1.NN>>NNC(=O)CC1CCCO1 | C(C)OC(CC1OCCC1)=O.O.NN>>O1C(CCC1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][O:10]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][O:10]1 | CCOC(=O)CC1CCCO1.NN | NNC(=O)CC1CCCO1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | C1CCOC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#8:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[#8:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[N;D1;H2:6] | 32 | [{"value": 32.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (rac.)-(tetrahydro-furan-2-yl)-acetic acid ethyl ester (3.84 g, 24 mmol) in n-butanol (24 mL) was treated with hydrazine hydrate (1.4 mL, 29 mmol) and the resulting mixture was then heated under reflux for 3 h. The solvent was evaporated and residual volatile components were azeotropically removed by coev... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1CCOC1 | HO- | C(CCC)O | null | null | CCOC(=O)CC1CCCO1.NN>C(CCC)O>NNC(=O)CC1CCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e61829b865e54994a2c8febfc8aed225 | CCOC(=O)CBr.O=C1COCCN1>>CCOC(=O)CN1CCOCC1=O | O=C1NCCOC1.[H-].[Na+].BrCC(=O)OCC>>C(C)OC(CN1C(COCC1)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[CH2:8][CH2:9][O:10][CH2:11][C:12]1=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][C:12]1=[O:13] | CCOC(=O)CBr.O=C1COCCN1 | CCOC(=O)CN1CCOCC1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7ca738da082545e6180e0dc731e19e09e00d305cddef3a2e00efa5971a996f47 | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1COCCN1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#8:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#8:9]-[C:8]-[C:7]-1=[O;D1;H0:6] | 28 | [{"value": 28.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-oxo-morpholine (6.5 g, 4 mmol) (Willey, Alan David; Kott, Kevin Lee; Miracle, Gregory Scot; Gosselink, Eugene Paul; Burckett-St. Laurent, James Charles Theophile Roger. Bleaching compositions containing bleach activators having alpha-modified lactam leaving-groups. PCT Int. Appl. (1996), WO 9622350 A1) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HBr | CN(C)C=O | null | null | CCOC(=O)CBr.O=C1COCCN1>CN(C)C=O>CCOC(=O)CN1CCOCC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f35efdd69a31478bb964ca8976c7d05e | CCOC(=O)CN1CCOCC1=O.NN>>NNC(=O)CN1CCOCC1=O | C(C)OC(CN1C(COCC1)=O)=O.O.NN>>O=C1N(CCOC1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][C:11]1=[O:12].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][C:11]1=[O:12] | CCOC(=O)CN1CCOCC1=O.NN | NNC(=O)CN1CCOCC1=O | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=C1COCCN1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | 56 | [{"value": 56.0, "product": "O=C1N(CCOC1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-oxo-morpholin-4-yl)-acetic acid ethyl ester in butanol was reacted with hydrazine hydrate at 100° C. for 6 h. Evaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the title compound as a white solid (yield: 56%). ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1COCC[NH]1 | HO- | C(CCC)O | null | null | CCOC(=O)CN1CCOCC1=O.NN>C(CCC)O>NNC(=O)CN1CCOCC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2dffd324c6984c8096162dbd1cc67372 | CO.Cc1cc(CC(=O)O)on1>>COC(=O)Cc1cc(C)no1 | CC1=NOC(=C1)CC(=O)O.CO>>COC(CC1=CC(=NO1)C)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][o:11]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([CH3:9])[n:10][o:11]1 | CO.Cc1cc(CC(=O)O)on1 | COC(=O)Cc1cc(C)no1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1cnoc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#8;a:5]:[#7;a:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[#7;a:6]:[#8;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C;D1;H3:7] | null | [] | null | null | null | null | A solution of 3-methyl-5-isoxazole acetic acid (10.2 g, 72.6 mmol) in methanol (100 mL) was treated with p-toluene-4-sulfonic acid monohydrate (1.0 g, cat.) and the resulting mixture was then heated under reflux for 4 h. After cooling, the mixture was then evaporated and the brownish residue stirred with saturated sodi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1cnoc1 | HO- | null | null | null | CO.Cc1cc(CC(=O)O)on1>>COC(=O)Cc1cc(C)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc87e9f8a2654a88b7073a18c13fa270 | CCOC(=O)Cc1ccc(C)nc1.NN>>Cc1ccc(CC(=O)NN)cn1 | C(C)OC(CC=1C=NC(=CC1)C)=O.O.NN>>CC1=CC=C(C=N1)CC(=O)NN | CCO[C:7]([CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:12][cH:11]1)=[O:8].[NH2:9][NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][NH2:10])[cH:11][n:12]1 | CCOC(=O)Cc1ccc(C)nc1.NN | Cc1ccc(CC(=O)NN)cn1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5]:[#7;a:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7] | 72 | [{"value": 72.0, "product": "CC1=CC=C(C=N1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (6-methyl-pyridin-3-yl)-acetic acid ethyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was then heated under reflux for 20 h. Evaporation of all volatiles and crystallization from n-butanol and toluene afforded the title compound as a white... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(CCC)O | null | null | CCOC(=O)Cc1ccc(C)nc1.NN>C(CCC)O>Cc1ccc(CC(=O)NN)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e30211f9728d442e8d7980840172db51 | COC(=O)Cc1nc(C)sc1C.NN>>Cc1nc(CC(=O)NN)c(C)s1 | COC(CC=1N=C(SC1C)C)=O.O.NN>>CC=1SC(=C(N1)CC(=O)NN)C | CO[C:6]([CH2:5][c:4]1[n:3][c:2]([CH3:1])[s:12][c:10]1[CH3:11])=[O:7].[NH2:8][NH2:9]>>[CH3:1][c:2]1[n:3][c:4]([CH2:5][C:6](=[O:7])[NH:8][NH2:9])[c:10]([CH3:11])[s:12]1 | COC(=O)Cc1nc(C)sc1C.NN | Cc1nc(CC(=O)NN)c(C)s1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cscn1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[#7;a:5]):[c:6]:[#16;a:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[#16;a:7]:[c:6]:[c:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[N;D1;H2:8]):[#7;a:5] | 68 | [{"value": 68.0, "product": "CC=1SC(=C(N1)CC(=O)NN)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2,5-dimethyl-thiazol-4-yl)-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was then heated under reflux for 20 h. Evaporation of all volatiles and crystallization from n-butanol and toluene afforded the title compound as a ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cscn1 | HO- | C(CCC)O | null | null | COC(=O)Cc1nc(C)sc1C.NN>C(CCC)O>Cc1nc(CC(=O)NN)c(C)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d595f510ea5c44a6b4f39160500eb79e | CCOC(=O)CBr.CCc1ncc[nH]1>>CCOC(=O)Cn1ccnc1CC | C(C)C=1NC=CN1.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(=NC=C1)CC)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[cH:8][cH:9][n:10][c:11]1[CH2:12][CH3:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][n:10][c:11]1[CH2:12][CH3:13] | CCOC(=O)CBr.CCc1ncc[nH]1 | CCOC(=O)Cn1ccnc1CC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b4d548919e87a11a7ba36f860f40bb0a2fa6336f94f13f3a92653c45462e51d0 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[C:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | 30.4 | [{"value": 30.0, "product": "C(C)OC(CN1C(=NC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.4, "product": "C(C)OC(CN1C(=NC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Ethyl-imidazole (10.0 g, 104 mmol) was dissolved in acetone (80 mL) and then ethyl bromoacetate (17.4 g, 104 mmol) and potassium carbonate (2.6 g, 18.7 mmol) was added and the resulting mixture was heated under reflux for 12 h. After filtration and evaporation the residue was extracted with water and dichloromethane.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1 | HBr | CC(=O)C | null | null | CCOC(=O)CBr.CCc1ncc[nH]1>CC(=O)C>CCOC(=O)Cn1ccnc1CC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e0afe34ff914098b8cee6118339d5a9 | CCOC(=O)Cn1ccnc1CC.NN>>CCc1nccn1CC(=O)NN | C(C)OC(CN1C(=NC=C1)CC)=O.O.NN>>C(C)C=1N(C=CN1)CC(=O)NN | CCO[C:9]([CH2:8][n:7]1[c:3]([CH2:2][CH3:1])[n:4][cH:5][cH:6]1)=[O:10].[NH2:11][NH2:12]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][n:7]1[CH2:8][C:9](=[O:10])[NH:11][NH2:12] | CCOC(=O)Cn1ccnc1CC.NN | CCc1nccn1CC(=O)NN | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1c[nH]cn1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 94 | [{"value": 94.0, "product": "C(C)C=1N(C=CN1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2-ethyl-imidazol-1-yl)-acetic acid ethyl ester in butanol was reacted with hydrazine hydrate (1.2 equivalents) at 100° C. for 6 h. Evaporation of all volatiles and crystallization from methanol/diisopropylether afforded the title compound as a white solid (yield: 94%). MS: m/e=169.3 [M+H... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ncc[nH]1 | HO- | C(CCC)O | null | null | CCOC(=O)Cn1ccnc1CC.NN>C(CCC)O>CCc1nccn1CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-156099e39bfa4256ba89fb82a1ddee4f | COC(=O)CN1CCOCC1.NN>>NNC(=O)CN1CCOCC1 | COC(CN1CCOCC1)=O.O.NN>>N1(CCOCC1)CC(=O)NN | CO[C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1 | COC(=O)CN1CCOCC1.NN | NNC(=O)CN1CCOCC1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | C1COCCN1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 68 | [{"value": 68.0, "product": "N1(CCOCC1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, morpholin-4-yl-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (1.2 equivalents) at 100° C. for 1 h. Evaporation of all volatiles and crystallization from n-butanol/toluene afforded the title compound as a white solid (yield: 68%). 1H-NMR (300 MHz, DMSO): δ=2.40 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1COCC[NH]1 | HO- | C(CCC)O | null | null | COC(=O)CN1CCOCC1.NN>C(CCC)O>NNC(=O)CN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12fafd759ff24cf8b857870d0ddfbd33 | COC(=O)Cc1ccno1.NN>>NNC(=O)Cc1ccno1 | COC(CC1=CC=NO1)=O.O.NN>>O1N=CC=C1CC(=O)NN | CO[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][n:9][o:10]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][n:9][o:10]1 | COC(=O)Cc1ccno1.NN | NNC(=O)Cc1ccno1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cnoc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#8;a:5]:[#7;a:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[#7;a:6]:[#8;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7] | 41 | [{"value": 41.0, "product": "O1N=CC=C1CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, isoxazol-5-yl-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 4 h. Evaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnoc1 | HO- | C(CCC)O | null | null | COC(=O)Cc1ccno1.NN>C(CCC)O>NNC(=O)Cc1ccno1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92db03ef5bef403a9021ddf50163f35d | COC(=O)Cc1cc(C)on1.NN>>Cc1cc(CC(=O)NN)no1 | COC(CC1=NOC(=C1)C)=O.O.NN>>CC1=CC(=NO1)CC(=O)NN | CO[C:6]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[o:11][n:10]1)=[O:7].[NH2:8][NH2:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6](=[O:7])[NH:8][NH2:9])[n:10][o:11]1 | COC(=O)Cc1cc(C)on1.NN | Cc1cc(CC(=O)NN)no1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cnoc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#7;a:5]:[#8;a:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[#8;a:6]:[#7;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7] | 90 | [{"value": 90.0, "product": "CC1=CC(=NO1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (5-methyl-isoxazol-3-yl)-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 90 min. Evaporation of all volatiles afforded the title compound as a white solid (yield: 90%). 1H-NMR (300 MHz, DMSO): δ=2... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnoc1 | HO- | C(CCC)O | null | null | COC(=O)Cc1cc(C)on1.NN>C(CCC)O>Cc1cc(CC(=O)NN)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ba7cf02516c4ae1890a4787209f4f0a | CCOC(=O)Cc1c(C)noc1C.NN>>Cc1noc(C)c1CC(=O)NN | C(C)OC(CC=1C(=NOC1C)C)=O.O.NN>>CC1=NOC(=C1CC(=O)NN)C | CCO[C:9]([CH2:8][c:7]1[c:2]([CH3:1])[n:3][o:4][c:5]1[CH3:6])=[O:10].[NH2:11][NH2:12]>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[CH2:8][C:9](=[O:10])[NH:11][NH2:12] | CCOC(=O)Cc1c(C)noc1C.NN | Cc1noc(C)c1CC(=O)NN | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cnoc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]1:[c:5]:[#7;a:6]:[#8;a:7]:[c:8]:1.[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]1:[c:5]:[#7;a:6]:[#8;a:7]:[c:8]:1 | 87 | [{"value": 87.0, "product": "CC1=NOC(=C1CC(=O)NN)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3,5-dimethyl-isoxazol-4-yl)-acetic acid ethyl ester (Bacon, Edward R.; Daum, Sol J.; Singh, Baldev. 6-Substituted pyrazolo[3,4-d]pyrimidin-4-ones and compositions and methods of use as c-GMP phosphodiesterase inhibitors. PCT Int. Appl. (1996), WO 9628429 A1) in butanol was reacted with h... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnoc1 | HO- | C(CCC)O | null | null | CCOC(=O)Cc1c(C)noc1C.NN>C(CCC)O>Cc1noc(C)c1CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-631d905e8e454e15aa32371b58415fcf | CCOC(=O)Cc1c(C)n[nH]c1C.NN>>Cc1n[nH]c(C)c1CC(=O)NN | O.NN.C(C)OC(CC=1C(=NNC1C)C)=O.N1N=CC(=C1)CC(=O)O>>CC1=NNC(=C1CC(=O)NN)C | CCO[C:9]([CH2:8][c:7]1[c:2]([CH3:1])[n:3][nH:4][c:5]1[CH3:6])=[O:10].[NH2:11][NH2:12]>>[CH3:1][c:2]1[n:3][nH:4][c:5]([CH3:6])[c:7]1[CH2:8][C:9](=[O:10])[NH:11][NH2:12] | CCOC(=O)Cc1c(C)n[nH]c1C.NN | Cc1n[nH]c(C)c1CC(=O)NN | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cn[nH]c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1.[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | 68 | [{"value": 68.0, "product": "CC1=NNC(=C1CC(=O)NN)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (Rainer, Georg. 4-Pyrazoleacetic acid derivatives. U.S. (1979), U.S. Pat. No. 4,146,721) in butanol was reacted with hydrazine hydrate (3 equivalents) and the resulting mixture was heated under reflux for 6 h. Evaporation of all volat... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cn[nH]c1 | HO- | C(CCC)O | null | null | CCOC(=O)Cc1c(C)n[nH]c1C.NN>C(CCC)O>Cc1n[nH]c(C)c1CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-477da8e56cc646649a05e152319b7a14 | CCOC(=O)Cn1ccccc1=O.NN>>NNC(=O)Cn1ccccc1=O | C(C)OC(CN1C(C=CC=C1)=O)=O.O.NN>>O=C1N(C=CC=C1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1=[O:12].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1=[O:12] | CCOC(=O)Cn1ccccc1=O.NN | NNC(=O)Cn1ccccc1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 78 | [{"value": 78.0, "product": "O=C1N(C=CC=C1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester (Begley, William J. et. al. Journal of the Chemical Society, Perkin Transactions 1 (1981), (9), 2620-4) in ethanol was reacted with hydrazine hydrate (1.1 equivalents) at 60° C. for 36 h. The mixture was cooled to rt and the precipitated pro... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1ccccc1=O.NN>C(C)O>NNC(=O)Cn1ccccc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e5b8b40a88e48a4b53eaef1fa584e19 | CCOC(=O)Cn1ccc(C)n1.NN>>Cc1ccn(CC(=O)NN)n1 | C(C)OC(CN1N=C(C=C1)C)=O.O.NN>>CC1=NN(C=C1)CC(=O)NN | CCO[C:7]([CH2:6][n:5]1[cH:4][cH:3][c:2]([CH3:1])[n:11]1)=[O:8].[NH2:9][NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][n:5]([CH2:6][C:7](=[O:8])[NH:9][NH2:10])[n:11]1 | CCOC(=O)Cn1ccc(C)n1.NN | Cc1ccn(CC(=O)NN)n1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cn[nH]c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 95 | [{"value": 95.0, "product": "CC1=NN(C=C1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-methyl-pyrazol-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 4 h. The mixture was then cooled to rt and the precipitated product was filtered off and crystallized from ethanol. The title... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cc[nH]n1 | HO- | C(C)O | null | null | CCOC(=O)Cn1ccc(C)n1.NN>C(C)O>Cc1ccn(CC(=O)NN)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88dd805681fd48d29b7b3167014fdb42 | Cc1cc(CC(=O)N(C)N)n(C)n1>>Cc1cc(CC(=O)O)n(C)n1 | CN(N)C(CC=1N(N=C(C1)C)C)=O.O1CCOCC1.Cl>>CN1N=C(C=C1CC(=O)O)C | CN(N)[C:6]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:11][n:9]1[CH3:10])=[O:7]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6](=[O:7])[OH:8])[n:9]([CH3:10])[n:11]1 | Cc1cc(CC(=O)N(C)N)n(C)n1 | Cc1cc(CC(=O)O)n(C)n1 | null | null | null | Miscellaneous | Oxidation of amide to carboxylic acid | 788cfd031b45a2f6597e703155f8c5868dd6c4f3d2f8420e0be522ea5feb8537 | be4116036c7f3c305b8ba0bb9e668ed0c313cd7be6981ff859d2456353d4d83d | c1cn[nH]c1 | C-N(-N)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#7;a:5]:[#7;a:6]>>[#7;a:6]:[#7;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;D1;H1:7] | null | [] | null | null | null | null | To a solution of (2,5-dimethyl-2H-pyrazol-3-yl)-acetic acid N-methyl-hydrazide (9.1 g, 41 mmol) in dioxane (50 mL) aqueous sodium hydroxide solution was added (5 N, 50 mL) and the and the resulting mixture was heated under reflux for 4 h. After addition of hydrochloric acid (5 N, 50 mL), all volatiles were evaporated. ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Carboxylic acid | null | null | c1cc[nH]n1 | Other | null | null | null | Cc1cc(CC(=O)N(C)N)n(C)n1>>Cc1cc(CC(=O)O)n(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3000970f3aab44dca80e5aea02dd10b8 | CCOC(=O)Cc1cc(C)nn1C.NN>>Cc1cc(CC(=O)NN)n(C)n1 | C(C)OC(CC=1N(N=C(C1)C)C)=O.O.NN>>CN1N=C(C=C1CC(=O)NN)C | CCO[C:6]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:12][n:10]1[CH3:11])=[O:7].[NH2:8][NH2:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6](=[O:7])[NH:8][NH2:9])[n:10]([CH3:11])[n:12]1 | CCOC(=O)Cc1cc(C)nn1C.NN | Cc1cc(CC(=O)NN)n(C)n1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cn[nH]c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#7;a:5]:[#7;a:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[#7;a:6]:[#7;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7] | 78 | [{"value": 78.0, "product": "CN1N=C(C=C1CC(=O)NN)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2,5-dimethyl-2H-pyrazol-3-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) at reflux for 16 h. Evaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the title compound as a wh... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cc[nH]n1 | HO- | C(C)O | null | null | CCOC(=O)Cc1cc(C)nn1C.NN>C(C)O>Cc1cc(CC(=O)NN)n(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5397f43a2b4c41b0bcaf62759bb6b2b8 | CCOC(=O)Cn1nccc1C.NN>>Cc1ccnn1CC(=O)NN | C(C)OC(CN1N=CC=C1C)=O.O.NN>>CC1=CC=NN1CC(=O)NN | CCO[C:8]([CH2:7][n:6]1[c:2]([CH3:1])[cH:3][cH:4][n:5]1)=[O:9].[NH2:10][NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][n:6]1[CH2:7][C:8](=[O:9])[NH:10][NH2:11] | CCOC(=O)Cn1nccc1C.NN | Cc1ccnn1CC(=O)NN | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cn[nH]c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 95 | [{"value": 95.0, "product": "CC1=CC=NN1CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (5-methyl-pyrazol-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 8 h. The mixture was cooled to rt and the precipitated product was filtered off, dried and crystallized from toluene. The tit... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cc[nH]n1 | HO- | C(C)O | null | null | CCOC(=O)Cn1nccc1C.NN>C(C)O>Cc1ccnn1CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df034769d2a5441a92f005e51f5705b4 | CCOC(=O)Cn1ccnn1.NN>>NNC(=O)Cn1ccnn1 | C(C)OC(CN1N=NC=C1)=O.O.NN>>N1(N=NC=C1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][n:9][n:10]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][n:9][n:10]1 | CCOC(=O)Cn1ccnn1.NN | NNC(=O)Cn1ccnn1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1c[nH]nn1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 73 | [{"value": 73.0, "product": "N1(N=NC=C1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | null | null | As described for example 112a, [1,2,3]triazol-1-yl-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture heated under reflux for 3 h. The mixture was cooled to 4° C. and the precipitated product was filtered off and dried to afford the title compound as a white ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1c[nH]nn1 | HO- | C(C)O | 4 | null | CCOC(=O)Cn1ccnn1.NN>C(C)O>NNC(=O)Cn1ccnn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a32ab292fd514910b7c2ce46dfbb02cb | CCN1CCNC(=O)C1=O.CCOC(=O)CBr>>CCOC(=O)CN1CCN(CC)C(=O)C1=O | ClCCl.C(C)N1C(C(NCC1)=O)=O.[H-].[Na+].BrCC(=O)OCC>>C(C)OC(CN1C(C(N(CC1)CC)=O)=O)=O | [NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH3:12])[C:13](=[O:14])[C:15]1=[O:16].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH3:12])[C:13](=[O:14])[C:15]1=[O:16] | CCN1CCNC(=O)C1=O.CCOC(=O)CBr | CCOC(=O)CN1CCN(CC)C(=O)C1=O | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | dd062c17fe507ad99abf24a700a336f6ef9f4e86b41755cea63190fe5fb3e4e4 | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1NCCNC1=O | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13]-1=[O;D1;H0:14]>>[C:6]-[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:11](=[O;D1;H0:12])-[C:13]-1=[O;D1;H0:14] | 72 | [{"value": 72.0, "product": "C(C)OC(CN1C(C(N(CC1)CC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 119a, 1-ethyl-piperazine-2,3-dione was reacted with sodium hydride followed by reaction with ethyl bromoacetate. Aqueous workup followed by chromatography (SiO2, dichloromethane:methanol=100:0 to 94:4) afforded the title compound as a light yellow oil (yield: 72%). MS: m/e=229.4 [M+H]+.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HBr | CO | null | null | CCN1CCNC(=O)C1=O.CCOC(=O)CBr>CO>CCOC(=O)CN1CCN(CC)C(=O)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12146869560145d38e0dc3c000add4d4 | CCOC(=O)CN1CCN(CC)C(=O)C1=O.NN>>CCN1CCN(CC(=O)NN)C(=O)C1=O | C(C)OC(CN1C(C(N(CC1)CC)=O)=O)=O.O.NN>>C(C)N1C(C(N(CC1)CC(=O)NN)=O)=O | CCO[C:8]([CH2:7][N:6]1[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:14](=[O:15])[C:12]1=[O:13])=[O:9].[NH2:10][NH2:11]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([CH2:7][C:8](=[O:9])[NH:10][NH2:11])[C:12](=[O:13])[C:14]1=[O:15] | CCOC(=O)CN1CCN(CC)C(=O)C1=O.NN | CCN1CCN(CC(=O)NN)C(=O)C1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=C1NCCNC1=O | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | 77 | [{"value": 77.0, "product": "C(C)N1C(C(N(CC1)CC(=O)NN)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (4-ethyl-2,3-dioxo-piperazin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) and the resulting mixture heated under reflux for 16 h. The precipitated product was filtered off and dried to afford the title compound as a white solid (yield: 77%)... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1C[NH]CC[NH]1 | HO- | C(C)O | null | null | CCOC(=O)CN1CCN(CC)C(=O)C1=O.NN>C(C)O>CCN1CCN(CC(=O)NN)C(=O)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c74e8da66e24b51963388efc6012b76 | COC(=O)Cc1ccon1.NN>>NNC(=O)Cc1ccon1 | COC(CC1=NOC=C1)=O.O.NN>>O1N=C(C=C1)CC(=O)NN | CO[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][o:9][n:10]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][o:9][n:10]1 | COC(=O)Cc1ccon1.NN | NNC(=O)Cc1ccon1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cnoc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#7;a:5]:[#8;a:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[#8;a:6]:[#7;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[N;D1;H2:7] | 78 | [{"value": 78.0, "product": "O1N=C(C=C1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, isoxazol-3-yl-acetic acid methyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) at rt for 16 h. After evaporation of the solvent the residue was chromatographed (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) to afford the title compound as a whit... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnoc1 | HO- | C(C)O | null | null | COC(=O)Cc1ccon1.NN>C(C)O>NNC(=O)Cc1ccon1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ab803f111ad4f6594fc701c9255f416 | CCOC(=O)Cn1nccn1.NN>>NNC(=O)Cn1nccn1 | C(C)OC(CN1N=CC=N1)=O.O.NN>>N=1N(N=CC1)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][n:6]1[n:7][cH:8][cH:9][n:10]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[n:7][cH:8][cH:9][n:10]1 | CCOC(=O)Cn1nccn1.NN | NNC(=O)Cn1nccn1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cn[nH]n1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 68 | [{"value": 68.0, "product": "N=1N(N=CC1)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, [1,2,3]triazol-2-yl-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture heated under reflux for 3 h. The mixture was cooled to rt and the precipitated product was filtered off and dried to afford the title compound as a white sol... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1c[nH]nn1 | HO- | C(C)O | null | null | CCOC(=O)Cn1nccn1.NN>C(C)O>NNC(=O)Cn1nccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c727e895427d48fdba1ecf5ca0cc5130 | Cc1c[nH]cn1.N#Cc1cc(Cl)ccc1F>>Cc1cn(-c2ccc(Cl)cc2C#N)cn1 | ClC=1C=CC(=C(C#N)C1)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1cc(Cl)ccc1F | Cc1cn(-c2ccc(Cl)cc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 63 | [{"value": 63.0, "product": "ClC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 5-chloro-2-fluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 20 h at 90° C. After aqueous workup and crystallization from ethyl acetate the title compound was obtained as a white solid (yield: 63%). MS: m/e=218.2 [M+H]+.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1cc(Cl)ccc1F>>Cc1cn(-c2ccc(Cl)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d88ae502f7b74708bcf0c12673cc5c7b | C=[N+](C)C.Cc1cn(-c2ccc(Cl)cc2C#N)cn1>>Cc1ncn(-c2ccc(Cl)cc2C#N)c1CN(C)C | ClC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>ClC=1C=CC(=C(C#N)C1)N1C=NC(=C1CN(C)C)C | [CH2:16]=[N+:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=[N+](C)C.Cc1cn(-c2ccc(Cl)cc2C#N)cn1 | Cc1ncn(-c2ccc(Cl)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 17 | [{"value": 17.0, "product": "ClC=1C=CC(=C(C#N)C1)N1C=NC(=C1CN(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 5-chloro-2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 16 h at 90° C. Evaporation of the solvent, aqueous workup and crystallization from ethyl acetate afforded the title compound as a white solid (yield: 17%). MS: m/e=275.1 [M+H]+.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccc(Cl)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(Cl)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f35d3a094b984bff9a5653e5dad4fa95 | COC(=O)c1cc(C)on1.NN>>Cc1cc(C(=O)NN)no1 | COC(=O)C1=NOC(=C1)C.O.NN>>CC1=CC(=NO1)C(=O)NN | CO[C:5]([c:4]1[cH:3][c:2]([CH3:1])[o:10][n:9]1)=[O:6].[NH2:7][NH2:8]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[NH:7][NH2:8])[n:9][o:10]1 | COC(=O)c1cc(C)on1.NN | Cc1cc(C(=O)NN)no1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1cnoc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#8;a:5]:[c:6]:[c:7]:1.[N;D1;H2:8]-[NH2;D1;+0:9]>>[N;D1;H2:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#8;a:5]:[c:6]:[c:7]:1 | 64 | [{"value": 64.0, "product": "CC1=CC(=NO1)C(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, 5-methyl-isoxazole-3-carboxylic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) at 100° C. for 2 h. Evaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the title compound as a white s... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1cnoc1 | HO- | C(CCC)O | null | null | COC(=O)c1cc(C)on1.NN>C(CCC)O>Cc1cc(C(=O)NN)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09e86028a29e4cf89a7faa423bf5a852 | Cc1c[nH]cn1.N#Cc1cc(I)ccc1F>>Cc1cn(-c2ccc(I)cc2C#N)cn1 | IC=1C=CC(=C(C#N)C1)N1C=NC=C1C.FC1=C(C#N)C=C(C=C1)I.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>IC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1cc(I)ccc1F | Cc1cn(-c2ccc(I)cc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 92 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-5-iodo-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 20 h at 90° C. Aqueous workup afforded a 1.9:1 mixture of the title compound and its regioisomer [5-iodo-2-(5-methyl-imidazol-1-yl)-benzonitrile] as a white solid (yield: 92%). MS: m/e=310.1 [M+H]+.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1cc(I)ccc1F>>Cc1cn(-c2ccc(I)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7e99499be19427c84b15411463fc75a | C=[N+](C)C.Cc1cn(-c2ccc(I)cc2C#N)cn1>>Cc1ncn(-c2ccc(I)cc2C#N)c1CN(C)C | IC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)I)C | [CH2:16]=[N+:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([I:10])[cH:11][c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([I:10])[cH:11][c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=[N+](C)C.Cc1cn(-c2ccc(I)cc2C#N)cn1 | Cc1ncn(-c2ccc(I)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 38 | [{"value": 38.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)I)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 5-iodo-2-(4-methyl-imidazol-1-yl)-benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 72 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3) afforded the title compound as a white solid (yield: 38%)... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccc(I)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(I)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3016bb3ae13d4daf9b8d7cb38c2a7512 | CCOC(=O)CN1CCOC1=O.NN>>NNC(=O)CN1CCOC1=O | C(C)OC(CN1C(OCC1)=O)=O.O.NN>>O=C1OCCN1CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][C:10]1=[O:11].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][C:10]1=[O:11] | CCOC(=O)CN1CCOC1=O.NN | NNC(=O)CN1CCOC1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=C1NCCO1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[N;D1;H2:8] | 77 | [{"value": 77.0, "product": "O=C1OCCN1CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2-oxo-oxazolidin-3-yl)-acetic acid ethyl ester (Potts, Kevin T.; Bhattacharjee, Debkumar; Kanemasa, Shuji. Journal of Organic Chemistry (1980), 45(24), 4985-8.) in ethanol was reacted with hydrazine hydrate (1 equivalent) at rt for 72 h. Evaporation of all volatiles and chromatography (S... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | C1COC[NH]1 | HO- | C(C)O | null | null | CCOC(=O)CN1CCOC1=O.NN>C(C)O>NNC(=O)CN1CCOC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74ccf69a957c42008a1be2a9ebfe8ffd | Cc1c[nH]cn1.N#Cc1cc(F)ccc1F>>Cc1cn(-c2ccc(F)cc2C#N)cn1 | FC1=C(C#N)C=C(C=C1)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>FC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1cc(F)ccc1F | Cc1cn(-c2ccc(F)cc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 41 | [{"value": 41.0, "product": "FC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2,5-difluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 20 h at 90° C. After aqueous workup and crystallization from ethyl acetate the title compound was obtained as a white solid (yield: 41%). MS: m/e=202.3 [M+H]+.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1cc(F)ccc1F>>Cc1cn(-c2ccc(F)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19612c2854304b128a256434079d562e | C=[N+](C)C.Cc1cn(-c2ccc(F)cc2C#N)cn1>>Cc1ncn(-c2ccc(F)cc2C#N)c1CN(C)C | FC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)F)C | [CH2:16]=[N+:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=[N+](C)C.Cc1cn(-c2ccc(F)cc2C#N)cn1 | Cc1ncn(-c2ccc(F)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 34 | [{"value": 34.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 5-fluoro-2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 24 h at 90° C. Evaporation of the solvent, aqueous workup and crystallization from ethyl acetate/diisopropylether afforded the title compound as a white solid (yield: 34%). MS: m/e=259.2 [M+H]+.... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccc(F)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(F)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbfa18bf9ced4f41a70d62c31320fbb7 | Cc1c[nH]cn1.N#Cc1cc(C(F)(F)F)ccc1F>>Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1 | CC1=CN=CN1C1=C(C#N)C=C(C=C1)C(F)(F)F.FC1=C(C#N)C=C(C=C1)C(F)(F)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>CC=1N=CN(C1)C1=C(C#N)C=C(C=C1)C(F)(F)F | [CH3:1][c:2]1[cH:3][nH:4][cH:17][n:18]1.F[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[C:15]#[N:16]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[C:15]#[N:16])[cH:17][n:18]1 | Cc1c[nH]cn1.N#Cc1cc(C(F)(F)F)ccc1F | Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-5-(trifluoromethyl)-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After aqueous workup and extraction with ethyl acetate the organic phase was dried over sodium sulfate and concentrated to afford a 3.4:1 mixture of the title compound an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1cc(C(F)(F)F)ccc1F>>Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c28d8651a79042e48de28c766b8131d8 | C=[N+](C)C.Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1>>Cc1ncn(-c2ccc(C(F)(F)F)cc2C#N)c1CN(C)C | CC=1N=CN(C1)C1=C(C#N)C=C(C=C1)C(F)(F)F.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)C(F)(F)F)C | [CH2:19]=[N+:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[C:16]#[N:17])[cH:18]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[C:16]#[N:17])[c:18]1[CH2:19][N:20]([CH3:21])[CH3:22] | C=[N+](C)C.Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1 | Cc1ncn(-c2ccc(C(F)(F)F)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH2;D2;+0:4]-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3] | 53 | [{"value": 53.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)C(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 2-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 16 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as a yellow oil that was sufficiently pure to be used in the next... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccc(C(F)(F)F)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(C(F)(F)F)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a812745423274ea5a7d04da5c3617f98 | Cc1c[nH]cn1.Cc1ccc(F)c(C#N)c1>>Cc1ccc(-n2cnc(C)c2)c(C#N)c1 | FC1=C(C#N)C=C(C=C1)C.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>CC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | [nH:6]1[cH:7][n:8][c:9]([CH3:10])[cH:11]1.F[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:15][c:12]1[C:13]#[N:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[cH:7][n:8][c:9]([CH3:10])[cH:11]2)[c:12]([C:13]#[N:14])[cH:15]1 | Cc1c[nH]cn1.Cc1ccc(F)c(C#N)c1 | Cc1ccc(-n2cnc(C)c2)c(C#N)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 48 | [{"value": 48.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-5-methyl-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After aqueous workup the title compound was obtained as a white solid (yield: 48%). MS: m/e=198.4 [M+H]+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HF | null | null | null | Cc1c[nH]cn1.Cc1ccc(F)c(C#N)c1>>Cc1ccc(-n2cnc(C)c2)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8ae426e86e24972b6e313864b0245ee | C=[N+](C)C.Cc1ccc(-n2cnc(C)c2)c(C#N)c1>>Cc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 | CC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)C)C | [CH2:12]=[N+:13]([CH3:14])[CH3:15].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[cH:7][n:8][c:9]([CH3:10])[cH:11]2)[c:16]([C:17]#[N:18])[cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[cH:7][n:8][c:9]([CH3:10])[c:11]2[CH2:12][N:13]([CH3:14])[CH3:15])[c:16]([C:17]#[N:18])[cH:19]1 | C=[N+](C)C.Cc1ccc(-n2cnc(C)c2)c(C#N)c1 | Cc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 249fb0d9f9284422773ed0273821c25f0e6f76099b8adfc8b3bfe580ab3e55d2 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH2;D2;+0:4]-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3] | 64 | [{"value": 64.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 5-methyl-2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 4 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as an oil that solidified upon standing (yield: 64%). MS: m/e=255.2 [M+H]+.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1ccc(-n2cnc(C)c2)c(C#N)c1>CN(C)C=O>Cc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5daee9a71dcd4164aade629674a17850 | COc1ccc(F)c(C#N)c1.Cc1c[nH]cn1>>COc1ccc(-n2cnc(C)c2)c(C#N)c1 | FC1=C(C#N)C=C(C=C1)OC.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>COC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C | F[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][c:13]1[C:14]#[N:15].[nH:7]1[cH:8][n:9][c:10]([CH3:11])[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]([CH3:11])[cH:12]2)[c:13]([C:14]#[N:15])[cH:16]1 | COc1ccc(F)c(C#N)c1.Cc1c[nH]cn1 | COc1ccc(-n2cnc(C)c2)c(C#N)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 72 | [{"value": 72.0, "product": "COC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-5-methoxy-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 48 h at 100° C. After aqueous workup and crystallization from ethyl acetate/diisopropylether the title compound was obtained as a white solid (yield: 72%). MS: m/e=214.1 [M+H]+.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HF | null | null | null | COc1ccc(F)c(C#N)c1.Cc1c[nH]cn1>>COc1ccc(-n2cnc(C)c2)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c73c22f5276475584cd66c6da07f980 | C=[N+](C)C.COc1ccc(-n2cnc(C)c2)c(C#N)c1>>COc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 | COC=1C=CC(=C(C#N)C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)OC)C | [CH2:13]=[N+:14]([CH3:15])[CH3:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]([CH3:11])[cH:12]2)[c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]([CH3:11])[c:12]2[CH2:13][N:14]([CH3:15])[CH3:16])[c:17]([C:18]#[N:19])[cH:20]1 | C=[N+](C)C.COc1ccc(-n2cnc(C)c2)c(C#N)c1 | COc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 249fb0d9f9284422773ed0273821c25f0e6f76099b8adfc8b3bfe580ab3e55d2 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH2;D2;+0:4]-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3] | 83 | [{"value": 83.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 5-methoxy-2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 16 h at 70° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as an oil (yield: 83%). MS: m/e=271.4 [M+H]+.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | null | CN(C)C=O | null | null | C=[N+](C)C.COc1ccc(-n2cnc(C)c2)c(C#N)c1>CN(C)C=O>COc1ccc(-n2cnc(C)c2CN(C)C)c(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-953fd019dabd4558a10ba291c9bfb23d | Fc1ccc(OC(F)(F)F)cc1.O=C=O>>O=Cc1cc(OC(F)(F)F)ccc1F | CN(C)C=O.C(C)(C)(C)[Li].FC1=CC=C(C=C1)OC(F)(F)F.C(=O)=O>>FC1=C(C=O)C=C(C=C1)OC(F)(F)F | [cH:3]1[cH:4][c:5]([O:6][C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][c:13]1[F:14].O=[C:2]=[O:1]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][c:13]1[F:14] | Fc1ccc(OC(F)(F)F)cc1.O=C=O | O=Cc1cc(OC(F)(F)F)ccc1F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 024699e76959a97c93dae17db880a1da93c50479e28cbf49bdeb80135dcc4c8b | 3c6b0d8e5d1da1ba2dcb896a8f9334c1841604d7035e307445ba5ecf475b5051 | c1ccccc1 | O=[C;H0;D2;+0:1]=[O;D1;H0:2].[F;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[F;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7]:[c:8] | 53 | [{"value": 53.0, "product": "FC1=C(C=O)C=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 mL) was cooled to <−70° C. and tert.-butyllithium (86 mL, 1.5 M in pentane, 129 mmol) was added at such a rate that temperature was kept <−70° C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 mL, 150 mmol) was added... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | null | 0.25 | Fc1ccc(OC(F)(F)F)cc1.O=C=O>C1CCOC1>O=Cc1cc(OC(F)(F)F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3211107e5894fde95e55084ef018fbe | NO.O=Cc1cc(OC(F)(F)F)ccc1F>>O/N=C/c1cc(OC(F)(F)F)ccc1F | FC1=C(C=O)C=C(C=C1)OC(F)(F)F.Cl.NO.C(C)(=O)[O-].[Na+]>>FC1=C(/C=N/O)C=C(C=C1)OC(F)(F)F | [OH:1][NH2:2].O=[CH:3][c:4]1[cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]1[F:15]>>[OH:1]/[N:2]=[CH:3]/[c:4]1[cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]1[F:15] | NO.O=Cc1cc(OC(F)(F)F)ccc1F | O/N=C/c1cc(OC(F)(F)F)ccc1F | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H1:6]/[N;H0;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 88 | [{"value": 88.0, "product": "FC1=C(/C=N/O)C=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "FC1=C(/C=N/O)C=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-fluoro-5-trifluoromethoxy-benzaldehyde (9.78 g, 47 mmol) in ethanol (50 mL) was treated with hydroxylamine HCl (3.59 g, 52 mmol) and sodium acetate (4.27 g, 52 mmol). The resulting mixture was heated under reflux for 2 h. The solvent was then evaporated and the residue stirred with water (50 mL). The pr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccccc1 | HO- | C(C)O | null | null | NO.O=Cc1cc(OC(F)(F)F)ccc1F>C(C)O>O/N=C/c1cc(OC(F)(F)F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fed7690638d9443b91f6c79a15da0e95 | O/N=C/c1cc(OC(F)(F)F)ccc1F>>N#Cc1cc(OC(F)(F)F)ccc1F | FC(C(=O)OC(C(F)(F)F)=O)(F)F.FC1=C(/C=N/O)C=C(C=C1)OC(F)(F)F.C(C)N(CC)CC>>FC1=C(C#N)C=C(C=C1)OC(F)(F)F | O/[N:1]=[CH:2]/[c:3]1[cH:4][c:5]([O:6][C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][c:13]1[F:14]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][C:7]([F:8])([F:9])[F:10])[cH:11][cH:12][c:13]1[F:14] | O/N=C/c1cc(OC(F)(F)F)ccc1F | N#Cc1cc(OC(F)(F)F)ccc1F | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccccc1 | O/[N;H0;D2;+0:1]=[CH;D2;+0:2]/[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "FC1=C(C#N)C=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "FC1=C(C#N)C=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of E-2-fluoro-5-trifluoromethoxy-benzaldehyde oxime (47.5 g, 213 mmol) in THF (400 mL) was added triethylamine (65.0 mL, 466 mmol). The mixture was cooled in an ice bath and trifluoroacetic anhydride (32.8 mL, 236 mmol) was added at such a rate that the temperature was kept <30° C. After 1 h at rt all vol... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1ccccc1 | HO- | C1CCOC1 | null | null | O/N=C/c1cc(OC(F)(F)F)ccc1F>C1CCOC1>N#Cc1cc(OC(F)(F)F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a7d48fb8a5447d6847e531f09c3f6a8 | Cc1c[nH]cn1.N#Cc1cc(OC(F)(F)F)ccc1F>>Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1 | CC1=CN=CN1C1=C(C#N)C=C(C=C1)OC(F)(F)F.FC1=C(C#N)C=C(C=C1)OC(F)(F)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>CC=1N=CN(C1)C1=C(C#N)C=C(C=C1)OC(F)(F)F | [CH3:1][c:2]1[cH:3][nH:4][cH:18][n:19]1.F[c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][c:15]1[C:16]#[N:17]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[C:16]#[N:17])[cH:18][n:19]1 | Cc1c[nH]cn1.N#Cc1cc(OC(F)(F)F)ccc1F | Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-5-trifluoromethoxy-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. Aqueous workup afforded a 3:1 mixture of the title compound and its regioisomer [2-(5-methyl-imidazol-1-yl)-5-trifluoromethoxy-benzonitrile] as a light brown viscous oil (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1cc(OC(F)(F)F)ccc1F>>Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46a6c402442a407db96fefbc47d9498a | C=[N+](C)C.Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1>>Cc1ncn(-c2ccc(OC(F)(F)F)cc2C#N)c1CN(C)C | CC=1N=CN(C1)C1=C(C#N)C=C(C=C1)OC(F)(F)F.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)OC(F)(F)F)C | [CH2:20]=[N+:21]([CH3:22])[CH3:23].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][c:16]2[C:17]#[N:18])[cH:19]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][c:16]2[C:17]#[N:18])[c:19]1[CH2:20][N:21]([CH3:22])[CH3:23] | C=[N+](C)C.Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1 | Cc1ncn(-c2ccc(OC(F)(F)F)cc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH2;D2;+0:4]-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3] | 38 | [{"value": 38.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=C(C=C1)OC(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 2-(4-methyl-imidazol-1-yl)-5-trifluoromethoxy benzonitrile (+regioisomer) was reacted with Eschenmoser's salt in DMF for 24 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography afforded the title compound as a colorless oil that was sufficiently pure to be used in the ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccc(OC(F)(F)F)cc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccc(OC(F)(F)F)cc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a854e4f858b74d69aec4de4b27066ade | Cc1c[nH]cn1.N#Cc1ccccc1F>>Cc1cn(-c2ccccc2C#N)cn1 | FC1=C(C#N)C=CC=C1.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>CC=1N=CN(C1)C1=C(C#N)C=CC=C1 | [CH3:1][c:2]1[cH:3][nH:4][cH:13][n:14]1.F[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]#[N:12]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]#[N:12])[cH:13][n:14]1 | Cc1c[nH]cn1.N#Cc1ccccc1F | Cc1cn(-c2ccccc2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 60 | [{"value": 60.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-fluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After aqueous workup the title compound was obtained as a white solid (yield: 60%). MS: m/e=184.2 [M+H]+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1ccccc1F>>Cc1cn(-c2ccccc2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50144101af994a68869211d3ed0fe9af | C=[N+](C)C.Cc1cn(-c2ccccc2C#N)cn1>>Cc1ncn(-c2ccccc2C#N)c1CN(C)C | CC=1N=CN(C1)C1=C(C#N)C=CC=C1.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C=CC=C1)C | [CH2:15]=[N+:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]#[N:13])[cH:14]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]#[N:13])[c:14]1[CH2:15][N:16]([CH3:17])[CH3:18] | C=[N+](C)C.Cc1cn(-c2ccccc2C#N)cn1 | Cc1ncn(-c2ccccc2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 57 | [{"value": 57.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 2-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 5 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 96:4) afforded the title compound as a light yellow oil (yield: 57%). MS: m/e=241.4 [M... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2ccccc2C#N)cn1>CN(C)C=O>Cc1ncn(-c2ccccc2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12cdd75d8c334dacbebca8990252bc91 | Cc1c[nH]cn1.N#Cc1c(F)cccc1F>>Cc1cn(-c2cccc(F)c2C#N)cn1 | ClCCl.FC1=C(C#N)C(=CC=C1)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C#N)C(=CC=C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([F:10])[c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1c(F)cccc1F | Cc1cn(-c2cccc(F)c2C#N)cn1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 29 | [{"value": 29.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2,6-difluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) the title compound was obtained as an off-white solid (yield: 29%). 1H-NMR (300 MHz, DMSO): δ=2.19 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | CO | null | null | Cc1c[nH]cn1.N#Cc1c(F)cccc1F>CO>Cc1cn(-c2cccc(F)c2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df2a07e78d594c3eb949a2ed98043806 | C=[N+](C)C.Cc1cn(-c2cccc(F)c2C#N)cn1>>Cc1ncn(-c2cccc(F)c2C#N)c1CN(C)C | FC1=C(C#N)C(=CC=C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>CN(C)CC1=C(N=CN1C1=C(C#N)C(=CC=C1)F)C | [CH2:16]=[N+:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([F:11])[c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([F:11])[c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=[N+](C)C.Cc1cn(-c2cccc(F)c2C#N)cn1 | Cc1ncn(-c2cccc(F)c2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 46 | [{"value": 46.0, "product": "CN(C)CC1=C(N=CN1C1=C(C#N)C(=CC=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 2-fluoro-6-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 7 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 97:3) afforded the title compound as a light yellow solid (yield: 46%). 1H-NM... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2cccc(F)c2C#N)cn1>CN(C)C=O>Cc1ncn(-c2cccc(F)c2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cda4f703e3f749998a1fababbc5c6b13 | Cc1c[nH]cn1.N#Cc1c(F)cccc1Cl>>Cc1cn(-c2cccc(Cl)c2C#N)cn1 | ClC1=C(C#N)C(=CC=C1)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+]>>ClC1=C(C#N)C(=CC=C1)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][nH:4][cH:14][n:15]1.F[c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]1[C:12]#[N:13]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]2[C:12]#[N:13])[cH:14][n:15]1 | Cc1c[nH]cn1.N#Cc1c(F)cccc1Cl | Cc1cn(-c2cccc(Cl)c2C#N)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]):[c:13]:1 | 73 | [{"value": 73.0, "product": "ClC1=C(C#N)C(=CC=C1)N1C=NC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84a, 2-chloro-6-fluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After aqueous workup and crystallization from ethyl acetate/diisopropylether the title compound was obtained as an off-white solid (yield: 73%). MS: m/e=218.2 [M+H]+.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | null | null | null | Cc1c[nH]cn1.N#Cc1c(F)cccc1Cl>>Cc1cn(-c2cccc(Cl)c2C#N)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6eb935ca30cc4fe5b614b76ce42cba50 | C=[N+](C)C.Cc1cn(-c2cccc(Cl)c2C#N)cn1>>Cc1ncn(-c2cccc(Cl)c2C#N)c1CN(C)C | ClC1=C(C#N)C(=CC=C1)N1C=NC(=C1)C.C[N+](=C)C.[I-]>>ClC1=C(C#N)C(=CC=C1)N1C=NC(=C1CN(C)C)C | [CH2:16]=[N+:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]2[C:13]#[N:14])[cH:15]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([Cl:11])[c:12]2[C:13]#[N:14])[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=[N+](C)C.Cc1cn(-c2cccc(Cl)c2C#N)cn1 | Cc1ncn(-c2cccc(Cl)c2C#N)c1CN(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 48f30e5b225a2160b703f5cfd14da61734d590f07d84c69ae9ed822475e2cacb | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-n2ccnc2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[cH;D2;+0:11]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 29 | [{"value": 29.0, "product": "ClC1=C(C#N)C(=CC=C1)N1C=NC(=C1CN(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 84b, 2-chloro-6-(4-methyl-imidazol-1-yl)-benzonitrile was reacted with Eschenmoser's salt in DMF for 5 h at 90° C. Evaporation of the solvent, aqueous workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) afforded the title compound as a white solid (yield: 29%). MS: m/e=275.... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | null | CN(C)C=O | null | null | C=[N+](C)C.Cc1cn(-c2cccc(Cl)c2C#N)cn1>CN(C)C=O>Cc1ncn(-c2cccc(Cl)c2C#N)c1CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f658d5b309bd4d8f99d01cf06c94cfd0 | CCOC(=O)Cn1c(C)cccc1=O.NN>>Cc1cccc(=O)n1CC(=O)NN | C(C)OC(CN1C(C=CC=C1C)=O)=O.O.NN>>CC1=CC=CC(N1CC(=O)NN)=O | CCO[C:10]([CH2:9][n:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1=[O:7])=[O:11].[NH2:12][NH2:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](=[O:7])[n:8]1[CH2:9][C:10](=[O:11])[NH:12][NH2:13] | CCOC(=O)Cn1c(C)cccc1=O.NN | Cc1cccc(=O)n1CC(=O)NN | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 88 | [{"value": 88.0, "product": "CC1=CC=CC(N1CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (6-methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester (Petride, Horia; Raileanu, Dan. Revue Roumaine de Chimie (1988), 33(7), 729-39.) in ethanol was reacted with hydrazine hydrate (1.8 equivalents) at rt for 96 h. The mixture was concentrated and crystallized from ethanol/diisopropyle... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1c(C)cccc1=O.NN>C(C)O>Cc1cccc(=O)n1CC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-240c2c563c7543ad9d8e9928e954eff1 | CCOC(=O)CBr.Cc1cccnc1O>>CCOC(=O)Cn1cccc(C)c1=O | OC1=NC=CC=C1C.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C(=CC=C1)C)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:8][cH:9][cH:10][c:11]([CH3:12])[c:13]1[OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][cH:10][c:11]([CH3:12])[c:13]1=[O:14] | CCOC(=O)CBr.Cc1cccnc1O | CCOC(=O)Cn1cccc(C)c1=O | null | null | CN(C)C=O | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[OH;D1;+0:13]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[c:7](-[C;D1;H3:6]):[c;H0;D3;+0:12]:1=[O;H0;D1;+0:13] | 84 | [{"value": 84.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 2-hydroxy-3-methyl-pyridine (4.1 g, 37 mmol), ethyl bromoacetate (5.9 g, 35 mmol) and potassium carbonate (4.9 g, 35 mmol) in DMF (60 ml) was stirred at rt for 16 h. After evaporation of the solvent and extractive workup (ethyl acetate/water) the organic phase was concentrated and chromatographed (SiO2, he... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | CN(C)C=O | null | 16 | CCOC(=O)CBr.Cc1cccnc1O>CN(C)C=O>CCOC(=O)Cn1cccc(C)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a53b2c8fed641548f22ade3e5cfc361 | CCOC(=O)Cn1cccc(C)c1=O.NN>>Cc1cccn(CC(=O)NN)c1=O | C(C)OC(CN1C(C(=CC=C1)C)=O)=O.O.NN>>CC=1C(N(C=CC1)CC(=O)NN)=O | CCO[C:8]([CH2:7][n:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:12]1=[O:13])=[O:9].[NH2:10][NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]([CH2:7][C:8](=[O:9])[NH:10][NH2:11])[c:12]1=[O:13] | CCOC(=O)Cn1cccc(C)c1=O.NN | Cc1cccn(CC(=O)NN)c1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 96 | [{"value": 96.0, "product": "CC=1C(N(C=CC1)CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 72 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 96%). MS: m/e=204.4 [... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1cccc(C)c1=O.NN>C(C)O>Cc1cccn(CC(=O)NN)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b26053b48ed4d74b4d504e79c64d4ac | CCOC(=O)CBr.Cc1ccnc(O)c1>>CCOC(=O)Cn1ccc(C)cc1=O | CCCCCCC.OC1=NC=CC(=C1)C.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C=C(C=C1)C)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]1[OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]1=[O:14] | CCOC(=O)CBr.Cc1ccnc(O)c1 | CCOC(=O)Cn1ccc(C)cc1=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[n;H0;D2;+0:12]:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:[c;H0;D3;+0:7]:1=[O;H0;D1;+0:6] | 77 | [{"value": 77.0, "product": "C(C)OC(CN1C(C=C(C=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 2-hydroxy-4-methyl-pyridine was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 40:60) afforded the title compound as a colorless liquid (yield: 77%). MS: m/e=196.1 [M+H]+.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)CBr.Cc1ccnc(O)c1>C(C)(=O)OCC>CCOC(=O)Cn1ccc(C)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a56cf2991a674d33a0e86788018668c2 | CCOC(=O)Cn1ccc(C)cc1=O.NN>>Cc1ccn(CC(=O)NN)c(=O)c1 | C(C)OC(CN1C(C=C(C=C1)C)=O)=O.O.NN>>CC1=CC(N(C=C1)CC(=O)NN)=O | CCO[C:7]([CH2:6][n:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:13][c:11]1=[O:12])=[O:8].[NH2:9][NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][n:5]([CH2:6][C:7](=[O:8])[NH:9][NH2:10])[c:11](=[O:12])[cH:13]1 | CCOC(=O)Cn1ccc(C)cc1=O.NN | Cc1ccn(CC(=O)NN)c(=O)c1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 94 | [{"value": 94.0, "product": "CC1=CC(N(C=C1)CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (4-methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 72 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 94%). MS: m/e=204.3 [... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1ccc(C)cc1=O.NN>C(C)O>Cc1ccn(CC(=O)NN)c(=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cd7251ca273483383aabefc3005cce2 | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F>>CCOC(=O)COc1ncccc1C(F)(F)F | CCCCCCC.OC1=NC=CC=C1C(F)(F)F.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(COC1=NC=CC=C1C(F)(F)F)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17] | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F | CCOC(=O)COc1ncccc1C(F)(F)F | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | 2 | [{"value": 2.0, "product": "C(C)OC(COC1=NC=CC=C1C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 2-hydroxy-3-(trifluoromethyl)-pyridine was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 40:60) afforded 2 compounds. The title compound was eluted first and was obtained as a colorless liquid (y... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F>C(C)(=O)OCC>CCOC(=O)COc1ncccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cf40cf18f0643898bde32008080295c | CCOC(=O)COc1ncccc1C(F)(F)F.NN>>NNC(=O)COc1ncccc1C(F)(F)F | C(C)OC(COC1=NC=CC=C1C(F)(F)F)=O.O.NN>>FC(C=1C(=NC=CC1)OCC(=O)NN)(F)F | CCO[C:3](=[O:4])[CH2:5][O:6][c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[n:8][cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | CCOC(=O)COc1ncccc1C(F)(F)F.NN | NNC(=O)COc1ncccc1C(F)(F)F | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 77 | [{"value": 77.0, "product": "FC(C=1C(=NC=CC1)OCC(=O)NN)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-trifluoromethyl-pyridin-2-yloxy)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 72 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 77%). MS: m/e=236.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)COc1ncccc1C(F)(F)F.NN>C(C)O>NNC(=O)COc1ncccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-278a7a96bc1d4e5eba84a67738ec2a56 | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F>>CCOC(=O)Cn1cccc(C(F)(F)F)c1=O | OC1=NC=CC=C1C(F)(F)F.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C(=CC=C1)C(F)(F)F)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]1[OH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]1=[O:17] | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F | CCOC(=O)Cn1cccc(C(F)(F)F)c1=O | null | null | null | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[c:13]:[n;H0;D2;+0:14]:[c;H0;D3;+0:15]:1-[OH;D1;+0:16]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[c:10](-[C:7](-[F;D1;H0:6])(-[F;D1;H0:8])-[F;D1;H0:9]):[c;H0;... | 84 | [{"value": 84.0, "product": "C(C)OC(CN1C(C(=CC=C1)C(F)(F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described in example 322a, reaction of 2-hydroxy-3-(trifluoromethyl)-pyridine with ethyl bromoacetate and potassium carbonate gave 2 products. The title compound was eluted second and was obtained as a colorless liquid (yield: 84%). MS: m/e=250.1[M+H]+.
Conditions: See reaction.notes.procedure_details.
Workup: gave ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | null | CCOC(=O)CBr.Oc1ncccc1C(F)(F)F>>CCOC(=O)Cn1cccc(C(F)(F)F)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3330386600d7404293cddcb9102ad6e0 | CCOC(=O)Cn1cccc(C(F)(F)F)c1=O.NN>>NNC(=O)Cn1cccc(C(F)(F)F)c1=O | C(C)OC(CN1C(C(=CC=C1)C(F)(F)F)=O)=O.O.NN>>O=C1N(C=CC=C1C(F)(F)F)CC(=O)NN | CCO[C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]1=[O:16].[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]1=[O:16] | CCOC(=O)Cn1cccc(C(F)(F)F)c1=O.NN | NNC(=O)Cn1cccc(C(F)(F)F)c1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 95 | [{"value": 95.0, "product": "O=C1N(C=CC=C1C(F)(F)F)CC(=O)NN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (2-oxo-3-trifluoromethyl-2H-pyridin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 72 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 95%). MS: m/... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1cccc(C(F)(F)F)c1=O.NN>C(C)O>NNC(=O)Cn1cccc(C(F)(F)F)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9f8e0146cd1486e80dc7c39ce60eb2b | CCOC(=O)CBr.COc1cccnc1O>>CCOC(=O)Cn1cccc(OC)c1=O | CCCCCCC.OC1=NC=CC=C1OC.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C(=CC=C1)OC)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]1[OH:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]1=[O:15] | CCOC(=O)CBr.COc1cccnc1O | CCOC(=O)Cn1cccc(OC)c1=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#8:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[OH;D1;+0:13]>>[#8:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]):[c;H0;D3;+0:12]:1=[O;H0;D1;+0:13] | 92 | [{"value": 92.0, "product": "C(C)OC(CN1C(C(=CC=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 2-hydroxy-3-methoxy-pyridine was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0: 100) afforded the title compound as a white solid (yield: 92%). MS: m/e=212.3[M+H]+.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)CBr.COc1cccnc1O>C(C)(=O)OCC>CCOC(=O)Cn1cccc(OC)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-009bb3719c1a404b88ea4d3fcf8de037 | CCOC(=O)Cn1cccc(OC)c1=O.NN>>COc1cccn(CC(=O)NN)c1=O | C(C)OC(CN1C(C(=CC=C1)OC)=O)=O.O.NN>>COC=1C(N(C=CC1)CC(=O)NN)=O | CCO[C:9]([CH2:8][n:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:13]1=[O:14])=[O:10].[NH2:11][NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7]([CH2:8][C:9](=[O:10])[NH:11][NH2:12])[c:13]1=[O:14] | CCOC(=O)Cn1cccc(OC)c1=O.NN | COc1cccn(CC(=O)NN)c1=O | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 83 | [{"value": 83.0, "product": "COC=1C(N(C=CC1)CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (3-methoxy-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 16 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 83%). MS: m/e=220.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1cccc(OC)c1=O.NN>C(C)O>COc1cccn(CC(=O)NN)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a2631986ac64ab8825363dad33fddaa | CCOC(=O)CBr.Cc1ccnc(O)c1>>CCOC(=O)Cn1cc(C)ccc1=O | CCCCCCC.OC1=NC=CC(=C1)C.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CN1C(C=CC(=C1)C)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[n:7]1[cH:12][cH:11][c:9]([CH3:10])[cH:8][c:13]1[OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][c:9]([CH3:10])[cH:11][cH:12][c:13]1=[O:14] | CCOC(=O)CBr.Cc1ccnc(O)c1 | CCOC(=O)Cn1cc(C)ccc1=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6dfdbac002000b49828e22c4b69d4571a0c0c3202697b85b5a08225e6955028a | 5e9e0b01f8c9a1c10ac2bdfadca2d4bb3d9d0593654f2be0a33adb4d01012cf3 | O=c1cccc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[c:7]1:[c:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[OH;D1;+0:12]):[cH;D2;+0:13]:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[cH;D2;+0:13]:[c:7](-[C;D1;H3:6]):[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:11]:1=[O;H0;D1;+0:12] | 76 | [{"value": 76.0, "product": "C(C)OC(CN1C(C=CC(=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 320a, 2-hydroxy-4-methyl-pyridine was reacted with ethyl bromoacetate and potassium carbonate. Extractive workup followed by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100) afforded the title compound as a colorless liquid (yield: 76%). MS: m/e=196.1 [M+H]+.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)CBr.Cc1ccnc(O)c1>C(C)(=O)OCC>CCOC(=O)Cn1cc(C)ccc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45e71c41ddfd47768b57c0412ff6d84f | CCOC(=O)Cn1cc(C)ccc1=O.NN>>Cc1ccc(=O)n(CC(=O)NN)c1 | C(C)OC(CN1C(C=CC(=C1)C)=O)=O.O.NN>>CC=1C=CC(N(C1)CC(=O)NN)=O | CCO[C:9]([CH2:8][n:7]1[c:5](=[O:6])[cH:4][cH:3][c:2]([CH3:1])[cH:13]1)=[O:10].[NH2:11][NH2:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](=[O:6])[n:7]([CH2:8][C:9](=[O:10])[NH:11][NH2:12])[cH:13]1 | CCOC(=O)Cn1cc(C)ccc1=O.NN | Cc1ccc(=O)n(CC(=O)NN)c1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | O=c1cccc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[N;D1;H2:5]-[NH2;D1;+0:6]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[N;D1;H2:5] | 92 | [{"value": 92.0, "product": "CC=1C=CC(N(C1)CC(=O)NN)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 112a, (5-methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (1.2 equivalents) at rt for 16 h. The mixture was concentrated and crystallized from ethanol/diisopropylether and the compound was obtained as a white solid (yield: 92%). MS: m/e=204.1 [... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccncc1 | HO- | C(C)O | null | null | CCOC(=O)Cn1cc(C)ccc1=O.NN>C(C)O>Cc1ccc(=O)n(CC(=O)NN)c1 |
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