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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-55924f439baf4eec911c51f073509950 | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCBr>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCBr)C=C1 | Br[CH2:11][CH2:12][CH2:13][CH2:14][Br:15].[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:16][CH2:17]3)[n:18][o:19][c:20]2[cH:21]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH2:16][CH2:17]3)[n:18][o:19][c:20]2[cH:21]1 | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | 8 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (12 g, 55 mmol), K2CO3 (13 g) and 1,4-dibromobutane (20 g, 9.3 mmol, 1.7 eq) in acetonitrile (300 ml) was stirred at room temperature overnight. The inorganic material was filtered. The solution was concentrated to ~80 ml, when crystals crashed out. The product ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | 8 | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9de078e66168457bb315d7d1372c9e07 | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)OCCBr>>C(\C=C\C(=O)O)(=O)O.C(C)(=O)OCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:10]-[C:11] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (3.5 g, 25 mmol), 2-bromoethyl acetate (4 g, 26.5 mmol) in acetonitrile (50 ml) was heated at reflux for 4 hours. After cooling to room temperature, the inorganic salts were filtered and washed with DCM (dichloromethane 50 ml). The orga... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd29025a102a48e9a4fe32bb9aa1b72b | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.ClCCN1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2CCOCC2)C=C1 | Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:19][CH2:20]3)[n:21][o:22][c:23]2[cH:24]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][N:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)[CH2:19][CH2:20]3)[... | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | null | null | C(C)#N.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), 2-chloroethyl morpholine hydrochloride (4.46 g, 29.7 mmol) and K2CO3 (7.3 g, 2.2 eq) in acetonitrile (60 ml) was heated at reflux for 24 hours. The crude mixture was diluted with DCM and filtered. The solvent was concentrated to an oil (~7.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1COCC[NH]1.c1ccc2oncc2c1 | HCl | C(C)#N.C(Cl)Cl | null | null | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(Cl)Cl>Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8bee3bfb2a50433ba754e6bd96348765 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1.Cl>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1 | [O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:1... | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | CCOCC.ClCCl.C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | null | null | [] | null | null | null | null | To a solution of 8.0 g of N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide in dichloromethane/ethanol (150 ml) was added 1M - HCl in ether. The salt crystallized out rapidly. It was filtered off, washed with ethanol and dried to afford 8.15 g with m.p.=257°-259° C, dec. Recrystallization provide... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | null | CCOCC.ClCCl.C(C)O | null | null | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>CCOCC.ClCCl.C(C)O>O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f61c855945b94f1ca7f24ef42d911d7d | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].COCCBr.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.COCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:4][CH2:3][O:2][CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.75 g, 17 mmol), K2CO3 (3 g, 21.7 mmol), bromoethyl methyl ether (2.84 g, 20.4 mmol) in acetonitrile (150 ml) was heated at reflux for 3.5 hours. The reaction was cooled. The inorganics were filtered and rinsed with DCM. The organic solution was concentrated d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>COCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bb738a891df04b59ad8b29472e39fecc | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)OCCCCBr.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(C)(=O)OCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[NH:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21][c:22]23)[CH2:23][CH2:24]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21]... | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (9.5 g, 41 mmol), K2CO3 (7.2 g, 51 mmol), and 4-bromobutyl acetate (10 g, 51 mmol) in acetonitrile (200 ml) was heated at reflux for 3.5 hours. At the end of the reaction, the solution was cooled and filtered. The inorganic salt was washed with DCM (50 ml). The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6caf8963624c4c5486cc8cef7dfc13b6 | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1>>CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCO)C=C1.C(C)N(CC)CC.C(Cl)Cl.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)OCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | N([CH2:2][CH3:1])([CH2:6][CH3:3])[CH2:8][CH3:9].[C:10](=[O:11])([OH:35])/[CH:36]=[CH:37]/[C:38](=[O:39])[OH:40].[OH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]... | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | C(C)O | C-C Coupling | OtherReaction | 751760910e5f360277c3f4d3befcb89bbe0e920df03a91877e36a8d024b51b87 | c343030799bb933f3375c7d72f59363fd1b700abfc69826f97b066628943b37c | c1ccc2c(C3CCNCC3)noc2c1 | [C;D1;H3:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C:7]-[C:8]-[OH;D1;+0:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-[OH;D1;+0:12])/[CH;D2;+0:13]=[C:14]/[C:15](=[O;D1;H0:16])-[O;D1;H1:17]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:18]-[CH2;D2;+0:3]-... | null | [] | null | null | 1 | HOUR | To a solution of 4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol (2.0 g, 6.84 mmol), triethylamine (1.0 g, 10 mmol) in DCM (70 ml) decanoyl chloride (1.7 g, 8.9 mmol) was added dropwise at room temperature. The mixture was stirred for 1 hour, then was concentrated to a crude solid. The solid was extracted i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Tertiary amine | Carboxylic acid.Ester | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(C)O | null | 1 | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1>C(C)O>CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b7a6381a31624f2abe3534bcc8534156 | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1>>CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCO)C=C1.C(CCCCCCCCC)(=O)Cl>>C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].[OH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][CH2... | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.C(C)O | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 20 | MINUTE | To a solution 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propanol (1.81 g, 6.5 mmol) triethylamine (0.9 g, 9.0 mmol) in DCM (45 ml) was added decanoyl chloride (1.5 g, 7.8 mmol) dropwise at room temperature. The mixture was stirred for 20 minutes, then concentrated down to a crude solid. The solid was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl.C(C)O | null | 0.333333 | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.C(C)O>CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6b0090ed138249c69201380b84c6c7ca | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>>NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.C(C)N(CC)CC.C(\C=C\C(=O)O)(=O)O.C(C)(=O)Cl>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCC(=O)N)C=C1 | Cl[C:2](=[O:3])[CH3:4].[NH2:1][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.C(C)O | Acylation | OtherReaction | 74356bef414ba31a0485b52d7495e90a08f4a5b89d028b8ec303ccdb6ed5504f | 5d86061e72bfd6a9511ca0dd8b67e7f96dd93b070d7199a24f9e8328c94bd93b | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].[#7:4]-[C:5]-[CH2;D2;+0:6]-[NH2;D1;+0:7]>>[#7:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:7])=[O;D1;H0:3] | null | [] | null | null | 4 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.56 g, 9.7 mmol) and triethylamine (1.45 g, 14.5 mmol) in DCM (50 ml) was treated with dropwise addition of acetyl chloride (1.0 g, 12.7 mmol) at room temperature. The mixture was stirred for 4 hours at room temperature. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Primary amide | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl.C(C)O | null | 4 | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.C(C)O>NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-acb1fa37cdaa4790bf36e0b4c1d1ccf1 | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-]>>Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.ClCCCN1CCCCC1.C(=O)([O-])[O-].[K+].[K+].O>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2CCCCC2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]3)[n:22][o:23][c:24]2[cH:25]1.[OH2:34].[O-:26][C:31](=[O:32])[O-:40]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][N:14]4[C... | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-] | Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N | Acylation | OtherReaction | 5abf4ce96638af1fef71fa30c86fff983bcc6ae0a81b871495c8ad14ff13da86 | 1e44655a39628ea3cd903509b7d5e10cb6ac6bc1b1eb03e5733de839f4a001b9 | c1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;D1;H0:12].[OH2;D0;+0:13]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8].[O;D1;H0:12]=[C;H0;D3;+0:10](-[O;D1;H1:14])/[C:15]=[C:16]/[C:17](-[O;D1;H1:18])=[O;H0;D1;+0:9].[O;D1;H1:19]-[C:20... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 g, 13.6 mmol), N-(3-chloropropyl)piperidine hydrochloride (4.05 g, 20.4 mmol), K2CO3 (6 g, 43.4 mmol), tetrabutylammonium hydrogen sulfate (phase transfer catalyst, 2.3 g) in acetonitrile (100 ml) and water (15 ml) was heated at reflux for 16 hours. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccc2oncc2c1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N | null | null | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N>Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e2975f1f2ea7449c8927f64803c30af1 | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.CN(CCCCl)C.C(=O)([O-])[O-].[K+].[K+].C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.CN(CCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1.[O-:23][C:24]([O-:25])=[O:29]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH... | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N.O.C(C)O | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;H0;D1;+0:12]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8].[O;D1;H1:13]-[C:14](=[O;H0;D1;+0:12])/[C:15]=[C:16]/[C;H0;D3;+0:10](=[O;H0;D1;+0:9])-[OH;D1;+0:11] | 56.9 | [{"value": 56.9, "product": "C(\\C=C\\C(=O)O)(=O)O.C(\\C=C\\C(=O)O)(=O)O.CN(CCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.05 g, 13.8 mmol), 3-dimethylaminopropyl chloride hydrochloride (3.4 g, 21 mmol), K2CO3 (6.2 g, 45 mmol), tetrabutylammonium hydrogen sulfate (phase transfer catalyst, 1.5 g) in acetonitrile (100 ml) and water (50 ml) was heated at 60° C. overnight. The aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O.C(C)O | 60 | null | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O.C(C)O>CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-be43b907ab2540ec8cab23f350f82a4d | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC=1C=C2C=CNC2=CC1.CC#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C3C=CNC3=CC2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[nH:19][cH:20][cH:21][c:22]2[cH:23]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:24][CH2:25]3)[n:26][o:27][c:28]2[cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][c:15]4[cH:16][cH:17... | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 123.4 | [{"value": 123.4, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C3C=CNC3=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.6 g, 11.8 mmol), K2CO3 (1.6 g, 11.6 mmol), KI (200 mg), 5-(3-chloropropoxy)indole (2.2 g, 10.5 mmol) and CH3CN (100 ml) was stirred at reflux under N2 for 18 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2oncc2c1 | HCl | O | null | null | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>O>Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-97225b9c9096405ebc773afa2b19a105 | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=C2C=CNC2=CC=C1.CC#N.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C3C=CNC3=CC=C2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[nH:20][cH:21][cH:22][c:23]12.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:24][CH2:25]3)[n:26][o:27][c:28]2[cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][c:15]4[cH:16][cH:17... | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCCN2CCC(c3noc4ccccc34)CC2)c2cc[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 103.5 | [{"value": 103.5, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C3C=CNC3=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 68 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.5 g, 16 mmol), K2CO3 (2.2 g, 16 mmol), KI (200 mg), 4-(3-chloropropoxy)indole (3.0 g, 14 mmol) and CH3CN (100 ml) was stirred at reflux under N2 for 7 hours and then at ambient temperature for 68 hours. Reflux was resumed for an additional 6 hours whereupon a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2oncc2c1 | HCl | O | null | 68 | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1>O>Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bd49ef3914f2487682f2523e95f2a150 | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1>>CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 | FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1.ClCCCOC1=C(C=C(C=C1)C(C)=O)O.C(=O)(O)[O-].[Na+].S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCCCOC2=C(C=C(C=C2)C(C)=O)OC>>FC1=CC2=C(C(=NS2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)O)C=C1 | Cl[CH2:11][CH2:10][CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:30][c:28]1[OH:29].[NH:12]1[CH2:13][CH2:14][CH:15]([c:16]2[n:17][s:18][c:19]3[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]... | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1 | CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 | null | null | O.CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3nsc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 97 | [{"value": 97.0, "product": "FC1=CC2=C(C(=NS2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (2.4 g, 10.1 mmol), 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (2.5 g, 11.1 mmol), NaHCO3, (0.94 g, 11.1 mmol), KI (100 mg) and CH3CN (1(30 ml) was stirred at reflux under N2 for 65 hours. The cooled reaction was poured into H2O and the aqueous mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2sncc2c1 | HCl | O.CC#N | null | null | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1>O.CC#N>CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-357efaa911ef4c019e648d9084143081 | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)C[C@H](CO)C)C=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:1... | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1 | C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | To a mixture of (R)-(-)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-1-propanol (7.26 g, 24.8 mmol), triethyl amine (3 ml, 30 mmol) in methylene chloride (DCM, 120 ml), methanesulfonyl chloride (3.13g, 27.3 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature for 1 hour, then c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl | null | 1 | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-484ddf404614445f9f6de7619e8291c6 | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(CO)(C)C>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CO)(C)C)C=C1 | Br[CH2:6][C:2]([CH3:1])([CH2:4][OH:5])[CH3:27].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1.[O-:23][C:28]([O-:25])=[O:29]>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18]... | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.C(C)#N | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[C:5]-[O;D1;H1:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11].[O-;H0;D1:12]-[C;H0;D3;+0:13](-[O-;H0;D1:14])=[O;D1;H0:15]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:16])-[C:5]-[O;D1;H1:6])-[C:10]-[C:11].[O;D1;H0:15]=[C;H0;D3;... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 g, 13.6 mmol), K2CO3 (12.5 g, 17.5 mmol), 3-bromo-2,2-dimethyl-1-propanol (3 g, 21 mmol, 1.5 eq.), tetra-butylammonium hydrogen sulfate (1 g, phase transfer catalyst) in water (5 ml) and acetonitrile (150 ml) was heated at reflux for 43 days. TLC showed a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(C)#N | null | null | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(C)#N>CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-122d0c56cdda4c498ef112e2cd7cb8e1 | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)C[C@@H](CO)C)C=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]... | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1 | C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | To a mixture of (S)-(+)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-1-propanol (8.8 g, 30 mmol), triethylamine (3.2 g, 32 mmol) in dichloromethane (DCM, 150 ml), methanesulfonyl chloride (4 g, 35 mmol) was added dropwise at 0° C. over 10 minutes. The mixture was stirred at room temperature for 1 hour,... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | ClCCl | null | 1 | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>ClCCl>C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-96709f122663497aba22bbf422d81999 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O>>CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | [NH4+].[Cl-].CCOC(=O)C.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(=O)OCC)C=C1.C[Mg]Br>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(C)(O)C)C=C1 | C([CH3:3])[O:4][C:2]([CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1)=[O:23].[CH2:24]([O:25][C:28]([CH3:27])=[O:29])[CH3:26]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([... | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O | CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | 07e99f91e500affa0451dbbfb1ccdfc6c2bf1d992b11b74db56debe2dbd4b3e4 | 15308189f1479c7a0725eea178834fcdf99915b1d89a0f1b88a28657dab684ab | c1ccc2c(C3CCNCC3)noc2c1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](-[CH3;D1;+0:5])=[O;D1;H0:6].[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[O;H0;D2;+0:11]-C-[CH3;D1;+0:12]>>[C:7]-[C:8]-[C;H0;D4;+0:9](-[C;D1;H3:13])(-[CH3;D1;+0:12])-[OH;D1;+0:11].[O;D1;H0:6]=[C;H0;D3;+0:4](-[O;D1;H1:14])/[CH;D2;+0:5]=[CH;D2;+0:1]/[C;H0;D3;+0:2]... | null | [] | null | null | 16 | HOUR | To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.21 g, 10 mmol) in tetrahydrofuran (THF, 100 ml), was added methylmagnesium bromide (10 ml, 30 mmol, 3M solution in ether) dropwise over 15 minutes at room temperature under N2. The resulting mixture was stirred for 16 hours. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid.Tertiary alcohol | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | Other | O1CCCC1 | null | 16 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O>O1CCCC1>CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0bb9f11325fc4360a6430779307c7ca3 | CCOC(=O)C(C)Br.Fc1ccc2c(C3CCNCC3)noc2c1>>CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrC(C(=O)OCC)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(=O)OCC)C=C1 | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[NH:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][o:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[CH2:22][CH2:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][o:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[CH2:2... | CCOC(=O)C(C)Br.Fc1ccc2c(C3CCNCC3)noc2c1 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c75fa98306ed1f74f6ec661a0622356cd27da947d5627f1d9753a66aa7c23912 | a0286fa141f0eb1490b0c8c39496a2920e05a12efb6a4295558085056c110e3f | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:10]-[C:11] | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5 g, 22.7 mmol), K2CO3 (3.8 g, 27.5 mmol) and ethyl bromopropionate (5 g, 27.6 mmol, 1.2 eq) in acetonitrile (200 ml) was heated at reflux for 16 hours. The mixture was cooled and filtered. The solvent was removed, and the residue was purified on a flash chroma... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Secondary amine | Ester.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | CCOC(=O)C(C)Br.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-74291959fa524be09e451123220ca837 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1.[BH4-].[Na+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17... | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 90 | [{"value": 90.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a suspension of N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide (7.8 g, 19.8 mmol) in methanol (250 ml) and DCM (30 ml) was added NaBH4 (1.7 g, 45.5 mmol) at room temperature under nitrogen. After stirring for 0.5 hours the homogeneous reaction mixture was concentrated. The remaining solid w... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(Cl)Cl.CO | null | 0.5 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.CO>O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-14011757043648f4b44214623ce6a978 | O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>O=C1c2ccccc2CN1CCN1CCC(c2noc3cc(F)ccc23)CC1 | C(=O)(O)[O-].[Na+].FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1.FC(C(=O)O)(F)F.C(C)[SiH](CC)CC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2)=O)C=C1 | O[CH:9]1[c:8]2[c:3]([cH:4][cH:5][cH:6][cH:7]2)[C:2](=[O:1])[N:10]1[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n:18][o:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n... | O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | O=C1c2ccccc2CN1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Reduction | OtherReaction | 6edf8215b233e57f6f4321f4b7bccecd4275fe90ce30e97960f31ca67074cfef | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | O=C1c2ccccc2CN1CCN1CCC(c2noc3ccccc23)CC1 | O-[CH;D3;+0:1]1-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-1:[c:8]>>[C:3]-[#7:2]1-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:6]-[C:4]-1=[O;D1;H0:5] | 79 | [{"value": 79.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydro-3-hydroxy-1H-isoindol-1-one (2.2 g, 5.6 mmol) was added a solution of trifluoroacetic acid (11.0 ml) in dichloromethane (30 ml) at room temperature, under nitrogen. Triethylsilane (1.5 ml) was then added and the reaction mixture was allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | Other | ClCCl | null | 18 | O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>ClCCl>O=C1c2ccccc2CN1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-93939fa9bb164986a5dea001fb41db72 | CN=C=O.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@@H](CCOC(N)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | C(=O)([O-])[O-].[K+].[K+].FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1.CN=C=O.C1CCOC1>>C(N)(OCC[C@@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C)=O | [CH3:1][N:7]=[C:6]=[O:5].OC1c2ccccc2C(=[O:8])N1[CH2:4][CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@@H:2]([CH2:3][CH2:4][O:5][C:6]([NH2:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20... | CN=C=O.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | C[C@@H](CCOC(N)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | null | C-C Coupling | OtherReaction | 53017254a6230e06d54a6df71090c280f25e867abecc594446c52b574a7e46ac | 57512f0c367b666e99a38eaae1d5a3161ab75ed5010663a43f9a8a698905be0d | c1ccc2c(C3CCNCC3)noc2c1 | O-C1-N(-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[#7:3](-[C:4])-[C:5])-C(=[O;H0;D1;+0:6])-c2:c:c:c:c:c:2-1.[CH3;D1;+0:7]-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;H0;D1;+0:10]>>[C:4]-[#7:3](-[CH2;D2;+0:2]-[C:11](-[CH3;D1;+0:7])-[C:12]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C;H0;D3;+0:9](-[NH2;D1;+0:8])=[O;H0;D1;+0:6])-[C:5] | 73 | [{"value": 73.0, "product": "C(N)(OCC[C@@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydro-3-hydroxy-1H-isoindol-1-one (3.1 g, 10.6 mmol) in dry THF (120 ml) was added methyl isocyanate (0.66 ml, 11.1 mmol) followed by milled K2CO3 (2.2 g, 15.9 mmol) at room temperature, under nitrogen. The reaction mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Tertiary amide.Secondary alcohol | Carbamic ester.Ether | c1ccc2c(c1)CNC2 | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | null | null | 72 | CN=C=O.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@@H](CCOC(N)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4adeacebf7a24fdca7f589616df037b7 | Cc1ccc(S(=O)(=O)[O-])cc1.Fc1ccc2c(C3CCNCC3)noc2c1>>Cc1ccc(S(=O)(=O)OCCC(C)O)cc1 | C([O-])([O-])=O.[K+].[K+].S(=O)(=O)([O-])C1=CC=C(C)C=C1.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1>>S(=O)(=O)(OCCC(C)O)C1=CC=C(C)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O-:9])[cH:15][cH:16]1.Fc1ccc2c([CH:12]3[CH2:11][CH2:10]NC[CH2:13]3)noc2c1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH:12]([CH3:13])[OH:14])[cH:15][cH:16]1 | Cc1ccc(S(=O)(=O)[O-])cc1.Fc1ccc2c(C3CCNCC3)noc2c1 | Cc1ccc(S(=O)(=O)OCCC(C)O)cc1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | d920f9e5a9eb20a0bfe9d685a7f4018d02ce8520ee8af4678553776a265bb4a3 | 36f1d5a01bfc6a51ca41548c13425da95a0757f3651ac1d5b3942affe5267fea | c1ccccc1 | F-c1:c:c:c2:c(-[CH;D3;+0:1]3-[C:2]-[CH2;D2;+0:3]-N-C-[CH2;D2;+0:4]-3):n:o:c:2:c:1.[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[#16:10](-[O-;H0;D1:11])(=[O;D1;H0:12])=[O;D1;H0:13]):[c:14]:[c:15]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[O;H0;D2;+0:11]-[CH2;D2;+0:3]-[C:2]-[CH;D3;+0:1](-[C... | null | [] | null | null | null | null | Racemic 3-hydroxybutyl tosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the racemic tosylate (9.2 g, 37.7 mmol) in acetonitrile (190 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (8.3 g, 37.7 mmol) followed by milled potassium carbonat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Secondary alcohol | C1CCNCC1.c1ccc2oncc2c1 | null | c1ccccc1 | HF | C(C)#N | null | null | Cc1ccc(S(=O)(=O)[O-])cc1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>Cc1ccc(S(=O)(=O)OCCC(C)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f2d7d41b97d14aacbf886ac2e8c8c7a2 | C[C@H](CO)CBr.Fc1ccc2c(C3CCNCC3)nsc2c1>>C[C@H](CO)CN1CCC(c2nsc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1.BrC[C@@H](CO)C.C(=O)([O-])[O-].[K+].[K+].C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NS2)C2CCN(CC2)C[C@@H](CO)C)C=C1 | Br[CH2:5][C@H:2]([CH3:1])[CH2:3][OH:4].[NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][s:12][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH2:20][CH2:21]1>>[CH3:1][C@H:2]([CH2:3][OH:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][s:12][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH2:20][CH2:21]1 | C[C@H](CO)CBr.Fc1ccc2c(C3CCNCC3)nsc2c1 | C[C@H](CO)CN1CCC(c2nsc3cc(F)ccc23)CC1 | null | S(=O)(=O)([O-])[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC | O.CC(=O)C.CC#N.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)nsc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4])-[C:8]-[C:9] | 69.1 | [{"value": 69.1, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC2=C(C(=NS2)C2CCN(CC2)C[C@@H](CO)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (4.6 g, 20 mmol), (R)-(-)-3-bromo-2-methyl-1-propanol (3.0 g, 20 mmol), K2CO3 (2.7 g, 20 mmol), tetrabutylammonium sulfate (0.058 g), CH3CN (95 ml) and H2O (19 ml) was stirred and refluxed for 4.5 hours. After standing at ambient temperature for 16 hours, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2sncc2c1 | HBr | S(=O)(=O)([O-])[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.O.CC(=O)C.CC#N.CCOC(=O)C | null | 16 | C[C@H](CO)CBr.Fc1ccc2c(C3CCNCC3)nsc2c1>S(=O)(=O)([O-])[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.O.CC(=O)C.CC#N.CCOC(=O)C>C[C@H](CO)CN1CCC(c2nsc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d000122fa51c4c28836bc544d29cda04 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>>O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 | FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O.Cl.CCOCC>>Cl.FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O | [O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([c:19]2[n:20][nH:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18... | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 | null | null | [] | null | null | 1 | HOUR | A 5.0 g sample of N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]-ethyl]phthalimide was suspended in methanol (130 ml) and was made acidic with ethereal-HCl. After stirring for 1 hour, anhydrous ether (100 ml) was added and the suspension was stirred for an additional 30 minutes. The solid was collected and dried to ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)C[NH]C2.C1C[NH]CC[NH]1.c1ccc2n[nH]cc2c1 | null | CO | null | 1 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>CO>O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-396556ae1b3b4f929d6c01b0f2affadd | CCOC(=O)CCBr.Fc1ccc2c(C3CCNCC3)nsc2c1>>CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1.BrCCC(=O)OCC.C(=O)([O-])[O-].[K+].[K+].Cl>>Cl.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(=O)OCC)C=C1 | Br[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][s:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[CH2:22][CH2:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][s:14][c:15]3[cH:16][c:17]([F:18])[cH:19][cH:20][c:21]23)[CH2:22... | CCOC(=O)CCBr.Fc1ccc2c(C3CCNCC3)nsc2c1 | CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1 | null | null | O.CCOCC.CC#N.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)nsc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:10]-[C:11] | 64 | [{"value": 64.0, "product": "Cl.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (6.0 g, 25 mmol), ethyl 3-bromopropionate (4.5 g, 25 mmol), K2CO3 (3.5 g) and CH3CN (100 ml) was stirred and refluxed for 16 hours. The reaction was poured into H2O, and after extractive workup with EtOAc, 6.0 g of an orange oil was realized. The oil was disso... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2sncc2c1 | HBr | O.CCOCC.CC#N.CCOC(=O)C | null | null | CCOC(=O)CCBr.Fc1ccc2c(C3CCNCC3)nsc2c1>O.CCOCC.CC#N.CCOC(=O)C>CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1c7812e2a7cc45e18a524f741551947d | CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O.[NH4+]>>CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | C(\C=C\C(=O)O)(=O)O.[NH4+].[Cl-].C[Mg]Br.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(=O)OCC)C=C1>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(C)(O)C)C=C1.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(C)(C)O)C=C1 | [C:2]([O:4][CH2:44][CH3:3])([CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][s:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1)=[O:26].[CH:1](\[C:24](=[O:45])[OH:47])=[CH:49]/[C:50](=[O:51])[OH:52].[NH4+:29]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n... | CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O.[NH4+] | CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | O.CCOCC.CCOC(=O)C.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 8f248116ffed31f1d98a0e4ed2541a05111a688ab82886ef09612f5482d54542 | 420e677e272f02a5b9ac5dcc53aa14a0da487831d1aab282fa7309c1e9a7f07b | c1ccc2c(C3CCNCC3)nsc2c1.c1ccc2c(C3CCNCC3)nsc2c1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7].[NH4+;D0:8].[O;D1;H0:9]=[C:10](-[O;D1;H1:11])/[CH;D2;+0:12]=[CH;D2;+0:13]/[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[OH;D1;+0:16]>>[C;D1;H3:17]-[C;H0;D4;+0:14](-[C;D1;H3:18])(-[OH;D1;+0:4])-[C:19]-[C:20]-[N;H0;D3;+0:8]1-[C:21]-[C:22]-[C:23]-... | 45.7 | [{"value": 45.7, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(C)(O)C)C=C1.FC1=CC2=C(C(=NS2)C2CCN(CC2)CCC(C)(C)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a stirred solution, under N2, of ethyl 3-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propionate (3.1 g, 9 mmol), in THF (100 ml) was added, dropwise, methylmagnesium bromide (9.0 ml, 27 mmol of a 3M solution in ether). The reaction was stirred at ambient temperature for 16 hours and then a saturated solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Aromatic halide.Carboxylic acid.Tertiary alcohol.Tertiary alcohol.Tertiary amine | null | C1CC[NH]CC1.c1ccc2sncc2c1 | C1CC[NH]CC1.c1ccc2sncc2c1.C1CC[NH]CC1.c1ccc2sncc2c1 | Other | O.CCOCC.CCOC(=O)C.C1CCOC1 | null | 16 | CCOC(=O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O.[NH4+]>O.CCOCC.CCOC(=O)C.C1CCOC1>CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.CC(C)(O)CCN1CCC(c2nsc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f5e57c23d08141b1919f4b2e6a6d5331 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1>>CCC(O)(CC)CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(=O)OCC)C=C1.C(C)[Mg]Br.C1CCOC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(CC)(CC)O)C=C1 | O([C:3](=[O:4])[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21][c:22]23)[CH2:23][CH2:24]1)[CH2:5][CH3:6]>>[CH3:1][CH2:2][C:3]([OH:4])([CH2:5][CH3:6])[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21][c:22]23)... | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1 | CCC(O)(CC)CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | acc71fe8769b79b54aa1556c6fe231efd2b33cf77e92a2d600083ad60281fa3e | a983d1549294a2208ae5c4170f0fa90cf362be77854bae41a5d52a70df2417b1 | c1ccc2c(C3CCNCC3)noc2c1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-O-[CH2;D2;+0:5]-[C;D1;H3:6]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[OH;D1;+0:4])(-[C:7]-[C;D1;H3:8])-[CH2;D2;+0:5]-[C;D1;H3:6] | 61 | [{"value": 61.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(CC)(CC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.9 g, 12.0 mmol) in THF (100 ml) was added ethylmagnesium bromide (12.0 ml, 36.0 mmol, 3.0M in ether) at room temperature under nitrogen (mild exotherm). The reaction mixture was stirred for 17 hours at which time it was carefully q... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Tertiary alcohol | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | null | null | null | 17 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1>>CCC(O)(CC)CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-96012c33cad64e728119cc0d8be3dbdd | CCCCCCCCCC(=O)Cl.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>CCCCCCCCCC(=O)OC1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | C(CCCCCCCCC)(=O)Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2O)=O)C=C1.CCN(CC)CC>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2=O)OC(CCCCCCCCC)=O)C=C1 | Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].[OH:12][CH:13]1[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20](=[O:21])[N:22]1[CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][CH:28]([c:29]2[n:30][o:31][c:32]3[cH:33][c:34]([F:35])[cH:36][cH:37][c:38]23)[CH2:39][CH2:40]1>>[CH3:1][CH2:2][CH2:3][CH... | CCCCCCCCCC(=O)Cl.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | CCCCCCCCCC(=O)OC1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C1c2ccccc2CN1CCN1CCC(c2noc3ccccc23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#7:6](-[C:7]=[O;D1;H0:8])-[C:9](-[OH;D1;+0:10])-[c:11]>>[C:5]-[#7:6](-[C:7]=[O;D1;H0:8])-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[c:11] | 83 | [{"value": 83.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2=O)OC(CCCCCCCCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl-2,3-dihydro-3-hydroxy-1H-isoindol-1-one (1.4 g, 3.5 mmol) in DCM (30 ml) was added Et3N (1.2 ml, 8.8 mmol) followed by decanoyl chloride at 0 C. under nitrogen. After stirring for 1 h in the cooling bath, the solvent was removed using a strea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl | null | 1 | CCCCCCCCCC(=O)Cl.O=C1c2ccccc2C(O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl>CCCCCCCCCC(=O)OC1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-37550048f837486e9cda2a9771b505eb | CC1(O)c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>>C=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | C(C)N(CC)CC.CCOCC.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2(C)O)=O)C=C1.Cl.Cl.CCOCC>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C3=CC=CC=C3C2=C)=O)C=C1 | O[C:2]1([CH3:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1>>[CH2:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][... | CC1(O)c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | C=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)(Cl)Cl.C(C)O | Functional Group Interconversion | OtherReaction | 12440afdbfc03b973584f51440930188851c9877e2aa841d73c307f73fea57de | 3970673bd1ec36ceedec2aab28891de56213076d8d43af2b68d8cd8a50b5b9ca | C=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | O-[C;H0;D4;+0:1]1(-[CH3;D1;+0:2])-[#7:3](-[C:4])-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]-1:[c:9]>>[C:4]-[#7:3]1-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1]-1=[CH2;D1;+0:2] | null | [] | null | null | 18 | HOUR | To the solution of 2,3-dihydro-2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-3-hydroxy-3-methyl-1H-isoindol-1-one (4.88 g, 11.9 mmol) in chloroform (50 ml) was added HCl.ether (1M, 20 ml) solution. A precipitate formed. This mixture was stirred for 18 hours at room temperature. The mixture was basified ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Enamine | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | C(Cl)(Cl)Cl.C(C)O | null | 18 | CC1(O)c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)(Cl)Cl.C(C)O>C=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8d53cdce15e84d5a858166223d24f7fd | CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCCCCCCCCC(=O)Cl>>CCCCCCCCCC(=O)OCC(C)CCN1CCC(c2noc3cc(F)ccc23)CC1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(C)(O)C)C=C1.C(C)N(CC)CC.C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)Cl>>C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)OCC(CCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | [OH:12][C:14]([CH3:13])([CH3:15])[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([c:22]2[n:23][o:24][c:25]3[cH:26][c:27]([F:28])[cH:29][cH:30][c:31]23)[CH2:32][CH2:33]1.Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](... | CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCCCCCCCCC(=O)Cl | CCCCCCCCCC(=O)OCC(C)CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)(Cl)Cl.C(C)O | Acylation | OtherReaction | 98017bac06eb42265c00528a12d8ad0fd443a81d4f2c4b4bd7765730c559bb5b | cda6b3bfc0599ee5e7303a58cf8c674c7577cf9fbc7c186a45060ebd8ab26e4f | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[CH3;D1;+0:9])-[OH;D1;+0:10]>>[C:5]-[C:6]-[CH;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 4 | HOUR | To a mixture of 4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-2-butanol (4.68 g, 15.3 mmol) and triethylamine (2.23 g, 22.3 mmol) in chloroform (20 ml) was added decanoyl chloride (3.5 g, 18.4 mmol, 1.2 eq) dropwise at 0° C. The reaction was stirred at ambient temperature for 4 hours. The solvent was re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary alcohol | Ester | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)(Cl)Cl.C(C)O | null | 4 | CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCCCCCCCCC(=O)Cl>C(Cl)(Cl)Cl.C(C)O>CCCCCCCCCC(=O)OCC(C)CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f91e5eb9886a4f248956debe7dafea26 | CCOC(=O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.[Cl-]>>CC(C)(O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.Cl | [NH4+].[Cl-].FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCC(=O)OCC.C[Mg]Br.CCOCC>>Cl.FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCC(C)(C)O | C(O[C:2](=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[n:12][nH:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1)[CH3:3].[Cl-:23]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[n:12][nH:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22... | CCOC(=O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.[Cl-] | CC(C)(O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 07357e6140e749f07059d3a4fc533a513848dc685ab1bb84c84e9780c186c553 | 046f8718a3cd4814f97a49894b6a7d3ed3f67ba38e8b5ed4b03fa3946a1eae8b | c1ccc2c(N3CCNCC3)n[nH]c2c1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-O-C-[CH3;D1;+0:5].[Cl-;H0;D0:6]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[C;D1;H3:7])(-[CH3;D1;+0:5])-[OH;D1;+0:4].[ClH;D0;+0:6] | null | [] | null | null | 5 | HOUR | To a stirred solution of ethyl 3-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]propionate (5.0 g, 16 mmol) in THF (120 ml) under N2 was added, dropwise, methylmagnesium bromide (15.6 ml of a 3.0M solution in Et2O; 0.047 mol). The temperature was maintained below 30° C. during the addition by using a water bath. After com... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Tertiary alcohol | null | null | C1C[NH]CC[NH]1.c1ccc2n[nH]cc2c1 | Other | C1CCOC1 | null | 5 | CCOC(=O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.[Cl-]>C1CCOC1>CC(C)(O)CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ae6a3e976f88478a822f50c674abec02 | BrCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(Br)C1CO1>>C(\C=C\C(=O)O)(=O)O.O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1 | Br[CH2:11][CH:12]1[CH2:13][O:14]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:15][CH2:16]3)[n:17][o:18][c:19]2[cH:20]1.[O-:21][C:26]([O-:23])=[O:27]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH:12]4[CH2:13][O:14]4)[CH2:15][CH2:16]3)[n:17][o:18][c:19]2[cH:20]1.[O:21... | BrCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O | null | null | C(C)#N | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc2c(C3CCN(CC4CO4)CC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9].[O-;H0;D1:10]-[C;H0;D3;+0:11](-[O-;H0;D1:12])=[O;D1;H0:13]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1)-[C:8]-[C:9].[O;D1;H0:13]=[C;H0;D3;+0:11](-[O;D1;H1:14])/[C:15]=[C:16]/[C:17](=[O;H0;D1;+0:10])-[OH;D1;+0:12] | 33.3 | [{"value": 33.3, "product": "C(\\C=C\\C(=O)O)(=O)O.O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (7.5 g, 54 mmol) and epibromohydrin (9 g, 54 mmol) in acetonitrile (150 ml) was heated at reflux for 16 hours. The mixture was filtered and concentrated to dryness. The crude product was purified by flash chromatography (SiO2, 180 g, elute... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CO1.c1ccc2oncc2c1 | Br- | C(C)#N | null | null | BrCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>C(C)#N>Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5158d88275a84b1ab6fe27be4636c400 | COc1ccc(Oc2ccc(OC)cc2CC2CO2)c(CC2CO2)c1.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1ccc(OCC(O)CN2CCC(c3noc4cc(F)ccc34)CC2)cc1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.O1C(CC2=C(C=CC(=C2)OC)OC2=C(C=C(C=C2)OC)CC2CO2)C1.C(C)(C)O>>COC1=CC=C(C=C1)OCC(CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)O | COc1ccc([O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][c:28]2CC2CO2)c([CH2:8][CH:9]2[O:10][CH2:11]2)c1.[NH:12]1[CH2:13][CH2:14][CH:15]([c:16]2[n:17][o:18][c:19]3[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([OH:10])[CH2:11][N:12]2[CH2:13][CH2:14... | COc1ccc(Oc2ccc(OC)cc2CC2CO2)c(CC2CO2)c1.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1ccc(OCC(O)CN2CCC(c3noc4cc(F)ccc34)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0c119f3232116620fd26db4595de0f51f57f5f1e2be7052db9dd4ad6e1ecaebd | 984ceb6f91816d007221e3a4779a894a11855fe8ab8f7efe1a441430ca84e080 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | C-O-c1:c:c:c(-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-C-C2-C-O-2):[c:5]:[c:6]):c(-[CH2;D2;+0:7]-[C:8]2-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-2):c:1.[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[CH2;D2;+0:9]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:7]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.4 g, 20 mmol) and 2,3-epoxypropyl-4-methoxyphenyl ether (3.7 g, 20.5 mmol) in isopropyl alcohol (80 ml) was heated to reflux for 2 hours. The mixture was cooled and the crystals were collected to yield 6.81 g (85%), m.p.=134°-135° C.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether.Secondary amine | Ether.Secondary alcohol.Tertiary amine | c1ccccc1.c1ccccc1.C1CO1.C1CO1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | null | null | null | COc1ccc(Oc2ccc(OC)cc2CC2CO2)c(CC2CO2)c1.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1ccc(OCC(O)CN2CCC(c3noc4cc(F)ccc34)CC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0d8d08e138c14826bc6a8685ca766fbb | COc1cc(C=O)ccc1OCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1>>COc1cc(C=O)ccc1OCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 | O1C(COC2=C(C=C(C=C2)C=O)OC)C1.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(COC2=C(C=C(C=C2)C=O)OC)O)C=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]1[O:14][CH2:15]1.[NH:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]([OH:14])[CH2:15... | COc1cc(C=O)ccc1OCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1 | COc1cc(C=O)ccc1OCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | c5753b22446d1ae5dcee7a30af0c7f96061ec363349faf28c9adeaca5e033c6d | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(OCCCN2CCC(c3noc4ccccc34)CC2)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:3](-[C:2]-[C:1])-[C:4]-[C:5] | 89.2 | [{"value": 86.0, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(COC2=C(C=C(C=C2)C=O)OC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(COC2=C(C=C(C=C2)C=O)OC)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | A stirred mixture of 4-(2,3-epoxypropoxy)-3-methoxyphenyl methanone (4.5 g, 22.5 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.36 g, 24.3 mmol) in isopropyl alcohol (150 ml) was heated at 55° C. for 16 hours. The mixture was cooled and the solvent was removed on a rotary evaporator. The residue was purified... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1.C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(C)(C)O | 55 | null | COc1cc(C=O)ccc1OCC1CO1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)(C)O>COc1cc(C=O)ccc1OCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7b5e29ce67f541e3a1994018ada2eb55 | COC(C)(CBr)OC.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | BrCC(C)(OC)OC.Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(C)(OC)OC>>Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(C)=O)C=C1 | CO[C:2]([CH3:1])([O:3]C)[CH2:4]Br.[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[CH3:1][C:2](=[O:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | COC(C)(CBr)OC.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.CCOCC.C(C)O | Acylation | OtherReaction | d23b9d90c7b3c8fd3f5d8058aca7739fc0697845334adb5675a3d3bdda2ffaa0 | 6d21f86f0fc57288cddd1d2cf1ba1e12b8fd22a393669b1d32626bf664aa05ab | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-O-C)-[O;H0;D2;+0:4]-C.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;H0;D1;+0:4])-[C:8]-[C:9] | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (7.45 g, 33.4 mmol), K2CO3 (5.5 g) and bromo-2,2-dimethoxypropane (6.84 g, 37.6 mmol) in acetonitrile (200 ml) was heated and stirred at reflux for 4 hours. An additional charge of bromo-2,2-dimethoxypropane (5.1 g, 28 mmol) was added and the mixture was refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Secondary amine | Ketone.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.CCOCC.C(C)O | null | null | COC(C)(CBr)OC.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.CCOCC.C(C)O>CC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-47d98c83c35742f2a2bc0bf5be443e7e | CCCCCCCCCCOC(=O)Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>>CCCCCCCCCCOn1nc(N2CCN(CCN3C(=O)c4ccccc4C3=O)CC2)c2ccc(F)cc21.Cl | ClC(=O)OCCCCCCCCCC.FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O>>Cl.C(CCCCCCCCC)ON1N=C(C2=CC=C(C=C12)F)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O | O=C([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[Cl:41].[nH:12]1[n:13][c:14]([N:15]2[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][N:21]3[C:22](=[O:23])[c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[C:30]3=[O:31])[CH2:32][CH2:33]2)[c:34]2[cH:35][cH:36][c:37]([F:38])[cH:39][c:40]12>>[CH3:1][CH2:2]... | CCCCCCCCCCOC(=O)Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 | CCCCCCCCCCOn1nc(N2CCN(CCN3C(=O)c4ccccc4C3=O)CC2)c2ccc(F)cc21.Cl | null | null | CCOCC | Miscellaneous | OtherReaction | e0b29cba72a42f654a54f41a2f1eb1247f630b1c53cc9f1f89bbb2f6d017d020 | 11873959194d43f291af7fba282284829cc9317bd0f9101d9a22013c97d9b731 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 | O=C(-[Cl;H0;D1;+0:1])-[O;H0;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[C:4]-[C:3]-[O;H0;D2;+0:2]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[c:6]:1:[c:5].[ClH;D0;+0:1] | null | [] | null | null | null | null | A mixture of decanyl chloroformate (2.4 g, 11 mmol), and N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide (3.9 g, 10 mmol) was warmed on the steam bath for 15 minutes. The reaction was allowed to cool to ambient temperature, and then ether was added to the residue. The resulting solid was filtered to ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | null | c1ccc2[nH]ncc2c1 | c1ccc2cn[nH]c2c1 | C1C[NH]CC[NH]1.c1ccc2c(c1)C[NH]C2.c1ccc2cn[nH]c2c1 | Other | CCOCC | null | null | CCCCCCCCCCOC(=O)Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>CCOCC>CCCCCCCCCCOn1nc(N2CCN(CCN3C(=O)c4ccccc4C3=O)CC2)c2ccc(F)cc21.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fc3e15c51e18496eb97fba070f3d1490 | COc1ccc(OC)c(O)c1.ClCCCBr>>COc1ccc(OC)c(OCCCCl)c1 | COC1=C(C=C(C=C1)OC)O.C(=O)([O-])[O-].[K+].[K+].ClCCCBr>>ClCCCOC1=C(C=CC(=C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([OH:10])[cH:15]1.Br[CH2:11][CH2:12][CH2:13][Cl:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([O:10][CH2:11][CH2:12][CH2:13][Cl:14])[cH:15]1 | COc1ccc(OC)c(O)c1.ClCCCBr | COc1ccc(OC)c(OCCCCl)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 86.2 | [{"value": 86.2, "product": "ClCCCOC1=C(C=CC(=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,5-dimethoxyphenol (29 g, 0.19 mol), K2CO3 (35 g), 3-chlorobromopropane (38.5 g, 0.25 mol) and acetone (250 ml) was stirred and refluxed for 6 hours, and then stirred at ambient temperature for 16 hours. The reaction was filtered, and the filtrate was concentrated to an orange liquid. The liquid was taken... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | COc1ccc(OC)c(O)c1.ClCCCBr>CC(=O)C>COc1ccc(OC)c(OCCCCl)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-54f6fc94a4794eb2bcc6cf161d9db11b | Fc1ccc2c(C3CCNCC3)noc2c1>>CCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CC)O)C=C1 | [CH2:1]1[CH:9]([c:10]2[n:11][o:4][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH2:8][CH2:7][NH:6][CH2:21]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH2:20][CH2:21]1 | Fc1ccc2c(C3CCNCC3)noc2c1 | CCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 1d12062e39a9332d8d7f641a66d131e17513fec9785c048d8eb1a17524acfdea | db2a794f46e2d6a7e5ac2e8df83539aaab70786dd0e2e0b7e375bc50a2a3a0e1 | c1ccc2c(C3CCNCC3)noc2c1 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[o;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](-[CH;D3;+0:7]2-[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-2):[c:13]:1:[c:14]>>[CH3;D1;+0:12]-[C:15]-[C:16](-[OH;D1;+0:4])-[C:17]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[CH;D3;+0:7](-[c:6]2:[n;H0;D2;+0:5]:[#8;a:18]:[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:13]:2:[... | 53.6 | [{"value": 53.6, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CC)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A stirred mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.5 g, 25 mmol) and 1,2-expoxybutane (1.89 g, 26.3 mmol) in isopropyl alcohol (1130 ml) was heated at 65 C. for 2 days. This mixture was cooled and the solvent was removed to leave a brown oil which was purified by flash chromatography over a silica gel... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Secondary alcohol.Tertiary amine | C1CCNCC1.c1ccc2oncc2c1 | C1CC[NH]CC1.c1ccc2oncc2c1 | C1CC[NH]CC1.c1ccc2oncc2c1 | Other | C(C)(C)O | null | 48 | Fc1ccc2c(C3CCNCC3)noc2c1>C(C)(C)O>CCC(O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7c1a7956b3b24488ab569314bb7dd9b9 | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21>>CCC(CN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 | N(=NC(=O)OCC)C(=O)OCC.FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CO)CC)C=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CN2C(C=3C(C2=O)=CC=CC3)=O)CC)C=C1 | O[CH2:4][CH:3]([CH2:2][CH3:1])[N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.[NH:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH2:2][CH:3]([CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=... | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21 | CCC(CN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 | null | null | CCOCC.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu_imide | 16aabf490ad1bd0cd53a985dff922c76188147a3ad5bf7d09c4c1e93a9e46a19 | 8a66434962da2945c8a8685e3bd4f60c7955241df224c95aa14ead6db9d240f9 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | O-[CH2;D2;+0:1]-[C:2](-[#7:3])-[C:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1>>[#7:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6](=[O;D1;H0:5])-[c:11]:[c:10]-[C:8]-1=[O;D1;H0:9] | 7.6 | [{"value": 7.6, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CN2C(C=3C(C2=O)=CC=CC3)=O)CC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of diethyl azodicarboxylate (DEAD, 4.9 g, 28.3 mmol) in THF (50 ml) was added dropwise to a solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol (6.9 g, 23.6 mmol), phthalimide (4.16 g, 1.2 eq), and triphenylphosphine (7.4 g, 28.3 mmol) in THF (200 ml) at room temperature. The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | CCOCC.C1CCOC1 | null | 24 | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21>CCOCC.C1CCOC1>CCC(CN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-54dce31dc7ad494799f38f67f46984df | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21>>CC(CCN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 | N(=NC(=O)OCC)C(=O)OCC.FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CO)CC)C=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)C(CCN2C(C=3C(C2=O)=CC=CC3)=O)C)C=C1 | O[CH2:1][CH:2]([CH2:3][CH3:4])[N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.[NH:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH:2]([CH2:3][CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=... | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21 | CC(CCN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 | null | null | CCOCC.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 16aabf490ad1bd0cd53a985dff922c76188147a3ad5bf7d09c4c1e93a9e46a19 | 8a66434962da2945c8a8685e3bd4f60c7955241df224c95aa14ead6db9d240f9 | O=C1c2ccccc2C(=O)N1CCCN1CCC(c2noc3ccccc23)CC1 | O-[CH2;D2;+0:1]-[C:2](-[#7:3])-[C:4]-[CH3;D1;+0:5].[O;D1;H0:6]=[C:7]1-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-1>>[#7:3]-[C:2](-[CH3;D1;+0:1])-[C:4]-[CH2;D2;+0:5]-[N;H0;D3;+0:8]1-[C:7](=[O;D1;H0:6])-[c:12]:[c:11]-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | 24 | HOUR | A solution of diethyl azodicarboxylate (DEAD, 4.9 g, 28.3 mmol) in THF (50 ml) was added dropwise to a solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butanol (6.9 g, 23.6 mmol), phthalimide (4.16 gm, 1.2 eq), and triphenylphosphine (7.4 g, 28.3 mmol) in THF (200 ml) at room temperature. The solution w... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | CCOCC.C1CCOC1 | null | 24 | CCC(CO)N1CCC(c2noc3cc(F)ccc23)CC1.O=C1NC(=O)c2ccccc21>CCOCC.C1CCOC1>CC(CCN1C(=O)c2ccccc2C1=O)N1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1ac63dbdb3784dbf9f872cfea6b00643 | CN1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1.O=C(Cl)Oc1ccccc1>>O=C(Oc1ccccc1)N1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 | C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)C1CCN(CC1)C.ClC(=O)OC1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)C1CCN(CC1)C(=O)OC1=CC=CC=C1 | C[N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][n:16]([C:17](=[O:18])[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][c:27]([F:28])[cH:29][cH:30][c:31]23)[CH2:32][CH2:33]1.Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][CH... | CN1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1.O=C(Cl)Oc1ccccc1 | O=C(Oc1ccccc1)N1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 | null | null | ClCCl | Protection | OtherReaction | 098d96013d8f515c8ca9e46982fe68daa1284f9999e2ea89d2ac209ec12fa538 | 0b52f7fe08d56743733fba6faa9ac2adb3359be0bf567eb74149abd092209076 | O=C(Oc1ccccc1)N1CCC(c2nn(C(=O)c3ccccc3)c3ccccc23)CC1 | C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[c:9]>>[C:3]-[C:2]-[N;H0;D3;+0:1](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[c:9])-[C:4]-[C:5] | 17.9 | [{"value": 17.9, "product": "C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)C1CCN(CC1)C(=O)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 1-benzoyl-6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole (2.0 g, 5.93 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.9 ml, 29.65 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 hours, refluxed for an additional 0.5 hours and subsequently conc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Tertiary amine | Carbamic ester | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccc2c[nH]nc2c1 | HCl | ClCCl | null | 24 | CN1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1.O=C(Cl)Oc1ccccc1>ClCCl>O=C(Oc1ccccc1)N1CCC(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-168771d1619a455a9c9aa30cb59740dc | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.N#CCCl>>N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | C(Cl)Cl.CCOC(=O)C.FC1=CC=C2C(=NNC2=C1)C1CCNCC1.C(=O)(O)[O-].[Na+].ClCC#N>>FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CC#N | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1.Cl[CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.N#CCCl | N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)n[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | 89.1 | [{"value": 89.1, "product": "FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-(6-fluoro-1H-indazol-3-yl)piperidine (4.95 g, 22.6 mmol) and NaHCO3 (2.1 g, 24.9 mmol) in dry acetonitrile (110 ml) was added chloroacetonitrile (1.6 ml, 24.9 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 22.5 hours, cooled to room temperature, and subse... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2n[nH]cc2c1 | HCl | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.N#CCCl>C(C)#N>N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1d1832c8d4744a10ac46c820c9778dbe | N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1>>NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CC#N.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN | [N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[NH2:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2c(C3CCNCC3)n[nH]c2c1 | [#7:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 90.5 | [{"value": 90.5, "product": "FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of [4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]-acetonitrile (6.1 g, 23.6 mmol) in dry THF (235 ml) was added (dropwise) lithium aluminum hydride (LAH) (28.4 mmol, 1.0M in THF) at room temperature, under nitrogen. Upon complete addition, the reaction mixture was warmed to reflux for 3 hours. After cooling... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC[NH]CC1.c1ccc2n[nH]cc2c1 | null | C1CCOC1 | null | null | N#CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1>C1CCOC1>NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ddb3ae200ad146ea8d751162fe71c70e | CO.NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>>O=C(O)/C=C\C(=O)O.O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | C(Cl)Cl.CO.FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN.FC=1C=C2C(C(=O)OC2=O)=CC1>>C(\C=C/C(=O)O)(=O)O.FC=1C=C2C(C(=O)N(C2=O)CCN2CCC(CC2)C2=NNC3=CC(=CC=C23)F)=CC1 | [OH:1][CH3:2].[NH2:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH:26]([c:27]2[n:28][nH:29][c:30]3[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]23)[CH2:37][CH2:38]1.[O:7]=[C:10]1[O:9][C:18](=[O:19])[c:17]2[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16]2>>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]\[C:6](=[O:7])[OH:8].[O:9]=[C:10]1[c:11]2[cH... | CO.NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21 | O=C(O)/C=C\C(=O)O.O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | null | null | CN(C)C=O | Acylation | OtherReaction | de8d4214a26065c388063a99020b9604bb7f2e179b525cbaa62edbdf2dfe01f7 | 1c309a47796de932bd4598cefda90275081567e21068d7c412a08ca7158eeecf | O=C1c2ccccc2C(=O)N1CCN1CCC(c2n[nH]c3ccccc23)CC1 | [CH3;D1;+0:1]-[OH;D1;+0:2].[C:3]-[C:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C;H0;D3;+0:7]1-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[C:3]-[C:4]-[N;H0;D3;+0:5]1-[C;H0;D3;+0:9](=[O;H0;D1;+0:8])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:7]-1=[O;D1;H0:6].[O;D1;H1:15]-[C;H0;D3;+0:1](=[O;H0;D1... | null | [] | null | null | 2.5 | HOUR | To a solution of 2-[4-(6-fluoro-1H-3-indazolyl)-1-piperidinyl]ethylamine (6.1 g, 23.3 mmol) in DMF (230 ml) was added 4-fluorophthalic anhydride (4.2 g, 25.5 mmol) at room temperature under nitrogen. The reaction mixture was warmed to 80 C. for 2.5 hours at which time it was allowed to cool to room temperature. The DMF... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine.Methanol | Carboxylic acid.Carboxylic acid.Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2n[nH]cc2c1 | Other | CN(C)C=O | null | 2.5 | CO.NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>CN(C)C=O>O=C(O)/C=C\C(=O)O.O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-37410465abd24107911681e9eeaefe12 | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.O=C(Cl)Oc1ccccc1>>O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C.ClC(=O)OC1=CC=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C(=O)OC1=CC=CC=C1 | C[N:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][n:16]([S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]23)[CH2:32][CH2:33]1.Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][N... | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.O=C(Cl)Oc1ccccc1 | O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | null | null | ClCCl | Protection | OtherReaction | d9e846a3c096957584b4d66e06b9953dc4a1cda5aed60d96d6d2e5ad6715b785 | 0b52f7fe08d56743733fba6faa9ac2adb3359be0bf567eb74149abd092209076 | O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-[#8:9]-[c:10]>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[#8:9]-[c:10])-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 55.1 | [{"value": 55.1, "product": "C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C(=O)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-benzenesulfonyl-3-(1-methyl-4-piperazinyl)-1H-indazole (2.1 g, 5.89 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.8 ml, 29.45 mmol) at room temperature. The reaction mixture was warmed to reflux for 2 hours, cooled to room temperature, and concentrated. The residue was diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Tertiary amine | Carbamic ester | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1[nH]nc2ccccc12 | HCl | ClCCl | null | null | CN1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1.O=C(Cl)Oc1ccccc1>ClCCl>O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2fd968492e0e4508ab345b373fb97e1b | O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1>>c1ccc2c(N3CCNCC3)n[nH]c2c1 | C1(=CC=CC=C1)S(=O)(=O)N1N=C(C2=CC=CC=C12)N1CCN(CC1)C(=O)OC1=CC=CC=C1.[OH-].[K+].Cl>>N1(CCNCC1)C1=NNC2=CC=CC=C12 | O=C(Oc1ccccc1)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[c:4]3[cH:3][cH:2][cH:1][cH:15][c:14]3[n:13](S(=O)(=O)c3ccccc3)[n:12]2)[CH2:11][CH2:10]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([N:6]3[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[n:12][nH:13][c:14]2[cH:15]1 | O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1 | c1ccc2c(N3CCNCC3)n[nH]c2c1 | null | null | C(C)O | Reduction | OtherReaction | 60035c41b56ad5eb4f62bce43e5fa5be3deffb0fdeaf67e7b38ad72c3fb1ed18 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc2c(N3CCNCC3)n[nH]c2c1 | O=C(-O-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5]2:[#7;a:6]:[n;H0;D3;+0:7](-S(=O)(=O)-c3:c:c:c:c:c:3):[c:8](:[c:9]):[c:10]:2)-[C:11]-[C:12]-1>>[c:9]:[c:8]1:[c:10]:[c:5](-[#7:4]2-[C:3]-[C:2]-[NH;D2;+0:1]-[C:12]-[C:11]-2):[#7;a:6]:[nH;D2;+0:7]:1 | 94.9 | [{"value": 94.9, "product": "N1(CCNCC1)C1=NNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 1-benzenesulfonyl-3-(1-phenoxycarbonyl-4-piperazinyl)-1H-indazole (31.3 g, 67.7 mmol) in ethanol (500 ml) was added 50% KOH (aq.) (100 g of KOH in 100 g H2O) at room temperature. The reaction mixture was warmed to reflux for 6.5 hours and cooled to room temperature. After adjusting the pH to about tw... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1n[nH]c2ccccc12 | C1C[NH]CCN1.c1ccc2n[nH]cc2c1 | C1C[NH]CCN1.c1ccc2n[nH]cc2c1 | HO- | C(C)O | null | null | O=C(Oc1ccccc1)N1CCN(c2nn(S(=O)(=O)c3ccccc3)c3ccccc23)CC1>C(C)O>c1ccc2c(N3CCNCC3)n[nH]c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b2a03606e23a4743aa62960aaf78ee48 | N#CCCl.c1ccc2c(N3CCNCC3)n[nH]c2c1>>N#CCN1CCN(c2n[nH]c3ccccc23)CC1 | N1(CCNCC1)C1=NNC2=CC=CC=C12.C(=O)(O)[O-].[Na+].ClCC#N>>N1N=C(C2=CC=CC=C12)N1CCN(CC1)CC#N | Cl[CH2:3][C:2]#[N:1].[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[CH2:17][CH2:18]1 | N#CCCl.c1ccc2c(N3CCNCC3)n[nH]c2c1 | N#CCN1CCN(c2n[nH]c3ccccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(N3CCNCC3)n[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 55.8 | [{"value": 55.8, "product": "N1N=C(C2=CC=CC=C12)N1CCN(CC1)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 3-piperazin-1-yl-1H-indazole (6.0 g, 29.7 mmol) and NaHCO3 (2.7 g, 32.7 mmol) in dry acetonitrile (125 ml) was added chloroacetonitrile (2.1 ml, 31.2 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 17.5 hours, cooled to room temperature, and subsequently fil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2n[nH]cc2c1 | HCl | C(C)#N | null | null | N#CCCl.c1ccc2c(N3CCNCC3)n[nH]c2c1>C(C)#N>N#CCN1CCN(c2n[nH]c3ccccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-20dca071c173476bb37a05ac767ae11a | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>>Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 | FC1=CC=C2C(=NNC2=C1)N1CCN(CC1)CCN1C(C2=CC=CC=C2C1=O)=O.C(C1=CC=CC=C1)(=O)Cl.C(C)O>>Cl.C(C1=CC=CC=C1)(=O)N1N=C(C2=CC=C(C=C12)F)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O | [Cl:1][C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([c:19]2[n:20][nH:21][c:30]3[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]23)[CH2:37][CH2:38]1>>[ClH:1].[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8... | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1 | Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 | null | null | CCOCC | Acylation | N-alkylation of secondary amines with alkyl halides | 49f82b4e585b34aaf01178ec8fb841682a20d4b7a3abe5926a9757992ea7cc47 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2nn(C(=O)c3ccccc3)c3ccccc23)CC1 | [Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[#7;a:11]:[nH;D2;+0:12]:1>>[ClH;D0;+0:1].[O;D1;H0:3]=[C;H0;D3;+0:2](-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[#7;a:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | null | [] | null | null | 2 | HOUR | A mixture of 2-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]ethyl]-1H-isoindol-1,3-(2H)-dione (6.0 g, 15 mmol) and benzoyl chloride (25 ml) was stirred at 175 C. under N2 for 2.0 hours. The reaction was cooled and diluted with anhydrous Et2O and the resultant hydrochloride salt was collected to yield 7.2 g. The compo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1ccc2n[nH]cc2c1 | c1ccc2c[nH]nc2c1 | c1ccc2c(c1)C[NH]C2.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c[nH]nc2c1 | null | CCOCC | null | 2 | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3cc(F)ccc23)CC1>CCOCC>Cl.O=C1c2ccccc2C(=O)N1CCN1CCN(c2nn(C(=O)c3ccccc3)c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e755616cf51348ab860fb16f4305485a | Cc1nc2ccccc2c(=O)n1CCCl.Fc1ccc2c(C3CCNCC3)noc2c1>>CC1Nc2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | N1CCC(CC1)C1=NOC2=C1C=CC(=C2)F.C(=O)([O-])[O-].[K+].[K+].ClCCN1C(=NC2=CC=CC=C2C1=O)C>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(NC3=CC=CC=C3C2=O)C)C=C1 | Cl[CH2:14][CH2:13][n:12]1[c:2]([CH3:1])[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1=[O:11].[NH:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[CH3:1][CH:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH... | Cc1nc2ccccc2c(=O)n1CCCl.Fc1ccc2c(C3CCNCC3)noc2c1 | CC1Nc2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Protection | OtherReaction | 30333abf78712c89f8817a5f0c424118f876d3fcd0edf79585058930e45a4cbb | d07559239c3992cdeb6b5d9d2745f66f2aaf80ec978b36e87e3e8216ecc9b602 | O=C1c2ccccc2NCN1CCN1CCC(c2noc3ccccc23)CC1 | Cl-[CH2;D2;+0:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c:6](:[c:7]):[c:8](:[c:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11]:1-[C;D1;H3:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[CH2;D2;+0:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](:[c:9])-[NH;D2;+0:... | null | [] | null | null | null | null | A stirred mixture of 3-(4-piperidinyl)-6-fluorobenzisoxazole (4 g, 18.2 mmol), K2CO3 (3.76 g, 27.2 mmol) and 3-(2-chloroethyl)-2-methyl-3H-4-quinazolinone (6.0 g, 27 mmol) in acetonitrile (300 ml) was heated at reflux for 16 hours. The reaction was complete as judged by TLC. The solids were filtered and the solvent was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amide.Secondary amine.Tertiary amine | c1ccc2ncncc2c1.C1CCNCC1 | c1ccc2c(c1)C[NH]CN2.C1CC[NH]CC1 | c1ccc2c(c1)C[NH]CN2.C1CC[NH]CC1.c1ccc2oncc2c1 | Other | C(C)#N | null | null | Cc1nc2ccccc2c(=O)n1CCCl.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>CC1Nc2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-05a17996f8da4e209b1d6ed89edfec9f | BrCc1ccccc1CBr.CC(O)CN1CCC(c2noc3cc(F)ccc23)C(N)C1>>Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1Cc2ccccc2C1 | NC1CN(CCC1C1=NOC2=C1C=CC(=C2)F)CC(C)O.C(=O)([O-])[O-].[K+].[K+].C(C)#N.Cl.BrCC=1C(=CC=CC1)CBr>>Cl.Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CC3=CC=CC=C3C2)O)C=C1 | Br[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]1[CH2:31]Br.[OH:3][CH:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]23)[CH:20]([NH2:23])[CH2:21]1)[CH3:22]>>[ClH:2].[OH:3][CH:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([c:10]2[n:11][o:12][c:13]3[cH:14][c:15]([F:16])[... | BrCc1ccccc1CBr.CC(O)CN1CCC(c2noc3cc(F)ccc23)C(N)C1 | Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1Cc2ccccc2C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 805939885373c5d9a597b701a9dea5f33d2f7bed849e018d3a63776e96d9def6 | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc2c(c1)CN(CCCN1CCC(c3noc4ccccc34)CC1)C2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH2;D2;+0:5]-Br):[c:6].[#8;a:7]:[#7;a:8]:[c:9]-[C:10]1-[C:11]-[C:12]-[#7:13](-[C:14]-[C:15](-[CH3;D1;+0:16])-[O;D1;H1:17])-[C:18]-[CH;D3;+0:19]-1-[NH2;D1;+0:20]>>[#8;a:7]:[#7;a:8]:[c:9]-[C:10]1-[C:11]-[C:12]-[#7:13](-[C:14]-[C:15](-[O;D1;H1:17])-[CH2;D2;+0:16]-[N;H0;D3;+0:20]2-[CH... | null | [] | null | null | null | null | To a stirred mixture of 1-(3-amino-2-hydroxypropyl-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.24 g, 7.6 mmol), K2CO3 (1.61 g, 11.7 mmol) in acetonitrile (100 ml) was added α,α'-dibromo-o-xylene (1.54 g, 6.1 mmol). The mixture was heated at reflux for 4 hours then cooled. The insolubles were filtered. The dark red ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)C[NH]C2 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)C[NH]C2 | HBr | C(C)O | null | null | BrCc1ccccc1CBr.CC(O)CN1CCC(c2noc3cc(F)ccc23)C(N)C1>C(C)O>Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1Cc2ccccc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9491a405059f484fa44d686675f7e65c | CC(C)[Si](OC1=CC(C)(Br)C(C)(Br)C=C1)(C(C)C)C(C)C.NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C([O-])[O-]>>CC(C)[Si](Oc1ccc2c(c1)CN(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2)(C(C)C)C(C)C.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.BrC1(C(C=C(C=C1)O[Si](C(C)C)(C(C)C)C(C)C)(C)Br)C.C(=O)([O-])[O-].[K+].[K+]>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2CC3=CC=C(C=C3C2)O[Si](C(C)C)(C(C)C)C(C)C)C=C1 | Br[C:8]1([CH3:9])[CH:7]=[C:6]([O:5][Si:4]([CH:2]([CH3:1])[CH3:3])([CH:33]([CH3:10])[CH3:11])[CH:36]([CH3:37])[CH3:38])[CH:50]=[CH:51][C:52]1(Br)[CH3:32].[NH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.[O-:39][C:44](=[O:45])[O... | CC(C)[Si](OC1=CC(C)(Br)C(C)(Br)C=C1)(C(C)C)C(C)C.NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C([O-])[O-] | CC(C)[Si](Oc1ccc2c(c1)CN(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2)(C(C)C)C(C)C.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 8f4ebc4c7275bd21b379c87db666a0f608686c78ef58173aaf9b7008f9d0f3cc | d407ac76aeb8d84aac4559a8333c394151a7dcf368abf8cc98a9e801d1292440 | c1ccc2c(c1)CN(CCN1CCC(c3noc4ccccc34)CC1)C2 | Br-[C;H0;D4;+0:1]1(-[CH3;D1;+0:2])-[C:3]=[CH;D2;+0:4]-[C;H0;D3;+0:5](-[#8:6]-[#14:7](-[C:8](-[C;D1;H3:9])-[C;D1;H3:10])(-[C:11](-[C;D1;H3:12])-[C;D1;H3:13])-[CH;D3;+0:14](-[CH3;D1;+0:15])-[CH3;D1;+0:16])=[CH;D2;+0:17]-[C;H0;D4;+0:18]-1(-Br)-[CH3;D1;+0:19].[C:20]-[C:21]-[NH2;D1;+0:22].[O-;H0;D1:23]-[C;H0;D3;+0:24](-[O-;... | null | [] | null | null | 18 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (1.52 g, 5.73 mmol), 1,2-dibromo-4-(triisopropylsilyl)oxy-xylene (2.4 g, 5.7 mmol) and K2CO3 (1.8 g, 13 mmol) in acetonitrile (300 ml) was stirred overnight (18 hours) at room temperature. The mixture was filtered and the solvent was stripped. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Primary amine | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary amine | C1=CCCC=C1 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | C(C)#N | null | 18 | CC(C)[Si](OC1=CC(C)(Br)C(C)(Br)C=C1)(C(C)C)C(C)C.NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C([O-])[O-]>C(C)#N>CC(C)[Si](Oc1ccc2c(c1)CN(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2)(C(C)C)C(C)C.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4e77acd1e4f04083aeadc5ba798b8b63 | O=C(O)/C=C\C(=O)O.O=C1c2ccccc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1>>Fc1ccc2c(C3CCN(CCN4Cc5ccccc5C4)CC3)n[nH]c2c1.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O | C(\C=C/C(=O)O)(=O)O.Cl.FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(\C=C/C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN1CC2=CC=CC=C2C1 | [O:28]=[C:29]([OH:30])/[CH:31]=[CH:32]\[C:41](=[O:42])[OH:43].[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][N:13]4[C:14](=[O:38])[c:15]5[cH:16][cH:17][cH:18][cH:19][c:20]5[C:21]4=[O:34])[CH2:22][CH2:23]3)[n:24][nH:25][c:26]2[cH:27]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH... | O=C(O)/C=C\C(=O)O.O=C1c2ccccc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | Fc1ccc2c(C3CCN(CCN4Cc5ccccc5C4)CC3)n[nH]c2c1.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O | null | null | CO.C1CCOC1 | Acylation | OtherReaction | dddcb52abc82387fe45591a9d5ec00818838cf455bba1040342b3d81659e6832 | d8447a054fe51d0821d183b441852de5b671d7470cbdfdf188e588112d89a5be | c1ccc2c(c1)CN(CCN1CCC(c3n[nH]c4ccccc34)CC1)C2 | [C:1]-[#7:2]1-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10].[O;D1;H0:11]=[C:12](-[O;D1;H1:13])/[C:14]=[CH;D2;+0:15]\[C;H0;D3;+0:16](=[O;D1;H0:17])-[O;D1;H1:18]>>[C:1]-[#7:2]1-[CH2;D2;+0:3]-[c:5](:[c:6]):[c:7](:[c:8])-[CH2;D2;+0:9]-1.[O;D1;H0:11]=[C:12](-[O;D1;H1:13])/[C:14... | null | [] | null | null | null | null | To a solution of N-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethyl]phthalimide hydrochloride (Example 183) (3.1 g, 7.91 mmol) in THF (100 ml) was added lithium aluminum hydride (16.6 ml of a 1.0M solution in THF, 16.6 mmol) at room temperature, under nitrogen. The reaction mixture was warmed to reflux for 6.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Substituted dicarboximide | Carboxylic acid.Carboxylic acid.Carboxylic acid | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | C1CC[NH]CC1.c1ccc2c(c1)C[NH]C2.c1ccc2n[nH]cc2c1 | Other | CO.C1CCOC1 | null | null | O=C(O)/C=C\C(=O)O.O=C1c2ccccc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1>CO.C1CCOC1>Fc1ccc2c(C3CCN(CCN4Cc5ccccc5C4)CC3)n[nH]c2c1.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d701f9475cb64dfd90d7e29bb3c0d34f | Fc1ccc2c(C3CCNCC3)noc2c1.NC(=O)CBr>>NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N)C=C1 | [NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1.Br[CH2:4][C:2]([NH2:1])=[O:3]>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | Fc1ccc2c(C3CCNCC3)noc2c1.NC(=O)CBr | NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4])-[C:8]-[C:9] | 33.1 | [{"value": 33.1, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (6.77 g, 30.7 mmol), K2CO3 (5 g, 36.2 mmol) and 2-bromoacetamide (4.46 g, 32.3 mmol) in acetonitrile (250 ml) was heated to reflux for 4 hours. The insolubles were filtered and rinsed with dichloromethane (DCM). The solvents were removed. The residual solid wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.NC(=O)CBr>C(C)#N>NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a9af6d8d94eb4f61a6d44e3436dd94b9 | BrCc1ccccc1CBr.NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1>>O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1Cc2ccccc2C1 | O.[H-].[Na+].FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N)C=C1.BrCC=1C(=CC=CC1)CBr>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N2CC3=CC=CC=C3C2)C=C1 | Br[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[CH2:28]Br.[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1)[NH2:20]>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[... | BrCc1ccccc1CBr.NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1Cc2ccccc2C1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 1dc38bde1432eeafb1ac224ea9a0502f6a4b2ab2423a3478e6d9f7d353241606 | b43b98d116fcaee9339f692697f01a5b1b5783354f893daa16f24a4196af7263 | O=C(CN1CCC(c2noc3ccccc23)CC1)N1Cc2ccccc2C1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH2;D2;+0:5]-Br):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])=[O;D1;H0:10]>>[C:7]-[C:8](=[O;D1;H0:10])-[N;H0;D3;+0:9]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:6])-[CH2;D2;+0:5]-1 | null | [] | null | null | 3 | HOUR | To a mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]acetamide (2.56 g, 9.2 mmol) in DMF (40 ml) was chipped in sodium hydride (770 mg, 60% in oil, 20.1 mmol) at room temperature under N2. The mixture was heated to 65 C. for 3 hours. α,α'-dibromoxylene (2.43 g, 9.2 mmol) was added and the resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amide | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C)C=O | null | 3 | BrCc1ccccc1CBr.NC(=O)CN1CCC(c2noc3cc(F)ccc23)CC1>CN(C)C=O>O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1Cc2ccccc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e32d36826f254cff9c34b065d63f6b1c | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N2CC3=CC=CC=C3C2)C=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N2CC3=CC=CC=C3C2)C=C1 | [O:29]=[C:30]([OH:31])/[CH:32]=[CH:33]/[C:34](=[O:35])[OH:36]>>[O:29]=[C:30]([OH:31])/[CH:32]=[CH:33]/[C:34](=[O:35])[OH:36] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | Free base (1 g, Example 243B) of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-1-(2,3-dihydro-1H-isoindol-2-yl)ethanone dissolved in hot ethanol (~10 ml) was treated with a solution of fumaric acid (306 mg) in hot ethanol. The mixture was cooled and the product collected, 1.2 gm, m.p. 223°-225° C.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | O=C(O)/C=C/C(=O)O>C(C)O>O=C(O)/C=C/C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fd2ae4ab2a1c40afbcab097f859e13b3 | NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>>O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | FC1=CC=C2C(=NNC2=C1)C1CCN(CC1)CCN.FC=1C=C2C(C(=O)OC2=O)=CC1.C(Cl)Cl.CO>>FC=1C=C2C(C(=O)N(C2=O)CCN2CCC(CC2)C2=NNC3=CC(=CC=C23)F)=CC1 | [NH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][nH:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]2[C:10]1=[O:11]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2... | NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21 | O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 | null | null | CN(C)C=O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2n[nH]c3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 37.8 | [{"value": 37.8, "product": "FC=1C=C2C(C(=O)N(C2=O)CCN2CCC(CC2)C2=NNC3=CC(=CC=C23)F)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution consisting of 2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethylamine (6.1 g, 23.2 mmol) in DMF (230 ml) was added 4-fluorophthalic anhydride (4.2 g, 25.5 mmol) at room temperature, under nitrogen. The reaction mixture was warmed to 80 C. for 2.5 hours at which time it was allowed to cool to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2n[nH]cc2c1 | HO- | CN(C)C=O | null | 2.5 | NCCN1CCC(c2n[nH]c3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>CN(C)C=O>O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2n[nH]c3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2308b72b301f418b918dc604005e2a31 | O=C1c2ccccc2C(=O)N1CCBr.c1ccc2c(N3CCNCC3)n[nH]c2c1>>O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 | N1N=C(C2=CC=CC=C12)N1CCNCC1.BrCCN1C(C=2C(C1=O)=CC=CC2)=O.C([O-])(O)=O.[Na+]>>N1N=C(C2=CC=CC=C12)N1CCN(CC1)CCN1C(C=2C(C1=O)=CC=CC2)=O | Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[NH:14]1[CH2:15][CH2:16][N:17]([c:18]2[n:19][nH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([c:... | O=C1c2ccccc2C(=O)N1CCBr.c1ccc2c(N3CCNCC3)n[nH]c2c1 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[O;D1;H0:7]=[C:6]-[#7:3](-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1)-[C:4]=[O;D1;H0:5] | null | [] | null | null | null | null | A suspension of 4-(1H-indazol-3-yl)piperazine (1.6 g, 7.9 mmol), N-(2-bromoethyl)phthalimide (2.1 g, 7.9 mmol), and sodium bicarbonate (0.7 g, 8.3 mmol) in acetonitrile (160 ml) was warmed to reflux for 24 hours. Upon cooling to room temperature, the reaction mixture was filtered through a pad of celite and the solids ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2c(c1)C[NH]C2.C1C[NH]CC[NH]1.c1ccc2n[nH]cc2c1 | HBr | C(C)#N | null | null | O=C1c2ccccc2C(=O)N1CCBr.c1ccc2c(N3CCNCC3)n[nH]c2c1>C(C)#N>O=C1c2ccccc2C(=O)N1CCN1CCN(c2n[nH]c3ccccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-93a1ba40cf7b4de0bc9321448825385b | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(CBr)N1CCc2ccccc21>>O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCc2ccccc21 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)N1CCC2=CC=CC=C12>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N2CCC3=CC=CC=C23)C=C1 | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1.Br[CH2:3][C:2](=[O:1])[N:20]1[CH2:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[C... | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(CBr)N1CCc2ccccc21 | O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCc2ccccc21 | null | null | C(C)O.C(Cl)Cl.C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2noc3ccccc23)CC1)N1CCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6])-[C:10]-[C:11] | null | [] | null | null | null | null | A stirred mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (10 g, 45.4 mmol), K2CO3 (7.2 g, 52.5 mmol) and N-(2-bromoacetyl)indoline (12 g, 50 mmol) in acetonitrile (300 ml) was heated at reflux for 4 hours. The mixture was cooled and filtered. The solution was concentrated down until solid appeared. The crystal... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)CC[NH]2 | HBr | C(C)O.C(Cl)Cl.C(C)#N.C(C)O | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(CBr)N1CCc2ccccc21>C(C)O.C(Cl)Cl.C(C)#N.C(C)O>O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa621b7359cb4d319daba7bfd23456f4 | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(Cl)CCl>>O=C(CCl)N1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(C)N(CC)CC.ClCC(=O)Cl>>ClCC(=O)N1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | [NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(Cl)CCl | O=C(CCl)N1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl.C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[C:8]-[C:9] | 37.1 | [{"value": 37.1, "product": "ClCC(=O)N1CCC(CC1)C1=NOC2=C1C=CC(=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.4 g, 20 mmol), triethylamine (2.1 g, 21 mmol) in chloroform (50 ml) was added to a solution of chloroacetyl chloride (2.5 g, 22 mmol) in chloroform (100 ml) dropwise at room temperature. The mixture was stirred for 2 hours. The solution was diluted with dich... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | ClCCl.C(Cl)(Cl)Cl | null | 2 | Fc1ccc2c(C3CCNCC3)noc2c1.O=C(Cl)CCl>ClCCl.C(Cl)(Cl)Cl>O=C(CCl)N1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ed493d0bff8042068a6067bd2293f00b | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.c1ccc2c(c1)CCNC2>>O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCc2ccccc2C1 | C(\C=C\C(=O)O)(=O)O.O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1.C1NCCC2=CC=CC=C12>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CC3=CC=CC=C3CC2)O)C=C1 | [O:17]1[CH:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([c:24]3[n:25][o:26][c:27]4[cH:28][c:29]([F:30])[cH:31][cH:32][c:33]34)[CH2:34][CH2:35]2)[CH2:36]1.[O:1]=[C:2](/[CH:4]=[CH:5]/[C:14](=[O:15])[OH:16])[OH:8].[NH:37]1[CH2:38][CH2:39][c:40]2[cH:41][cH:42][cH:43][cH:44][c:45]2[CH2:46]1>>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/... | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.c1ccc2c(c1)CCNC2 | O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCc2ccccc2C1 | null | null | C(C)(C)O.C(C)O | Acylation | OtherReaction | fcd14c9f7d7baf89c927fbfdd6609a5b0207f153b0bccf38dcbeab0821ce04e7 | eb32abec09cec5f0c9fb6955bb451f690c8c8ac754bdbe9dd50d24ad7d5de082 | c1ccc2c(c1)CCN(CCCN1CCC(c3noc4ccccc34)CC1)C2 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[c:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1.[O;D1;H0:10]=[C;H0;D3;+0:11](-[O;D1;H1:12])/[CH;D2;+0:13]=[C:14]/[C;H0;D3;+0:15](=[O;D1;H0:16])-[OH;D1;+0:17]>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:3](-[C:2]-[C:1])-[C:4]-[c:5].[C:18]=[C:19]/[C;H0;D3;+0:11](=[O;D1;H0:10])-[... | null | [] | null | null | null | null | A mixture of N-[3-(2,3-epoxy)propyl]-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.56 g, 12.9 mmol) and 1,2,3,4-tetrahydroisoquinoline (2.06 g, 15.4 mmol) in isopropyl alcohol (150 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was removed. The residual oil was purified by flash chromat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Secondary amine | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Secondary alcohol.Tertiary amine | C1CO1.c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CC[NH]C2 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)CC[NH]C2 | Other | C(C)(C)O.C(C)O | null | null | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.c1ccc2c(c1)CCNC2>C(C)(C)O.C(C)O>O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCc2ccccc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1fe0c39fcb28423da1462c68b96e45ba | COc1cc2c(cc1OC)CNCC2.Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1>>COc1cc2c(cc1OC)CN(CC(O)CN1CCC(c3noc4cc(F)ccc34)CC1)CC2 | O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1.C(=O)([O-])[O-].[K+].[K+].Cl.COC=1C=C2CCNCC2=CC1OC>>COC=1C=C2CCN(CC2=CC1OC)CC(CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][NH:12][CH2:33][CH2:34]2.[CH2:13]1[CH:14]([CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([c:21]3[n:22][o:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]34)[CH2:31][CH2:32]2)[O:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][N... | COc1cc2c(cc1OC)CNCC2.Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1 | COc1cc2c(cc1OC)CN(CC(O)CN1CCC(c3noc4cc(F)ccc34)CC1)CC2 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 5ce7ac738be0d4a61a1491ab19f5ee643e1b82bd5b0e5b68590ec8492f9baa73 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(c1)CCN(CCCN1CCC(c3noc4ccccc34)CC1)C2 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[c:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:3](-[C:4]-[c:5])-[C:2]-[C:1] | 11 | [{"value": 11.0, "product": "COC=1C=C2CCN(CC2=CC1OC)CC(CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A stirred mixture of 1-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.2 g, 11.6 mmol), K2CO3 (2 gm, 1.25 eq) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.3 g, 1.25 eq) in isopropyl alcohol (200 ml) was heated at reflux for 6 hours. The mixture was cooled and filtered. The solvent... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | c1ccc2c(c1)CCNC2.C1CO1 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(C)(C)O | null | 8 | COc1cc2c(cc1OC)CNCC2.Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1>C(C)(C)O>COc1cc2c(cc1OC)CN(CC(O)CN1CCC(c3noc4cc(F)ccc34)CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1d206f2f0d7e461992658e8c74435035 | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.O=C(CBr)N1CCc2ccccc2C1>>O=C(CN1CCC(c2n[nH]c3cc(F)ccc23)CC1)N1CCc2ccccc2C1 | FC1=CC=C2C(=NNC2=C1)C1CCNCC1.BrCC(=O)N1CC2=CC=CC=C2CC1.C([O-])(O)=O.[Na+]>>C1N(CCC2=CC=CC=C12)C(CN1CCC(CC1)C1=NNC2=CC(=CC=C12)F)=O | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1.Br[CH2:3][C:2](=[O:1])[N:20]1[CH2:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[CH2:29]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][nH:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][... | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.O=C(CBr)N1CCc2ccccc2C1 | O=C(CN1CCC(c2n[nH]c3cc(F)ccc23)CC1)N1CCc2ccccc2C1 | null | null | CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2n[nH]c3ccccc23)CC1)N1CCc2ccccc2C1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6])-[C:10]-[C:11] | 55.3 | [{"value": 55.3, "product": "C1N(CCC2=CC=CC=C12)C(CN1CCC(CC1)C1=NNC2=CC(=CC=C12)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-(6-fluoro-1H-indazol-3-yl)piperidine (4.8 g, 18.9 mmol) in CH3CN (200 ml) was added 2-bromo-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethanone (4.8 g, 18.9 mmol) and sodium bicarbonate (1.9 g, 22.7 mmol) at room temperature. The reaction mixture was warmed to reflux (4 hours), cooled to room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2n[nH]cc2c1.c1ccc2c(c1)CC[NH]C2 | HBr | CC#N | null | null | Fc1ccc2c(C3CCNCC3)n[nH]c2c1.O=C(CBr)N1CCc2ccccc2C1>CC#N>O=C(CN1CCC(c2n[nH]c3cc(F)ccc23)CC1)N1CCc2ccccc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-59c3f386a11441b28f8bd927f52f0783 | O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCCc2ccccc21>>Fc1ccc2c(C3CCN(CCN4CCCc5ccccc54)CC3)noc2c1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(=O)N2CCCC3=CC=CC=C23)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N#N>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2CCCC3=CC=CC=C23)C=C1 | O=[C:12]([CH2:11][N:10]1[CH2:9][CH2:8][CH:7]([c:6]2[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:28][c:27]3[o:26][n:25]2)[CH2:24][CH2:23]1)[N:13]1[CH2:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][N:13]4[CH2:14][CH2:15][CH2:16][c:17]5... | O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCCc2ccccc21 | Fc1ccc2c(C3CCN(CCN4CCCc5ccccc54)CC3)noc2c1 | null | null | C1CCOC1.C(C)O | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc2c(c1)CCCN2CCN1CCC(c2noc3ccccc23)CC1 | O=[C;H0;D3;+0:1](-[C:2]-[#7:3])-[#7:4](-[C:5])-[c:6]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[#7:4](-[C:5])-[c:6] | null | [] | null | null | 8 | HOUR | To a stirred solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethanone (5.5 g, 14 mmol) in THF (50 ml) was charged with lithium aluminum hydride (17 ml, 17 mmol, 1 M in ether) dropwise under N2 at room temperature. The mixture was stirred for 8 hours at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | C1CC[NH]CC1.c1ccc2c(c1)CCC[NH]2.c1ccc2oncc2c1 | Other | C1CCOC1.C(C)O | null | 8 | O=C(CN1CCC(c2noc3cc(F)ccc23)CC1)N1CCCc2ccccc21>C1CCOC1.C(C)O>Fc1ccc2c(C3CCN(CCN4CCCc5ccccc54)CC3)noc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-319ebce40947427bb72425925b81a1e7 | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.c1ccc2c(c1)CCCN2>>OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21 | C(\C=C\C(=O)O)(=O)O.O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1.N1CCCC2=CC=CC=C12>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CCCC3=CC=CC=C23)O)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CCCC3=CC=CC=C23)O)C=C1 | [O:9]1[CH:10]([CH2:41][N:42]2[CH2:43][CH2:44][CH:45]([c:46]3[n:47][o:48][c:49]4[cH:50][c:21]([F:22])[cH:53][cH:54][c:55]34)[CH2:56][CH2:57]2)[CH2:28]1.[CH2:11]1[NH:12][c:19]2[cH:20][cH:30][cH:31][cH:64][c:63]2[CH2:62][CH2:61]1>>[OH:9][CH:10]([CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([c:16]2[n:17][o:18][c:19]3[cH:20][c:21]... | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.c1ccc2c(c1)CCCN2 | OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21 | null | null | C(C)(C)O.C(C)O | Aromatic Heterocycle Formation | Ring opening of epoxide with amine | 94b694c4e807fd222f99678dc0a5d45efe518a58e1b83dc8276088547912789b | 72819d123292691faf3ac8d412eb31835c5af20978b0e5580d2e54f84a691f1b | c1ccc2c(c1)CCCN2CCCN1CCC(c2noc3ccccc23)CC1.c1ccc2c(c1)CCCN2CCCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[#7:2](-[CH2;D2;+0:3]-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-1)-[C:7].[F;D1;H0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]2:[#8;a:12]:[#7;a:13]:[c:14]:[c:15]:2:[c:16]:[cH;D2;+0:17]:1.[C:18]1-[CH2;D2;+0:19]-[CH2;D2;+0:20]-[NH;D2;+0:21]-[c;H0;D3;+0:22]2:[cH;D2;+0:23]:[cH;D2;+0:24]:[cH;D2;+0:25]:[cH;D2;+0:26]:[c;H0;... | null | [] | null | null | null | null | A stirred mixture of N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.41 g, 8.73 mmol), 1,2,3,4-tetrahydroquinoline (1.33 g, 10 mmol, in isopropyl alcohol (50 ml) was heated at reflux for 6 hours. The solution was cooled and the solvent was removed on a rotary evaporator. The crude solid was purified... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amine | Aromatic halide.Aromatic halide.Secondary alcohol.Secondary alcohol.Tertiary amine.Tertiary amine.Tertiary amine | C1CO1.c1ccc2oncc2c1.c1ccc2c(c1)CCCN2 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)CCC[NH]2.c1ccc2oncc2c1.c1ccc2c(c1)CCC[NH]2 | C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)CCC[NH]2.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccc2c(c1)CCC[NH]2 | Other | C(C)(C)O.C(C)O | null | null | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.c1ccc2c(c1)CCCN2>C(C)(C)O.C(C)O>OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5e80186788ea4c8dba389d2ffd945c9b | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>>Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCC(c2noc3cc(F)ccc23)CC1 | O1C(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)C1.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl>>Cl.Cl.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CN2CCC(CC2)C2=NOC3=C2C=CC(=C3)F)O)C=C1 | [O:3]1[CH:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH:9]([c:10]3[n:11][o:12][c:13]4[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]34)[CH2:20][CH2:21]2)[CH2:22]1.[NH:23]1[CH2:24][CH2:25][CH:26]([c:27]2[n:28][o:29][c:30]3[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]23)[CH2:37][CH2:38]1>>[ClH:2].[OH:3][CH:4]([CH2:5][N:6]1[CH2:7][CH2:8][CH:9]... | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.Fc1ccc2c(C3CCNCC3)noc2c1 | Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)(C)O.C(C)O | Functional Group Addition | Ring opening of epoxide with amine | 8f4365a4240bb3ef2b74683874d3e70abd097abb018b25f09bae9b0649035eec | 681442a3c8548b1c6358163a45643f5654b12c41787e3fd8f8f2669578ce05ac | c1ccc2c(C3CCN(CCCN4CCC(c5noc6ccccc56)CC4)CC3)noc2c1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH2;D2;+0:8]-[C:7](-[C:6])-[OH;D1;+0:9])-[C:4]-[C:5] | null | [] | 65 | CELSIUS | 16 | HOUR | A stirred mixture of 1-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (1.19 g, 4.3 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (0.95 g, 4.3 mmol) in isopropyl alcohol (50 ml) was heated at reflux for 1 hour, then stirred at 65° C. for 16 hours. The solvent was removed on a rotary evaporator. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1.C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1.C1CC[NH]CC1.c1ccc2oncc2c1 | Other | C(C)(C)O.C(C)O | 65 | 16 | Fc1ccc2c(C3CCN(CC4CO4)CC3)noc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)(C)O.C(C)O>Cl.OC(CN1CCC(c2noc3cc(F)ccc23)CC1)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b42dc69d37ed401ea18a2cfc9a9c9cda | CC#N.Cc1ccccc1S(=O)(=O)C1(c2ccccc2)C(=O)c2ccccc2C1=O.Fc1ccc2c(C3CCNCC3)noc2c1>>O=C1c2ccccc2C(=O)C1(CCN1CCC(c2noc3cc(F)ccc23)CC1)c1ccccc1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C=1(C(=CC=CC1)S(=O)(=O)C1(C(C2=CC=CC=C2C1=O)=O)C1=CC=CC=C1)C.C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2(C(C3=CC=CC=C3C2=O)=O)C2=CC=CC=C2)C=C1 | N#[C:13][CH3:12].Cc1ccccc1S(=O)(=O)[C:11]1([c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[NH:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[... | CC#N.Cc1ccccc1S(=O)(=O)C1(c2ccccc2)C(=O)c2ccccc2C1=O.Fc1ccc2c(C3CCNCC3)noc2c1 | O=C1c2ccccc2C(=O)C1(CCN1CCC(c2noc3cc(F)ccc23)CC1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 729f7b277b48207085eedff56635f4ec8447af58b5ecf5a967c1e85bb57b32a1 | 61ec31e5de7c3e957c4a7b4c9cf3e7ceec144bd85a9a8af1ace072d8f78459e9 | O=C1c2ccccc2C(=O)C1(CCN1CCC(c2noc3ccccc23)CC1)c1ccccc1 | C-c1:c:c:c:c:c:1-S(=O)(=O)-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]-[C:9]-1=[O;D1;H0:10].N#[C;H0;D2;+0:11]-[CH3;D1;+0:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5](=[O;D1;H0:6])-[c:7]:[... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.2 g, 10 mmol), K2CO3 (1.6 g, 11.6 mmol) and 2-toluenesulfonyl-2-phenyl-1,3-indandione (4.2 g, 10 mmol) in acetonitrile (50 ml) was heated at reflux for 3 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evapo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Nitrile.Secondary amine.Sulfone | Ketone.Ketone.Tertiary amine | c1ccccc1.c1ccc2c(c1)CCC2.C1CCNCC1 | c1ccc2c(c1)CCC2.C1CC[NH]CC1 | c1ccc2c(c1)CCC2.C1CC[NH]CC1.c1ccc2oncc2c1.c1ccccc1 | HO- | null | null | null | CC#N.Cc1ccccc1S(=O)(=O)C1(c2ccccc2)C(=O)c2ccccc2C1=O.Fc1ccc2c(C3CCNCC3)noc2c1>>O=C1c2ccccc2C(=O)C1(CCN1CCC(c2noc3cc(F)ccc23)CC1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0b3af418529e42ea893c111f8c64ed7e | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCl>>N#CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCC#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CC#N)C=C1 | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1.Cl[CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCl | N#CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 61.6 mmol) and 2-chloroacetonitrile (5.5 g, 73 mmol) in acetonitrile (250 ml) was heated at reflux for 24 hours. The insolubles were filtered off and rinsed with methylene chloride (DCM). During concentration of the solvents on the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCl>C(C)#N>N#CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bbfb3372b4664f4b919ced1da15d7803 | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCBr>>N#CCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCC#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC#N)C=C1 | [NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1.Br[CH2:4][CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCBr | N#CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3]#[N;D1;H0:4])-[C:8]-[C:9] | 31.5 | [{"value": 31.5, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 74 mmol) and 3-bromopropionitrile (8.2 g, 1.2 eq) in acetonitrile (300 ml) was heated at reflux for 24 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator and the crude pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.N#CCCBr>C(C)#N>N#CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-085bcf2d4a8b4502808e8f546ff0934f | COc1cc(C(C)=O)ccc1OCCCCl.O=C(O)C(F)(F)F>>COc1cc(C(=O)CO)ccc1OCCCCl | ClCCCOC1=C(C=C(C=C1)C(C)=O)OC.FC(C(=O)OI(OC(C(F)(F)F)=O)C1=CC=CC=C1)(F)F.O.C(F)(F)(F)C(=O)O>>ClCCCOC1=C(C=C(C=C1)C(CO)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH3:8])[cH:10][cH:11][c:12]1[O:13][CH2:14][CH2:15][CH2:16][Cl:17].O=C(C(F)(F)F)[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][OH:9])[cH:10][cH:11][c:12]1[O:13][CH2:14][CH2:15][CH2:16][Cl:17] | COc1cc(C(C)=O)ccc1OCCCCl.O=C(O)C(F)(F)F | COc1cc(C(=O)CO)ccc1OCCCCl | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 31a4c12379bf4facf310e0d1fac7911d9643a30c73ba661e8d6534bbcf168fd3 | c5fc43da3490b0b186f4f65ac0b981fa3cf81ba2f542cb3439cd24a6541bfbba | c1ccccc1 | F-C(-F)(-F)-C(=O)-[OH;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[O;D1;H0:4]=[C:3](-[c:5])-[CH2;D2;+0:2]-[OH;D1;+0:1] | 32.8 | [{"value": 32.8, "product": "ClCCCOC1=C(C=C(C=C1)C(CO)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodo]benzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3CN (90 ml) was refluxed for 3 hours. The CH3CN was removed under reduced pressure and the resulting yellow liquid was partitioned between H2O and... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Ketone | Ketone.Primary alcohol | null | null | c1ccccc1 | HF | CC#N | null | null | COc1cc(C(C)=O)ccc1OCCCCl.O=C(O)C(F)(F)F>CC#N>COc1cc(C(=O)CO)ccc1OCCCCl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2c930f18473f49e79a37a4dcae2cce3b | C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1>>C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1 | C(C1=CC=CC=C1)OC1=CC=2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3C2C=C1)OCCOC(CCCC1=CC=C(C=C1)N(CCCl)CCCl)=O>>OC1=CC=2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3C2C=C1)OCCOC(CCCC1=CC=C(C=C1)N(CCCl)CCCl)=O | c1ccc(C[O:10][c:9]2[cH:8][cH:7][c:6]3[c:12]([cH:11]2)[CH2:13][CH2:14][C@@H:15]2[C@@H:5]3[CH2:4][CH2:3][C@@:2]3([CH3:1])[C@H:16]2[CH2:17][CH2:18][C@@H:19]3[O:20][CH2:21][CH2:22][O:23][C:24](=[O:25])[CH2:26][CH2:27][CH2:28][c:29]2[cH:30][cH:31][c:32]([N:33]([CH2:34][CH2:35][Cl:36])[CH2:37][CH2:38][Cl:39])[cH:40][cH:41]2)... | C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1 | C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1 | null | [Pd] | O1CCOCC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCCc1ccccc1)OCCO[C@H]1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 1 | HOUR | 10% palladium on carbon (320.7 mg) was placed into an eggplant type flask (100 ml), followed by dropwise addition of 1,4-dioxane (15 ml) at 0° C. To this mixture was added a 1,4-dioxane (15 ml) solution of 1-[3-benzyloxy-1,3,5(10)-estratriene-17β-oxy]-2-[4-[p-[bis(2-chloroethyl)amino]-phenyl]-butyryloxy]ethane (I-5) dr... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@@H]3CC[C@H]21.c1ccccc1 | Other | [Pd].O1CCOCC1 | null | 1 | C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1>[Pd].O1CCOCC1>C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2OCCOC(=O)CCCc1ccc(N(CCCl)CCCl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f2c33553b284f46a23392b59f9c40f9 | CCOP(C)(=O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1>>CP(=O)(O)CC[C@H](N)C(=O)O | C(C1=CC=CC=C1)OC(=O)N1COC([C@@H]1CCP(=O)(C)OCC)=O.Cl>>Cl.N[C@@H](CCP(O)(=O)C)C(=O)O | CC[O:4][P:2]([CH3:1])(=[O:3])[CH2:5][CH2:6][C@@H:7]1[N:8](C(=O)OCc2ccccc2)C[O:11][C:9]1=[O:10]>>[CH3:1][P:2](=[O:3])([OH:4])[CH2:5][CH2:6][C@H:7]([NH2:8])[C:9](=[O:10])[OH:11] | CCOP(C)(=O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1 | CP(=O)(O)CC[C@H](N)C(=O)O | null | null | null | Reduction | OtherReaction | 52a4afec2b7b72de683fb376b73a6612ab9aec96e23f3f92f66aa4e5f6103577 | 4b696b0cbdbebf7009d6d110fab9caa4ca7439f26b30158b2f202f142b660eeb | null | C-C-[O;H0;D2;+0:1]-[#15:2](-[C;D1;H3:3])(=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]1-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-[N;H0;D3;+0:11]-1-C(=O)-O-C-c1:c:c:c:c:c:1>>[C;D1;H3:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[C:5]-[C:6]-[C:7](-[NH2;D1;+0:11])-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10] | 82.1 | [{"value": 82.1, "product": "Cl.N[C@@H](CCP(O)(=O)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.50 g (1.4 mmol) of (4S)-3-benzyloxycarbonyl-4-{2-[ethoxy (methyl)phosphinyl]ethyl}-1,3-oxazolidin-5-one (from Example 12) are, as described in DE-A-3,817,956, hydrolyzed by heating in 6 N hydrochloric acid. 0.25 g (82.1% of theory) of L-homoalanin-4-yl(methyl)phosphinic acid hydrochloride are obtained as a white soli... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether | Carboxylic acid.Primary amine | C1COC[NH]1.c1ccccc1 | null | null | HO- | null | null | null | CCOP(C)(=O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1>>CP(=O)(O)CC[C@H](N)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4902632df18446baba38307038fb3a54 | O=C(O)C1CC1>>O=CC1CC1 | C1(CC1)C(=O)O.C1(CC1)C(=O)O.C1(CC1)C(=O)O>>C1(CC1)C=O.C1CC1C(=O)O | O[C:8](=[O:7])[CH:9]1[CH2:10][CH2:11]1>>[O:7]=[CH:8][CH:9]1[CH2:10][CH2:11]1 | O=C(O)C1CC1 | O=CC1CC1 | null | [Co].[Pt] | null | Reduction | OtherReaction | 78999da0d33b2c10ff8c3d41626c41ea14d2697ff6d1d7e5baf78453ec38592a | f41d7c101137b93550fdf296ceb4547d1ce640e4cbceb5b7b006723d153456c9 | C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]1-[C:4]-[C:5]-1 | null | [] | null | null | null | null | Disclosed is a process for the conversion of off-color cyclopropanecarboxylic acid (CPC-Acid) to CPC-Acid having a color value (platinum-cobalt scale) of less than about 10 by the steps of (1) heating off-color CPC-Acid produced by the oxidation of cyclopropanecarboxaldehyde with molecular oxygen with a strong acid; an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | C1CC1 | Other | [Co].[Pt] | null | null | O=C(O)C1CC1>[Co].[Pt]>O=CC1CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-06766ac25d6b48cc939c274d6b783b58 | C1CCOC1.CCCCOB(OCCCC)OCCCC>>O=Cc1ccc(B(O)O)cc1 | [Mg].B(OCCCC)(OCCCC)OCCCC.C1CCOC1.C1CCOC1.C1CCOC1.C1CCOC1.COCCO[AlH2-]OCCOC.[Na+].BrCCBr>>C(=O)C1=CC=C(C=C1)B(O)O | C1O[CH2:5][CH2:4][CH2:3]1.CCCC[O:8][B:7]([O:1][CH2:2][CH2:11][CH2:10][CH3:6])[O:9]CCCC>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([B:7]([OH:8])[OH:9])[cH:10][cH:11]1 | C1CCOC1.CCCCOB(OCCCC)OCCCC | O=Cc1ccc(B(O)O)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b8c9b7445db3e533304aaebfe565dc5cd66e5b97d48dc63b999843b95edda633 | 954326100edd89bd63184c1d4de194aa650da391de981b7d65fb83dc23c81f28 | c1ccccc1 | C-C-C-C-[O;H0;D2;+0:1]-[B;H0;D3;+0:2](-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7])-[O;H0;D2;+0:8]-C-C-C-C.C1-O-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1>>[O;H0;D1;+0:3]=[CH;D2;+0:4]-[c;H0;D3;+0:11]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[B;H0;D3;+0:2](-[OH;D1;+0:1])-[OH;D1;+0:8]):[cH... | null | [] | null | null | 30 | MINUTE | Under an argon atmosphere, 3.65 g of magnesium turnings are covered with 15 ml of anhydrous THF and treated with 0.5 ml of 1,2-dibromoethane. Gentle warming leads to a vigorous reaction. After the reaction has subsided, the solvent is pipetted off with a pipette, treated with 40 ml of anhydrous THF and 1/3 of a solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde.Boronic acid | C1CCOC1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 0.5 | C1CCOC1.CCCCOB(OCCCC)OCCCC>>O=Cc1ccc(B(O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bdaa0f9bbc2a40cdb25fd2d294344c32 | CCCN=C=O.NS(=O)(=O)c1ccccc1Br>>Brc1ccccc1.CCCS(=O)(=O)NC(N)=O | OS(=O)(=O)[O-].[Na+].BrC1=C(C=CC=C1)S(=O)(=O)N.C(=O)([O-])[O-].[K+].[K+].C(CC)N=C=O>>BrC1=CC=CC=C1.C(CC)S(=O)(=O)NC(=O)N | [CH3:8][CH2:9][CH2:10][N:14]=[C:15]=[O:17].[Br:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:11](=[O:12])(=[O:13])[NH2:16]>>[Br:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1.[CH3:8][CH2:9][CH2:10][S:11](=[O:12])(=[O:13])[NH:14][C:15]([NH2:16])=[O:17] | CCCN=C=O.NS(=O)(=O)c1ccccc1Br | Brc1ccccc1.CCCS(=O)(=O)NC(N)=O | null | null | COC(C)(C)OC | Acylation | OtherReaction | 64210a8cdea5e6abfcd951826d7deabe3ec6162a5a9fd79927d8f6e0bb93dfd7 | 0fe1082098d61e5130a83440c9351817ede5cdd433bfc65ee308ef6fab351022 | c1ccccc1 | [Br;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[S;H0;D4;+0:5](-[NH2;D1;+0:6])(=[O;D1;H0:7])=[O;D1;H0:8]):[c:9]:[c:10].[C;D1;H3:11]-[C:12]-[CH2;D2;+0:13]-[N;H0;D2;+0:14]=[C;H0;D2;+0:15]=[O;D1;H0:16]>>[Br;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:9]:[c:10].[C;D1;H3:11]-[C:12]-[CH2;D2;+0:13]-[S;H0;D4;+0:5](=[O;D1;H0:7])(=[O;D1;H... | null | [] | 0 | CELSIUS | 12 | HOUR | 3.5 g (15mmol) of 2-bromobenzenesulfonamide and 4.1 g K2CO3 are refluxed in dimethoxypropane for 1 hour. After that time 3 ml of n-propylisocyanate are added via a syringe. After additional 12 hours, the solution is cooled to 0° C., the pH is adjusted to 5-6 using 5% NaHSO4 and this mixture is extracted twice with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | Sulfonamide.Urea | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | COC(C)(C)OC | 0 | 12 | CCCN=C=O.NS(=O)(=O)c1ccccc1Br>COC(C)(C)OC>Brc1ccccc1.CCCS(=O)(=O)NC(N)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8d9322228f549dd86a0241ae2cb5e96 | Nc1ccccc1S(N)(=O)=O.[I-]>>NS(=O)(=O)c1ccccc1I | [I-].[K+].NC1=C(C=CC=C1)S(=O)(=O)N.N(=O)[O-].[Na+]>>IC1=C(C=CC=C1)S(=O)(=O)N | N[c:10]1[c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:6][cH:7][cH:8][cH:9]1.[I-:11]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[I:11] | Nc1ccccc1S(N)(=O)=O.[I-] | NS(=O)(=O)c1ccccc1I | null | null | O.OS(=O)(=O)O | Functional Group Interconversion | OtherReaction | f4fea6a3c7b007f3829d29d893f3499a4094808c0f3b2211f4c3483919a690d8 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6].[I-;H0;D0:7]>>[#16:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[I;H0;D1;+0:7]):[c:2]:[c:3] | 69.5 | [{"value": 62.0, "product": "IC1=C(C=CC=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "IC1=C(C=CC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | 2-aminobenzene sulfonamide (3.5 g) in conc. H2SO4, 98% (25 ml) are heated at 60° to give a clear solution. 20 g of ice is then added and the solution is cooled to 0° C. NaNO2 (1.45 g) in water (4 ml) is added dropwise very carefully without exceeding 5°-6° C. The reaction mixture is stirred at 5°-6° C. for 3 hours. A s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O.OS(=O)(=O)O | 0 | 3 | Nc1ccccc1S(N)(=O)=O.[I-]>O.OS(=O)(=O)O>NS(=O)(=O)c1ccccc1I |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b7ffa34e30a64a33926146bd0b212434 | CCCN=C=O.NS(=O)(=O)c1ccccc1I>>CCCS(=O)(=O)NC(N)=O.Ic1ccccc1 | C(CC)N=C=O.IC1=C(C=CC=C1)S(=O)(=O)N.C(=O)([O-])[O-].[K+].[K+].CC(=O)C.C(C)(C)OC(C)C>>IC1=CC=CC=C1.C(CC)S(=O)(=O)NC(=O)N | [CH3:1][CH2:2][CH2:3][N:9]=[C:8]=[O:10].[S:4](=[O:5])(=[O:6])([NH2:7])[c:17]1[c:12]([I:11])[cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[NH:7][C:8]([NH2:9])=[O:10].[I:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCCN=C=O.NS(=O)(=O)c1ccccc1I | CCCS(=O)(=O)NC(N)=O.Ic1ccccc1 | null | null | CC(=O)C | Acylation | OtherReaction | 64210a8cdea5e6abfcd951826d7deabe3ec6162a5a9fd79927d8f6e0bb93dfd7 | 0fe1082098d61e5130a83440c9351817ede5cdd433bfc65ee308ef6fab351022 | c1ccccc1 | [C;D1;H3:1]-[C:2]-[CH2;D2;+0:3]-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[I;D1;H0:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[S;H0;D4;+0:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]):[c:15]:[c:16]>>[C;D1;H3:1]-[C:2]-[CH2;D2;+0:3]-[S;H0;D4;+0:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[C;H0;D3;+0:5](-[NH2;D1;+0:4])=[O;... | null | [] | null | null | null | null | To a stirred solution of 2-iodo benzene sulfonamide (4 g) in acetone (40 ml) solid K2CO3 (3.92 g) is added in one portion and the mixture is refluxed under N2 -atmosphere, n-propyl isocyanate is added dropwise to the heated mixture. After 2 hours reflux, the reaction is cooled to room temperature and concentrated to dr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | Sulfonamide.Urea | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CC(=O)C | null | null | CCCN=C=O.NS(=O)(=O)c1ccccc1I>CC(=O)C>CCCS(=O)(=O)NC(N)=O.Ic1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-99941482ecf24c6ebdb6ea32e9152dd5 | O=C(O)c1cc(F)c([N+](=O)[O-])cc1Cl.[F-]>>O=C(O)c1cc(F)c(F)cc1Cl | [F-].[K+].ClC1=C(C(=O)O)C=C(C(=C1)[N+](=O)[O-])F>>ClC1=C(C(=O)O)C=C(C(=C1)F)F | O=[N+]([O-])[c:8]1[c:6]([F:7])[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:11]([Cl:12])[cH:10]1.[F-:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[Cl:12] | O=C(O)c1cc(F)c([N+](=O)[O-])cc1Cl.[F-] | O=C(O)c1cc(F)c(F)cc1Cl | null | null | C1CCCS1(=O)=O | Functional Group Interconversion | OtherReaction | 8f7bc091dc518c08e5d782f7be171f96724683a8b47732ef73a42794602da354 | 0a14f7867b85468f63360cd013871971003c6f72f5faa0cf46cb11776a5452b5 | c1ccccc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[F-;H0;D0:7]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[F;H0;D1;+0:7]):[c:2]:[c:3] | 24 | [{"value": 24.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | The combined benzoic acids made in each of Examples 3, 11 and 12 (consisting of compounds 5 and 6 in a ratio of about 2:1) were converted to the corresponding acid chlorides as in Example 4. The acid chlorides (2 g, 8.4 mmol) were dissolved in 4 ml of tetramethylenesulfone and treated with spray-dried KF (2.0 g, 34.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCCS1(=O)=O | 150 | null | O=C(O)c1cc(F)c([N+](=O)[O-])cc1Cl.[F-]>C1CCCS1(=O)=O>O=C(O)c1cc(F)c(F)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f20e599b4b974f9f93ef7af1788114bb | COc1cccc(C(C)N)c1>>COc1cccc([C@@H](C)N)c1 | C([C@H](O)C1=CC=CC=C1)(=O)O.COC=1C=C(C(C)N)C=CC1>>COC=1C=C([C@@H](C)N)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([CH3:9])[NH2:10])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C@@H:8]([CH3:9])[NH2:10])[cH:11]1 | COc1cccc(C(C)N)c1 | COc1cccc([C@@H](C)N)c1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 83 | [{"value": 83.0, "product": "COC=1C=C([C@@H](C)N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.4, "product": "COC=1C=C([C@@H](C)N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 14.0 g (92.0 mmol) of (R)-(-)- mandelic acid (Aldrich, 99+%), 14.0 g (92.7 mmol) of (±) 3-methoxy-α-methylbenzylamine and 500 mL of isopropanol was brought to reflux and gravity filtered while hot. The solution was then seeded at 50° C. with diastereomerically-pure seeds. After cooling to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)(C)O | null | null | COc1cccc(C(C)N)c1>C(C)(C)O>COc1cccc([C@@H](C)N)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1b27e7ea017449b68acfe3c2babcd2ac | CCOC(=O)C(Cc1ccccc1Cl)C(=O)OCC>>O=C(O)CCc1ccccc1Cl | ClC1=C(CC(C(=O)OCC)C(=O)OCC)C=CC=C1.CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C>>ClC1=C(C=CC=C1)CCC(=O)O | CCOC(=O)[CH:4]([C:2](=[O:1])[O:3]CC)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12] | CCOC(=O)C(Cc1ccccc1Cl)C(=O)OCC | O=C(O)CCc1ccccc1Cl | null | null | Cl | Reduction | OtherReaction | 5ba27bafcd96d74a94be636caed9361c02821d71f9ddac00396de4e018da642b | 6d9edf77f3bf4688cdf5f5c3ccf062016b04f2e19a67399a3ca7c7e8d575cc5a | c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-C>>[O;D1;H0:5]=[C:4](-[OH;D1;+0:6])-[CH2;D2;+0:1]-[C:2]-[c:3] | 93.4 | [{"value": 93.4, "product": "ClC1=C(C=CC=C1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "ClC1=C(C=CC=C1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a 50 liter flask was added diethyl o-chlorobenzylmalonate (6067 g, 21.31 mol), glacial acetic. acid (1090 mL), and concentrated hydrochloric acid (16,000 mL). The reaction was then heated at reflux for 21 hours and 13 minutes. Additional concentrated hydrochloric acid (1840 mL, 5520 mL total) was added at 3.5, 13.5,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid | null | null | c1ccccc1 | HO- | Cl | null | 0.083333 | CCOC(=O)C(Cc1ccccc1Cl)C(=O)OCC>Cl>O=C(O)CCc1ccccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cf2a01af2af748529f5ae4365cbce0cf | COc1cc(C=O)cc([N+](=O)[O-])c1O>>O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C=O)C=C1[N+](=O)[O-])OC.Br>>OC=1C=C(C=O)C=C(C1O)[N+](=O)[O-] | C[O:6][c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]1[OH:8]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | COc1cc(C=O)cc([N+](=O)[O-])c1O | O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 17.1 g of 4-hydroxy-3-methoxy-5-nitrobenzaldehyde are treated with 170 ml of constant-boiling hydrobromic acid and heated under reflux for 3.5 hours. After cooling the separated precipitate is filtered under suction, washed twice with ice-water and taken up in ethyl acetate. The organic phase is washed twice with 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | null | COc1cc(C=O)cc([N+](=O)[O-])c1O>C(Cl)Cl>O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9211ecccd6cb4d37b207ab7b66aeb29d | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1cccnc1>>COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1 | Cl.C(C)(C)(C)[Li].C(C1=CC=CC=C1)OC1=C(C=C(C=C1)Br)OC.N1=CC(=CC=C1)C=O>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(O)C=1C=NC=CC1)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:15][cH:14]1.[CH:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][c... | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1cccnc1 | COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(COc2ccc(Cc3cccnc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | aa) 10 ml of tert.butyl lithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 4.1 g of 4-(benzyloxy)-3-methoxy-bromobenzene dissolved in 40 ml of tetrahydrofuran. After stirring at -70° for 2 hours. 1 ml of pyridine-3-carbaldehyde is added within 5 minutes The reaction mixture is stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.c1ccccc1 | Br- | O1CCCC1 | null | 2 | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1cccnc1>O1CCCC1>COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7842e662cbba4ebaae8e916b05890726 | COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1OC)C(O)C=1C=NC=CC1.[Mn](=O)(=O)(=O)[O-].[K+].[Mn](=O)(=O)(=O)[O-].[K+]>>N1=CC(=CC=C1)C(=O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][... | COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1 | COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1 | null | null | O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccc(OCc2ccccc2)cc1)c1cccnc1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | null | [] | null | null | 30 | MINUTE | ba) 3.2 g of alpha-[4-(benzyloxy)-5-methoxyphenyl]-3-pyridinemethanol suspended in 50 ml of water are treated with 2.5 g of potassium permanganate, whereupon the mixture is stirred at 90° for 30 minutes After adding a further 1.0 g of potassium permanganate and stirring for a further 30 minutes at 90° the mixture is co... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | null | O | null | 0.5 | COc1cc(C(O)c2cccnc2)ccc1OCc1ccccc1>O>COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3e0e85f92d4a47c49517786c0f10563e | COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2cccnc2)ccc1O | N.Br.N1=CC(=CC=C1)C(=O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OC>>N1=CC(=CC=C1)C(=O)C1=CC(=C(C=C1)O)OC | c1ccc(C[O:17][c:16]2[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][cH:11][n:12][cH:13]3)[cH:14][cH:15]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:16]1[OH:17] | COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1 | COc1cc(C(=O)c2cccnc2)ccc1O | null | null | C(C)(=O)O.C(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1cccnc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 3 | HOUR | ca) 50 ml of 33 percent hydrobromic acid in acetic acid are added dropwise within 15 minutes at 10° to 20 g of 4-(benzyloxy)-3-methoxyphenyl 3-pyridyl ketone dissolved in 200 ml of methylene chloride. After stirring at 20° for 3 hours, the reaction mixture is poured into a mixture of 100 ml of conc. aqueous ammonia and... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccncc1 | Other | C(C)(=O)O.C(Cl)Cl | null | 3 | COc1cc(C(=O)c2cccnc2)ccc1OCc1ccccc1>C(C)(=O)O.C(Cl)Cl>COc1cc(C(=O)c2cccnc2)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2486e2aedec54c30a9098cef9551b3d9 | COc1cc(C(=O)c2cccnc2)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O | N.[N+](=O)(O)[O-].N1=CC(=CC=C1)C(=O)C1=CC(=C(C=C1)O)OC>>N1=CC(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][cH:15][c:19]1[OH:20].O[N+:16](=[O:17])[O-:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[OH:20] | COc1cc(C(=O)c2cccnc2)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C(c1ccccc1)c1cccnc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 2 | HOUR | da) 0.38 ml of 65 percent nitric acid is added dropwise at room temperature to 1.15 g of 4-hydroxy-3-methoxyphenyl 3-pyridyl ketone dissolved in 15 ml of acetic acid. After stirring for 2 hours, the reaction mixture is poured into 120 ml of ice-water, whereupon the mixture is adjusted to pH 5 with conc. ammonia and the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | C(C)(=O)O | null | 2 | COc1cc(C(=O)c2cccnc2)ccc1O.O=[N+]([O-])O>C(C)(=O)O>COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e70b0aee5d954f049be917209400519e | COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O>>O=C(c1cccnc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | N1=CC(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.Br>>Br.N1=CC(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:13][c:12]1[cH:11][c:10]([C:3](=[O:2])[c:4]2[cH:5][cH:6][cH:7][n:8][cH:9]2)[cH:20][c:16]([N+:17](=[O:18])[O-:19])[c:14]1[OH:15]>>[O:2]=[C:3]([c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[cH:11][c:12]([OH:13])[c:14]([OH:15])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O | O=C(c1cccnc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1cccnc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | 3.5 g of 4-hydroxy-3-methoxy-5-nitrophenyl 3-pyridyl ketone dissolved in 70 ml of 48 percent aqueous hydrobromic acid are stirred at 100° for 18 hours. The reaction mixture is subsequently evaporated under reduced pressure. The residue is recrystallized from water. There is obtained 3,4-dihydroxy-5-nitrophenyl 3-pyridy... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccncc1.c1ccccc1 | Other | null | null | 18 | COc1cc(C(=O)c2cccnc2)cc([N+](=O)[O-])c1O>>O=C(c1cccnc1)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d4b0e25814394c5996579e53795ab646 | O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | N1=CC=C(C=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.CS(=O)(=O)O>>CS(=O)(=O)O.N1=CC=C(C=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | [O:6]=[C:7]([c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][c:16]([OH:17])[c:18]([OH:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1>>[O:6]=[C:7]([c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][c:16]([OH:17])[c:18]([OH:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1 | O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)c1ccncc1 | null | null | [] | null | null | null | null | 13.2 g of 3,4-dihydroxy-5-nitrophenyl 4-pyridyl ketone are suspended in 500 ml of methanol and treated while stirring with 4.88 g of methanesulfonic acid. The suspension is heated under reflux for 60 minutes. It is subsequently cooled to 10°, the crystals are filtered under suction and washed twice with 30 ml of methan... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.c1ccccc1 | null | CO | null | null | O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1>CO>O=C(c1ccncc1)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f7329e3b88654b54961703a743b4acdf | COc1cc(C(=O)O)cc([N+](=O)[O-])c1O>>O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C(=O)O)C=C1[N+](=O)[O-])OC>>OC=1C=C(C(=O)O)C=C(C1O)[N+](=O)[O-] | C[O:7][c:6]1[cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]1[OH:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | COc1cc(C(=O)O)cc([N+](=O)[O-])c1O | O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 2.6 g of 4-hydroxy-3-methoxy-5-nitrobenzoic acid in 26 ml of constant-boiling hydrobromic acid is heated under reflux for 2 hours. After cooling the solvent is distilled in a water-jet vacuum. The crystalline residue is recrystallized from 50 ml of water at boiling temperature. There is obtained 3,4-dihyd... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | Br | null | null | COc1cc(C(=O)O)cc([N+](=O)[O-])c1O>Br>O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-937c87110d0d45dda472aad6af96b732 | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][c]1ccccc1>>COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC | C1(=CC=CC=C1)[Li].COC=1C=C(C=O)C=C(C1OC)[N+](=O)[O-].S(O)(O)(=O)=O>>COC=1C=C(C(C2=CC=CC=C2)O)C=C(C1OC)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21].[Li][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21] | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][c]1ccccc1 | COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | b69e6463bf3d042723585d322bbfaf490e3496166187a5cef2788ca3e5e5105d | 1cd650c3a5fed462f5dff3a656d16c03fda05f3a76e0703b4e579a9400688788 | c1ccc(Cc2ccccc2)cc1 | [Li]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | 25 ml of 2M phenyl lithium solution (in benzene/ether (7:3)) are added dropwise within 15 minutes to 10.0 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 150 ml of tetrahydrofuran and the mixture is stirred at 0° for 1 hour and at 20° for 2 hours. The mixture is subsequently treated with 150 ml of 2N sulfuric acid ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aryl lithium | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Li | O1CCCC1 | null | 2 | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][c]1ccccc1>O1CCCC1>COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0475c0f1d7974a6f82a47be0e46d3829 | COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(C2=CC=CC=C2)O)C=C(C1OC)[N+](=O)[O-].[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>COC=1C=C(C(=O)C2=CC=CC=C2)C=C(C1OC)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21] | COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccccc1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | 2.5 g of 3,4-dimethoxy-5-nitrobenzhydrol dissolved in 50 ml of methylene chloride are treated with 2.2 g of pyridinium chlorochromate, whereupon the mixture is stirred at room temperature for 2 hours. The insoluble constituents are subsequently filtered. The filtrate is evaporated and the residue is chromatographed on ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | COc1cc(C(O)c2ccccc2)cc([N+](=O)[O-])c1OC>C(Cl)Cl>COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b5876ade9b14469b9de2e28870a9aa3c | COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC>>O=C(c1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | COC=1C=C(C(=O)C2=CC=CC=C2)C=C(C1OC)[N+](=O)[O-]>>OC=1C=C(C(=O)C2=CC=CC=C2)C=C(C1O)[N+](=O)[O-] | C[O:12][c:11]1[cH:10][c:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[cH:19][c:15]([N+:16](=[O:17])[O-:18])[c:13]1[O:14]C>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][c:11]([OH:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC | O=C(c1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(C)(=O)O.Br | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 0.5 g of 3,4-dimethoxy-5-nitrobenzophenone is stirred at 110° for 30 hours in a mixture of 4 ml of acetic acid and 4 ml of 48 percent aqueous hydrobromic acid. The reaction mixture is subsequently evaporated to dryness. The residue is taken up in methylene chloride. It is washed with water, dried over sodium sulfate an... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O.Br | null | null | COc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1OC>C(C)(=O)O.Br>O=C(c1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-81f3d141da514f0f96dce4afc62bffb3 | CCOC(=O)CC(=O)OCC.COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC>>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1 | C(CC(=O)OCC)(=O)OCC.[Mg].C(Cl)(Cl)(Cl)Cl.COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-]>>COC=1C=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C1OC)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[C:12](=[O:13])[c:14]1[cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[c:22]([N+:23](=[O:24])[O-:25])[cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[C:12](=[O:13])[c:14]1[cH:15][c:16]([O:17][CH3:18])[c:19... | CCOC(=O)CC(=O)OCC.COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1 | null | null | O1CCCC1.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | OtherReaction | 872dd4ea89053916cf9ee557745988425973a0fb6c3fde7e681bde82864a0018 | a7050091370b27e4945622bf444949c46249e49bd26e357ae44671cc72030a02 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4.9 g of magnesium are suspended in 15 ml of absolute ethanol and, after adding 1 ml of carbon tetra- chloride, warmed until the reaction starts. A solution of 31.8 g of diethyl malonate in 19.9 ml of absolute ethanol and 80 ml of absolute toluene is then added dropwise while stirring so that the temperature lies betwe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone | null | null | c1ccccc1 | HCl | O1CCCC1.C1(=CC=CC=C1)C.C(C)O | null | null | CCOC(=O)CC(=O)OCC.COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC>O1CCCC1.C1(=CC=CC=C1)C.C(C)O>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-47867be4c54344eb8b7bb41ae167e225 | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC>>CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(C)=O.Br>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C)=O | C[O:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]1[O:9]C>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC | CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 2.5 | HOUR | 2 g of 3',4'-dimethoxy-5'-nitroacetophenone are treated with 30 ml of constant-boiling hydrobromic acid and stirred at 140° for 2.5 hours. After cooling the mixture is poured into 200 ml of ice-water and extracted three times with 100 ml of ethyl acetate each time. The organic phase is washed twice with 25 ml of sodium... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | null | null | 2.5 | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC>>CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7a444300f0c04c30917512361c20cb37 | COc1cc(C(=O)C(C)C)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O | OC1=C(C=C(C=C1)C(C(C)C)=O)OC.[N+](=O)(O)[O-]>>OC1=C(C=C(C=C1[N+](=O)[O-])C(C(C)C)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH:8]([CH3:9])[CH3:10])[cH:11][cH:12][c:16]1[OH:17].O[N+:13](=[O:14])[O-:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH:8]([CH3:9])[CH3:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[OH:17] | COc1cc(C(=O)C(C)C)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O | null | null | C(C)(=O)O.C(Cl)Cl | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 15 | MINUTE | 15.0 g of 4'-hydroxy-3'-methoxy-2-methyl-propiophenone are dissolved in 300 ml of glacial acetic acid and 7.65 ml of 50.5 percent nitric acid (11.2N) in 40 ml of glacial acetic acid are added dropwise thereto while stiring within 15 minutes. After 15 minutes the reaction mixture is poured into ice-water and the separat... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)O.C(Cl)Cl | null | 0.25 | COc1cc(C(=O)C(C)C)ccc1O.O=[N+]([O-])O>C(C)(=O)O.C(Cl)Cl>COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4ffbdfe2562042f4a856dda077ba7130 | COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O>>CC(C)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C=C1[N+](=O)[O-])C(C(C)C)=O)OC.Cl.N1=CC=CC=C1>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(C)C)=O | C[O:9][c:8]1[cH:7][c:6]([C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[cH:16][c:12]([N+:13](=[O:14])[O-:15])[c:10]1[OH:11]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1 | COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O | CC(C)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 45 | MINUTE | 8.0 g of 4'-hydroxy-3'-methoxy-2-methyl-5'-nitropropiophenone are treated with 64 g of pyridine hydrochloride and stirred at 180° for 45 minutes. After cooling the reaction mixture is poured into 500 ml of ice-water, whereupon it is made acid with 20 ml of 3N hydrochloric acid and extracted with methylene chloride. The... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | Cl | null | 0.75 | COc1cc(C(=O)C(C)C)cc([N+](=O)[O-])c1O>Cl>CC(C)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-317668bfe5d940f4b07d61cba8c14e90 | COc1ccccc1O>>CCCC(=O)c1ccc(O)c(OC)c1 | C=1(C(O)=CC=CC1)OC>>OC1=C(C=C(C=C1)C(CCC)=O)OC | [cH:1]1[cH:2][cH:3][c:4]([OH:5])[c:11]([O:12][CH3:13])[cH:14]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([O:12][CH3:13])[cH:14]1 | COc1ccccc1O | CCCC(=O)c1ccc(O)c(OC)c1 | null | [Cl-].[Zn+2].[Cl-] | C(CCC)(=O)OC(CCC)=O | Functional Group Interconversion | OtherReaction | 6b0bcea7a1717486cfb77951a1fb31d502cd1b161ed87bdfaa8c84808b7bbd10 | e4f47ce21f7381226f2f8ecf7d48480a5b717fe4b61f5111779df9f9f55f1559 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[OH;D1;+0:9]>>[C;D1;H3:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:10](-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[CH3;D1;+0:5]):[c:11]:[c:12]:[c:13]:1-[O;D1;H1:14] | null | [] | null | null | null | null | 100 g of guaiacol are dissolved in 136.4 g of butyric anhydride, treated with 120 g of zinc chloride, heated for 3 minutes as given in Example 6.a and then worked-up as described there. The crude product obtained after high vacuum distillation is chromatographed with toluene on 600 g of silica gel. After recrystallizat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ketone.Ether.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cl-].[Zn+2].[Cl-].C(CCC)(=O)OC(CCC)=O | null | null | COc1ccccc1O>[Cl-].[Zn+2].[Cl-].C(CCC)(=O)OC(CCC)=O>CCCC(=O)c1ccc(O)c(OC)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ee3c9125e5b24e7db7b7ab3cba151dd9 | CCCC(=O)c1ccc(O)c(OC)c1.O=[N+]([O-])O>>CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | [N+](=O)(O)[O-].OC1=C(C=C(C=C1)C(CCC)=O)OC>>OC1=C(C=C(C=C1[N+](=O)[O-])C(CCC)=O)OC | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([OH:12])[cH:13][cH:17]1.O[N+:14](=[O:15])[O-:16]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([OH:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CCCC(=O)c1ccc(O)c(OC)c1.O=[N+]([O-])O | CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 10 | MINUTE | 6.5 ml of 11.2N nitric acid are added dropwise to a solution of 12.7 g of 4'-hydroxy-3'-methoxybutyrophenone in 250 ml of glacial acetic acid while stirring within 10 minutes. The reaction mixture is subsequently stirred for 15 minutes, poured into ice-water, the separated precipitate is filtered under suction, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)O | null | 0.166667 | CCCC(=O)c1ccc(O)c(OC)c1.O=[N+]([O-])O>C(C)(=O)O>CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2e698d9c28294f70adc4c0cd77715ebf | CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1>>CCCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C=C1[N+](=O)[O-])C(CCC)=O)OC.Cl.N1=CC=CC=C1>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(CCC)=O | C[O:9][c:8]1[cH:7][c:6]([C:4]([CH2:3][CH2:2][CH3:1])=[O:5])[cH:16][c:12]([N+:13](=[O:14])[O-:15])[c:10]1[OH:11]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1 | CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | CCCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 40 | MINUTE | 10.2 g of 4'-hydroxy-3'-methoxy-5'-nitrobutyrophenone are treated with 80 g of pyridine hydrochloride and stirred at 200° for 40 minutes. After cooling the reaction mixture is poured into 500 ml of ice-water. The mixture is treated with 30 ml of 3N hydrochloric acid and extracted with methylene chloride. The organic ph... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | Cl | null | 0.666667 | CCCC(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1>Cl>CCCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-651a4401373a4a5aa560714774938900 | O=C(O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1>>COC(=O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | OC=1C=C(C=CC(=O)O)C=C(C1O)[N+](=O)[O-].Cl.C(C)(C)OC(C)C>>OC=1C=C(C=CC(=O)OC)C=C(C1O)[N+](=O)[O-] | [OH:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | O=C(O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | COC(=O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]=[C:5]-[c:6]>>[C;D1;H3:7]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[C:4]=[C:5]-[c:6] | null | [] | null | null | null | null | 2.25 g of 3,4-dihydroxy-5-nitrocinnamic acid are dissolved in 50 ml of methanol and hydrochloric acid gas is introduced into this solution for 10 minutes. After 1 hour 50 ml of isopropyl ether are added thereto, and the separated precipitate is filtered under suction and washed with isopropyl ether. After recrystalliza... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | Other | CO | null | null | O=C(O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1>CO>COC(=O)C=Cc1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5d6d7b4d3eb340209d13e1773fcc3c68 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.NCCc1ccccc1>>COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-].C1(=CC=CC=C1)CCN.C(C)N(CC)CC>>COC=1C=C(C(=O)NCCC2=CC=CC=C2)C=C(C1OC)[N+](=O)[O-] | Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:18]([N+:19](=[O:20])[O-:21])[cH:17]1)=[O:7].[NH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21]... | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.NCCc1ccccc1 | COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 1.49 g of 2-phenylethylamine in 100 ml of methylene chloride is treated with 1.26 g of triethylamine. A solution of 3.0 g of 3,4-dimethoxy-5-nitrobenzoyl chloride in 100 ml of methylene chloride is added dropwise thereto while stirring, whereupon the mixture is stirred for a further 15 minutes. The organi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.NCCc1ccccc1>C(Cl)Cl>COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC |
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