dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f63e52fc4e484a91b3e232e390750d6f | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-]>>N#Cc1ncc(Br)cc1[N+](=O)[O-] | NC1=NC=C(C=C1[N+](=O)[O-])Br.C(C)(C)(C)ON=O.C(C)#N>>BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-] | C[C:2]#[N:1].N[c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[N:1]#[C:2][c:3]1[n:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12] | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-] | N#Cc1ncc(Br)cc1[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 7be32428aabd580dfbed2e434f7904a98f0e54bc30b8b5f4dba0a6d14252e209 | 5270ba81df65d040f7a2858a28254c13e4f1fb0313393de6d45aa339bf5619bd | c1ccncc1 | C-[C;H0;D2;+0:1]#[N;D1;H0:2].N-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[#7;+:7]):[c:8]>>[#7;+:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[C;H0;D2;+0:1]#[N;D1;H0:2]):[#7;a:4]:[c:5] | 41 | [{"value": 41.0, "product": "BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 2-amino-5-bromo-3-nitropyridine (2.18 g, 10 mmol), cuprous cyanide (1.33 g, 15 mmol) and tert-butylnitrite (2.0 mL, 15 mmol) in acetonitrile (50 mL) at 60° C. for 2 hours. Cool the solution and partitioned between ethyl acetate (100 mL) and saturated aqueous NaHCO3 (100 mL). Extract the aqueous layer... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | CC#N.Nc1ncc(Br)cc1[N+](=O)[O-]>>N#Cc1ncc(Br)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b19e67aa6484aacaa880438d505242b | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-]>>Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | BrC=1C=C(C(=NC1)C#N)[N+](=O)[O-].[Br-].CC=1C(=NC=CC1)[Zn+]>>CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-] | [Zn+][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1.Br[c:8]1[cH:9][n:10][c:11]([C:12]#[N:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([C:12]#[N:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-] | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1 | C-C Coupling | OtherReaction | e4ecd4c8f01d2effb96acd4b7efc6dcca828274ea1bedd77506f1b8e3573c914 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccnc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[Zn+]):[#7;a:11]:[c:12]>>[C;D1;H3:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[#7;a:11]:[c:12] | 88 | [{"value": 88.0, "product": "CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5-bromo-3-nitropyridine-2-carbonitrile (228 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg), 3-methyl-2-pyridylzinc bromide (0.5 M in THF, 3 mL, 1.5 mmol) in THF (5 mL) at 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | Br-.Zn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1 | null | null | Cc1cccn[c]1[Zn+].N#Cc1ncc(Br)cc1[N+](=O)[O-]>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1>Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ec110cfd6604b6995af219e708ec667 | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1>>Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 | CC=1C(=NC=CC1)C=1C=C(C(=NC1)C#N)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-].C(C)O>>NC=1C(=NC=C(C1)C1=NC=CC=C1C)C(=O)N | [O-][N+:16](=[O:14])[c:15]1[c:11]([C:12]#[N:13])[n:10][cH:9][c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]2)[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([C:12]([NH2:13])=[O:14])[c:15]([NH2:16])[cH:17]1 | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1 | Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 | null | [Fe] | O | Functional Group Interconversion | OtherReaction | ede7d2a6ee11f3b3697b1dfb480a8f492854589e148f2058b38ac2e2cd797a36 | cb5481c22f68622a17796d4a172dd074a4fb2bd7f9c138bcaa93b97fc12e084f | c1ccc(-c2cccnc2)nc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[N+;H0;D3:7](-[O-])=[O;H0;D1;+0:8]):[c:9]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:8])-[c:3](:[#7;a:4]:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:9] | 94 | [{"value": 94.0, "product": "NC=1C(=NC=C(C1)C1=NC=CC=C1C)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Heat a solution of 5-(3-methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile (1 g, 4.1 mmol), iron (2.3 g, 40 mmol) and calcium chloride (560 mg, 5 mmol) in ethanol (15 mL) and water (4 mL) to reflux for 1 hour. Cool the mixture, filter through Celite and wash with ethyl acetate. Evaporate the filtrate and re-dissolve the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitro group | Primary amide.Primary amine | null | null | c1ccncc1.c1ccncc1 | Other | [Fe].O | null | null | Cc1cccnc1-c1cnc(C#N)c([N+](=O)[O-])c1>[Fe].O>Cc1cccnc1-c1cnc(C(N)=O)c(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d541d70246742768408266a370c8bc3 | COCc1nc2cc(-c3ncccc3C(F)(F)F)cnc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>>COCc1nc(Cl)c2ncc(-c3ncccc3C(F)(F)F)cc2n1 | P(=O)(Cl)(Cl)Cl.FC(C=1C(=NC=CC1)C1=CC=2N=C(NC(C2N=C1)=O)COC)(F)F.N1=C(C=CC=C1C)C>>ClC=1C2=C(N=C(N1)COC)C=C(C=N2)C2=NC=CC=C2C(F)(F)F | O=[c:6]1[nH:5][c:4]([CH2:3][O:2][CH3:1])[n:24][c:23]2[c:8]1[n:9][cH:10][c:11](-[c:12]1[n:13][cH:14][cH:15][cH:16][c:17]1[C:18]([F:19])([F:20])[F:21])[cH:22]2.O=P(Cl)(Cl)[Cl:7]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]([Cl:7])[c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][cH:14][cH:15][cH:16][c:17]3[C:18]([F:19])([F:20])[F:21])[cH:... | COCc1nc2cc(-c3ncccc3C(F)(F)F)cnc2c(=O)[nH]1.O=P(Cl)(Cl)Cl | COCc1nc(Cl)c2ncc(-c3ncccc3C(F)(F)F)cc2n1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 333a0516a9bcf357e640bc314ff77fe9ec1320c775bca1158466fec62a1bdede | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cnc3cncnc3c2)nc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[C:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[#7;a:10]:[c:11]>>[C:5]-[c:4]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[#7;a:10]:[c:11]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:3]:1 | null | [] | null | null | null | null | Dissolve 7-(3-trifluoromethyl-pyridin-2-yl)-2-methoxymethyl-3H-pyrido[3,2-d]pyrimidin-4-one (276 mg, 0.822 mmol) in CHCl3 (25 mL) and 2,6-lutidine (294 mg, 2.74 mmol). Add phosphorous oxycloride (0.255 mL, 2.74 mmol) dropwise and heat the resulting solution to reflux for 24 hours. Cool the solution and remove the solve... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2cncnc2c1 | c1cnc2cncnc2c1 | c1cnc2cncnc2c1.c1ccncc1 | HCl | C(Cl)(Cl)Cl | null | null | COCc1nc2cc(-c3ncccc3C(F)(F)F)cnc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>COCc1nc(Cl)c2ncc(-c3ncccc3C(F)(F)F)cc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9baff1f9762947f78bec357af27b36b8 | CCOCC.N#Cc1ncccc1Cl>>CC(=O)c1ncccc1Cl | ClC=1C(=NC=CC1)C#N.C1CCOC1.C(C)OCC.Cl>>C(C)(=O)C1=NC=CC=C1Cl | CC[O:3]C[CH3:1].N#[C:2][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[Cl:10]>>[CH3:1][C:2](=[O:3])[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[Cl:10] | CCOCC.N#Cc1ncccc1Cl | CC(=O)c1ncccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 643b9d210906c1df38fa997852698e729d0316bdb35f50266fb1b09ae476eb8e | a7c966337c9a564ffde7cdff914cb3598adf1a30626c7d972cd5f8fafc6bcb42 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-C-[CH3;D1;+0:2].N#[C;H0;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[CH3;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 2 | HOUR | Dissolve 3-chloro-2-cyanopyridine (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33:565-571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MeMgl in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Ketone | null | null | c1ccncc1 | Other | null | null | 2 | CCOCC.N#Cc1ncccc1Cl>>CC(=O)c1ncccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ceca5cd1c6a4e9aa6e737c0719f58ab | COCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2Cl)nc1N>>COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1 | [OH-].[Na+].N1=CC=CC=C1.COCC(=O)Cl.NC1=C(C=CC(=N1)C1=NC=CC=C1Cl)C(=O)N>>ClC=1C(=NC=CC1)C=1C=CC2=C(N=C(NC2=O)COC)N1 | O=[C:4](Cl)[CH2:3][O:2][CH3:1].[NH2:5][c:6]1[n:7][c:8](-[c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[Cl:15])[cH:16][cH:17][c:18]1[C:19](=[O:20])[NH2:21]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]2[n:7][c:8](-[c:9]3[n:10][cH:11][cH:12][cH:13][c:14]3[Cl:15])[cH:16][cH:17][c:18]2[c:19](=[O:20])[nH:21]1 | COCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2Cl)nc1N | COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 614645d801f7c5726ec106aa02b43279861de36ea60b67b39b15bd956115aa68 | 02d67ba88d19cec9fd983cfc9ce8356800130d81fa7c25da407b402df0800696 | O=c1[nH]cnc2nc(-c3ccccn3)ccc12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[NH2;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[#7;a:11]:[c:12]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[#7;a:11]:[c:12]):[c:7](:[c:8]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:4]:1 | null | [] | null | null | 8 | HOUR | Dissolve 6-amino-3′-chloro-[2,2′]bipyridinyl-5-carboxylic acid amide (0.5 g, 2.02 mmol) in anhydrous THF (10 mL) under N2 atmosphere. Add drop wise pyridine (0.36 g, 4.04 mmol) and methoxyacetyl chloride (0.48 g, 4.04 mmol) to the reaction mixture and stir at room temperature overnight. Add 10% aq. NaOH (10 mL) and ref... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Primary amine | null | c1ccncc1 | c1ccc2cncnc2n1 | c1ccc2cncnc2n1.c1ccncc1 | HCl | C1CCOC1 | null | 8 | COCC(=O)Cl.NC(=O)c1ccc(-c2ncccc2Cl)nc1N>C1CCOC1>COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3cbbc97b49b4f18939c73ad6166cc7a | COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>>COCc1nc(Cl)c2ccc(-c3ncccc3Cl)nc2n1 | ClC=1C(=NC=CC1)C=1C=CC2=C(N=C(NC2=O)COC)N1.N1=C(C=CC=C1C)C.O=P(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)COC)N=C(C=C2)C2=NC=CC=C2Cl | O=[c:6]1[nH:5][c:4]([CH2:3][O:2][CH3:1])[n:21][c:20]2[c:8]1[cH:9][cH:10][c:11](-[c:12]1[n:13][cH:14][cH:15][cH:16][c:17]1[Cl:18])[n:19]2.O=P(Cl)(Cl)[Cl:7]>>[CH3:1][O:2][CH2:3][c:4]1[n:5][c:6]([Cl:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[n:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[n:19][c:20]2[n:21]1 | COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl | COCc1nc(Cl)c2ccc(-c3ncccc3Cl)nc2n1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d47976970a5d5230c47ef65f20d9160cb77827992ffb6b76ceab53d201153dd5 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ccc3cncnc3n2)nc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[C:5]):[#7;a:6]:[c:7](:[#7;a:8]:[c:9]):[c:10]:1:[c:11]>>[C:5]-[c:4]1:[#7;a:6]:[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:3]:1 | null | [] | null | null | null | null | Reflux a mixture of 7-(3-chloro-pyridin-2-yl)-2-methoxymethyl-3H-pyrido[2,3-d]pyrimidin-4-one (0.25 g), 2,6-lutidine (0.44 g), and POCl3 (0.51 g) in CHCl3 (5 mL) for 20 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between EtOAc and saturated NaHCO3 solution. Wash the EtOAc porti... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2n1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccncc1 | HCl | C(Cl)(Cl)Cl | null | null | COCc1nc2nc(-c3ncccc3Cl)ccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>COCc1nc(Cl)c2ccc(-c3ncccc3Cl)nc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a91ff830304340ea99b8ec6790e64c8a | Nc1cccc2cnccc12.O=C(Cl)C(Cl)(Cl)Cl>>O=C(Nc1cccc2cnccc12)C(Cl)(Cl)Cl | NC1=C2C=CN=CC2=CC=C1.ClC(C(=O)Cl)(Cl)Cl>>ClC(C(=O)NC1=C2C=CN=CC2=CC=C1)(Cl)Cl | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12.Cl[C:2](=[O:1])[C:14]([Cl:15])([Cl:16])[Cl:17]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[C:14]([Cl:15])([Cl:16])[Cl:17] | Nc1cccc2cnccc12.O=C(Cl)C(Cl)(Cl)Cl | O=C(Nc1cccc2cnccc12)C(Cl)(Cl)Cl | null | null | ClCCl.CCN(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2cnccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 65.1 | [{"value": 65.0, "product": "ClC(C(=O)NC1=C2C=CN=CC2=CC=C1)(Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.1, "product": "ClC(C(=O)NC1=C2C=CN=CC2=CC=C1)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | A solution of 5-aminoisoquinoline (1.0 g, 6.9 mmol) in dichloromethane (40 mL) and Et3N (1 mL) at 5° C. was treated with trichloroacetyl chloride (1.38 g, 7.6 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 14 hours, concentrated, diluted with ethyl acetate and washed with 1N HCl. The aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2cnccc2c1 | HCl | ClCCl.CCN(CC)CC | null | 14 | Nc1cccc2cnccc12.O=C(Cl)C(Cl)(Cl)Cl>ClCCl.CCN(CC)CC>O=C(Nc1cccc2cnccc12)C(Cl)(Cl)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-024b250d20b24d2abbbcdd14f7613d24 | C1CCC2=NCCCN2CC1.CCOC(C)=O.NCCc1cccc(F)c1>>O=C(NCCc1cccc(F)c1)Nc1cccc2cnccc12 | C(C)(=O)OCC.C1CCC2=NCCCN2CC1.FC=1C=C(C=CC1)CCN>>FC=1C=C(C=CC1)CCNC(=O)NC1=C2C=CN=CC2=CC=C1 | [N:13]1=[C:18]2[N:20]([CH2:19][CH2:16][CH2:17][CH2:22][CH2:23]2)[CH2:21][CH2:15][CH2:14]1.CCO[C:2](C)=[O:1].[NH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1)[NH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][c... | C1CCC2=NCCCN2CC1.CCOC(C)=O.NCCc1cccc(F)c1 | O=C(NCCc1cccc(F)c1)Nc1cccc2cnccc12 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 3611f44769d386b1bfe0c5b8c8d1388cb7f87a5a7a8498354be7aa1dd3b6c426 | 1da510b4e3613d637593754dc05473127c6553dbe8838e5750afa76b7abe6f45 | O=C(NCCc1ccccc1)Nc1cccc2cnccc12 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[CH2;D2;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[N;H0;D3;+0:6]2-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12]-2=[N;H0;D2;+0:13]-1.[C:14]-[C:15]-[NH2;D1;+0:16]>>[C:14]-[C:15]-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[c;H0;D3;+0:3]1... | 65 | [{"value": 65.0, "product": "FC=1C=C(C=CC1)CCNC(=O)NC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 1A (0.65 g, 2.25 mmol), DBU (0.85 g, 5.6 mmol) and 2-(3-fluorophenyl)ethylamine (0.35 g, 2.5 mmol) in acetonitrile (50 mL) were refluxed for 10 hours. The mixture was cooled, concentrated, diluted with ethyl acetate, washed twice with aqueous ammonium chloride and concentrated to dryness. The s... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Tertiary amine | Urea | C1CCC2=NCCCN2CC1 | c1ccc2cnccc2c1 | c1ccccc1.c1ccc2cnccc2c1 | HO- | C(C)#N | null | null | C1CCC2=NCCCN2CC1.CCOC(C)=O.NCCc1cccc(F)c1>C(C)#N>O=C(NCCc1cccc(F)c1)Nc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53554113e33343818790da31833728e8 | Cc1cc2c(N)cccc2nn1.O=C(Cl)C(Cl)(Cl)Cl>>Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1 | CC=1N=NC=2C=CC=C(C2C1)N.ClC(C(=O)Cl)(Cl)Cl>>ClC(C(=O)NC1=C2C=C(N=NC2=CC=C1)C)(Cl)Cl | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([NH2:6])[cH:13][cH:14][cH:15][c:16]2[n:17][n:18]1.Cl[C:7](=[O:8])[C:9]([Cl:10])([Cl:11])[Cl:12]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([NH:6][C:7](=[O:8])[C:9]([Cl:10])([Cl:11])[Cl:12])[cH:13][cH:14][cH:15][c:16]2[n:17][n:18]1 | Cc1cc2c(N)cccc2nn1.O=C(Cl)C(Cl)(Cl)Cl | Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1 | null | null | C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2nnccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6]):[c:12] | null | [] | null | null | null | null | The title compound was prepared using 3-methylcinnolin-5-amine (commercially available Maybridge), triethylamine, trichloroacetyl chloride and the procedure described in Example 1A.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2nnccc2c1 | HCl | C(C)N(CC)CC | null | null | Cc1cc2c(N)cccc2nn1.O=C(Cl)C(Cl)(Cl)Cl>C(C)N(CC)CC>Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd3cfb7d3b544124813d63fb69494554 | Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1.NCc1ccc(Cl)c(Cl)c1>>Cc1cc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc2nn1 | ClC=1C=C(CN)C=CC1Cl.ClC(C(=O)NC1=C2C=C(N=NC2=CC=C1)C)(Cl)Cl.C1CCC2=NCCCN2CC1>>ClC=1C=C(CNC(=O)NC2=C3C=C(N=NC3=CC=C2)C)C=CC1Cl | ClC(Cl)(Cl)[C:7]([NH:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:24][n:23][c:22]2[cH:21][cH:20][cH:19]1)=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([NH:6][C:7](=[O:8])[NH:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]3)[cH:19][cH:20][c... | Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1.NCc1ccc(Cl)c(Cl)c1 | Cc1cc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc2nn1 | null | null | null | Acylation | OtherReaction | ffe5fdd6070c0c75bd20e0ee13bc090c32d3281269178f04f3649ea77b9456e8 | 56b69d37f244d2e25fa681709adac1c85312cc9ccbfef016678a99d56e55b4c6 | O=C(NCc1ccccc1)Nc1cccc2nnccc12 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | The title compound was prepared using 3,4-dichlorobenzylamine, the product from Example 16A, DBU and the procedure described in Example 1B. MS (ESI+) m/z 362 (M+)+; 1H NMR (DMSO-d6) δ 2.88 (s, 3H), 4.36 (d, 2H), 7.10 (t, 1H), 7.34 (dd, 1H), 7.59 (m, 2H), 7.76 (t, 1H), 8.04 (d, 2H), 8.19 (d, 1H), 8.93 (s, 1H).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2nnccc2c1 | HCl | null | null | null | Cc1cc2c(NC(=O)C(Cl)(Cl)Cl)cccc2nn1.NCc1ccc(Cl)c(Cl)c1>>Cc1cc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc2nn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-264a7560bdc047b6b11ed3aa62c5ca72 | O=C1CCC(=O)N1Br.c1ccc2cnccc2c1>>Brc1cccc2cnccc12 | C1=NC=CC2=CC=CC=C12.OS(=O)(=O)O.[NH4+].[OH-].BrN1C(CCC1=O)=O>>BrC1=C2C=CN=CC2=CC=C1 | O=C1CCC(=O)N1[Br:1].[cH:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | O=C1CCC(=O)N1Br.c1ccc2cnccc2c1 | Brc1cccc2cnccc12 | null | null | CCCCCCC | Functional Group Interconversion | Bromination | 9cac9f3adaa01c5b3ba77ecc78b3325ca368823796a491b3ff1d81b1acdc724d | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2cnccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | null | [] | -10 | CELSIUS | null | null | Concentrated H2SO4 (260 mL) was cooled to −25° C. while stirring with a mechanical stirrer. Isoquinoline (30 mL, 0.25 mol) was added slowly so the temperature did not exceed 0° C. After the addition was complete, the red solution was recooled to −25° C. and treated with N-bromosuccinimide (55.49 g, 0.31 mol) in small p... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | CCCCCCC | -10 | null | O=C1CCC(=O)N1Br.c1ccc2cnccc2c1>CCCCCCC>Brc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e82ad2e910d1448f86a850a6cac03894 | Brc1cccc2cnccc12>>O=[N+]([O-])c1ccc(Br)c2ccncc12 | BrC1=C2C=CN=CC2=CC=C1.[N+](=O)([O-])[O-].[K+]>>BrC1=C2C=CN=CC2=C(C=C1)[N+](=O)[O-] | [cH:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]12>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]12 | Brc1cccc2cnccc12 | O=[N+]([O-])c1ccc(Br)c2ccncc12 | null | null | [OH-].[NH4+] | Functional Group Addition | OtherReaction | af041d80e34a3ce46b5eb910f230615587e5ab9eb4305ac845f1ae2dbd577a25 | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2cnccc2c1 | [c:1]:[#7;a:2]:[c:3]:[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:9]-[#7;+:10](=[O;D1;H0:11])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](:[c:5]):[c:3]:[#7;a:2]:[c:1] | null | [] | null | null | 1 | HOUR | The diethyl ether solution from Example 57A was treated with potassium nitrate (10.1 g, 100 mmol). After stirring for one hour, The mixture was poured onto ice and neutralized with concentrated ammonium hydroxide (˜300 ml). The crude product was collected by filtration, dried, and recrystalization from methanol to prov... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | [OH-].[NH4+] | null | 1 | Brc1cccc2cnccc12>[OH-].[NH4+]>O=[N+]([O-])c1ccc(Br)c2ccncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdbc8cf33a7841f9b75f923182e141ef | O=[N+]([O-])c1ccc(Br)c2ccncc12>>Nc1cccc2ccncc12 | BrC1=C2C=CN=CC2=C(C=C1)[N+](=O)[O-]>>C1=NC=CC2=CC=CC(=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](Br)[c:6]2[cH:7][cH:8][n:9][cH:10][c:11]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][n:9][cH:10][c:11]12 | O=[N+]([O-])c1ccc(Br)c2ccncc12 | Nc1cccc2ccncc12 | null | [Pd] | null | Reduction | OtherReaction | 33243a7a0a86654ba62ab63c9b0595dc06b3b2ec6c8d660470131d23402a9f9a | 7a1074c91f17781b9c7c26911e795314b42511dc69433b1dc4bc93ccba503456 | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:1>>[NH2;D1;+0:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:11]2:[c:10]:[c:9]:[#7;a:8]:[c:7]:[c:6]:1:2 | null | [] | null | null | null | null | The product from Example 57B was treated with Pd/C under a hydrogen atmosphere to provide the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Br- | [Pd] | null | null | O=[N+]([O-])c1ccc(Br)c2ccncc12>[Pd]>Nc1cccc2ccncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b30b419672b0479ba052baffaacb2fbf | Nc1cccc2ccncc12.O=C(Cl)C(Cl)(Cl)Cl>>O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl | C1=NC=CC2=CC=CC(=C12)N.ClC(C(=O)Cl)(Cl)Cl>>ClC(C(=O)NC=1C=CC=C2C=CN=CC12)(Cl)Cl | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]12.Cl[C:2](=[O:1])[C:14]([Cl:15])([Cl:16])[Cl:17]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]12)[C:14]([Cl:15])([Cl:16])[Cl:17] | Nc1cccc2ccncc12.O=C(Cl)C(Cl)(Cl)Cl | O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2cnccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6]):[c:12] | null | [] | null | null | null | null | The product from Example 57C and trichloroacetylchloride were processed as described in Example 1A to provide the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2cnccc2c1 | HCl | null | null | null | Nc1cccc2ccncc12.O=C(Cl)C(Cl)(Cl)Cl>>O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9ac0b31af9b424dafeeed6462c070b2 | NCc1ccc(C(F)(F)F)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl>>O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2ccncc12 | FC(C1=CC=C(CN)C=C1)(F)F.ClC(C(=O)NC=1C=CC=C2C=CN=CC12)(Cl)Cl.C1CCC2=NCCCN2CC1>>C1=NC=CC2=CC=CC(=C12)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1.ClC(Cl)(Cl)[C:2](=[O:1])[NH:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22][n:23][cH:24][c:25]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1)[NH:15][c:16]1[cH:17][cH:18][cH:19][c:20]2... | NCc1ccc(C(F)(F)F)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl | O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2ccncc12 | null | null | null | Acylation | OtherReaction | ffe5fdd6070c0c75bd20e0ee13bc090c32d3281269178f04f3649ea77b9456e8 | 56b69d37f244d2e25fa681709adac1c85312cc9ccbfef016678a99d56e55b4c6 | O=C(NCc1ccccc1)Nc1cccc2ccncc12 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | The title compound was prepared using 4-(trifluoromethyl)benzylamine, the product from Example 57D, DBU and the procedure described in Example 1B. MS (ESI+) m/z 346 (M+H)+; 1H NMR (DMSO-d6) δ 9.58 (s, 1H), 9.10 (s, 1H), 8.49 (d, 1H), 8.12 (d, 1H), 7.81-7.54 (m, 7H), 7.20 (t, 1H), 4.47 (d, 2H); Anal. Calcd for C18H14F3N... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | HCl | null | null | null | NCc1ccc(C(F)(F)F)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl>>O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2ccncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f92abbcdc3c94b179fa768fab3bf8f4d | NCc1ccc(Br)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl>>O=C(NCc1ccc(Br)cc1)Nc1cccc2ccncc12 | O.BrC1=CC=C(CN)C=C1.ClC(C(=O)NC=1C=CC=C2C=CN=CC12)(Cl)Cl.C1CCC2=NCCCN2CC1>>BrC1=CC=C(CNC(=O)NC=2C=CC=C3C=CN=CC23)C=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.ClC(Cl)(Cl)[C:2](=[O:1])[NH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][n:20][cH:21][c:22]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][n:20][cH:21][c:22]12 | NCc1ccc(Br)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl | O=C(NCc1ccc(Br)cc1)Nc1cccc2ccncc12 | null | null | CO | Acylation | OtherReaction | ffe5fdd6070c0c75bd20e0ee13bc090c32d3281269178f04f3649ea77b9456e8 | 56b69d37f244d2e25fa681709adac1c85312cc9ccbfef016678a99d56e55b4c6 | O=C(NCc1ccccc1)Nc1cccc2ccncc12 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | The title compound was prepared using 4-bromobenzylamine, the product from Example 57D, DBU and the procedure described in Example 1B. MS (ESI+) m/z 356 (M+H)+; 1H NMR (DMSO-d6) δ 9.52 (s, 1H), 9.15 (s, 1H), 8.49 (d, 1H), 8.11 (d, 1H), 7.77 (d, 1H), 7.67 (t, 1H), 7.55 (m, 3H) 7.32 (d, 2H), 7.25 (t, 1H), 4.34 (d, 2H); A... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | HCl | CO | null | null | NCc1ccc(Br)cc1.O=C(Nc1cccc2ccncc12)C(Cl)(Cl)Cl>CO>O=C(NCc1ccc(Br)cc1)Nc1cccc2ccncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac589d79f7aa450e9af1dc8575d8944e | O=C(O)Cc1ccccc1C(=O)O.[NH4+]>>O=C1Cc2ccccc2C(=O)N1 | C(=O)(O)CC1=C(C(=O)O)C=CC=C1.[NH4+].[OH-]>>C1(NC(CC2=CC=CC=C12)=O)=O | O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](O)=[O:11].[NH4+:12]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[NH:12]1 | O=C(O)Cc1ccccc1C(=O)O.[NH4+] | O=C1Cc2ccccc2C(=O)N1 | null | null | null | Acylation | OtherReaction | 8c6e19b6d9556b641f610ee6f3892dfc89bcb6dcf68cea638ca6db03bf9c2edb | 286fbd2cccb868855ca34a2d629ab8d8113cbdbf5f1fb5f1c2174808f1aa7a3a | O=C1Cc2ccccc2C(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]-[C;H0;D3;+0:7](-O)=[O;D1;H0:8].[NH4+;D0:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:6]-[c:5]:[c:3]-1:[c:4] | 74 | [{"value": 74.0, "product": "C1(NC(CC2=CC=CC=C12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 8 | HOUR | 2-(Carboxymethyl)benzoic acid (10 g, 55.6 mmol) was dissolved in concentrated NH4OH (15 mL) and then was evaporated to dryness under reduced pressure. The process was repeated with additional NH4OH (5 mL). The resulting residue was treated with 1,2-dichlorobenzene (20 mL) and heated with stirring at 200° C. without a c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Unsubstituted dicarboximide | null | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | null | 200 | 8 | O=C(O)Cc1ccccc1C(=O)O.[NH4+]>>O=C1Cc2ccccc2C(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc77105416774ff4acba9c435d4af89e | Clc1cc2ccccc2c(Cl)n1>>Clc1cc2ccccc2cn1 | ClC1=NC(=CC2=CC=CC=C12)Cl.Cl.[Sn]>>ClC=1N=CC2=CC=CC=C2C1 | Cl[c:10]1[c:9]2[c:4]([cH:3][c:2]([Cl:1])[n:11]1)[cH:5][cH:6][cH:7][cH:8]2>>[Cl:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10][n:11]1 | Clc1cc2ccccc2c(Cl)n1 | Clc1cc2ccccc2cn1 | null | null | C(C)(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 5f52289b2baf4c41a4fd744ce2a94a34156399db711c7ce043a5818b3fd25f7a | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2cnccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]>>[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:4](:[c:5]):[c:6] | 23 | [{"value": 23.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 57.5 | CELSIUS | null | null | The product from Example 60B (6.73 g, 33.8 mmol) was suspended in glacial acetic acid (37 mL) and concentrated HCl (13 mL), treated with tin powder (12.1 g, 101.9 mmol), and heated at 55-60° C. for 3 hours with stirring. The mixture was allowed to cool to room temperature and the precipitated tin salts were removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | C(C)(=O)O | 57.5 | null | Clc1cc2ccccc2c(Cl)n1>C(C)(=O)O>Clc1cc2ccccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d5ccbe39f41541a1a5bf6cc3514f6406 | Nc1cccc2cnccc12.O=C(Cl)Cl>>O=C=Nc1cccc2cnccc12 | C(=O)(Cl)Cl.NC1=C2C=CN=CC2=CC=C1>>N(=C=O)C1=C2C=CN=CC2=CC=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12 | Nc1cccc2cnccc12.O=C(Cl)Cl | O=C=Nc1cccc2cnccc12 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc2cnccc2c1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosgene (20 ml, 20% in toluene from Fluka) in CH2Cl2 (300 mL) at 0° C. was treated with DMAP (10 g) in CH2Cl2 (100 mL) slowly. After complete addition, the mixture was treated with 5-aminoisoquinoline (5 g) in CH2Cl2 (100 mL) dropwise. The mixture was allowed to warm to room temperature and then stirred overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccc2cnccc2c1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | Nc1cccc2cnccc12.O=C(Cl)Cl>CN(C)C=1C=CN=CC1.C(Cl)Cl>O=C=Nc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a014e40984194ad18ac351616be7b53c | N#Cc1ccc(CO)cc1.O=C=Nc1cccc2cnccc12>>N#Cc1ccc(COC(=O)Nc2cccc3cnccc23)cc1 | C(#N)C1=CC=C(CO)C=C1.N(=C=O)C1=C2C=CN=CC2=CC=C1>>C1=NC=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)C#N)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:22][cH:23]1.[C:9](=[O:10])=[N:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]12>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][n:18][cH:19][cH:20][c:21]23)[cH:22][cH:23]1 | N#Cc1ccc(CO)cc1.O=C=Nc1cccc2cnccc12 | N#Cc1ccc(COC(=O)Nc2cccc3cnccc23)cc1 | null | null | null | Protection | OtherReaction | 8d2aa5da7fec498749aba98cc9467e8d82c146f343570568bec74a92b10e0ae2 | e505c5de73b3f9ad0414c141c59109424d376f26a728bbd154d3edfd03d2f50a | O=C(Nc1cccc2cnccc12)OCc1ccccc1 | [O;D1;H0:1]=[C;H0;D2;+0:2]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[O;H0;D2;+0:7]-[C:8]-[c:9] | 44 | [{"value": 44.0, "product": "C1=NC=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Cyanobenzyl alcohol (150 mg, 1.13 mmol) diethyl ether (10 mL) was treated with the product from Example 61A as an ethereal solution. The mixture was stirred for 2 hours, filtered, and the filter cake was washed with diethyl ether to provide the title compound as an off-white solid (150 mg, 44%). 1H HMR (300 MHz, DMSO... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | null | null | 2 | N#Cc1ccc(CO)cc1.O=C=Nc1cccc2cnccc12>>N#Cc1ccc(COC(=O)Nc2cccc3cnccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-896af839f2e74d45a7df1a4bdd6efa4e | Cc1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1>>Cc1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 | CC=1N=CC=2C=CC=C(C2C1)N.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(C=C1)CNC(=O)NC1=C2C=C(N=CC2=CC=C1)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([NH2:6])[cH:18][cH:19][cH:20][c:21]2[cH:22][n:23]1.[C:7](=[O:8])=[N:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([NH:6][C:7](=[O:8])[NH:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[cH:18][cH:19][cH:20][c:21]2[cH:22][n:23]1 | Cc1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1 | Cc1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | null | [] | 80 | CELSIUS | null | null | The product from Example 63A (500 mg, 3.1 mmol) in toluene (10 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.5 mL, 3.57 mmol) with stirring and then the mixture was heated at 80° C. overnight. The mixture was allowed to cool to room temperature, filtered, the filter cake was washed with toluene, and allow... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1(=CC=CC=C1)C | 80 | null | Cc1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1>C1(=CC=CC=C1)C>Cc1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09aa8922b041445ba2af6c40b03ec737 | Nc1cccc2c(Cl)nccc12.O=C=NCc1ccc(Br)cc1>>O=C(NCc1ccc(Br)cc1)Nc1cccc2c(Cl)nccc12 | ClC1=NC=CC=2C(=CC=CC12)N.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(C=C1)CNC(=O)NC1=C2C=CN=C(C2=CC=C1)Cl | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]([Cl:19])[n:20][cH:21][cH:22][c:23]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]([Cl:19])[n:20][cH:21][cH:22][c:23]12 | Nc1cccc2c(Cl)nccc12.O=C=NCc1ccc(Br)cc1 | O=C(NCc1ccc(Br)cc1)Nc1cccc2c(Cl)nccc12 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | 63.1 | [{"value": 63.0, "product": "BrC1=CC=C(C=C1)CNC(=O)NC1=C2C=CN=C(C2=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "BrC1=CC=C(C=C1)CNC(=O)NC1=C2C=CN=C(C2=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90° C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1(=CC=CC=C1)C | 90 | null | Nc1cccc2c(Cl)nccc12.O=C=NCc1ccc(Br)cc1>C1(=CC=CC=C1)C>O=C(NCc1ccc(Br)cc1)Nc1cccc2c(Cl)nccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53af5ae1b742411193551ab8a30ba92a | Cc1nccc2c(N)cccc12.O=C=NCc1ccc(Br)cc1>>Cc1nccc2c(NC(=O)NCc3ccc(Br)cc3)cccc12 | CC1=NC=CC=2C(=CC=CC12)N.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(C=C1)CNC(=O)NC1=C2C=CN=C(C2=CC=C1)C | [CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]2[c:7]([NH2:8])[cH:20][cH:21][cH:22][c:23]12.[C:9](=[O:10])=[N:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]2[c:7]([NH:8][C:9](=[O:10])[NH:11][CH2:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]3)[cH:20][cH:21][cH:22][c:23]12 | Cc1nccc2c(N)cccc12.O=C=NCc1ccc(Br)cc1 | Cc1nccc2c(NC(=O)NCc3ccc(Br)cc3)cccc12 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[C:8]-[c:9])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | null | null | The product from Example 65A (480 mg, 3.04 mmol) in toluene (9 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.43, 3.07 mmol) with stirring. After heating the mixture at 90° C. for 1 hour, the mixture was allowed to cool to room temperature, filtered, and the filter cake washed with toluene to provide the t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1(=CC=CC=C1)C | 90 | null | Cc1nccc2c(N)cccc12.O=C=NCc1ccc(Br)cc1>C1(=CC=CC=C1)C>Cc1nccc2c(NC(=O)NCc3ccc(Br)cc3)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d8ab7911edad41d98ae14adb182cb303 | C1COCCN1.N#Cc1ccc(F)cc1>>N#Cc1ccc(N2CCOCC2)cc1 | FC1=CC=C(C#N)C=C1.N1CCOCC1.O>>N1(CCOCC1)C1=CC=C(C#N)C=C1 | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:14][cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1 | C1COCCN1.N#Cc1ccc(F)cc1 | N#Cc1ccc(N2CCOCC2)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 80 | [{"value": 80.0, "product": "N1(CCOCC1)C1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "N1(CCOCC1)C1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 4-Fluorobenzonitrile (1 g, 8.26 mmol) and morpholine (2.2 mL, 25.2 mmol) were combined in DMSO (25 mL) and heated at 100° C. for 2.5 hours. The mixture was allowed to cool to room temperature, poured into water, and extracted with diethyl ether. The organic extracts were combined, washed with water and brine, dried ove... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HF | CS(=O)C | 100 | null | C1COCCN1.N#Cc1ccc(F)cc1>CS(=O)C>N#Cc1ccc(N2CCOCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52820bdcd91c4280adbd2ff3d769d0df | N#Cc1ccc(N2CCOCC2)cc1>>NCc1ccc(N2CCOCC2)cc1 | O.[OH-].[Na+].N1(CCOCC1)C1=CC=C(C#N)C=C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>N1(CCOCC1)C1=CC=C(C=C1)CN | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1 | N#Cc1ccc(N2CCOCC2)cc1 | NCc1ccc(N2CCOCC2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(N2CCOCC2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 23 | [{"value": 23.0, "product": "N1(CCOCC1)C1=CC=C(C=C1)CN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.5, "product": "N1(CCOCC1)C1=CC=C(C=C1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 66A (1.24 g, 6.6 mmol) in THF (25 mL) was treated with LiAlH4 (2.5 g, 65.9 mmol) at 0° C. The mixture was allowed to warm to room temperature and then refluxed for 1 hour. The mixture was allowed to cool to room temperature and then treated with 1N NaOH carefully followed by water. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | null | C1CCOC1 | null | null | N#Cc1ccc(N2CCOCC2)cc1>C1CCOC1>NCc1ccc(N2CCOCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efd459b996964986839ace8df6a1ab67 | NCc1ccc(N2CCOCC2)cc1.O=C=Nc1cccc2cnccc12>>O=C(NCc1ccc(N2CCOCC2)cc1)Nc1cccc2cnccc12 | N1(CCOCC1)C1=CC=C(C=C1)CN.N(=C=O)C1=C2C=CN=CC2=CC=C1>>C1=NC=CC2=C(C=CC=C12)NC(=O)NCC1=CC=C(C=C1)N1CCOCC1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1.[O:1]=[C:2]=[N:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][n:24][cH:25][cH:26][c:27]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1)[NH:17][c:18]1[cH:1... | NCc1ccc(N2CCOCC2)cc1.O=C=Nc1cccc2cnccc12 | O=C(NCc1ccc(N2CCOCC2)cc1)Nc1cccc2cnccc12 | null | null | C(C)OCC | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccc(N2CCOCC2)cc1)Nc1cccc2cnccc12 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:4]=[C;H0;D3;+0:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | The product from Example 66B (285 mg, 1.48 mmol) in diethyl ether (10 mL) was treated with the product from Example 61A. The mixture was filtered and the filter cake purified by chromatography (95:5 CH2Cl2—MeOH, eluant) to provide that title compound as a white solid. The corresponding di-hydrochloride salt was prepare... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.C1COCC[NH]1.c1ccc2cnccc2c1 | null | C(C)OCC | null | null | NCc1ccc(N2CCOCC2)cc1.O=C=Nc1cccc2cnccc12>C(C)OCC>O=C(NCc1ccc(N2CCOCC2)cc1)Nc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55648e4dd72e4918928f020267c3f81b | CC1CNCC(C)O1.N#Cc1ccc(F)cc1>>CC1CN(c2ccc(CN)cc2)CC(C)O1 | FC1=CC=C(C#N)C=C1.CC1CNCC(O1)C>>CC1CN(CC(O1)C)C1=CC=C(C=C1)CN | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:13][CH:14]([CH3:15])[O:16]1.F[c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:11][cH:12]2)[CH2:13][CH:14]([CH3:15])[O:16]1 | CC1CNCC(C)O1.N#Cc1ccc(F)cc1 | CC1CN(c2ccc(CN)cc2)CC(C)O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bb2821dd35ce6e07ed9e7459ce7cc81854777a952694d10cc051b50745e098b9 | 8974feeb75b9b5e4f2e6d12ce58009881c023f2cc77ffb861190d06c60e864aa | c1ccc(N2CCOCC2)cc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7]:[c:8]:1.[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[NH2;D1;+0:6]-[CH2;D2;+0:5]-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-2):[c:8]:[c:7]:1 | null | [] | null | null | null | null | 4-Fluorobenzonitrile and 2,6-dimethylmorpholine were processed as described in Examples 66A and 66B to provide the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrile.Secondary amine | Primary amine.Tertiary amine | C1COCCN1.c1ccccc1 | C1COCC[NH]1.c1ccccc1 | C1COCC[NH]1.c1ccccc1 | Other | null | null | null | CC1CNCC(C)O1.N#Cc1ccc(F)cc1>>CC1CN(c2ccc(CN)cc2)CC(C)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a13c289538cb4cf1970503aeab75eba8 | CC1CN(c2ccc(CN)cc2)CC(C)O1.O=C=Nc1cccc2cnccc12>>CC1CN(c2ccc(CNC(=O)Nc3cccc4cnccc34)cc2)CC(C)O1 | CC1CN(CC(O1)C)C1=CC=C(C=C1)CN.N(=C=O)C1=C2C=CN=CC2=CC=C1>>CC1CN(CC(O1)C)C1=CC=C(C=C1)CNC(=O)NC1=C2C=CN=CC2=CC=C1 | [CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:24][cH:25]2)[CH2:26][CH:27]([CH3:28])[O:29]1.[C:11](=[O:12])=[N:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([CH2:9][NH:10][C:11](=[O:12])[NH:13][c:14]3[cH:15][cH:16][c... | CC1CN(c2ccc(CN)cc2)CC(C)O1.O=C=Nc1cccc2cnccc12 | CC1CN(c2ccc(CNC(=O)Nc3cccc4cnccc34)cc2)CC(C)O1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccc(N2CCOCC2)cc1)Nc1cccc2cnccc12 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:4]=[C;H0;D3;+0:5](-[NH;D2;+0:1]-[C:2]-[c:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | The product from Example 67A and the product from Example 61A were processed as described in Example 66C to provide a waxy material which was purified by chromatography (95:5 CH2Cl2—MeOH, eluant) to provide the title compound as a white solid. The corresponding di-hydrochloride salt was prepared using methanolic HCl. 1... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1COCC[NH]1.c1ccccc1.c1ccc2cnccc2c1 | null | null | null | null | CC1CN(c2ccc(CN)cc2)CC(C)O1.O=C=Nc1cccc2cnccc12>>CC1CN(c2ccc(CNC(=O)Nc3cccc4cnccc34)cc2)CC(C)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-50ac4b0f356f49b4ae8d04d06aaeaf3c | Clc1ccc(N2CCNCC2)cc1Cl.O=C=Nc1cccc2cnccc12>>O=C(Nc1cccc2cnccc12)N1CCN(c2ccc(Cl)c(Cl)c2)CC1 | ClC=1C=C(C=CC1Cl)N1CCNCC1.N(=C=O)C1=C2C=CN=CC2=CC=C1>>ClC=1C=C(C=CC1Cl)N1CCN(CC1)C(=O)NC1=C2C=CN=CC2=CC=C1 | [NH:14]1[CH2:15][CH2:16][N:17]([c:18]2[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]2)[CH2:26][CH2:27]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[N:14]1[CH2:15][CH2:16][N:17]([c:18]2[cH:19][... | Clc1ccc(N2CCNCC2)cc1Cl.O=C=Nc1cccc2cnccc12 | O=C(Nc1cccc2cnccc12)N1CCN(c2ccc(Cl)c(Cl)c2)CC1 | null | null | C(C)OCC | Acylation | Urea synthesis via isocyanate and secondary amine | 6c56e6fc0929cf5b2c535d5ee3915e354a1b28cb53e352800366a2a7d763c4a8 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(Nc1cccc2cnccc12)N1CCN(c2ccccc2)CC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 80 | [{"value": 80.0, "product": "ClC=1C=C(C=CC1Cl)N1CCN(CC1)C(=O)NC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(3,4-Dichlorophenyl)piperazine (1280 mg, 5.55 mmol) in diethyl ether (30 mL) was treated with the product from Example 61A (˜40 mL). The mixture was filtered, the filter cake washed with diethyl ether, and dried under reduced pressure to provide the title compound as a white solid (1.78 g, 80%). 1H NMR (300 MHz, DMSO... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2cnccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)OCC | null | null | Clc1ccc(N2CCNCC2)cc1Cl.O=C=Nc1cccc2cnccc12>C(C)OCC>O=C(Nc1cccc2cnccc12)N1CCN(c2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8421b9e4bc34d96b0274bd79553161f | Brc1cccc2cnccc12.CCOC(=O)C(=O)OCC>>CCOC(=O)C(=O)c1cccc2cnccc12 | [NH4+].[Cl-].C(C(=O)OCC)(=O)OCC.BrC1=C2C=CN=CC2=CC=C1.C(CCC)[Li]>>C1=NC=CC2=C(C=CC=C12)C(C(=O)OCC)=O | Br[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12.CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12 | Brc1cccc2cnccc12.CCOC(=O)C(=O)OCC | CCOC(=O)C(=O)c1cccc2cnccc12 | null | null | C1CCOC1 | C-C Coupling | Ester and halide to ketone | c2f0786450e86e8f47917ca1d9f974bf315ab7618b97528e08a0299591acc115 | dd03ca4e617545414fae7e22c410ecd4f78e4fd10d5a86bce7e36a4a1d0f1e9d | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.C-C-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 35.2 | [{"value": 35.0, "product": "C1=NC=CC2=C(C=CC=C12)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.2, "product": "C1=NC=CC2=C(C=CC=C12)C(C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The product from Example 57A (11.80 g, 56.6 mmol) in THF (200 mL) at −78° C. was treated with n-butyllithium (30 mL, 75.0 mmol, 2.5M in hexanes) dropwise. After 30 minutes, the mixture was treated with diethyl oxalate (25.0 mL, 184 mmol). After 20 minutes, the solution was allowed to warm to room temperature and was tr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ketone | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | C1CCOC1 | null | 0.5 | Brc1cccc2cnccc12.CCOC(=O)C(=O)OCC>C1CCOC1>CCOC(=O)C(=O)c1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f81aba286c6c4712992f65f7c6a08880 | CC(=O)Cl.CCOC(=O)C(O)c1cccc2cnccc12>>CCOC(=O)C(OC(C)=O)c1cccc2cnccc12 | OC(C(=O)OCC)C1=C2C=CN=CC2=CC=C1.C(C)(=O)Cl>>C(C)(=O)OC(C(=O)OCC)C1=C2C=CN=CC2=CC=C1 | Cl[C:8]([CH3:9])=[O:10].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([OH:7])[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][cH:18][cH:19][c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([O:7][C:8]([CH3:9])=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][cH:18][cH:19][c:20]12 | CC(=O)Cl.CCOC(=O)C(O)c1cccc2cnccc12 | CCOC(=O)C(OC(C)=O)c1cccc2cnccc12 | null | null | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc2cnccc2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](-[OH;D1;+0:9])-[c:10]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](-[c:10])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 67.2 | [{"value": 67.0, "product": "C(C)(=O)OC(C(=O)OCC)C1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.2, "product": "C(C)(=O)OC(C(=O)OCC)C1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The product of Example 70B (1.0202 g, 4.41 mmol) in pyridine (15 mL) was treated with acetyl chloride (0.35 mL, 4.92 mmol) dropwise. The solution was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was purified by column chromatography (2% methanol/CH2CH2) to provide the tit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccc2cnccc2c1 | HCl | N1=CC=CC=C1 | null | 4 | CC(=O)Cl.CCOC(=O)C(O)c1cccc2cnccc12>N1=CC=CC=C1>CCOC(=O)C(OC(C)=O)c1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2cd6e83b53a34d02a19b609fd0150a3d | CCOC(=O)C(OC(C)=O)c1cccc2cnccc12>>CCOC(=O)Cc1cccc2cnccc12 | C(C)(=O)OC(C(=O)OCC)C1=C2C=CN=CC2=CC=C1>>C1=NC=CC2=C(C=CC=C12)CC(=O)OCC | CC(=O)O[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12 | CCOC(=O)C(OC(C)=O)c1cccc2cnccc12 | CCOC(=O)Cc1cccc2cnccc12 | null | null | C(C)O | Reduction | OtherReaction | 33f176f6ce02426b2726e71e3c19f64673952a2b50dd48518b89a08efe25965b | b45711df98eaf2a3f54e3027da3f1b57580ab2f6d54e9ac2a56731961e64969a | c1ccc2cnccc2c1 | C-C(=O)-O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[c:6](:[c:7]):[c:8]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[c:6](:[c:7]):[c:8] | 82.6 | [{"value": 67.0, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 6 | HOUR | The product of Example 70C (1.43 g, 5.23 mmol) in absolute ethanol (200 mL) was treated with dry 10% Pd/C (0.122 g) and triethylamine (10.4 mL). The reaction mixture was stirred at 60° C. for 6 hours under H2 (60 psi), filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | c1ccc2cnccc2c1 | HO- | C(C)O | 60 | 6 | CCOC(=O)C(OC(C)=O)c1cccc2cnccc12>C(C)O>CCOC(=O)Cc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b94a35791cae4b8ea43dc8ab5851d733 | CCOC(=O)Cc1cccc2cnccc12.NCc1ccc(C(F)(F)F)cc1>>O=C(Cc1cccc2cnccc12)NCc1ccc(C(F)(F)F)cc1 | Cl.C1=NC=CC2=C(C=CC=C12)CC(=O)OCC.C[Al](C)C.[NH4+].[OH-].FC(C1=CC=C(CN)C=C1)(F)F>>C1=NC=CC2=C(C=CC=C12)CC(=O)NCC1=CC=C(C=C1)C(F)(F)F | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12.[NH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[NH:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([C:20]([F:21])(... | CCOC(=O)Cc1cccc2cnccc12.NCc1ccc(C(F)(F)F)cc1 | O=C(Cc1cccc2cnccc12)NCc1ccc(C(F)(F)F)cc1 | null | null | ClCCl.O.C(Cl)Cl | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(Cc1cccc2cnccc12)NCc1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 37 | [{"value": 37.0, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)NCC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)NCC1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The product from Example 70D (0.207 g, 0.96 mmol) in dichloromethane (10 mL) was treated with trimethylaluminum (1 mL, 2.0 mmol, 2M in toluene) dropwise. After 30 minutes, the mixture was teated with 4-(trifluoromethyl)benzylamine (0.350 g, 2.0 mmol) in dichloromethane (2 mL) and then refluxed for 16 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2cnccc2c1.c1ccccc1 | HO- | ClCCl.O.C(Cl)Cl | null | 0.5 | CCOC(=O)Cc1cccc2cnccc12.NCc1ccc(C(F)(F)F)cc1>ClCCl.O.C(Cl)Cl>O=C(Cc1cccc2cnccc12)NCc1ccc(C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9178f29f1218402098e6fa03da8337ae | COC(=O)c1cc2ccccc2cn1.O=[N+]([O-])[O-]>>COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1 | C1=NC(=CC2=CC=CC=C12)C(=O)OC.[N+](=O)([O-])[O-].[Na+]>>[N+](=O)([O-])C1=C2C=C(N=CC2=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:12][cH:13][cH:14][c:15]2[cH:16][n:17]1.[O-][N+:9](=[O:10])[O-:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17]1 | COC(=O)c1cc2ccccc2cn1.O=[N+]([O-])[O-] | COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1 | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with NO3 salt | dcb421e65a8922cd9594f5567e7ba6ab06a8bfe0650592bab8d9da3689fbb53d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2cnccc2c1 | [O-]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | 96.2 | [{"value": 96.0, "product": "[N+](=O)([O-])C1=C2C=C(N=CC2=CC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.2, "product": "[N+](=O)([O-])C1=C2C=C(N=CC2=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methyl isoquinoline-3-carboxylate (9.58 g, 51.2 mmol) in concentrated H2SO4 (100 mL) at 0° C. was treated with sodium nitrate (4.79 g, 56.4 mmol) in small portions such that the temperature was maintained below 5° C. Ten minutes after addition was complete, the reaction mixture was allowed to warm to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | OS(=O)(=O)O | null | 2 | COC(=O)c1cc2ccccc2cn1.O=[N+]([O-])[O-]>OS(=O)(=O)O>COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01fb787146f347a1af791d906562fe79 | COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1>>COC(=O)c1cc2c(N)cccc2cn1 | [N+](=O)([O-])C1=C2C=C(N=CC2=CC=C1)C(=O)OC.CO.C(Cl)Cl>>NC1=C2C=C(N=CC2=CC=C1)C(=O)OC | O=[N+:9]([O-])[c:8]1[c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:15][cH:14][c:13]2[cH:12][cH:11][cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([NH2:9])[cH:10][cH:11][cH:12][c:13]2[cH:14][n:15]1 | COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1 | COC(=O)c1cc2c(N)cccc2cn1 | null | [Fe] | C(C)(=O)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | The product of Example 71A (10.33 g, 44.5 mmol) in acetic acid/water (3/1) (320 mL) was treated with iron powder (5.06 g, 90.7 mmol). After stirring for 16 hours at room temperature, the reaction mixture was filtered the filtrate concentrated under reduced pressure to approximately half the original volume. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | [Fe].C(C)(=O)O.O | null | 16 | COC(=O)c1cc2c([N+](=O)[O-])cccc2cn1>[Fe].C(C)(=O)O.O>COC(=O)c1cc2c(N)cccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa24ed6b072c4b2588f2110a59e2631e | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1>>COC(=O)c1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 | NC1=C2C=C(N=CC2=CC=C1)C(=O)OC.C1(=CC=CC=C1)C.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([NH2:9])[cH:21][cH:22][cH:23][c:24]2[cH:25][n:26]1.[C:10](=[O:11])=[N:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]3)... | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1 | COC(=O)c1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[C:8]-[c:9])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 85.3 | [{"value": 85.0, "product": "BrC1=CC=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "BrC1=CC=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The product of Example 71B (0.156 g, 0.77 mmol) in THF:toluene (10 mL, 1:1) was treated with a solution of 1-bromo-4-(isocyanatomethyl)benzene (0.201 g, 0.95 mmol) in THF (1.0 mL). After stirring for 16 hours at room temperature, the reaction mixture was concentrated under reduced pressure and the residue was triturate... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1CCOC1 | null | 16 | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Br)cc1>C1CCOC1>COC(=O)c1cc2c(NC(=O)NCc3ccc(Br)cc3)cccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0698f79948cc4b37adf3f01e3952f75c | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Cl)cc1Cl>>COC(=O)c1cc2c(NC(=O)NCc3ccc(Cl)cc3Cl)cccc2cn1 | NC1=C2C=C(N=CC2=CC=C1)C(=O)OC.C1(=CC=CC=C1)C.ClC1=C(C=CC(=C1)Cl)CN=C=O>>ClC1=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=CC(=C1)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([NH2:9])[cH:22][cH:23][cH:24][c:25]2[cH:26][n:27]1.[C:10](=[O:11])=[N:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]1[Cl:21]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:... | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Cl)cc1Cl | COC(=O)c1cc2c(NC(=O)NCc3ccc(Cl)cc3Cl)cccc2cn1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[C:8]-[c:9])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 73 | [{"value": 73.0, "product": "ClC1=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "ClC1=C(CNC(=O)NC2=C3C=C(N=CC3=CC=C2)C(=O)OC)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The product of Example 71B (0.156 g, 0.77 mmol) in THF:toluene (10 mL, 1:1) was treated with a solution of 2,4-dichloro-1-(isocyanatomethyl)benzene (0.195 g, 0.97 mmol) in THF (1.0 mL). After stirring for 16 hours at room temperature, the reaction mixture was concentrated under reduced pressure and the residue was trit... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1CCOC1 | null | 16 | COC(=O)c1cc2c(N)cccc2cn1.O=C=NCc1ccc(Cl)cc1Cl>C1CCOC1>COC(=O)c1cc2c(NC(=O)NCc3ccc(Cl)cc3Cl)cccc2cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c15f0d07ca94425cb81ba6badf1891b1 | BrBr.Nc1cccc2cnccc12>>Nc1ccc(Br)c2cnccc12 | [OH-].[Na+].NC1=C2C=CN=CC2=CC=C1.[Cl-].[Cl-].[Cl-].[Al+3].BrBr>>BrC1=CC=C(C=2C=CN=CC12)N | Br[Br:6].[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:7]2[cH:8][n:9][cH:10][cH:11][c:12]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]2[cH:8][n:9][cH:10][cH:11][c:12]12 | BrBr.Nc1cccc2cnccc12 | Nc1ccc(Br)c2cnccc12 | null | null | C(C)(=O)OCC | Functional Group Interconversion | Bromination | dd766f53887400b5e199d60af04f01509e5613a22375639572626e4514c9ae8d | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2cnccc2c1 | Br-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[c:4]:[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6]):[c:4]:[#7;a:3]:[c:2] | 69.7 | [{"value": 35.0, "product": "BrC1=CC=C(C=2C=CN=CC12)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "BrC1=CC=C(C=2C=CN=CC12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | 5-Aminoisoquinoline (5.50 g, 38.1 mmol) and aluminium trichloride (15.1 g, 113 mmol) were combined and heated at 80° C. in a 3-necked flask equipped with a dropping funnel, stirrer bar, needle and sintered glass tube. Bromine (3.04 g, 19.05 mmol) was dripped onto the sintered glass funnel and the vapour diffused onto t... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | C(C)(=O)OCC | 80 | 2 | BrBr.Nc1cccc2cnccc12>C(C)(=O)OCC>Nc1ccc(Br)c2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2dd9c98cd52743aeb03c3f220dba9b0f | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(Cl)cc1Cl>>O=C(NCc1ccc(Cl)cc1Cl)Nc1ccc(Br)c2cnccc12 | BrC1=CC=C(C=2C=CN=CC12)N.C1(=CC=CC=C1)C.ClC1=C(C=CC(=C1)Cl)CN=C=O>>BrC=1C=CC(=C2C=CN=CC12)NC(=O)NCC1=C(C=C(C=C1)Cl)Cl | [NH2:13][c:14]1[cH:15][cH:16][c:17]([Br:18])[c:19]2[cH:20][n:21][cH:22][cH:23][c:24]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12])[NH:13][c:14]1[cH:15][cH:16][c:17]([Br:18])[c:19]2[cH:20][n:21][cH:22][cH:23]... | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(Cl)cc1Cl | O=C(NCc1ccc(Cl)cc1Cl)Nc1ccc(Br)c2cnccc12 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | 80.5 | [{"value": 78.0, "product": "BrC=1C=CC(=C2C=CN=CC12)NC(=O)NCC1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "BrC=1C=CC(=C2C=CN=CC12)NC(=O)NCC1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The product from Example 73A (120 mg, 0.52 mmol) in THF:toluene (1.4, 5 mL) was treated with a solution of 2,4-dichloro-1-(isocyanatomethyl)benzene (108 mg, 0.52 mmol) in THF (0.5 mL). After stirring for 16 hours at room temperature, the mixture was filtered and the filter cake dried under reduced pressure to provide t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1CCOC1 | null | 16 | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(Cl)cc1Cl>C1CCOC1>O=C(NCc1ccc(Cl)cc1Cl)Nc1ccc(Br)c2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64d581fdecb8443b8ea98f84eff7dba9 | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(F)cc1>>O=C(NCc1ccc(F)cc1)Nc1ccc(Br)c2cnccc12 | FC1=CC=C(C=C1)CN=C=O.BrC1=CC=C(C=2C=CN=CC12)N>>BrC=1C=CC(=C2C=CN=CC12)NC(=O)NCC1=CC=C(C=C1)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12 | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(F)cc1 | O=C(NCc1ccc(F)cc1)Nc1ccc(Br)c2cnccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | null | [] | null | null | null | null | The title compound was prepared using 1-fluoro-4-(isocyanatomethyl)benzene, the product of Example 73A and the procedure described in Example 73B (white solid, 108 mg, 65%) MS (ESI+) m/z 376 (M+H)+; MS (ESI−) m/z 374 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.35 (d, 5.8, 2H), 7.12 (m, 1H), 7.18 (m, 2H), 7.40 (m, 1H), 7.91 (... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | null | null | null | Nc1ccc(Br)c2cnccc12.O=C=NCc1ccc(F)cc1>>O=C(NCc1ccc(F)cc1)Nc1ccc(Br)c2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc1f90ba027d43989e6d6e60ee769702 | Nc1ccc(Br)c2cnccc12.O=C=NCc1cccc(F)c1>>O=C(NCc1cccc(F)c1)Nc1ccc(Br)c2cnccc12 | FC1=CC(=CC=C1)CN=C=O.BrC1=CC=C(C=2C=CN=CC12)N>>BrC=1C=CC(=C2C=CN=CC12)NC(=O)NCC1=CC(=CC=C1)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1)[NH:12][c:13]1[cH:14][cH:15][c:16]([Br:17])[c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12 | Nc1ccc(Br)c2cnccc12.O=C=NCc1cccc(F)c1 | O=C(NCc1cccc(F)c1)Nc1ccc(Br)c2cnccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | null | [] | null | null | null | null | The title compound was prepared using 1-fluoro-3-(isocyanatomethyl)benzene, the product of Example 73A and the procedure described in Example 73 (white solid, 108 mg, 65%). MS (ESI+) m/z 376 (M+H)+; MS (ESI−) m/z 374 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.39 (d, 5.8, 2H), 7.09 (m, 1H), 7.17 (m, 2H), 7.40 (m, 1H), 7.91 (... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | null | null | null | Nc1ccc(Br)c2cnccc12.O=C=NCc1cccc(F)c1>>O=C(NCc1cccc(F)c1)Nc1ccc(Br)c2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58ebfe9b7cb34e039a7f12d2ebcbb5ef | CC(C)(C(=O)O)c1ccc(Cl)cc1.O=S(Cl)Cl>>CC(C)(C(=O)Cl)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)C(C(=O)O)(C)C.S(=O)(Cl)Cl>>ClC1=CC=C(C=C1)C(C(=O)Cl)(C)C | O[C:4]([C:2]([CH3:1])([CH3:3])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)=[O:5].O=S(Cl)[Cl:6]>>[CH3:1][C:2]([CH3:3])([C:4](=[O:5])[Cl:6])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1 | CC(C)(C(=O)O)c1ccc(Cl)cc1.O=S(Cl)Cl | CC(C)(C(=O)Cl)c1ccc(Cl)cc1 | null | null | CCCCCC.C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[c:7]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[c:7])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | 98 | [{"value": 98.0, "product": "ClC1=CC=C(C=C1)C(C(=O)Cl)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "ClC1=CC=C(C=C1)C(C(=O)Cl)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2-(4-Chlorophenyl)-2-methylpropanoic acid (3.85 g, 19.4 mmol) in toluene (5 mL) was treated with thionyl chloride (5.00 g, 3.1 mL) and heated at 80° C. for 2 hours. The cooled solution was concentrated under reduced pressure to provide a yellow oil containing a crystalline residue. The mixture was dissolved in hexane, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CCCCCC.C1(=CC=CC=C1)C | 80 | null | CC(C)(C(=O)O)c1ccc(Cl)cc1.O=S(Cl)Cl>CCCCCC.C1(=CC=CC=C1)C>CC(C)(C(=O)Cl)c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db14f5bfc589491191cd8ac60651eaa1 | CC(C)(C(=O)Cl)c1ccc(Cl)cc1>>CC(C)(N=C=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)C(C(=O)Cl)(C)C.[N-]=[N+]=[N-].[Na+].CC(=O)C>>ClC1=CC=C(C=C1)C(C)(C)N=C=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)=[O:6]>>[CH3:1][C:2]([CH3:3])([N:4]=[C:5]=[O:6])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1 | CC(C)(C(=O)Cl)c1ccc(Cl)cc1 | CC(C)(N=C=O)c1ccc(Cl)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | fbf2339641ff0cdb5e15752f21553572109b22d0761d12b2dad0b963d5d29fa7 | cc08743a6a6e57f91530e729ed5783f6b5577caba801cdc96f6a1c4a9df32591 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C;H0;D4;+0:3](-[C;D1;H3:5])(-[#7:9]=[C;H0;D2;+0:1]=[O;D1;H0:2])-[c:6](:[c:7]):[c:8] | 96 | [{"value": 96.0, "product": "ClC1=CC=C(C=C1)C(C)(C)N=C=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | The product of Example 76A (4.00 g, 19.4 mmol) in acetone (9 mL) at 0° C. was treated with a solution of sodium azide (1.27 g) in water (9 mL) dropwise over 15 minutes. After stirring for 30 minutes at 0° C., the mixture was extracted with toluene (20 mL). The organic extract was dried with MgSO4, filtered, and the fil... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Isocyanate | null | null | c1ccccc1 | null | O | 0 | 0.5 | CC(C)(C(=O)Cl)c1ccc(Cl)cc1>O>CC(C)(N=C=O)c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1299c6fa1584a449bf4be13c0a1832e | CC(C)(N=C=O)c1ccc(Cl)cc1.Nc1cccc2cnccc12>>CC(C)(NC(=O)Nc1cccc2cnccc12)c1ccc(Cl)cc1 | NC1=C2C=CN=CC2=CC=C1.ClC1=CC=C(C=C1)C(C)(C)N=C=O>>ClC1=CC=C(C=C1)C(C)(C)NC(=O)NC1=C2C=CN=CC2=CC=C1 | [CH3:1][C:2]([CH3:3])([N:4]=[C:5]=[O:6])[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12>>[CH3:1][C:2]([CH3:3])([NH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12)[c:18]1[cH:19][cH:20][c:21]([Cl:22]... | CC(C)(N=C=O)c1ccc(Cl)cc1.Nc1cccc2cnccc12 | CC(C)(NC(=O)Nc1cccc2cnccc12)c1ccc(Cl)cc1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 34 | [{"value": 34.0, "product": "ClC1=CC=C(C=C1)C(C)(C)NC(=O)NC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using 5-aminoisoquinoline, the product of Example 76B and the procedure described in Example 73B except that THF was used as solvent. The product was recrystallized from ethyl acetate to provide the title compound as a white solid (840 mg, 34%). MS (ESI+) m/z 355 (M+H)+; MS (ESI−) m/z 35... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2cnccc2c1.c1ccccc1 | null | C1CCOC1 | null | null | CC(C)(N=C=O)c1ccc(Cl)cc1.Nc1cccc2cnccc12>C1CCOC1>CC(C)(NC(=O)Nc1cccc2cnccc12)c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5792bf11df114477af29d7fe662be805 | Nc1cccc2cnccc12.O=C(C(F)(F)F)C(F)(F)F>>Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 | NC1=C2C=CN=CC2=CC=C1.O.O.O.O.O.O.FC(C(=O)C(F)(F)F)(F)F>>NC1=C2C=CN=CC2=CC=C1C(C(F)(F)F)(C(F)(F)F)O | [NH2:1][c:2]1[cH:3][cH:14][cH:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]12.[C:4](=[O:5])([C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13]>>[NH2:1][c:2]1[c:3]([C:4]([OH:5])([C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]12 | Nc1cccc2cnccc12.O=C(C(F)(F)F)C(F)(F)F | Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | null | C-C Coupling | OtherReaction | ddb379ad63d99a5f7ded013bf598cb3b376f94f1ff8e2a4b87fa503953b27a47 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc2cnccc2c1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10].[N;D1;H2:11]-[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:[c:16]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5](-[OH;D1;+0:6])(-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:12](-[N;D1;H2:11]):[c:13]... | 30 | [{"value": 30.0, "product": "NC1=C2C=CN=CC2=CC=C1C(C(F)(F)F)(C(F)(F)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "NC1=C2C=CN=CC2=CC=C1C(C(F)(F)F)(C(F)(F)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 5-Aminoisoquinoline (288 mg, 2.00 mmol) and p-toluenesulfonic acid (5 mg) were combined and treated with hexafluoroacetone hexahydrate (0.29 mL, 462 mg, 2.10 mmol). The mixture was stirred in a sealed pressure tube and heated to 150° C. for 18 hours. The reaction was allowed to cool to room temperature and partitioned ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | 150 | null | Nc1cccc2cnccc12.O=C(C(F)(F)F)C(F)(F)F>C1(=CC=C(C=C1)S(=O)(=O)O)C>Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-419f73c2ccd540af8eda4c2260f31adf | Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12.O=C=NCc1ccc(Br)cc1>>O=C(NCc1ccc(Br)cc1)Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 | BrC1=CC=C(C=C1)CN=C=O.NC1=C2C=CN=CC2=CC=C1C(C(F)(F)F)(C(F)(F)F)O>>BrC1=CC=C(CNC(=O)NC2=C3C=CN=CC3=CC=C2C(C(F)(F)F)(C(F)(F)F)O)C=C1 | [NH2:12][c:13]1[c:14]([C:15]([OH:16])([C:17]([F:18])([F:19])[F:20])[C:21]([F:22])([F:23])[F:24])[cH:25][cH:26][c:27]2[cH:28][n:29][cH:30][cH:31][c:32]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH:12][c:13]1[c:14]([C... | Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12.O=C=NCc1ccc(Br)cc1 | O=C(NCc1ccc(Br)cc1)Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2cnccc12 | [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]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8]-[c:9] | null | [] | null | null | null | null | The title compound was prepared using 1-bromo-4-(isocyanatomethyl)benzene, the product of Example 77A and the procedure described in Example 73B except that THF was used as solvent (white solid, 840 mg, 34%). MS (ESI+) m/z 376 (M+H)+; MS (ESI−) m/z 374 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.35 (d, 5.8, 2H), 7.12 (m, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2cnccc2c1 | null | C1CCOC1 | null | null | Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12.O=C=NCc1ccc(Br)cc1>C1CCOC1>O=C(NCc1ccc(Br)cc1)Nc1c(C(O)(C(F)(F)F)C(F)(F)F)ccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ab03b67d609402ea896932a96ef91f3 | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Br)cc1>>O=C(NCc1ccc(Br)cc1)Nc1cccc2[nH]ccc12 | CCCCCC.NC1=C2C=CNC2=CC=C1.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(CNC(=O)NC2=C3C=CNC3=CC=C2)C=C1 | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[nH:18][cH:19][cH:20][c:21]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[nH:18][cH:19][cH:20][c:21]12 | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Br)cc1 | O=C(NCc1ccc(Br)cc1)Nc1cccc2[nH]ccc12 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:6] | null | [] | null | null | null | null | 4-aminoindole (0.13 g, 1 mmol) in THF (3 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.23 g, 1.1 mmol) for 3 hours at ambient temperature. Hexane was added to the reaction mixture to precipitate 0.26 g of the title compound as a tan solid. mp 198° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.30 (d, 2H), 6.51 (t, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | C1CCOC1 | null | null | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Br)cc1>C1CCOC1>O=C(NCc1ccc(Br)cc1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-60f6a2e647de494cbda989dfd2269117 | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Cl)c(Cl)c1>>O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ccc12 | CCCCCC.NC1=C2C=CNC2=CC=C1.ClC1=C(C=C(C=C1)CN=C=O)Cl>>ClC=1C=C(CNC(=O)NC2=C3C=CNC3=CC=C2)C=CC1Cl | [NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[nH:19][cH:20][cH:21][c:22]12.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1)[NH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[nH:19][cH:20][cH:21][c:22]12 | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Cl)c(Cl)c1 | O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ccc12 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:6] | null | [] | null | null | null | null | 4-Aminoindole (0.13 g, 1 mmol) in THF (3 mL) was treated with 1,2-dichloro-4-(isocyanatomethyl)benzene (0.22 g, 1.1 mmol) for 3 h at ambient temperature. Hexane was added to the reaction mixture to precipitate 0.25 g of the title compound as a tan solid. mp 201° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.23 (d, 2H), 6.36 (s, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | C1CCOC1 | null | null | Nc1cccc2[nH]ccc12.O=C=NCc1ccc(Cl)c(Cl)c1>C1CCOC1>O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-494f09c94a034747a59f95e195d1f93c | Nc1cccc2[nH]ccc12.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=C=Nc1cccc2[nH]ccc12 | NC1=C2C=CNC2=CC=C1.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>N(=C=O)C1=C2C=CNC2=CC=C1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12.ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12 | Nc1cccc2[nH]ccc12.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=C=Nc1cccc2[nH]ccc12 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 38334b31448e1d8428e2cb6569eceaecc2305b2359c734a98433aa0746ff9140 | a539b8d5e65abe163774733461d6850ba8234d38df1df3c2ccdeef5ce9de389b | c1ccc2[nH]ccc2c1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[#7;a:3]:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8]>>[#7;a:3]:[c:4]:[c:5]:[c:6](-[N;H0;D2;+0:7]=[C;H0;D2;+0:1]=[O;D1;H0:2]):[c:8] | 187.3 | [{"value": 187.3, "product": "N(=C=O)C1=C2C=CNC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Aminoindole (0.5 g, 3.78 mmol) in toluene (50 mL) was treated with triphosgene (0.4 g, 1.35 mmol) and heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in diethyl ether, filtered, and the filtrate was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | Isocyanate | null | null | c1ccc2[nH]ccc2c1 | HCl | C1(=CC=CC=C1)C | null | null | Nc1cccc2[nH]ccc12.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C1(=CC=CC=C1)C>O=C=Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d5461ba09a34288a079fb380b35d5b0 | NCc1ccc(C(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2[nH]ccc12 | CCCCCC.N(=C=O)C1=C2C=CNC2=CC=C1.FC(C1=CC=C(CN)C=C1)(F)F>>N1C=CC2=C(C=CC=C12)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1.[O:1]=[C:2]=[N:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[nH:21][cH:22][cH:23][c:24]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1)[NH:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[nH:21][cH:22][cH:2... | NCc1ccc(C(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12 | O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2[nH]ccc12 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:8] | null | [] | null | null | 3 | HOUR | The product of Example 80A (0.15 g, 1 mmol) in THF (3 mL) was treated with 4-(trifluoromethyl)benzylamine (0.19 g, 1.1 mmol) at ambient temperature. After stirring for 3 hours, hexane was added to the reaction mixture to precipitate the title compound as a solid. mp 178° C. 1H NMR (300 MHz, DMSO-d6) δ 4.43 (d, 2H), 6.5... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | C1CCOC1 | null | 3 | NCc1ccc(C(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12>C1CCOC1>O=C(NCc1ccc(C(F)(F)F)cc1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-402b7bfa394a4b7fa357526ecefe2b68 | NCc1ccc(OC(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(OC(F)(F)F)cc1)Nc1cccc2[nH]ccc12 | FC(OC1=CC=C(CN)C=C1)(F)F.N(=C=O)C1=C2C=CNC2=CC=C1>>N1C=CC2=C(C=CC=C12)NC(=O)NCC1=CC=C(C=C1)OC(F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1.[O:1]=[C:2]=[N:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH:22][cH:23][cH:24][c:25]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH:22]... | NCc1ccc(OC(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12 | O=C(NCc1ccc(OC(F)(F)F)cc1)Nc1cccc2[nH]ccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:8] | 65.8 | [{"value": 65.8, "product": "N1C=CC2=C(C=CC=C12)NC(=O)NCC1=CC=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(Trifluoromethoxy)benzylamine (0.21 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound (0.23 g). mp 177° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.36 (d, 2H), 6.52 (m, 1H), 6.95 (m, 3H), 7.24 (t, 1H), 7.36 (d, 2H), 7.48 (d, 2H), 7.63 (dd, 1H), 8... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | NCc1ccc(OC(F)(F)F)cc1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(OC(F)(F)F)cc1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e762148a3b14b59a7a4bdab88a889fc | NCc1ccc(C(F)(F)F)c(F)c1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(C(F)(F)F)c(F)c1)Nc1cccc2[nH]ccc12 | FC=1C=C(CN)C=CC1C(F)(F)F.N(=C=O)C1=C2C=CNC2=CC=C1>>FC=1C=C(CNC(=O)NC2=C3C=CNC3=CC=C2)C=CC1C(F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13]([F:14])[cH:15]1.[O:1]=[C:2]=[N:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH:22][cH:23][cH:24][c:25]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13]([F:14])[cH:15]1)[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH:2... | NCc1ccc(C(F)(F)F)c(F)c1.O=C=Nc1cccc2[nH]ccc12 | O=C(NCc1ccc(C(F)(F)F)c(F)c1)Nc1cccc2[nH]ccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:8] | 68.3 | [{"value": 68.3, "product": "FC=1C=C(CNC(=O)NC2=C3C=CNC3=CC=C2)C=CC1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Fluoro-4-(trifluoromethyl)benzylamine (0.22 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound (0.24 g). mp 198° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.43 (d, 2H), 6.52 (m, 1H), 6.98 (m, 3H), 7.26 (m, 1H), 7.39 (m, 2H), 7.57 (dd, 1H), 7.77 (t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | NCc1ccc(C(F)(F)F)c(F)c1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(C(F)(F)F)c(F)c1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27e36248124042f48c694f29083cf12b | NCc1ccc(Cl)c(C(F)(F)F)c1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(Cl)c(C(F)(F)F)c1)Nc1cccc2[nH]ccc12 | ClC1=C(C=C(CN)C=C1)C(F)(F)F.N(=C=O)C1=C2C=CNC2=CC=C1>>ClC1=C(C=C(CNC(=O)NC2=C3C=CNC3=CC=C2)C=C1)C(F)(F)F | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1.[O:1]=[C:2]=[N:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH:22][cH:23][cH:24][c:25]12>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[nH... | NCc1ccc(Cl)c(C(F)(F)F)c1.O=C=Nc1cccc2[nH]ccc12 | O=C(NCc1ccc(Cl)c(C(F)(F)F)c1)Nc1cccc2[nH]ccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:8] | null | [] | null | null | null | null | 4-Chloro-3-(trifluoromethyl)benzylamine (0.27 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound. mp 197° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.42 (d, 2H), 6.52 (m, 1H), 6.96 (m, 3H), 7.25 (m, 1H), 7.56 (dd, 1H), 7.67 (dd, 1H), 7.70 (t, 1H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | NCc1ccc(Cl)c(C(F)(F)F)c1.O=C=Nc1cccc2[nH]ccc12>>O=C(NCc1ccc(Cl)c(C(F)(F)F)c1)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d4d3376ae5c496abd9fa1a3e8ebab41 | NCCc1ccc(Cl)cc1Cl.O=C=Nc1cccc2[nH]ccc12>>O=C(NCCc1ccc(Cl)cc1Cl)Nc1cccc2[nH]ccc12 | ClC1=C(C=CC(=C1)Cl)CCN.N(=C=O)C1=C2C=CNC2=CC=C1>>ClC1=C(C=CC(=C1)Cl)CCNC(=O)NC1=C2C=CNC2=CC=C1 | [NH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13].[O:1]=[C:2]=[N:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[nH:20][cH:21][cH:22][c:23]12>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13])[NH:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[nH:20][cH:21][cH:22][c:23]12 | NCCc1ccc(Cl)cc1Cl.O=C=Nc1cccc2[nH]ccc12 | O=C(NCCc1ccc(Cl)cc1Cl)Nc1cccc2[nH]ccc12 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:11]-[C:10]-[C:9]):[c:8] | null | [] | null | null | null | null | 2-(2,4-Dichlorophenyl)ethylamine (0.21 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1. mmol) were treated as described in Example 80B to provide the title compound. mp 170° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.90 (m, 2H), 3.31 (m, 2H), 6.47 (m, 2H), 6.93 (m, 2H), 7.23 (m, 1H), 7.40 (m, 2H), 7.60 (m, 2H), 8.15 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | NCCc1ccc(Cl)cc1Cl.O=C=Nc1cccc2[nH]ccc12>>O=C(NCCc1ccc(Cl)cc1Cl)Nc1cccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec18f9e730094a60b26101a5f64a6926 | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(C(F)(F)F)cc1>>O=C(Nc1cccc2[nH]ccc12)OCc1ccc(C(F)(F)F)cc1 | FC(C1=CC=C(C=C1)CO)(F)F.N(=C=O)C1=C2C=CNC2=CC=C1.C(C)N(CC)CC>>N1C=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)C(F)(F)F)=O | [O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12.[OH:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12)[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]... | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(C(F)(F)F)cc1 | O=C(Nc1cccc2[nH]ccc12)OCc1ccc(C(F)(F)F)cc1 | null | null | C1CCOC1 | Protection | OtherReaction | 8d2aa5da7fec498749aba98cc9467e8d82c146f343570568bec74a92b10e0ae2 | e505c5de73b3f9ad0414c141c59109424d376f26a728bbd154d3edfd03d2f50a | O=C(Nc1cccc2[nH]ccc12)OCc1ccccc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[OH;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:9]-[C:10]-[c:11]):[c:8] | 53.8 | [{"value": 53.8, "product": "N1C=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [4-(Trifluoromethyl)phenyl]methanol (0.09 g, 0.55 mmol) and the product of Example 80A (0.08 g, 0.5 mmol) in THF (5 mL) were heated at reflux for 16 hours with a catalytic amount of triethylamine. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel e... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | null | C1CCOC1 | null | null | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(C(F)(F)F)cc1>C1CCOC1>O=C(Nc1cccc2[nH]ccc12)OCc1ccc(C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25703e41bebf41a49b262861f5add80d | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(OC(F)(F)F)cc1>>O=C(Nc1cccc2[nH]ccc12)OCc1ccc(OC(F)(F)F)cc1 | FC(OC1=CC=C(C=C1)CO)(F)F.N(=C=O)C1=C2C=CNC2=CC=C1.C(C)N(CC)CC>>N1C=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)OC(F)(F)F)=O | [O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12.[OH:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12)[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F... | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(OC(F)(F)F)cc1 | O=C(Nc1cccc2[nH]ccc12)OCc1ccc(OC(F)(F)F)cc1 | null | null | C1CCOC1 | Protection | OtherReaction | 8d2aa5da7fec498749aba98cc9467e8d82c146f343570568bec74a92b10e0ae2 | e505c5de73b3f9ad0414c141c59109424d376f26a728bbd154d3edfd03d2f50a | O=C(Nc1cccc2[nH]ccc12)OCc1ccccc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7]):[c:8].[OH;D1;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:9]-[C:10]-[c:11]):[c:8] | 54.4 | [{"value": 54.4, "product": "N1C=CC2=C(C=CC=C12)NC(OCC1=CC=C(C=C1)OC(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [4-(Trifluoromethoxy)pheny]methanol (0.13 g, 0.7 mmol) and the product of Example 80A (0.1 g, 0.63 mmol) in THF (5 mL) were heated at reflux for 16 hours with a catalytic amount of triethylamine. The reaction mixture was concentrated under reduced pressure and the residue was triturated with diethyl ether/hexane to pro... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | null | C1CCOC1 | null | null | O=C=Nc1cccc2[nH]ccc12.OCc1ccc(OC(F)(F)F)cc1>C1CCOC1>O=C(Nc1cccc2[nH]ccc12)OCc1ccc(OC(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93c3b299313148d6920bcc1b4881ba30 | Cc1[nH]c2cccc(N)c2c1C.O=C=NCc1ccc(Br)cc1>>Cc1[nH]c2cccc(NC(=O)NCc3ccc(Br)cc3)c2c1C | CCCCCC.CC=1NC2=CC=CC(=C2C1C)N.BrC1=CC=C(C=C1)CN=C=O>>BrC1=CC=C(CNC(=O)NC2=C3C(=C(NC3=CC=C2)C)C)C=C1 | [CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([NH2:9])[c:21]2[c:22]1[CH3:23].[C:10](=[O:11])=[N:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]3)[c:21]2[c:22]1[CH3:2... | Cc1[nH]c2cccc(N)c2c1C.O=C=NCc1ccc(Br)cc1 | Cc1[nH]c2cccc(NC(=O)NCc3ccc(Br)cc3)c2c1C | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[C:10]-[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:6] | null | [] | null | null | 3 | HOUR | 2,3-Dimethyl-4-aminoindole (0.11 g, 0.7 mmol) in THF (3 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.17 g, 0.8 mmol) at ambient temperature. After stirring for 3 hours at ambient temperature, hexane was added to the reaction mixture to precipitate the title compound as a tan solid (0.12 g). mp 190° C. 1H... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | null | C1CCOC1 | null | 3 | Cc1[nH]c2cccc(N)c2c1C.O=C=NCc1ccc(Br)cc1>C1CCOC1>Cc1[nH]c2cccc(NC(=O)NCc3ccc(Br)cc3)c2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f3cfefeb8ee42058587f4c73297002d | O=[N+]([O-])c1cccc2[nH]ncc12>>Nc1cccc2[nH]ncc12 | [BH4-].[Na+].[N+](=O)([O-])C1=C2C=NNC2=CC=C1>>N1N=CC=2C(=CC=CC12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][n:8][cH:9][c:10]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][n:8][cH:9][c:10]12 | O=[N+]([O-])c1cccc2[nH]ncc12 | Nc1cccc2[nH]ncc12 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | 75.1 | [{"value": 75.1, "product": "N1N=CC=2C(=CC=CC12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 4-Nitro-1H-indazole (1.63 g, 10 mmol) in ethanol (100 mL) was treated with BiCl3 (3.46 g, 11 mmol) followed by a portionwise addition of NaBH4. The reaction mixture was stirred at ambient temperature for 20 minutes and filtered through Celite. The filtrate was evaporated under reduced pressure and the residue was parti... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]ncc2c1 | Other | C(C)O | null | 0.333333 | O=[N+]([O-])c1cccc2[nH]ncc12>C(C)O>Nc1cccc2[nH]ncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1cd8c040b014a86b3af0bab367a7a2d | COC(=O)Cl.O=[N+]([O-])c1cccc2[nH]ncc12>>COC(=O)n1ncc2c([N+](=O)[O-])cccc21 | O.[H-].[Na+].[N+](=O)([O-])C1=C2C=NNC2=CC=C1.COC(=O)Cl>>[N+](=O)([O-])C1=C2C=NN(C2=CC=C1)C(=O)OC | Cl[C:3]([O:2][CH3:1])=[O:4].[nH:5]1[n:6][cH:7][c:8]2[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15][c:16]12>>[CH3:1][O:2][C:3](=[O:4])[n:5]1[n:6][cH:7][c:8]2[c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][cH:15][c:16]12 | COC(=O)Cl.O=[N+]([O-])c1cccc2[nH]ncc12 | COC(=O)n1ncc2c([N+](=O)[O-])cccc21 | null | null | CN(C)C=O | Acylation | N-alkylation of secondary amines with alkyl halides | 7faa17e35f4b23d2a80e9918e1703cff18db9438f8afa208f5b9468b7244c1c3 | d03c43b1eb3e007d0a26c663cd0f6b51f594c27d1ade9616fb1640d35a60bddb | c1ccc2[nH]ncc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[c:5]:[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[n;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[c:6]:1:[c:5] | null | [] | null | null | 1 | HOUR | Sodium hydride (0.3 g, 12.5 mmol) suspended in DMF (5 mL) at 0° C. was treated with 4-nitro-1H-indazole (1.33 g, 10 mmol). After stirring at room temperature for 1 hours, the mixture was treated with methylchloroformate (0.9 mL). After stirring at room temperature for 3 hours, the mixture was carefully treated with wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ether | c1ccc2[nH]ncc2c1 | c1cccc2[nH]ncc12 | c1cccc2[nH]ncc12 | HCl | CN(C)C=O | null | 1 | COC(=O)Cl.O=[N+]([O-])c1cccc2[nH]ncc12>CN(C)C=O>COC(=O)n1ncc2c([N+](=O)[O-])cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76f351b7aaeb48c2a08b8b641d36c13e | COC(=O)n1ncc2c([N+](=O)[O-])cccc21>>COC(=O)n1ncc2c(N)cccc21 | [BH4-].[Na+].[N+](=O)([O-])C1=C2C=NN(C2=CC=C1)C(=O)OC>>NC1=C2C=NN(C2=CC=C1)C(=O)OC | O=[N+:10]([O-])[c:9]1[c:8]2[cH:7][n:6][n:5]([C:3]([O:2][CH3:1])=[O:4])[c:14]2[cH:13][cH:12][cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[n:5]1[n:6][cH:7][c:8]2[c:9]([NH2:10])[cH:11][cH:12][cH:13][c:14]12 | COC(=O)n1ncc2c([N+](=O)[O-])cccc21 | COC(=O)n1ncc2c(N)cccc21 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | 83.7 | [{"value": 83.7, "product": "NC1=C2C=NN(C2=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | The product of Example 90A (1.66 g, 7.5 mmol) in ethanol (20 mL) was treated with BiCl3 (8.2 g, 2.6 mmol) followed by the addition of NaBH4 (1.13 g, 30.5 mmol). The reaction mixture was stirred at room temperature for 20 minutes, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cccc2[nH]ncc12 | Other | C(C)O | null | 0.333333 | COC(=O)n1ncc2c([N+](=O)[O-])cccc21>C(C)O>COC(=O)n1ncc2c(N)cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0799dee62d2d45c1bc621be2a0256ced | COC(=O)n1ncc2c(N)cccc21.O=C=NCc1ccc(Cl)c(Cl)c1>>COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21 | CCCCCC.NC1=C2C=NN(C2=CC=C1)C(=O)OC.ClC1=C(C=C(C=C1)CN=C=O)Cl>>ClC=1C=C(CNC(=O)NC2=C3C=NN(C3=CC=C2)C(=O)OC)C=CC1Cl | [CH3:1][O:2][C:3](=[O:4])[n:5]1[n:6][cH:7][c:8]2[c:9]([NH2:10])[cH:23][cH:24][cH:25][c:26]12.[C:11](=[O:12])=[N:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[n:5]1[n:6][cH:7][c:8]2[c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[c:20]([C... | COC(=O)n1ncc2c(N)cccc21.O=C=NCc1ccc(Cl)c(Cl)c1 | COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1cccc2[nH]ncc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1.[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[C:12]-[c:13]>>[O;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1)-[NH;D2;+0:11]-[C:12]-[c:13] | null | [] | null | null | 3 | HOUR | The product of Example 90B (0.19 g, 1 mmol) in THF (3 mL) was treated with 1,2-dichloro-4-(isocyanatomethyl)benzene (0.22 g, 1.1 mmol) at ambient temperature. After stirring for 3 hours, hexane was added to the reaction mixture to precipitate the title compound as a tan solid (0.25 g). 1H NMR (300 MHz, DMSO-d6) δ 4.38 ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1cccc2[nH]ncc12 | null | C1CCOC1 | null | 3 | COC(=O)n1ncc2c(N)cccc21.O=C=NCc1ccc(Cl)c(Cl)c1>C1CCOC1>COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e811c5f2db5a4baba03798fd855c4f85 | COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21>>O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ncc12 | ClC=1C=C(CNC(=O)NC2=C3C=NN(C3=CC=C2)C(=O)OC)C=CC1Cl.[OH-].[K+].C(Cl)Cl.O>>ClC=1C=C(CNC(=O)NC2=C3C=NNC3=CC=C2)C=CC1Cl | COC(=O)[n:19]1[c:18]2[cH:17][cH:16][cH:15][c:14]([NH:13][C:2](=[O:1])[NH:3][CH2:4][c:5]3[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]3)[c:22]2[cH:21][n:20]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1)[NH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[nH:19][n:20][cH:21][c:22]12 | COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21 | O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ncc12 | null | null | CO | Reduction | OtherReaction | b2164736883446cc727e745d0b4fddbc945c5a6fa5cfea478691c70222eeb795 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=C(NCc1ccccc1)Nc1cccc2[nH]ncc12 | C-O-C(=O)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1:[c:6]>>[c:6]:[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | The product of Example 90C (0.25 g, 0.6 mmol) was heated at reflux in methanol (5 mL) and 0.5N KOH (1 mL) for 0.5 hours. The reaction mixture was allowed to cool to ambient temperature, pH was adjusted to 5, and volume was reduced under reduced pressure. Methylene chloride and water was added, the phases were separated... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1cccc2[nH]ncc12 | c1ccc2[nH]ncc2c1 | c1ccccc1.c1ccc2[nH]ncc2c1 | HO- | CO | null | null | COC(=O)n1ncc2c(NC(=O)NCc3ccc(Cl)c(Cl)c3)cccc21>CO>O=C(NCc1ccc(Cl)c(Cl)c1)Nc1cccc2[nH]ncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-28b7ce7cf2a34f658965fc61001c81c1 | C=C(C)CC(O)(C(=O)OCC)C(F)(F)F.COc1ccc(F)cc1>>CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F | C(C)OC(C(CC(=C)C)(C(F)(F)F)O)=O.FC1=CC=C(C=C1)OC.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)OC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)(C(F)(F)F)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([OH:7])([CH2:8][C:9]([CH3:10])=[CH2:11])[C:21]([F:22])([F:23])[F:24].[cH:12]1[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]1[O:19][CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([OH:7])([CH2:8][C:9]([CH3:10])([CH3:11])[c:12]1[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]1[O:19][CH3:20])[C:21... | C=C(C)CC(O)(C(=O)OCC)C(F)(F)F.COc1ccc(F)cc1 | CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F | null | null | null | C-C Coupling | Friedel-Crafts alkylation | f6021e53f57d07d48a856391b21137517c9bd669381174a55381b6219a6afd68 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH2;D1;+0:8].[#8:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[#8:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[CH3;D1;+0:8])-[C:5]-[C:4]-[C:2](-[#8:1])=[O;D1;H0:3]):[c:13]:[c:14] | 71 | [{"value": 71.0, "product": "C(C)OC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)(C(F)(F)F)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a mixture of 5.9 g (26.1 mmol) of the above 2-hydroxy-4-methyl-2-trifluoromethylpent-4-enoic acid ethyl ester in 30 mL of 4-fluoroanisole was added 5.2 g (39.4 mmol) of aluminum chloride in several portions. The mixture became exothermic and turned black with the first addition and was cooled with an ice-water bath.... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | null | null | 72 | C=C(C)CC(O)(C(=O)OCC)C(F)(F)F.COc1ccc(F)cc1>>CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f255b62e0074ac9bcc1cd1bc6738ed5 | CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F>>COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F | C(C)OC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)(C(F)(F)F)O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>FC=1C=CC(=C(C1)C(CC(CO)(O)C(F)(F)F)(C)C)OC | CCO[C:16]([C:14]([CH2:13][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1)([CH3:11])[CH3:12])([OH:15])[C:18]([F:19])([F:20])[F:21])=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([OH:15])([CH2:16][OH:17])[C:18]([F:19])([F:20])[F:21] | CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F | COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[C:4]-[C:3](-[O;D1;H1:5])(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 92.9 | [{"value": 92.0, "product": "FC=1C=CC(=C(C1)C(CC(CO)(O)C(F)(F)F)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "FC=1C=CC(=C(C1)C(CC(CO)(O)C(F)(F)F)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a chilled solution (ice-water bath) of 6 g (17.0 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 60 mL of dry THF, 2.4 g (61.5 mmol) of lithium aluminum hydride was added in portions. After the addition, the cold bath was removed and the mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 8 | CCOC(=O)C(O)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F>C1CCOC1>COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b41be51826db4d2eb77745541df9b0f1 | COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F>>COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F | FC=1C=CC(=C(C1)C(CC(CO)(O)C(F)(F)F)(C)C)OC.I(=O)(=O)(=O)[O-].[Na+]>>FC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)=O)(F)F | OC[C:14]([CH2:13][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1)([CH3:11])[CH3:12])([OH:15])[C:16]([F:17])([F:18])[F:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14](=[O:15])[C:16]([F:17])([F:18])[F:19] | COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F | COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F | null | null | CCCCCC.CCOCC.CO | Miscellaneous | OtherReaction | 81a20ed57ee1ee8b55e4a533e6a354ed57ac5ba5659b8e1dd3b74910e43debde | d8333db1a8553533b9f31a51fd46ac10421b6606be90ce648ca3b16dc0428896 | c1ccccc1 | O-C-[C;H0;D4;+0:1](-[OH;D1;+0:2])(-[C:3]-[C:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8] | 87.6 | [{"value": 87.0, "product": "FC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "FC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 4.9 g (15.8 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol in 100 mL of MeOH was added 10 g (45.9 mmol) of sodium periodate. The mixture was stirred for 4 hours and was then diluted with 100 mL of ether and 100 mL of hexane, filtered through diatomaceous eart... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ketone | null | null | c1ccccc1 | HO- | CCCCCC.CCOCC.CO | null | 4 | COc1ccc(F)cc1C(C)(C)CC(O)(CO)C(F)(F)F>CCCCCC.CCOCC.CO>COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5aea3bb6c7145c0a83278b7a1d1572c | CC(C)(C)S(N)=O.COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F>>COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F | FC(C(CC(C)(C)C1=C(C=CC(=C1)F)OC)=O)(F)F.C(C)(C)(C)S(=O)N>>FC=1C=CC(=C(C1)C(C/C(/C(F)(F)F)=N/S(=O)C(C)(C)C)(C)C)OC | [NH2:15][S:16](=[O:17])[C:18]([CH3:19])([CH3:20])[CH3:21].O=[C:14]([CH2:13][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1)([CH3:11])[CH3:12])[C:22]([F:23])([F:24])[F:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13]/[C:14](=[N:15]/[S:16](=[O:17])[C:18]([CH3:1... | CC(C)(C)S(N)=O.COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F | null | null | [Cl-].[Na+].O.CCO.CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C:8]-[#16:9](-[NH2;D1;+0:10])=[O;D1;H0:11]>>[C:3]-[C:2]/[C;H0;D3;+0:1](=[N;H0;D2;+0:10]/[#16:9](-[C:8])=[O;D1;H0:11])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7] | 44 | [{"value": 44.0, "product": "FC=1C=CC(=C(C1)C(C/C(/C(F)(F)F)=N/S(=O)C(C)(C)C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "FC=1C=CC(=C(C1)C(C/C(/C(F)(F)F)=N/S(=O)C(C)(C)C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 500 mg (1.8 mmol) of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one and 0.86 mL (3.6 mmol) of a solution of Ti(OEt)4 in EtOH (˜20% Ti) in 7 mL of THF was added 240 mg (2 mmol) t-butylsulfinamide. The reaction was warmed at reflux for 6 h and then cooled to room temperature, diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1 | HO- | [Cl-].[Na+].O.CCO.CCOC(=O)C.C1CCOC1 | null | null | CC(C)(C)S(N)=O.COc1ccc(F)cc1C(C)(C)CC(=O)C(F)(F)F>[Cl-].[Na+].O.CCO.CCOC(=O)C.C1CCOC1>COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad8536782cee4311a9561ad7db6d3bb1 | CC(C)([CH2][Mg][Cl])c1ccccc1.CCOC(=O)C(=O)C(F)(F)F>>CCOC(=O)C(O)(CC(C)(C)c1ccccc1)C(F)(F)F | CC(C[Mg]Cl)(C)C1=CC=CC=C1.FC(C(C(=O)OCC)=O)(F)F>>C(C)OC(C(CC(C)(C1=CC=CC=C1)C)(C(F)(F)F)O)=O | [Cl][Mg][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[C:18]([F:19])([F:20])[F:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([OH:7])([CH2:8][C:9]([CH3:10])([CH3:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C:18]([F:19])([F:20])[F:21] | CC(C)([CH2][Mg][Cl])c1ccccc1.CCOC(=O)C(=O)C(F)(F)F | CCOC(=O)C(O)(CC(C)(C)c1ccccc1)C(F)(F)F | null | null | C(C)OCC.C1CCOC1 | C-C Coupling | Grignard from ketone to alcohol | c19641c06a40b22fede7d393a1da1cf27beb2cebc8cc85022080aa1ae052c9db | 652461eb0cd30990fcbed359f728e518ea93a58c037f4fc210fcb30d2dae5f8d | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[CH2;D2;+0:5]-[Mg]-[Cl].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[CH2;D2;+0:5]-[C:2](-[C;D1;H3:1])(-[C;D1;H3:3])-[c:4])-[C:12](-[F;D1;H0:... | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a room temperature solution of 45 mL (22.5 mmol) of a 0.5 M solution of 2-methyl-2-phenylpropylmagnesium chloride in diethyl ether was added 38 g (22.5 mmol) of ethyl trifluoropyruvate in 10 mL of anhydrous THF. The reaction became slightly warm to the touch and a white precipitate quickly developed. After 2 hours, ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone.Ester | Ester.Tertiary alcohol | null | null | c1ccccc1 | Mg | C(C)OCC.C1CCOC1 | null | 2 | CC(C)([CH2][Mg][Cl])c1ccccc1.CCOC(=O)C(=O)C(F)(F)F>C(C)OCC.C1CCOC1>CCOC(=O)C(O)(CC(C)(C)c1ccccc1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f92c4dbb5644799998fc794518485ad | CC(C)=CC(=O)C(F)(F)F.Fc1cc[c]([Mg][Br])cc1>>CC(C)(CC(=O)C(F)(F)F)c1ccc(F)cc1 | CCOCC.C1CCOC1.FC(C(C=C(C)C)=O)(F)F.FC1=CC=C(C=C1)[Mg]Br>>FC(C(CC(C)(C)C1=CC=C(C=C1)F)=O)(F)F | [CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[C:7]([F:8])([F:9])[F:10].[Br][Mg][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[C:7]([F:8])([F:9])[F:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | CC(C)=CC(=O)C(F)(F)F.Fc1cc[c]([Mg][Br])cc1 | CC(C)(CC(=O)C(F)(F)F)c1ccc(F)cc1 | null | [Cu]I | CCOCC | C-C Coupling | OtherReaction | acaaa339865910ee0f39da9928705a9efb5b9d834fb78bc685b81a374a75bca3 | 135f2ea95ad9a9b731f59e3aadf4d42e0f9aa41135665e9340592661a7692c1c | c1ccccc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C;H0;D3;+0:7](-[C;D1;H3:8])=[CH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[C;D1;H3:6]-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15])-[c;H0;D3;+0:1... | null | [] | null | null | 2 | HOUR | To a 2 M ether/THF solution of the above 1,1,1-trifluoro-4-methylpent-3-en-2-one was added 3.8 g of CuI and 10 mL of 2 M ether solution of 4-fluorophenylmagnesium bromide at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous ammonium chloride and e... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br-.Mg | [Cu]I.CCOCC | null | 2 | CC(C)=CC(=O)C(F)(F)F.Fc1cc[c]([Mg][Br])cc1>[Cu]I.CCOCC>CC(C)(CC(=O)C(F)(F)F)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f6a1e981b314c1c9c77fdfca8695d2a | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1ccccn1>>COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccccn1)C(F)(F)F | FC=1C=CC(=C(C1)C(C/C(/C(F)(F)F)=N/S(=O)C(C)(C)C)(C)C)OC.[Li]C(C)(C)C.CC1=NC=CC=C1>>FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=NC=CC=C1)N)(C)C)OC | CC(C)(C)S(=O)/[N:15]=[C:14](/[CH2:13][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1)([CH3:11])[CH3:12])[C:23]([F:24])([F:25])[F:26].[CH3:16][c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([NH2:15])([CH2:16][c:17]... | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1ccccn1 | COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccccn1)C(F)(F)F | null | null | CCCCC.C1CCOC1 | C-C Coupling | OtherReaction | ea3670267116d5783ab698a14a0529569267399ee692198612de216b6780a4f2 | a891e3efbb7d17d9024318bc2cb873f9c84846ffdaa21e6d4dd6f86dbec3bf20 | c1ccc(CCCCc2ccccn2)cc1 | C-C(-C)(-C)-S(=O)/[N;H0;D2;+0:1]=[C;H0;D3;+0:2](/[C:3]-[C:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[CH3;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[C:4]-[C:3]-[C;H0;D4;+0:2](-[NH2;D1;+0:1])(-[CH2;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8] | 25.2 | [{"value": 25.0, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=NC=CC=C1)N)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=NC=CC=C1)N)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a chilled (−78 C.) solution of 0.05 mL (0.514 mmol) of 2-methylpyridine in 3 mL of dry THF was added 0.23 mL (0.4 mmol) of a 1.7 M solution of t-BuLi in pentane. The mixture turned a bright orange. After 10 min, a solution of 98 mg (0.257 mmol) of 2-methyl-propane-2-sulfinic acid [3-(5-fluoro-2-methoxy-phenyl)-3-met... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | CCCCC.C1CCOC1 | null | 0.166667 | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1ccccn1>CCCCC.C1CCOC1>COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccccn1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbe22f1cc4b247bc8ad311fec8f58b7a | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1cc2ccccc2[nH]1>>COc1ccc(F)cc1C(C)(C)CC(N)(Cc1cc2ccccc2[nH]1)C(F)(F)F | FC=1C=CC(=C(C1)C(C/C(/C(F)(F)F)=N/S(=O)C(C)(C)C)(C)C)OC.CC(C)(C)[O-].[K+].[Li]CCCC.CC=1NC2=CC=CC=C2C1>>FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC=1NC2=CC=CC=C2C1)N)(C)C)OC | CC(C)(C)S(=O)/[N:15]=[C:14](/[CH2:13][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1)([CH3:11])[CH3:12])[C:26]([F:27])([F:28])[F:29].[CH3:16][c:17]1[cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[nH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([N... | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1cc2ccccc2[nH]1 | COc1ccc(F)cc1C(C)(C)CC(N)(Cc1cc2ccccc2[nH]1)C(F)(F)F | null | null | C(C)OCC.C1CCOC1 | C-C Coupling | OtherReaction | ea3670267116d5783ab698a14a0529569267399ee692198612de216b6780a4f2 | a891e3efbb7d17d9024318bc2cb873f9c84846ffdaa21e6d4dd6f86dbec3bf20 | c1ccc(CCCCc2cc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-S(=O)/[N;H0;D2;+0:1]=[C;H0;D3;+0:2](/[C:3]-[C:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[CH3;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[C:4]-[C:3]-[C;H0;D4;+0:2](-[NH2;D1;+0:1])(-[CH2;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8] | 33 | [{"value": 33.0, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC=1NC2=CC=CC=C2C1)N)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a chilled (−78 C.) solution of 40 mg (0.30 mmol) of 2-methylindole in 3 mL of diethyl ether was added 0.56 mL (0.91 mmol) of a 1.6 M solution of n-BuLi in hexanes. The resulting orange solution was stirred for 5 min and treated with 0.60 mL (0.60 mmol) of a solution of 1 M solution of KOt-Bu in THF. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | C(C)OCC.C1CCOC1 | -78 | 0.083333 | COc1ccc(F)cc1C(C)(C)C/C(=N/S(=O)C(C)(C)C)C(F)(F)F.Cc1cc2ccccc2[nH]1>C(C)OCC.C1CCOC1>COc1ccc(F)cc1C(C)(C)CC(N)(Cc1cc2ccccc2[nH]1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-78f61fc663da4dc2a337552f1b74b830 | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>>CNC(Cc1ccnc2ccccc12)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F | C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N)(C)C)OC.C=O>>FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC)(C)C)OC | O=[CH2:1].[NH2:2][C:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)([CH2:15][C:16]([CH3:17])([CH3:18])[c:19]1[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]1[O:26][CH3:27])[C:28]([F:29])([F:30])[F:31]>>[CH3:1][NH:2][C:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)([C... | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F | CNC(Cc1ccnc2ccccc12)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F | null | null | ClC(C)Cl | Heteroatom Alkylation and Arylation | Reductive methylation of primary amine with formaldehyde | 51d235def9103cd7a524cbedb590276839772d481304df37a121e64cb81721f4 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc(CCCCc2ccnc3ccccc23)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[C:4])(-[NH2;D1;+0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[C:2]-[C:3](-[C:4])(-[NH;D2;+0:5]-[CH3;D1;+0:1])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 55.2 | [{"value": 55.0, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 3-(5-fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) and formaldehyde (8 μL, 0.1 mmol) in dichloroethane (2 mL) was stirred for 30 min at room temperature in the presence of 4A molecular sieves (200 mg). The reaction mixture was acidified with aceti... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | null | null | c1ccc2ncccc2c1.c1ccccc1 | Other | ClC(C)Cl | null | 16 | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>ClC(C)Cl>CNC(Cc1ccnc2ccccc12)(CC(C)(C)c1cc(F)ccc1OC)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-06a1b845d841460fa85679daee335f1f | CC(=O)OC(C)=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>>COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(NC(C)=O)C(F)(F)F | FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N)(C)C)OC.C(C)(=O)OC(C)=O>>FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC(C)=O)(C)C)OC | CC(=O)O[C:27]([CH3:28])=[O:29].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([CH2:15][c:16]1[cH:17][cH:18][n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12)([NH2:26])[C:30]([F:31])([F:32])[F:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3... | CC(=O)OC(C)=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F | COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(NC(C)=O)C(F)(F)F | null | null | ClC(C)Cl | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(CCCCc2ccnc3ccccc23)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[C:6])(-[NH2;D1;+0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]>>[C:4]-[C:5](-[C:6])(-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11] | 74 | [{"value": 74.0, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC(C)=O)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)NC(C)=O)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 16 | HOUR | A solution of 3-(5-fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) in dichloroethane (4 mL) was treated with acetic anhydride (71 μL, 1.0 mmol). The mixture was stirred for 16 h at 85° C. and quenched with NaHCO3 (sat, 4 mL). Phases were separated and the aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | ClC(C)Cl | 85 | 16 | CC(=O)OC(C)=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>ClC(C)Cl>COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(NC(C)=O)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27986a26fcae4b74a8276a0be92b4c2c | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>>COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(N(C)C)C(F)(F)F | C(#N)[BH3-].[Na+].FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N)(C)C)OC.C=O.C(C)(=O)O>>FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N(C)C)(C)C)OC | O=[CH2:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([CH2:15][c:16]1[cH:17][cH:18][n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12)([NH2:26])[C:29]([F:30])([F:31])[F:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][C:14](... | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F | COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(N(C)C)C(F)(F)F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccc(CCCCc2ccnc3ccccc23)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[C:4])(-[NH2;D1;+0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[C:2]-[C:3](-[C:4])(-[N;H0;D3;+0:5](-[C;D1;H3:10])-[CH3;D1;+0:1])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9] | 28 | [{"value": 28.0, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N(C)C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.9, "product": "FC=1C=CC(=C(C1)C(CC(C(F)(F)F)(CC1=CC=NC2=CC=CC=C12)N(C)C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of 3-(5-Fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) and the formaldehyde (1.49 ml, 20 mmol) in acetonitrile (2 ml) was stirred for 30 minutes at room temperature. The reaction mixture was acidified with acetic acid (57 μL, 1.0 mmol) and treated wit... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2ncccc2c1 | null | C(C)#N | null | 15 | C=O.COc1ccc(F)cc1C(C)(C)CC(N)(Cc1ccnc2ccccc12)C(F)(F)F>C(C)#N>COc1ccc(F)cc1C(C)(C)CC(Cc1ccnc2ccccc12)(N(C)C)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-701b5f1c918649d0a0cd6ae9ff8a1478 | BrCc1ccccc1.CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(C(=O)OC(C)(C)C)CC2)cc1>>CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(Cc3ccccc3)CC2)cc1 | C(C)(C)(C)OC(=O)N1CCC(CC1)=C(C1=CC=C(C=C1)C(N(CC)CC)=O)Br.C(=O)(C(F)(F)F)O.C(C1=CC=CC=C1)Br.C(C)N(CC)CC>>C(C)N(C(C1=CC=C(C=C1)C(=C1CCN(CC1)CC1=CC=CC=C1)Br)=O)CC | Br[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][C:14](=[C:12]([c:11]2[cH:10][cH:9][c:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[cH:28][cH:27]2)[Br:13])[CH2:26][CH2:25]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12]([Br:13])=[C:14]... | BrCc1ccccc1.CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(C(=O)OC(C)(C)C)CC2)cc1 | CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(Cc3ccccc3)CC2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 2748de0f66b24d9234b7038da32a953a331d785cf6b99b2cb684608e577382cc | a8bb195a563e3d75cf4b5698f17ee0104c6036dda9c0d819e472675fa1d5becb | C(=C1CCN(Cc2ccccc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[C:8](=[C:9])-[C:10]-[C:11]-1>>[C:9]=[C:8]1-[C:7]-[C:6]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]-[C:10]-1 | 64 | [{"value": 64.0, "product": "C(C)N(C(C1=CC=C(C=C1)C(=C1CCN(CC1)CC1=CC=CC=C1)Br)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Compound 6, prepared in Example 1 (v) above (6.122 g, 13.4 mmoL), was treated with TFA (13 mL) in dichloromethane (80 mL) at room temperature. After 2 h, the reaction mixture was washed with 2M sodium hydroxide (25 mL) and the organic layer was separated. The organic layer was dried (MgSO), filtered and concentrated. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Boc | Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | ClCCl | 0 | 2 | BrCc1ccccc1.CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(C(=O)OC(C)(C)C)CC2)cc1>ClCCl>CCN(CC)C(=O)c1ccc(C(Br)=C2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7993330f56544394abc27c1cca50f87f | COC(=O)c1cc(OC)cc(C(=O)OC)c1>>COC(=O)c1cc(OC)cc(C(=O)O)c1 | COC(C1=CC(C(=O)OC)=CC(=C1)OC)=O.[OH-].[Na+]>>COC(C1=CC(C(=O)O)=CC(=C1)OC)=O | C[O:14][C:12]([c:11]1[cH:10][c:7]([O:8][CH3:9])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15]1)=[O:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15]1 | COC(=O)c1cc(OC)cc(C(=O)OC)c1 | COC(=O)c1cc(OC)cc(C(=O)O)c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 75.1 | [{"value": 75.0, "product": "COC(C1=CC(C(=O)O)=CC(=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "COC(C1=CC(C(=O)O)=CC(=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of dimethyl-5-methoxy-isophthalate (6.4 g, 28.5 mmol) in methanol (143 mL) was treated with 1 N sodium hydroxide (25.6 mL, 25.6 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 8 | COC(=O)c1cc(OC)cc(C(=O)OC)c1>CO>COC(=O)c1cc(OC)cc(C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-49f67a00773e439ca0f77853451bc9f9 | COC(=O)c1cc(OC)cc(C(N)=O)c1>>COC(=O)c1cc(C#N)cc(OC)c1 | COC(C1=CC(C(=O)N)=CC(=C1)OC)=O.N1=CC=CC=C1.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>COC(C1=CC(=CC(=C1)OC)C#N)=O | O=[C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][c:11]([O:12][CH3:13])[cH:10]1)[NH2:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]#[N:9])[cH:10][c:11]([O:12][CH3:13])[cH:14]1 | COC(=O)c1cc(OC)cc(C(N)=O)c1 | COC(=O)c1cc(C#N)cc(OC)c1 | null | null | ClCCl | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccccc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | 98.6 | [{"value": 98.0, "product": "COC(C1=CC(=CC(=C1)OC)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "COC(C1=CC(=CC(=C1)OC)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A suspension of 5-methoxy-isophthalamic acid methyl ester (4.0 g, 19.1 mmol) in a dichloromethane (80 mL) at 0° C. was treated with pyridine (6.3 mL, 77.0 mmol) and then trifluoroacetic anhydride drop-wise (6.5 mL, 46 mmol). The reaction was stirred at 0° C. for 20 min. and then stirred overnight at room temperature. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1 | HO- | ClCCl | 0 | 0.333333 | COC(=O)c1cc(OC)cc(C(N)=O)c1>ClCCl>COC(=O)c1cc(C#N)cc(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4151484a7b049b5ab77f711a10b50be | COC(=O)c1cc(C#N)cc(OC)c1>>COc1cc(C#N)cc(C(=O)O)c1 | COC(C1=CC(=CC(=C1)OC)C#N)=O.[OH-].[Li+]>>C(#N)C=1C=C(C(=O)O)C=C(C1)OC | C[O:12][C:10]([c:9]1[cH:8][c:5]([C:6]#[N:7])[cH:4][c:3]([O:2][CH3:1])[cH:13]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13]1 | COC(=O)c1cc(C#N)cc(OC)c1 | COc1cc(C#N)cc(C(=O)O)c1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 77 | [{"value": 77.0, "product": "C(#N)C=1C=C(C(=O)O)C=C(C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "C(#N)C=1C=C(C(=O)O)C=C(C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 2 | HOUR | A solution of 3-cyano-5-methoxy-benzoic acid methyl ester (3.4 g, 18.7 mmol) in THF (45 mL) was treated with 0.5 N lithium hydroxide (45 mL, 22.4 mmol). The reaction was stirred at 75° C. for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH 2) by... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C1CCOC1 | 75 | 2 | COC(=O)c1cc(C#N)cc(OC)c1>C1CCOC1>COc1cc(C#N)cc(C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b79f67932a94e14accfc8c088e94cde | Fc1cc(Br)cc(-n2ccnc2)c1>>N#Cc1cc(F)cc(-n2ccnc2)c1 | FC=1C=C(C=C(C1)Br)N1C=NC=C1.CN(C)C=O.[Br-]>>FC=1C=C(C=C(C1)C#N)N1C=NC=C1 | Br[c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[n:9]2[cH:10][cH:11][n:12][cH:13]2)[cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[n:9]2[cH:10][cH:11][n:12][cH:13]2)[cH:14]1 | Fc1cc(Br)cc(-n2ccnc2)c1 | N#Cc1cc(F)cc(-n2ccnc2)c1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-n2ccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | A solution of 3-fluoro-5-bromo-(1H-imidazol-1-yl)-benzene in DMF (36 mL) was treated with zinc cyanide and tetrakis(triphenylphosphine)palladium(0). The reaction mixture was heated under an argon atmosphere for 18 h at 80° C. when GC-MS indicated complete disappearance of starting bromide and presence of product molecu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | 80 | null | Fc1cc(Br)cc(-n2ccnc2)c1>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>N#Cc1cc(F)cc(-n2ccnc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-31068ea7e3ba4a8ab43d092f97804004 | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N>>CC(C)(C)OC(=O)N1CCCCC1C#N | N.C(C)N(CC)CC.C(C)(C)(C)OC(=O)N1C(CCCC1)C(=O)O.ClC(=O)OCC>>C(C)(C)(C)OC(=O)N1C(CCCC1)C#N | O=[C:14](O)[CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1.[NH3:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:14]#[N:15] | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N | CC(C)(C)OC(=O)N1CCCCC1C#N | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 6daec5e71bbc82d6d1305b776bb14d16edf8cd607701702401322171e2ae3591 | fe1b71f0ae392b327c6a5cc3c2c245a8e15960efcad58e19a65ce9bcf5ea8243 | C1CCNCC1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12].[NH3;D0;+0:13]>>[C:3]-[C:2](-[C;H0;D2;+0:1]#[N;H0;D1;+0:13])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12] | 80.4 | [{"value": 74.0, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | Piperidine-1,2-dicarboxylic acid-1-tert-butyl ester (12.8 g, 55.6 mmol) and THF (170 mL) were added to a 500 mL round bottom flask equipped with stir bar. The solution was cooled to −20° C. and triethylamine (10.1 mL, 72.3 mmol) was added followed by ethyl chloroformate (5.32 mL, 55.6 mmol). The resulting white precipi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Nitrile | null | null | C1CC[NH]CC1 | HO- | C1CCOC1 | -20 | null | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N>C1CCOC1>CC(C)(C)OC(=O)N1CCCCC1C#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3edc9b2b8f3444c9ae70e7c1766ffe10 | CC(C)(C)OC(=O)N1CCCCC1C(N)=O>>CC(C)(C)OC(=O)N1CCCCC1C#N | C(C(=O)Cl)(=O)Cl.C(C)(C)(C)OC(=O)N1C(CCCC1)C(N)=O.N1=CC=CC=C1.CN(C)C=O>>C(C)(C)(C)OC(=O)N1C(CCCC1)C#N | O=[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1)[NH2:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:14]#[N:15] | CC(C)(C)OC(=O)N1CCCCC1C(N)=O | CC(C)(C)OC(=O)N1CCCCC1C#N | null | null | C(C)#N | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | C1CCNCC1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]>>[C:4]-[C:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13] | 97.4 | [{"value": 97.0, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | Acetonitrile (220 mL) and DMF (3.82 mL, 49.4 mmol) were added to a 500 mL round bottom flask equipped with stir bar. Cooled the mixture down to −5° C. and to it added oxalyl chloride (24.7 mL, 49.4 mmol, 2 M dichloromethane). The resulting mixture was stirred for 15 min. This was followed by addition of solution of 2-c... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | C1CC[NH]CC1 | HO- | C(C)#N | -5 | null | CC(C)(C)OC(=O)N1CCCCC1C(N)=O>C(C)#N>CC(C)(C)OC(=O)N1CCCCC1C#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9abdd14d13e4aaab88e0d197f3e87dd | N#Cc1cccs1.NO>>N=C(NO)c1cccs1 | C(C)O.S1C(=CC=C1)C#N.Cl.NO.[OH-].[Na+]>>ONC(=N)C=1SC=CC1 | [N:1]#[C:2][c:5]1[cH:6][cH:7][cH:8][s:9]1.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][cH:7][cH:8][s:9]1 | N#Cc1cccs1.NO | N=C(NO)c1cccs1 | null | null | ClCCl.O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccsc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 88 | [{"value": 88.0, "product": "ONC(=N)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To an ethanol (5 mL) solution of 2-thiophenecarbonitrile (525.5 mg, 5 mmol), 5 M hydroxylamine hydrochloride (1.1 mL) and 1 M sodium hydroxide (5.5 mL) were added. After the reaction mixture was heated at 80° C. for 3 h, water and dichloromethane were added. The organic layer was dried, concentrated and triturated with... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1ccsc1 | null | ClCCl.O | 80 | null | N#Cc1cccs1.NO>ClCCl.O>N=C(NO)c1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08c518ddca984a52aaff357143fecc4d | CCc1cccc(C#N)c1.NO>>CCc1cccc(C(=N)NO)c1 | C(C)C=1C=C(C#N)C=CC1.Cl.NO.[OH-].[Na+]>>C(C)C=1C=C(C(=N)NO)C=CC1 | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]#[N:9])[cH:12]1.[NH2:10][OH:11]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[NH:9])[NH:10][OH:11])[cH:12]1 | CCc1cccc(C#N)c1.NO | CCc1cccc(C(=N)NO)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 46 | [{"value": 46.0, "product": "C(C)C=1C=C(C(=N)NO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Ethyl-benzonitrile (400 mg, 3.05 mmol) with 5 M hydroxylamine hydrochloride (0.61 mL) and 1 M sodium hydroxide (3.05 mL) in ethanol (3 mL) were stirred at room temperature for 60 h. Work up as in example 4 afforded 230 mg (46%) of 3-ethyl-N-hydroxy-benzamidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1ccccc1 | null | C(C)O | null | null | CCc1cccc(C#N)c1.NO>C(C)O>CCc1cccc(C(=N)NO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-36199a77d7744869bd14dc8e316823d6 | CN(C)C=O.Cc1cc[c]([Mg][Br])nc1>>Cc1ccc(C=O)nc1 | CC=1C=CC(=NC1)[Mg]Br.C1CCOC1.CN(C)C=O>>CC=1C=CC(=NC1)C=O | CN(C)[CH:6]=[O:7].[Br][Mg][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:9][n:8]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[n:8][cH:9]1 | CN(C)C=O.Cc1cc[c]([Mg][Br])nc1 | Cc1ccc(C=O)nc1 | null | null | null | C-C Coupling | OtherReaction | 9604d2e886e0bc8c47ad2945f9a5a6e743d4e4a6997677963260fd89592474cd | a58e2418b13d3d8c24c7fc0b5536d7cd7f384640d0a25ca1c1aac16b0b551ae5 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Br]-[Mg]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7] | 62.6 | [{"value": 62.6, "product": "CC=1C=CC(=NC1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To the 0.25 M 5-methyl-2-pyridinylmagnesium bromide of THF solution (20 mL, 5 mmol), DMF (0.773 mL, 10 mmol) was added at room temperature under argon. The reaction mixture was stirred for 10 min. and concentrated in vacuo. The residue was quenched with saturated ammonium chloride and dichloromethane. The organic layer... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Mg | null | null | 0.166667 | CN(C)C=O.Cc1cc[c]([Mg][Br])nc1>>Cc1ccc(C=O)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdf2fac1990c44f1be6a980ba0fd2b04 | CN(C)C=O.Cc1ccn[c]([Mg][Br])c1>>Cc1ccnc(C=O)c1 | CC1=CC(=NC=C1)[Mg]Br.C1CCOC1.CN(C)C=O>>CC1=CC(=NC=C1)C=O | CN(C)[CH:7]=[O:8].[Br][Mg][c:6]1[n:5][cH:4][cH:3][c:2]([CH3:1])[cH:9]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH:7]=[O:8])[cH:9]1 | CN(C)C=O.Cc1ccn[c]([Mg][Br])c1 | Cc1ccnc(C=O)c1 | null | null | null | C-C Coupling | OtherReaction | 9604d2e886e0bc8c47ad2945f9a5a6e743d4e4a6997677963260fd89592474cd | a58e2418b13d3d8c24c7fc0b5536d7cd7f384640d0a25ca1c1aac16b0b551ae5 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Br]-[Mg]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7] | 71.5 | [{"value": 71.5, "product": "CC1=CC(=NC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methyl-pyridine-2-carbaldehyde (433 mg, 71.5%) was obtained from 0.25 M 4-methyl-2-pyridinylmagnesium bromide of THF solution (20 mL, 5 mmol) with DMF (0.773 mL, 10 mmol) at room temperature under argon.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Mg | null | null | null | CN(C)C=O.Cc1ccn[c]([Mg][Br])c1>>Cc1ccnc(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fafd068689ee495580217a21665ecd92 | CN(C)C=O.Cc1cccn[c]1[Mg][Br]>>Cc1cccnc1C=O | CC=1C(=NC=CC1)[Mg]Br.C1CCOC1.CN(C)C=O>>CC=1C(=NC=CC1)C=O | CN(C)[CH:8]=[O:9].[Br][Mg][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]=[O:9] | CN(C)C=O.Cc1cccn[c]1[Mg][Br] | Cc1cccnc1C=O | null | null | null | C-C Coupling | OtherReaction | 9604d2e886e0bc8c47ad2945f9a5a6e743d4e4a6997677963260fd89592474cd | a58e2418b13d3d8c24c7fc0b5536d7cd7f384640d0a25ca1c1aac16b0b551ae5 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Br]-[Mg]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[C;D1;H3:7]):[c:8]>>[C;D1;H3:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[CH;D2;+0:1]=[O;D1;H0:2]):[#7;a:4]:[c:5] | 33 | [{"value": 33.0, "product": "CC=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methyl-pyridine-2-carbaldehyde (200 mg, 33.0%) was obtained from 0.25 M 3-methyl-2-pyridinylmagnesium bromide of THF solution (20 mL, 5 mmol) with DMF (0.773 mL, 10 mmol) at room temperature under argon.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Mg | null | null | null | CN(C)C=O.Cc1cccn[c]1[Mg][Br]>>Cc1cccnc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1f40f47ba5b4ffdb0a8c6d6403695d0 | CCO.O=C(O)c1ccc(F)cn1>>CCOC(=O)c1ccc(F)cn1 | FC=1C=CC(=NC1)C(=O)O.C(C)O.Cl>>C(C)OC(=O)C1=NC=C(C=C1)F | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][n:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][n:12]1 | CCO.O=C(O)c1ccc(F)cn1 | CCOC(=O)c1ccc(F)cn1 | null | null | O1CCOCC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 49.3 | [{"value": 49.3, "product": "C(C)OC(=O)C1=NC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Fluoro-pyridine-2-carboxylic acid (200 mg, 1.13 mmol) was mixed with ethanol (6 mL) and 4 M HCl in dioxane (0.5 mL) at 90° C. for 20 h. The mixture was concentrated and mixed with saturated sodium carbonate and dichloromethane. The dichloromethane layer was washed with brine, dried to give 94 mg (49.3%) of 5-fluoro-p... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | O1CCOCC1 | null | null | CCO.O=C(O)c1ccc(F)cn1>O1CCOCC1>CCOC(=O)c1ccc(F)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4e88c7a4f2f4535a5b7fe669b0b17f4 | CCOC(=O)c1ccc(F)cn1>>O=Cc1ccc(F)cn1 | C(C)OC(=O)C1=NC=C(C=C1)F.C1(=CC=CC=C1)C>>FC=1C=CC(=NC1)C=O | CCO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][n:9]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][n:9]1 | CCOC(=O)c1ccc(F)cn1 | O=Cc1ccc(F)cn1 | null | null | ClCCl.CC(C)C[AlH]CC(C)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 56.1 | [{"value": 54.7, "product": "FC=1C=CC(=NC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "FC=1C=CC(=NC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To 5-fluoro-pyridine-2-carboxylic acid ethyl ester (94 mg, 0.556 mmol) in dichloromethane (4.0 mL), 1 M DIBAL in toluene (1.23 mL, 1.23 mmol) was added at room temperature and the mixture was stirred for 30 min. The reaction mixture was quenched with 2 M sodium carbonate and extracted with dichloromethane. The dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccncc1 | HO- | ClCCl.CC(C)C[AlH]CC(C)C | null | 0.5 | CCOC(=O)c1ccc(F)cn1>ClCCl.CC(C)C[AlH]CC(C)C>O=Cc1ccc(F)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c1c154152fe45b2afb28915615593be | O=C(O)c1ccc(Cl)cn1>>O=Cc1ccc(Cl)cn1 | ClC=1C=CC(=NC1)C(=O)O.C(C)O.Cl>>ClC=1C=CC(=NC1)C=O | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][n:9]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][n:9]1 | O=C(O)c1ccc(Cl)cn1 | O=Cc1ccc(Cl)cn1 | null | null | O1CCOCC1 | Reduction | OtherReaction | 78999da0d33b2c10ff8c3d41626c41ea14d2697ff6d1d7e5baf78453ec38592a | f41d7c101137b93550fdf296ceb4547d1ce640e4cbceb5b7b006723d153456c9 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 52 | [{"value": 52.0, "product": "ClC=1C=CC(=NC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "ClC=1C=CC(=NC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 76.3%) was obtained obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid (200 mg, 1.03 mmol) with ethanol (3 mL) and 4M HCl in dioxane (0.5 mL) at 90° C. for 20 h. 5-Chloro-pyridine-2-carbaldehyde (58 mg, 52%) was obtained as described in ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | c1ccncc1 | Other | O1CCOCC1 | null | null | O=C(O)c1ccc(Cl)cn1>O1CCOCC1>O=Cc1ccc(Cl)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c969145559604c7d8937ea3bf6a22d15 | COC(=O)C1CCCCN1.O=Cc1ccccn1>>COC(=O)C1CCCCN1Cc1ccccn1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].Cl.N1C(C(=O)OC)CCCC1.N1=C(C=CC=C1)C=O.C(C)N(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>>COC(=O)C1N(CCCC1)CC1=NC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][NH:10]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1 | COC(=O)C1CCCCN1.O=Cc1ccccn1 | COC(=O)C1CCCCN1Cc1ccccn1 | null | null | ClC(C)Cl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCCCC2)nc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11])-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:6]-[C:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[C:13]-[C:14] | 93.6 | [{"value": 93.6, "product": "COC(=O)C1N(CCCC1)CC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "COC(=O)C1N(CCCC1)CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Methyl pipecolinate hydrochloride (9.0 g, 50 mmol) was mixed with pyridine-2-carbaldehyde (5.4 g, 50 mmol) and triethylamine (5.05 g, 50 mmol) in dichloroethane (180 mL) at room temperature. Sodium triacetoxyborohydride (14.8 g, 70 mmol) was added in one portion. After the reaction mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1 | Other | ClC(C)Cl | null | 1.5 | COC(=O)C1CCCCN1.O=Cc1ccccn1>ClC(C)Cl>COC(=O)C1CCCCN1Cc1ccccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd10f91b73694d80bba3c4a92731a1f1 | Cc1cccc(C(=O)O)n1>>CC1CCCC(C(=O)O)N1 | CC1=CC=CC(=N1)C(=O)O>>CC1CCCC(N1)C(=O)O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[n:10]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([C:7](=[O:8])[OH:9])[NH:10]1 | Cc1cccc(C(=O)O)n1 | CC1CCCC(C(=O)O)N1 | null | [Pt](=O)=O | O.C(C)O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[n;H0;D2;+0:10]:1>>[C;D1;H3:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])-[NH;D2;+0:10]-1 | 98.3 | [{"value": 98.3, "product": "CC1CCCC(N1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "CC1CCCC(N1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 6-Methyl-pyridine-2-carboxylic acid (4.11 g, 30 mmol) was mixed with platinum(IV) oxide (35 mg, 0.154 mmol) in ethanol (50 mL) and water (25 mL) and stirred under hydrogen for 3 days. The reaction mixture was filtered through the celite and concentrated to dry. The residue was triturated with diethyl ether to give 4.1 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Pt](=O)=O.O.C(C)O | null | 72 | Cc1cccc(C(=O)O)n1>[Pt](=O)=O.O.C(C)O>CC1CCCC(C(=O)O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed65202826954bf3adb9a2a7abfbaabc | COC(=O)C1CC(O)CCN1C(=O)OC(C)(C)C>>COC(=O)C1CC(=O)CCN1C(=O)OC(C)(C)C | OS(=O)(=O)[O-].[Na+].COC(=O)C1N(CCC(C1)O)C(=O)OC(C)(C)C.CS(=O)C.C(C(=O)Cl)(=O)Cl>>COC(=O)C1N(CCC(C1)=O)C(=O)OC(C)(C)C | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][C:7](=[O:8])[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | COC(=O)C1CC(O)CCN1C(=O)OC(C)(C)C | COC(=O)C1CC(=O)CCN1C(=O)OC(C)(C)C | null | null | ClCCl.CCN(CC)CC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | eb1454704a72f81f212192eafcb78e0711de77dd6074b9d7e49d38205debb755 | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCNCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5]-[C:6]-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5]-[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-1 | 88.2 | [{"value": 88.0, "product": "COC(=O)C1N(CCC(C1)=O)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "COC(=O)C1N(CCC(C1)=O)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a mixture of oxalyl chloride ((15 mL, 30 mmol, 2 M dichloromethane) in CH2Cl2 (100 mL) cooled to −78° C. was added DMSO (4.5 mL, 63.4 mmol). The mixture was stirred at this temperature for 1 h, after which 4-hydroxy-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2.0 g, 7.71 mmol dissolved in CH2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | null | ClCCl.CCN(CC)CC.C(Cl)Cl | -78 | 1 | COC(=O)C1CC(O)CCN1C(=O)OC(C)(C)C>ClCCl.CCN(CC)CC.C(Cl)Cl>COC(=O)C1CC(=O)CCN1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f98dd5e94fc24360a3b4c09c127afdb6 | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N#Cc1cccc(C(=N)NO)c1>>CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1 | C(C)(C)(C)OC(=O)N1C(CCCC1)C(=O)O.C(C)N(CC)CC.ClC(=O)OCC(C)C.C(#N)C=1C=C(C(=N)NO)C=CC1>>C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N | O=[C:14](O)[CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1.[NH:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]#[N:23])[cH:24]1)[NH:25][OH:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[c:14]1[n:15][c:16](-[c:17]2[cH... | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N#Cc1cccc(C(=N)NO)c1 | CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1 | null | null | ClCCl.O.CN(C)C=O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2noc(C3CCCCN3)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12].[NH;D1;+0:13]=[C;H0;D3;+0:14](-[NH;D2;+0:15]-[OH;D1;+0:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:14](-[c;H0;D3;+0:17](:[c:18]:[... | 98.5 | [{"value": 98.4, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a mixture of piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5.32 g, 23.2 mmol) and triethylamine (4.04 g, 40 mmol) in THF (50 mL), isobutyl chloroformate (3.0 mL, 25.5 mmol) was added dropwise. After the mixture was stirred at room temperature for 45 min, 3-cyano-N-hydroxy-benzamidine (3.7 g, 23.2 mmol) and DM... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | C1CC[NH]CC1.c1ncon1.c1ccccc1 | HO- | ClCCl.O.CN(C)C=O.C1CCOC1 | null | 0.75 | CC(C)(C)OC(=O)N1CCCCC1C(=O)O.N#Cc1cccc(C(=N)NO)c1>ClCCl.O.CN(C)C=O.C1CCOC1>CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1699df2f672043e7829a1f11eb94148c | CC1CCCC(C(=O)O)N1C(=O)OC(C)(C)C.N#Cc1cccc(C(=N)NO)c1>>CC1CCCC(c2nc(-c3cccc(C#N)c3)no2)N1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(CCCC1C)C(=O)O.ClC(=O)OCC(C)C.C(#N)C=1C=C(C(=N)NO)C=CC1.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1C(CCCC1C)C1=NC(=NO1)C1=CC(=CC=C1)C#N | O=[C:7](O)[CH:6]1[CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:20]1[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].[NH:8]=[C:9]([c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17]1)[NH:18][OH:19]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17]3... | CC1CCCC(C(=O)O)N1C(=O)OC(C)(C)C.N#Cc1cccc(C(=N)NO)c1 | CC1CCCC(c2nc(-c3cccc(C#N)c3)no2)N1C(=O)OC(C)(C)C | null | null | CN(C)C=O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2noc(C3CCCCN3)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12].[NH;D1;+0:13]=[C;H0;D3;+0:14](-[NH;D2;+0:15]-[OH;D1;+0:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[C:12]-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:1... | 48.6 | [{"value": 46.2, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1C)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1C)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (340 mg, 46.2%) was prepared according to the procedure in Example 25 from 6-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (486 mg, 2 mmol) with isobutyl chloroformate (273.16 mg, 2.0 mmol) and triethylamine... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | C1CC[NH]CC1.c1ncon1.c1ccccc1 | HO- | CN(C)C=O.C1CCOC1 | null | null | CC1CCCC(C(=O)O)N1C(=O)OC(C)(C)C.N#Cc1cccc(C(=N)NO)c1>CN(C)C=O.C1CCOC1>CC1CCCC(c2nc(-c3cccc(C#N)c3)no2)N1C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58507d49889e46be85380f27529308d1 | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.N#Cc1cccc(C(=O)Cl)c1>>CC(C)(C)OC(=O)N1CCCCC1c1noc(-c2cccc(C#N)c2)n1 | CN(C)C=O.C(#N)C=1C=C(C(=O)Cl)C=CC1.C(C)(C)(C)OC(=O)N1C(CCCC1)C(NO)=N.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC=C1)C#N | O[NH:15][C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[NH:26].Cl[C:17](=[O:16])[c:18]1[cH:19][cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[c:14]1[n:15][o:16][c:17](-[c:1... | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.N#Cc1cccc(C(=O)Cl)c1 | CC(C)(C)OC(=O)N1CCCCC1c1noc(-c2cccc(C#N)c2)n1 | null | null | ClCCl.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 35a949425cd7c777a41d64382aaf5f09103d9c9391a5f137dd482762a199998b | 7f85aea1a67b85d56267cd6d88af12850e1092108f42124a342198b2ffd2e0d0 | c1ccc(-c2nc(C3CCCCN3)no2)cc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].O-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[C:11](-[C:12])-[#7:13](-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20])-[C:21]>>[C:12]-[C:11](-[c;H0;D3;+0:9]1:[n;H0;D2;+0:8]:[o;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D... | 22.3 | [{"value": 22.3, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 50 mL round bottom flask equipped with stir bar, added 2-(N-hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (327 mg, 1.34 mmol), dichloromethane (5 mL) and triethylamine (0.56 mL, 4.03 mmol). To this stirred mixture was added a solution of 3-cyanobenzoyl chloride (222 mg, 1.34 mmol) in dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | null | null | c1ncon1 | C1CC[NH]CC1.c1ncon1.c1ccccc1 | HCl | ClCCl.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.N#Cc1cccc(C(=O)Cl)c1>ClCCl.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCCCC1c1noc(-c2cccc(C#N)c2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c116e83071ab4eae99b80de63e45af7c | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.COc1ccc(C#N)c(C(=O)O)c1>>COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1 | C(#N)C1=C(C(=O)O)C=C(C=C1)OC.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O.C(C)(C)(C)OC(=O)N1C(CCCC1)C(NO)=N>>C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC(=C1)OC)C#N | [NH:11]=[C:12]([CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[NH:26][OH:27].O=[C:10](O)[c:9]1[c:5]([C:6]#[N:7])[cH:8][cH:4][c:3]([O:2][CH3:1])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][c:9](-[c:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2... | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.COc1ccc(C#N)c(C(=O)O)c1 | COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1 | null | null | CN(C)C=O.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | fb0af6d623a6fb0dc430126834eabf3f72dc4d55326f21657754c4c7ce40679a | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2nc(C3CCCCN3)no2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[#8:5]):[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[C:9]#[N;D1;H0:10].[C:11]-[C:12](-[C;H0;D3;+0:13](=[NH;D1;+0:14])-[NH;D2;+0:15]-[OH;D1;+0:16])-[#7:17](-[C:18](=[O;D1;H0:19])-[#8:20]-[C:21](-[C;D1;H3:22])(-[C;D1;H3:23])-[C;D1;H3:24])-[C:25]>>[#8:5]-[c:4]1:[c:3]:[c;H0;... | 56 | [{"value": 56.0, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC(=C1)OC)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.7, "product": "C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC(=C1)OC)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | 8 | HOUR | DMF (2.0 mL) was added to a mixture of cyano-5-methoxybenzoic acid (160 mg, 0.90 mmol), EDCI (176 mg, 0.92 mmol), HOBt (124.3 mg, 0.92 mmol) and 2-(N-hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (224 mg, 0.92 mmol) at room temperature and stirred overnight. The reaction mixture was diluted with e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | c1ccccc1 | c1ccccc1.c1ncon1 | c1ccccc1.c1ncon1.C1CC[NH]CC1 | HO- | CN(C)C=O.C(C)(=O)OCC | 135 | 8 | CC(C)(C)OC(=O)N1CCCCC1C(=N)NO.COc1ccc(C#N)c(C(=O)O)c1>CN(C)C=O.C(C)(=O)OCC>COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-66a50e87870749f6a6723fc9a87525a5 | CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1>>N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1 | C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N>>N1C(CCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | CC(C)(C)OC(=O)[N:17]1[CH:12]([c:11]2[o:10][n:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:19]3)[n:18]2)[CH2:13][CH2:14][CH2:15][CH2:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]3)[n:18]2)[cH:19]1 | CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1 | N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1 | null | null | C(=O)O | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2noc(C3CCCCN3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[c:5](:[#7;a:6]):[#8;a:7]:[#7;a:8])-[C:9]>>[#7;a:6]:[c:5](-[C:4](-[C:9])-[NH;D2;+0:1]-[C:2]-[C:3]):[#8;a:7]:[#7;a:8] | 77.4 | [{"value": 73.4, "product": "N1C(CCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "N1C(CCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | 2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (8.1 g) was mixed with 96% formic acid (80 mL) and heated at 45° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ncon1.C1CCNCC1 | HO- | C(=O)O | 45 | null | CC(C)(C)OC(=O)N1CCCCC1c1nc(-c2cccc(C#N)c2)no1>C(=O)O>N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbd37b52b58d4dac829cc80eb1f6e6a3 | COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1>>COc1cc(C#N)cc(-c2nc(C3CCCCN3Cc3ccccn3)no2)c1 | C(C)(C)(C)OC(=O)N1C(CCCC1)C1=NOC(=N1)C1=CC(=CC(=C1)OC)C#N.FC(C(=O)O)(F)F>>COC=1C=C(C#N)C=C(C1)C1=NC(=NO1)C1N(CCCC1)CC1=NC=CC=C1 | O=[C:19](O[C:23]([CH3:21])([CH3:22])[CH3:24])[N:18]1[CH:13]([c:12]2[n:11][c:10](-[c:9]3[cH:8][c:5]([C:6]#[N:7])[cH:4][c:3]([O:2][CH3:1])[cH:28]3)[o:27][n:26]2)[CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][c:9](-[c:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2... | COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1 | COc1cc(C#N)cc(-c2nc(C3CCCCN3Cc3ccccn3)no2)c1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | de7153b84dda2e90c71480994df0a3f3b8dc2f891c32890ceec26a6aefcdf10b | 2c72fed15cc3edd74b0482c8ecd787e13465f4faff387e244477a633fd9b8e38 | c1ccc(-c2nc(C3CCCCN3Cc3ccccn3)no2)cc1 | O=[C;H0;D3;+0:1](-O-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[CH3;D1;+0:5])-[#7:6](-[C:7])-[C:8]>>[C:7]-[#7:6](-[CH2;D2;+0:1]-[c:9]1:[#7;a:10]:[cH;D2;+0:5]:[cH;D2;+0:2]:[cH;D2;+0:4]:[cH;D2;+0:3]:1)-[C:8] | null | [] | null | null | null | null | To a solution of 2-[5-(3-cyano-5-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester (162 mg, 0.42 mmol) in dichloromethane (4 mL) cooling in an ice-bath was added trifluoroacetic acid (2 mL). The ice-bath was removed after 30 min. and then left stirring for an additional hour. After th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | null | null | c1ccncc1 | c1ccccc1.c1ncon1.C1CC[NH]CC1.c1ccncc1 | null | ClCCl | null | null | COc1cc(C#N)cc(-c2nc(C3CCCCN3C(=O)OC(C)(C)C)no2)c1>ClCCl>COc1cc(C#N)cc(-c2nc(C3CCCCN3Cc3ccccn3)no2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ab5f886a86e44dfae5f95c005cece48 | ClCc1ccc2ccccc2n1.N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1>>N#Cc1cccc(-c2noc(C3CCCCN3Cc3ccc4ccccc4n3)n2)c1 | N1C(CCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1.Cl.ClCC1=NC2=CC=CC=C2C=C1.C(C)(C)N(CC)C(C)C.Cl>>N1=C(C=CC2=CC=CC=C12)CN1C(CCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[n:28]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]3)[n:29]2)[cH:30]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]... | ClCc1ccc2ccccc2n1.N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1 | N#Cc1cccc(-c2noc(C3CCCCN3Cc3ccc4ccccc4n3)n2)c1 | null | null | O.CCOCC.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2noc(C3CCCCN3Cc3ccc4ccccc4n3)n2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]):[#8;a:13]:[#7;a:14]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[C:11]-[C:12]):[#8;a:13]:[#7;a:14] | null | [] | null | null | null | null | 3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (50.8 mg, 0.2 mmol) was mixed with 2-(chloromethyl)quinoline monohydrochloride (47.1 mg, 0.22 mmol) and diisopropylethylamine (129.3 mg, 1.0 mmol) in DMF (2 mL) at 80° C. for 20 h. The reaction mixture was poured into water and extracted with dichloromethane. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ncon1.C1CC[NH]CC1.c1ccc2ncccc2c1 | HCl | O.CCOCC.CN(C)C=O | null | null | ClCc1ccc2ccccc2n1.N#Cc1cccc(-c2noc(C3CCCCN3)n2)c1>O.CCOCC.CN(C)C=O>N#Cc1cccc(-c2noc(C3CCCCN3Cc3ccc4ccccc4n3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5aa70eb55f574960b7a7ce073d20565d | COC(=O)C1CCCCN1Cc1ccccn1.COc1cccc(C(=N)NO)c1>>COc1cccc(-c2noc(C3CCCCN3Cc3ccccn3)n2)c1 | COC(=O)C1N(CCCC1)CC1=NC=CC=C1.ONC(C1=CC(=CC=C1)OC)=N.CC(C)([O-])C.[Na+]>>COC=1C=C(C=CC1)C1=NOC(=N1)C1N(CCCC1)CC1=NC=CC=C1 | CO[C:11](=O)[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([NH:9][OH:10])=[NH:25])[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][c:19]3... | COC(=O)C1CCCCN1Cc1ccccn1.COc1cccc(C(=N)NO)c1 | COc1cccc(-c2noc(C3CCCCN3Cc3ccccn3)n2)c1 | null | null | ClCCl.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 88b71cc25219a15819c3a3f01bd6e17c339fa66cdf2edd95092bad2351ca17df | b2e640ad6adb277738cae8a944067d998d1107d1f884bf69b59d55eb50b99f16 | c1ccc(-c2noc(C3CCCCN3Cc3ccccn3)n2)cc1 | C-O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[#7:4](-[C:5])-[C:6].[NH;D1;+0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[OH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[n;H0;D2;+0:9]:[o;H0;D2;+0:10]:1)-[#7:4](-[C:5])-[C... | null | [] | null | null | null | null | 1-Pyridin-2-ylmethyl-piperidine-2-carboxylic acid methyl ester (50 mg, 0.213 mmol) was mixed with N-hydroxy-3-methoxy-benzamidine (29 mg, 0.174 mmol) and sodium tert-butoxide (19 mg, 0.20 mmol) in toluene (0.5 mL) in a sealed vial at 130° C. for 10 min. The reaction mixture was cooled down and diluted with dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1CC[NH]CC1.c1ccncc1 | HO- | ClCCl.C1(=CC=CC=C1)C | null | null | COC(=O)C1CCCCN1Cc1ccccn1.COc1cccc(C(=N)NO)c1>ClCCl.C1(=CC=CC=C1)C>COc1cccc(-c2noc(C3CCCCN3Cc3ccccn3)n2)c1 |
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