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-0387783899c642a8b7eb4ba379bcdf5d | ord-39687a43224143b2a901aec5623ec2e7 | Fc1cccc(CNCCBr)c1.Oc1cccc(-c2noc3ccsc23)c1>>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | [Na].O1N=C(C2=C1C=CS2)C=2C=C(C=CC2)O.BrCCNCC1=CC(=CC=C1)F>>FC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1 | Br[CH2:10][CH2:9][NH:8][CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:26]1.[OH:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19][c:20]4[cH:21... | Fc1cccc(CNCCBr)c1.Oc1cccc(-c2noc3ccsc23)c1 | Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Add dichloromethane to 3-thieno[2,3-d]isoxazol-3-yl-phenol (10 g, 0.046 mol) or the appropriately protected 3-thieno[2,3-d]isoxazol-3-yl-phenol as is known in the art, and stir with sodium hydroxide (1M; 28 mL) to form the sodium salt. Combine the sodium salt from 3-thieno[2,3-d]isoxazol-3-yl-phenol, (2-bromo-ethyl)-(3... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C1(=CC=CC=C1)C | null | null | Fc1cccc(CNCCBr)c1.Oc1cccc(-c2noc3ccsc23)c1>C1(=CC=CC=C1)C>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96ec3a24686b406a85e6ce4079bf506b | NCc1cccc(F)c1.OCCCl>>OCCNCc1cccc(F)c1 | FC=1C=C(CN)C=CC1.ClCCO.[OH-].[Na+]>>FC=1C=C(CNCCO)C=CC1 | [NH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1.Cl[CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1 | NCc1cccc(F)c1.OCCCl | OCCNCc1cccc(F)c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | Combine 3-fluorobenzylamine (31.1 g, 0.248 mol), 2-chloroethanol (10 g, 0.124 mol) and water (30 g, 1.66 mol) and heat on a steam-bath for ˜5 hours. Add sodium hydroxide (15 g, 0.373 mol) to the cooled solution and heat the resulting mixture on a steam-bath for ˜30 minutes. Add water (˜50 mL) to dissolve the inorganic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HCl | O | null | null | NCc1cccc(F)c1.OCCCl>O>OCCNCc1cccc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bfb9478b47f4e919a8a0e2f00a8190d | CC(C)(C)OC(=O)N(CCO)Cc1cccc(F)c1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1 | C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.CC(C)(C)OC(N(CCO)CC1=CC(=CC=C1)F)=O.FC=1C=C(CNCCO)C=CC1>>C(C)(C)(C)OC(=O)N(CCOS(=O)(=O)C1=CC=C(C=C1)C)CC1=CC(=CC=C1)F | [OH:9][CH2:10][CH2:11][N:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([F:19])[cH:20]1)[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:29][cH:28]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][c... | CC(C)(C)OC(=O)N(CCO)Cc1cccc(F)c1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCNCc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Add p-toluenesulfonyl-chloride (0.71 g, 3.71 mmol), portionwise, to a mixture of (3-fluoro-benzyl)-(2-hydroxy-ethyl)-carbamic acid dimethyl-ethyl ester (1 g, 3.71 mmol, prepared from 2-(3-fluoro-benzylamino)-ethanol by methods as are known in the art), triethylamine (0.751 g, 7.4 mmol) and dichloromethane (6 mL). Stir ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)(C)OC(=O)N(CCO)Cc1cccc(F)c1.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1dd22aeb2ee24793a8ccc69ebe25774c | Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1.Oc1cccc(-c2noc3ccsc23)c1>>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | C(C)(C)(C)OC(=O)N(CCOS(=O)(=O)C1=CC=C(C=C1)C)CC1=CC(=CC=C1)F.O1N=C(C2=C1C=CS2)C=2C=C(C=CC2)O>>FC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1 | Cc1ccc(S(=O)(=O)O[CH2:10][CH2:9][N:8](C(=O)OC(C)(C)C)[CH2:7][c:6]2[cH:5][cH:4][cH:3][c:2]([F:1])[cH:26]2)cc1.[OH:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]... | Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1.Oc1cccc(-c2noc3ccsc23)c1 | Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 261ae411c4608578c0c14d59f131d847b957a660c39a648f88d7da982bfaf4d2 | 8037a620c8dfb4103dc042c9904bc09f0a447fc8e392686dda758ffbc1676a14 | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[N;H0;D3;+0:3](-[C:4]-[c:5])-C(=O)-O-C(-C)(-C)-C):c:c:1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[c:5]):[c:9] | null | [] | null | null | null | null | The title compound is prepared from a mixture of toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester and 3-thieno[2,3-d]isoxazol-3-yl-phenol essentially as described in Example 3, Scheme I, Step F. It is understood by one skilled in the art that the nitrogen may be deprotected by acid hy... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Carbamic ester.Ether.Aromatic alcohol.Boc | Ether.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | TsOH.HO- | null | null | null | Cc1ccc(S(=O)(=O)OCCN(Cc2cccc(F)c2)C(=O)OC(C)(C)C)cc1.Oc1cccc(-c2noc3ccsc23)c1>>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dcbe5d9d92e4048baae54673195caa5 | COc1cccc(C(=O)c2sccc2Br)c1.NO>>COc1cccc(C(=NO)c2sccc2Br)c1 | C(Cl)Cl.BrC1=C(SC=C1)C(=O)C1=CC(=CC=C1)OC.Cl.NO.N1=CC=CC=C1>>BrC1=C(SC=C1)C(=NO)C1=CC(=CC=C1)OC | O=[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17]1)[c:11]1[s:12][cH:13][cH:14][c:15]1[Br:16].[NH2:9][OH:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[N:9][OH:10])[c:11]2[s:12][cH:13][cH:14][c:15]2[Br:16])[cH:17]1 | COc1cccc(C(=O)c2sccc2Br)c1.NO | COc1cccc(C(=NO)c2sccc2Br)c1 | null | null | CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1ccccc1)c1cccs1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[#16;a:4]:[c:5])-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[O;D1;H1:10]>>[O;D1;H1:10]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1](-[c:2](:[c:3]):[#16;a:4]:[c:5])-[c:6](:[c:7]):[c:8] | 87 | [{"value": 87.0, "product": "BrC1=C(SC=C1)C(=NO)C1=CC(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "BrC1=C(SC=C1)C(=NO)C1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Stir a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone (7 g, 0.024 mol), hydroxylamine hydrochloride (3.09 g, 0.048 mol) and pyridine (40 mL) overnight at room temperature, and then heat the mixture (100° C.–105° C.) for four hours. TLC (DCM) shows that the reaction is complete. Quench the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccsc1 | HO- | CCCCCC | null | null | COc1cccc(C(=O)c2sccc2Br)c1.NO>CCCCCC>COc1cccc(C(=NO)c2sccc2Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4403c65bc86f4873a07629c666db5d15 | COc1cccc(C(=NO)c2sccc2Br)c1>>COc1cccc(-c2noc3ccsc23)c1 | BrC1=C(SC=C1)C(=NO)C1=CC(=CC=C1)OC.[OH-].[K+].C(C)OCCO>>COC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[c:11]1[cH:12][cH:13][s:14][c:15]1[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16]1)=[N:9][OH:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]3[cH:12][cH:13][s:14][c:15]23)[cH:16]1 | COc1cccc(C(=NO)c2sccc2Br)c1 | COc1cccc(-c2noc3ccsc23)c1 | null | [Cu](Cl)Cl | CCCCCC | Aromatic Heterocycle Formation | OtherReaction | 2aa0bbcf926ff92c73dd6b64fe58b598a4cca2e0111b30ba67f5d6c2ad7ef4ba | c3af886e80a4d8a4db0b9015a14ae7edf5d5d18deb2717f7ce3620ceac08ea61 | c1ccc(-c2noc3ccsc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1-[C;H0;D3;+0:6](=[N;H0;D2;+0:7]-[OH;D1;+0:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[o;H0;D2;+0:8]:[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#16;a:4]:[c:5]:2:1):[c:12]:[c:13] | 68 | [{"value": 68.0, "product": "COC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "COC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reflux a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone oxime (10 g, 0.032 mol), KOH (3.6 g, 0.064 mol dissolved in 10 mL water) and 2-ethoxyethanol (40 mL) under nitrogen for one hour at 105–110° C. Add copper chloride (0.16 g, 0.0016 mol) whereupon the reaction mixture becomes dark brown in color. Heat ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Oxime | null | c1ccsc1 | c1cc2oncc2s1 | c1ccccc1.c1cc2oncc2s1 | HBr | [Cu](Cl)Cl.CCCCCC | null | null | COc1cccc(C(=NO)c2sccc2Br)c1>[Cu](Cl)Cl.CCCCCC>COc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-130240c6a61a4ba39e2fdcb60136612f | COc1cccc(-c2noc3ccsc23)c1>>Oc1cccc(-c2noc3ccsc23)c1 | ClCCl.COC=1C=C(C=CC1)C1=NOC2=C1SC=C2.Cl.N1=CC=CC=C1.C(C)(=O)OCC>>O1N=C(C2=C1C=CS2)C=2C=C(C=CC2)O | C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]3[cH:11][cH:12][s:13][c:14]23)[cH:15]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]3[cH:11][cH:12][s:13][c:14]23)[cH:15]1 | COc1cccc(-c2noc3ccsc23)c1 | Oc1cccc(-c2noc3ccsc23)c1 | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2noc3ccsc23)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 40 | [{"value": 40.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(C=CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "O1N=C(C2=C1C=CS2)C=2C=C(C=CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | Combine and stir under nitrogen at 140° C. a mixture of 3-(3-methoxyphenyl)thieno[2,3-d]isoxazole (8 g, 0.035 mol) and pyridine hydrochloride (80 g, 0.69 mol) for nine hours. TLC (ethyl acetate: dichloromethane) shows the reaction is complete. Cool the reaction mixture to room temperature, and pour into water. Extract ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2oncc2s1 | Other | O | 140 | null | COc1cccc(-c2noc3ccsc23)c1>O>Oc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7618583492454d46a32c9c9120713d00 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F>>Fc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.FC1=C(CN)C=CC=C1.C([O-])([O-])=O.[K+].[K+]>>FC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1 | Br[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:2... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F | Fc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N.O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 94.1 | [{"value": 94.0, "product": "FC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.1, "product": "FC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Combine a mixture (1 mmol total) of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole with 2-fluorobenzylamine (0.63 g, 5.0 mmol), potassium carbonate (0.41 g, 3.0 mmol) and a mixture of acetonitrile:water (80:20) and heat (80° C.) for 30 hours. Cool the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N.O | 80 | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F>C(C)#N.O>Fc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-598260d8b1be4001a4fe9d3ea45a3d59 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1>>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.FC1=CC=C(CN)C=C1.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:26][cH:27]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19][c:2... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1 | Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 94 | [{"value": 94.0, "product": "FC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[(3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-fluorobenzylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1>>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-753b8f4b0e8840059f919aa58a8e8fe8 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1>>Clc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClC1=CC=C(CN)C=C1.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:26][cH:27]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19][c... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1 | Clc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-chlorobenzylamine and potassium carbonate essentially as described above in example 4. Purity by LC/MS (APCI)=100%, [M+H]+=399 m/e.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1>>Clc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6ff9daab63b4b308f667c53494f9a38 | COc1ccc(CN)cc1.ClCCCOc1cccc(-c2noc3ccsc23)c1>>COc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.COC1=CC=C(CN)C=C1.C([O-])([O-])=O.[K+].[K+]>>COC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:27][cH:28]1.Cl[CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[cH:22][cH:23][s:24][c:25]23)[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17](-[c:18]3... | COc1ccc(CN)cc1.ClCCCOc1cccc(-c2noc3ccsc23)c1 | COc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 100 | [{"value": 100.0, "product": "COC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-methoxybenzylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HCl | null | null | null | COc1ccc(CN)cc1.ClCCCOc1cccc(-c2noc3ccsc23)c1>>COc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bb6ce2fe8a0479ca1d5204a25a71496 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1>>c1cc(OCCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.S1C(=CC=C1)CN.C([O-])([O-])=O.[K+].[K+]>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC=1SC=CC1)C=CC2 | Br[CH2:7][CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:25][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:15]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][s:14]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][s:14]2)[cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][c... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1 | c1cc(OCCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#16;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#16;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 94 | [{"value": 94.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC=1SC=CC1)C=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 2-thiophenemethylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccsc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1>>c1cc(OCCCNCc2cccs2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92bcf849b3e149aea25a639e139f430f | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccsc1>>CN(CCCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.S1C=C(C=C1)CN.C([O-])([O-])=O.[K+].[K+]>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCN(C)C1=CSC=C1)C=CC2 | Cl[CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][o:14][c:15]3[cH:16][cH:17][s:18][c:19]23)[cH:20]1.[CH2:1]([NH2:2])[c:21]1[cH:22][cH:23][s:24][cH:25]1>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][o:14][c:15]3[cH:16][cH:17][s:18][c:19]23)[cH:20]1)[c:21]... | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccsc1 | CN(CCCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 759837460ae987655812772f1b53f40ef362c59fbf901b7e1cbb138d78cadf1c | f9bb8e657c4b6e8753cee787f1ab908d7e19aa5ff94862f2f6aa0ac4d358a8ab | c1cc(OCCCNc2ccsc2)cc(-c2noc3ccsc23)c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[CH3;D1;+0:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1 | 86 | [{"value": 86.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCCN(C)C1=CSC=C1)C=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-thiophenemethylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Tertiary amine | c1ccsc1 | c1ccsc1 | c1ccccc1.c1cc2oncc2s1.c1ccsc1 | HCl | null | null | null | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccsc1>>CN(CCCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0e631025f7e4cd3bcc06cf3c21e7e9a | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1>>c1cncc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.NCC=1C=NC=CC1.C([O-])([O-])=O.[K+].[K+]>>N1=CC(=CC=C1)CNCCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[cH:1]1[cH:2][n:3][cH:4][c:5]([CH2:6][NH2:7])[cH:26]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19][c:20]4[c... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1 | c1cncc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cncc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:4]:[c:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3] | 77 | [{"value": 77.0, "product": "N1=CC(=CC=C1)CNCCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-(aminomethyl)pyridine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1>>c1cncc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb7c9101f37f44f4aa6d125230905285 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCC(O)c1ccccc1>>OC(CNCCCOc1cccc(-c2noc3ccsc23)c1)c1ccccc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.NCC(O)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)C(CNCCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2)O | Br[CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][c:13](-[c:14]2[n:15][o:16][c:17]3[cH:18][cH:19][s:20][c:21]23)[cH:22]1.[OH:1][CH:2]([CH2:3][NH2:4])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[OH:1][CH:2]([CH2:3][NH:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][c:13](-[c:14]2[n:15][o:16][c:17]3[cH:18]... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCC(O)c1ccccc1 | OC(CNCCCOc1cccc(-c2noc3ccsc23)c1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 100 | [{"value": 100.0, "product": "C1(=CC=CC=C1)C(CNCCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 2-amino-1-phenylethanol and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromethane:m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1cc2oncc2s1.c1ccccc1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCC(O)c1ccccc1>>OC(CNCCCOc1cccc(-c2noc3ccsc23)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8285a2268d0743a5afb92970bebc1927 | ClCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1>>c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C1(=CC=CC=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Cl[CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[cH:22][cH:23][s:24][c:25]23)[cH:26]1.[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:27][CH2:28]2)[cH:29][cH:30]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11][O:12][c:13]3[cH:14][cH:15][c... | ClCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1 | c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 94 | [{"value": 94.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 1-phenylpiperazine and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromethane:methan... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cc2oncc2s1 | HCl | null | null | null | ClCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1>>c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f34ce8945daf4fefa0c5f1821d2e0803 | BrCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccc(N2CCNCC2)cc1>>Fc1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.FC1=CC=C(C=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(C=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[F:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:28][CH2:29]2)[cH:30][cH:31]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12][O:13][c:14]3[cH:15... | BrCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccc(N2CCNCC2)cc1 | Fc1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 100 | [{"value": 100.0, "product": "FC1=CC=C(C=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 1-(4-fluorophenyl) piperazine and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccc(N2CCNCC2)cc1>>Fc1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cba101c4b95b4347a538db4ed690cbcd | ClCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccccc1N1CCNCC1>>Fc1ccccc1N1CCN(CCCOc2cccc(-c3noc4ccsc34)c2)CC1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.FC1=C(C=CC=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C=CC=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Cl[CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[n:22][o:23][c:24]3[cH:25][cH:26][s:27][c:28]23)[cH:29]1.[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:30][CH2:31]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][O:15][... | ClCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccccc1N1CCNCC1 | Fc1ccccc1N1CCN(CCCOc2cccc(-c3noc4ccsc34)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#7:4]-[C:5]-[C:6]-1 | 100 | [{"value": 100.0, "product": "FC1=C(C=CC=C1)N1CCN(CC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 1-(2-fluorophenyl) piperazine and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cc2oncc2s1 | HCl | null | null | null | ClCCCOc1cccc(-c2noc3ccsc23)c1.Fc1ccccc1N1CCNCC1>>Fc1ccccc1N1CCN(CCCOc2cccc(-c3noc4ccsc34)c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0f1ba7fd1aa4441a926a53d857380d8 | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.O.Cl.NCC1=CC=C(C=C1)S(=O)(=O)N.C([O-])([O-])=O.[K+].[K+]>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC1=CC=C(C=C1)S(=O)(=O)N)C=CC2 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:28]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:29][cH:30]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2... | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(S(N)(=O)=O)cc1 | NS(=O)(=O)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 27 | [{"value": 27.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC1=CC=C(C=C1)S(=O)(=O)N)C=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-(aminomethyl) benzenesulfonamide hydrochloride monohydrate and potassium carbonate essentially as described above in example 4 except that the column is elute... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HCl | null | null | null | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35056de0b49747e79ad154c41ebc6c38 | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCCc1ccc(S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(CCNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.ClCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.NCCC1=CC=C(C=C1)S(=O)(=O)N.C([O-])([O-])=O.[K+].[K+]>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCCC1=CC=C(C=C1)S(=O)(=O)N)C=CC2 | Cl[CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[n:22][o:23][c:24]3[cH:25][cH:26][s:27][c:28]23)[cH:29]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH2:11])[cH:30][cH:31]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH2:... | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCCc1ccc(S(N)(=O)=O)cc1 | NS(=O)(=O)c1ccc(CCNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | 35 | [{"value": 35.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCCC1=CC=C(C=C1)S(=O)(=O)N)C=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-(2-aminoethyl) benzenesulfonamide and potassium carbonate essentially as described above in example 4 except that the column is eluted using a graded solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HCl | null | null | null | ClCCCOc1cccc(-c2noc3ccsc23)c1.NCCc1ccc(S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(CCNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a23060077fa4a118beecc9e547f6e26 | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1ccccc1CN>>COc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].COC1=C(CN)C=CC=C1>>COC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1 | Br[CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH2:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:2... | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1ccccc1CN | COc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 90 | [{"value": 90.0, "product": "COC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "COC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.324 g, 1 mmol), potassium carbonate (0.28 g, 2 mmol), 2-methoxybenzylamine (0.686 g, 5 mmol) and acetonitrile (anhydrous, 4 mL) and heat at 75° C. for 16.5 hours. Cool the reaction mixture and filter through a Waters Sep-Pak silica gel cartridge (1 g) using et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | 75 | null | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1ccccc1CN>C(C)#N>COc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4586749449f49b7a34f6eb5ab7dee40 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1>>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=CC=C(CN)C=C1>>FC1=CC=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20][cH:21... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1 | Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-fluorobenzylamine and acetonitrile essentially as described above in example 18 except that the column is eluted using a solvent gradient of 40% ethyl acetate in heptane, to 100% ethyl acetate. Purity by LC/... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1>C(C)#N>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90a534bf732d457b95655893e415f5c6 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1>>Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].ClC1=CC=C(CN)C=C1>>ClC1=CC=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25][cH:26]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20][cH:... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1 | Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-chlorobenzylamine and acetonitrile essentially as described above in example 18 except that the column is eluted using a gradient of 40% ethyl acetate in heptane, to 100% ethyl acetate. Purity by LC/MS (APCI... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)cc1>C(C)#N>Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19feb8fd6be947428311b8d3944003e3 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccc(F)c1>>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC=1C=C(CN)C=CC1>>FC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1 | Br[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:26]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19][c:20]4[cH:21... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccc(F)c1 | Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3-fluorobenzylamine and acetonitrile essentially as described above in example 18 except that the column is eluted using a graded solvent mixture of 40% ethyl acetate in heptane to 100% ethyl acetate. Purity b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccc(F)c1>C(C)#N>Fc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c61cccd74a44b228ecf09c6ef86bcb1 | BrCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1>>Cc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(CN)C=C1>>CC1=CC=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20][c... | BrCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1 | Cc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-methylbenzylamine and acetonitrile essentially as described above in example 18. Purity by LC/MS (APCI)=100%, [M+H]+=365.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1>C(C)#N>Cc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0edf5ca02a324a7d8ed1899271441890 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)c(Cl)c1>>Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1Cl | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].ClC=1C=C(CN)C=CC1Cl>>ClC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1Cl | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25][c:26]1[Cl:27]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:2... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)c(Cl)c1 | Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3,4-dichlorobenzylamine and acetonitrile essentially as described above in example 18 except that the column is eluted using a graded solvent mixture of 40% ethyl acetate in heptane, to 100% ethyl acetate. Pur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(Cl)c(Cl)c1>C(C)#N>Clc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c632d1f03ef4ea1ad693653be4afc16 | BrCCOc1cccc(-c2noc3ccsc23)c1.CNc1ccsc1>>CN(CCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].S1C=C(C=C1)NC.C(C)#N>>O1N=C(C2=C1C=CS2)C=2C=C(OCCN(C)C1=CSC=C1)C=CC2 | Br[CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[n:12][o:13][c:14]3[cH:15][cH:16][s:17][c:18]23)[cH:19]1.[CH3:1][NH:2][c:20]1[cH:21][cH:22][s:23][cH:24]1>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[n:12][o:13][c:14]3[cH:15][cH:16][s:17][c:18]23)[cH:19]1)[c:20]1[cH:21][cH:22][s:2... | BrCCOc1cccc(-c2noc3ccsc23)c1.CNc1ccsc1 | CN(CCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCNc2ccsc2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C;D1;H3:4]-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1 | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, thiophen-3-yl-methylamine (prepared according to Synthetic Metals, 26 (1988)153–168) and acetonitrile essentially as described above in example 18, except that water (0.40 mL) is added to the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1cc2oncc2s1.c1ccsc1 | HBr | O | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.CNc1ccsc1>O>CN(CCOc1cccc(-c2noc3ccsc23)c1)c1ccsc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31d4c4ba7e91456ba2cba1421a535cbb | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1>>c1cc(OCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].S1C(=CC=C1)CN>>O1N=C(C2=C1C=CS2)C=2C=C(OCCNCC=1SC=CC1)C=CC2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:24][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:14]1.[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][s:13]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1 | c1cc(OCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCNCc2cccs2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#16;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#16;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[#8:3] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, C-Thiophen-2-yl-methylamine and acetonitrile essentially as described above in example 18 except that the column is eluted using a graded solvent mixture of 40% ethyl acetate in heptane, to 100% ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccsc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccs1>C(C)#N>c1cc(OCCNCc2cccs2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f2d65abc2e648ce8229b3de35ed1ffc | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1>>c1cncc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].NCC=1C=NC=CC1>>N1=CC(=CC=C1)CNCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[cH:1]1[cH:2][n:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25]1>>[cH:1]1[cH:2][n:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20][cH:21][s:2... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1 | c1cncc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cncc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7;a:4]:[c:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:4]:[c:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[#8:3] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3-(aminomethyl)pyridine and acetonitrile essentially as described above in example 18 except that the Waters Sep-Pak filtration is eluted with 10% methanol in dichloromethane and the column is eluted using a g... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1cccnc1>C(C)#N>c1cncc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1574d05012d74272a3de0a8a27865291 | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2>>c1cc(OCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C1NCCC2=CC=CC=C12>>O1N=C(C2=C1C=CS2)C=2C=C(OCCN1CC3=CC=CC=C3CC1)C=CC2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:27][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:17]1.[NH:7]1[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16]2)[cH:17][c:18](-[c:... | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2 | c1cc(OCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7901d50fadd7b2205ca48bcd0c91a7ce2a4caa7c5b18385de4e67176215faa6e | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | 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:7]-[c:8])-[C:5]-[C:4] | 61.5 | [{"value": 56.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCN1CC3=CC=CC=C3CC1)C=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCN1CC3=CC=CC=C3CC1)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.400 g, 1.23 mmol), potassium carbonate (0.345 g, 2.50 mmol), 1,2,3,4-tetrahydroisoquinoline (0.532 g, 3.99 mmol) and acetonitrile (5.0 mL) and heat at 75° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CC[NH]C2 | c1ccccc1.c1ccc2c(c1)CC[NH]C2.c1cc2oncc2s1 | HBr | C(C)#N | 75 | null | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2>C(C)#N>c1cc(OCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7425231cb5054edb8397a2b558164d3f | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F>>FC(F)(F)c1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC(C1=C(CN)C=CC=C1)(F)F>>O1N=C(C2=C1C=CS2)C=2C=C(OCCNCC1=C(C=CC=C1)C(F)(F)F)C=CC2 | Br[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[n:22][o:23][c:24]3[cH:25][cH:26][s:27][c:28]23)[cH:29]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][NH2:12]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][NH:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:1... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F | FC(F)(F)c1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 96.4 | [{"value": 96.0, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCNCC1=C(C=CC=C1)C(F)(F)F)C=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.4, "product": "O1N=C(C2=C1C=CS2)C=2C=C(OCCNCC1=C(C=CC=C1)C(F)(F)F)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.771 mmol), potassium carbonate (0.205 g, 1.48 mmol), 2-(trifluoromethyl)benzylamine (0.676 mg, 3.86 mmol) and acetonitrile (4 mL) essentially as described above in example 18 except that the reaction is run overnight an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F>C(C)#N>FC(F)(F)c1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e293192327034fc7bb34b90469c081a3 | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1>>c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].N1CCCCC1>>N1(CCCCC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:23][c:14](-[c:15]2[n:16][o:17][c:18]3[cH:19][cH:20][s:21][c:22]23)[cH:13]1.[NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14](-[c:15]2[n:16][o:17][c:18]3[cH:19][cH:20][s:21][c:22]23)... | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1 | c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | 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 | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, piperidine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a graded solvent mixture of 5% eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cc2oncc2s1 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1>C(C)#N>c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24c6c61dbc584bdfb406fd2f7c551df0 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F>>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=C(CN)C=CC(=C1)F>>FC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC(=C1)F | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[c:25]([F:26])[cH:27]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F | Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2,4-difluorobenzylamine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a graded solvent mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F>C(C)#N>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42b086f70dad42e785a111a2ef18aa2a | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F>>Fc1cccc(F)c1CNCCOc1cccc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=C(CN)C(=CC=C1)F>>FC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C(=CC=C1)F | Br[CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH2:10]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20]... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F | Fc1cccc(F)c1CNCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2,6-difluorobenzylamine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a solvent gradient of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F>C(C)#N>Fc1cccc(F)c1CNCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb43606501f3400b8d4cf5f8ac7ab8df | BrCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2>>c1cc(OCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:28][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:18]1.[NH2:7][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:16]1)[CH2:17]2>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][NH:7][C:8]23[CH2:9][CH:10]4[CH2:11][CH:12]([CH2:13][CH:14]([CH2:15]4)[C... | BrCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2 | c1cc(OCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5](-[NH2;D1;+0:6])(-[C:7])-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])(-[C:7])-[C:8] | null | [] | null | null | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 1-adamantanamine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a graded solvent mixture of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cc2oncc2s1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2>C(C)#N>c1cc(OCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c9f9bf27da0426b8c2c143da023701a | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1>>FC(F)(F)c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC(C1=CC=C(CN)C=C1)(F)F>>O1N=C(C2=C1C=CS2)C=2C=C(OCCNCC1=CC=C(C=C1)C(F)(F)F)C=CC2 | Br[CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:28][cH:29]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][c:... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | 8 | HOUR | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-(trifluoromethyl)benzylamine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a solvent grad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | 8 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1>C(C)#N>FC(F)(F)c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4538b46408a348e9ba852736e080caa3 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F>>Fc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=C(CN)C=CC=C1>>FC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[cH:22][cH:23][s:24][c:25]23)[cH:26]1.[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F | Fc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 83.4 | [{"value": 83.0, "product": "FC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "FC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.40 g, 1.23 mmol), potassium carbonate (0.341 g, 2.47 mmol), 2-fluorobenzylamine (0.626 g, 5.0 mmol) and acetonitrile (5.0 mL) and heat at 80° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Com... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | 80 | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1F>C(C)#N>Fc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78522ad5249c4db88db521174abeeb45 | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl>>Clc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].ClC1=C(CN)C=CC=C1>>ClC1=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[cH:22][cH:23][s:24][c:25]23)[cH:26]1.[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl | Clc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2-chlorobenzylamine and acetonitrile essentially as described above in example 35. Purity by LC/MS (APCI)=99%, [M+H]+=385.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl>C(C)#N>Clc1ccccc1CNCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f69e3581a28d42ec827522042311ea49 | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1>>COc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].COC=1C=C(CN)C=CC1>>COC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[n:19][o:20][c:21]3[cH:22][cH:23][s:24][c:25]23)[cH:26]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17](-[c:18]3[n:19][o:... | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1 | COc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3-methoxybenzylamine and acetonitrile essentially as described above in example 35, except that the column is eluted with a graded solvent mixture of 50% ethyl acetate in heptane to 100% ethyl acetate. Purity ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1>C(C)#N>COc1cccc(CNCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ea839edd9684efa8e7e543e86d05ace | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1>>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1F | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC=1C=C(CN)C=CC1F>>FC=1C=C(CNCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1F | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:25][c:26]1[F:27]>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[cH:20][... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1 | Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3,4-difluorobenzylamine and acetonitrile essentially as described above in example 35. Purity by LC/MS (APCI)=100%, [M+H]+=387.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1>C(C)#N>Fc1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e25271e79aec4857a9780483483882d6 | BrCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21>>c1cc(OCCNC2CCc3ccccc32)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].NC1CCC2=CC=CC=C12>>C1(CCC2=CC=CC=C12)NCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:27][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:17]1.[NH2:7][CH:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][NH:7][CH:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[cH:17][c:18](-[c:... | BrCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21 | c1cc(OCCNC2CCc3ccccc32)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCNC2CCc3ccccc32)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])-[c:7] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy]phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 1-aminoindan and acetonitrile essentially as described above in example 35. Purity by LC/MS (APCI)=99%, [M+H]+=377.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC2.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21>C(C)#N>c1cc(OCCNC2CCc3ccccc32)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f27a956677fb4f649e90173553ade153 | BrCCOc1cccc(-c2noc3ccsc23)c1.CC1CCNCC1>>CC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].CC1CCNCC1>>CC1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][c:13](-[c:14]2[n:15][o:16][c:17]3[cH:18][cH:19][s:20][c:21]23)[cH:22]1.[CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:23][CH2:24]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][cH:12][c:13](-[c:14]3[n:15][o:16][c:17]4[cH:18][cH:19][s:20][c:21]34)[cH:... | BrCCOc1cccc(-c2noc3ccsc23)c1.CC1CCNCC1 | CC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | 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] | 96.3 | [{"value": 96.0, "product": "CC1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "CC1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.77 mmol), potassium carbonate (0.22 g, 1.59 mmol), 4-methylpiperidine (0.382 g, 3.85 mmol) and acetonitrile (4.0 mL) and heat at 75° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Com... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | 75 | null | BrCCOc1cccc(-c2noc3ccsc23)c1.CC1CCNCC1>C(C)#N>CC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00713097cc4a4a48b60bcfb12597d27b | BrCCOc1cccc(-c2noc3ccsc23)c1.CCCC1CCNCC1>>CCCC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].CCCC1CCNCC1>>C(CC)C1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1.[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][NH:7][CH2:25][CH2:26]1>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[n:17][o:18][c:19]4[... | BrCCOc1cccc(-c2noc3ccsc23)c1.CCCC1CCNCC1 | CCCC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | 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 | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-N-propylpiperidine and acetonitrile essentially as described above in example 40. Purity by LC/MS (APCI)=96%, [M+H]+=371.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.CCCC1CCNCC1>C(C)#N>CCCC1CCN(CCOc2cccc(-c3noc4ccsc34)c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b8f5125ade54344922446ec574bdd1c | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNC1>>c1cc(OCCN2CCCC2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].N1CCCC1>>N1(CCCC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:22][c:13](-[c:14]2[n:15][o:16][c:17]3[cH:18][cH:19][s:20][c:21]23)[cH:12]1.[NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][c:13](-[c:14]2[n:15][o:16][c:17]3[cH:18][cH:19][s:20][c:21]23)[cH:22]1 | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNC1 | c1cc(OCCN2CCCC2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCN2CCCC2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[C:8]-[C:7]-1 | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, pyrrolidine and acetonitrile essentially as described above in example 40. Purity by LC/MS (APCI)=100%, [M+H]+=315.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.C1CCNC1>C(C)#N>c1cc(OCCN2CCCC2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c2c563a30e04c3f95fd9e00eaaedf6d | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N>>c1cc(OCCN2CCCCCC2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C(C)#N>>N1(CCCCCC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:24][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:14]1.[N:7]#[C:8][CH3:9]>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:24]1 | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N | c1cc(OCCN2CCCCCC2)cc(-c2noc3ccsc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b697c8a97978543d6599ef196eeefebcaa0de0cac88091a715eb342d7457f73a | 847e4f3388be6b412c30a1e0dac5815a9121e7f38de3cc603b5da6c43822a22c | c1cc(OCCN2CCCCCC2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[CH3;D1;+0:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, hexamethyleneimine and acetonitrile essentially as described above in example 40. Purity by LC/MS (APCI)=99%, [M+H]+=343.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile | Tertiary amine | null | C1CCC[NH]CC1 | c1ccccc1.C1CCC[NH]CC1.c1cc2oncc2s1 | Br- | null | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N>>c1cc(OCCN2CCCCCC2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03c115600f4b416989c82dc4c42a665d | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N>>c1cc(OCCN2CCCCCCC2)cc(-c2noc3ccsc23)c1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C(C)#N>>N1(CCCCCCC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:25][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:15]1.[N:7]#[C:14][CH3:13]>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1 | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N | c1cc(OCCN2CCCCCCC2)cc(-c2noc3ccsc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 69e2c4f8ad85beb4d1f67b28a25ca428b847f8d7a4ff44ac52b368686d5f3c89 | 847e4f3388be6b412c30a1e0dac5815a9121e7f38de3cc603b5da6c43822a22c | c1cc(OCCN2CCCCCCC2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[CH3;D1;+0:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:7]-[C:8])-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, heptamethyleneimine and acetonitrile essentially as described above in example 40. Purity by LC/MS (APCI)=99%, [M+H]+=357.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile | Tertiary amine | null | C1CCC[NH]CCC1 | c1ccccc1.C1CCC[NH]CCC1.c1cc2oncc2s1 | Br- | null | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.CC#N>>c1cc(OCCN2CCCCCCC2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6fb58ddbaab45e5bfb690a1b57001be | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1>>c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][o:17][c:18]3[cH:19][cH:20][s:21][c:22]23)[cH:23]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:24][cH:25]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[n:16][o:17][c:18]4[cH:19][cH:20][s:21][c:... | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1 | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)NCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, and benzylamine in two separate reactions using acetonitrile and 90% aqueous acetonitrile, respectively, essentially as described above in example 18 except that the reaction mixtures are filtered through 2 g ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1>>c1ccc(CNCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a208bef3d67408193e3c036ee51db44 | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1>>c1ccc(N2CCN(CCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | BrCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)N1CCNCC1>>C1(=CC=CC=C1)N1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:26][CH2:27]2)[cH:28][cH:29]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][c:12]3[cH:13][cH:14][cH:15][c:16](-[c:... | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1 | c1ccc(N2CCN(CCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 66 | [{"value": 66.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, and N-phenylpiperazine essentially as described in example 27 except that the freebase is dried to give the title compound (330 mg, 66%). Mp=91–93° C. Microanalysis (C, H, N) is consistent with the final compo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cc2oncc2s1 | HBr | null | null | null | BrCCOc1cccc(-c2noc3ccsc23)c1.c1ccc(N2CCNCC2)cc1>>c1ccc(N2CCN(CCOc3cccc(-c4noc5ccsc45)c3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a99c1c0c4a2345f79a71dc7c55462a97 | BrCCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1>>Cc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(CN)C=C1.C(C)#N>>CC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1 | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19]... | BrCCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1 | Cc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | ClCCl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 80 | [{"value": 80.0, "product": "CC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "CC1=CC=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Mix 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole (0.400 g, 1.18 mmol), potassium carbonate (0.326 g, 2.36 mmol), 4-methylbenzylamine (0.606, 5.00 mmol) and acetonitrile (5.0 mL) and heat (75° C.), overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Com... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | ClCCl.C(C)(=O)OCC | 75 | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.Cc1ccc(CN)cc1>ClCCl.C(C)(=O)OCC>Cc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59efbbf68f2849e5bdb962a83e5a0ddb | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl>>Clc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].ClC1=C(CN)C=CC=C1.C(C)#N>>ClC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC=C1 | Br[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH2:9]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl | Clc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2-chlorobenzylamine and acetonitrile essentially as described above in example 48 except that the crude product is dissolve in DCM and purified by using a step gradient of 50% ethyl acetate in heptane, to 100... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(Cl)Cl | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1Cl>C(Cl)Cl>Clc1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ad9440d1efb4de2a501b320e0a53821 | BrCCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1>>COc1cccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].COC=1C=C(CN)C=CC1>>COC=1C=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1 | Br[CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]3[cH:23][cH:24][s:25][c:26]23)[cH:27]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][c:18](-... | BrCCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1 | COc1cccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3-methoxybenzylamine and acetonitrile essentially as described above in example 48. Purity by LC/MS (APCI)=93%, [M+H]+=395.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.COc1cccc(CN)c1>C(C)#N>COc1cccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fa4f018d6864d4eb84a21dad9652244 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1>>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1F | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC=1C=C(CN)C=CC1F>>FC=1C=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC1F | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:26][c:27]1[F:28]>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:19... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1 | Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3,4-difluorobenzylamine and acetonitrile essentially as described above in example 48. Purity by LC/MS (APCI)=98%, [M+H]+=401.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)c(F)c1>C(C)#N>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24432a42b1bc400c9ec4d5b008a2d3e7 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21>>CC(CNC1CCc2ccccc21)Oc1cccc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].NC1CCC2=CC=CC=C12>>C1(CCC2=CC=CC=C12)NCC(C)OC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:3][CH2:1][CH2:2][O:14][c:15]1[cH:16][cH:17][cH:18][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:28]1.[NH2:4][CH:5]1[CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[CH3:1][CH:2]([CH2:3][NH:4][CH:5]1[CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21)[O:14][c:15]1[cH:16][cH:17][cH... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21 | CC(CNC1CCc2ccccc21)Oc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b600a81df87bea1685df54aaf8b30bd23674e9b7dd2a3cc8662e71bd3684ebef | d995b0d46e4aacf6b403d700b3e57edde7ae1aa34d450d1418ad3604b33a8a71 | c1cc(OCCNC2CCc3ccccc32)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[#8:4]-[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[CH;D3;+0:3](-[CH3;D1;+0:2])-[#8:4]-[c:5])-[c:9] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 1-aminoindan, and acetonitrile essentially as described above in example 48. Purity by LC/MS (APCI)=97%, [M+H]+=391.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Ether.Secondary amine | null | null | c1ccc2c(c1)CCC2.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1CCc2ccccc21>C(C)#N>CC(CNC1CCc2ccccc21)Oc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f77f59c78fe45488d2967a1da89ce66 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1Cc2ccccc2C1>>c1cc(OCCCNC2Cc3ccccc3C2)cc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].NC1CC2=CC=CC=C2C1>>C1C(CC2=CC=CC=C12)NCCCOC1=CC(=CC=C1)C1=NOC2=C1SC=C2 | Br[CH2:7][CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:28][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:18]1.[NH2:8][CH:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH2:7][NH:8][CH:9]2[CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH2:17]2)[c... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1Cc2ccccc2C1 | c1cc(OCCCNC2Cc3ccccc3C2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCCNC2Cc3ccccc3C2)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2-aminoindan, and acetonitrile essentially as described above in example 48. Purity by LC/MS (APCI)=99%, [M+H]+=391.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC2.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC1Cc2ccccc2C1>C(C)#N>c1cc(OCCCNC2Cc3ccccc3C2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f77827b82f184b44a8fecc9f72a1fa72 | BrCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2>>c1cc(OCCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C1NCCC2=CC=CC=C12.C(C)#N>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCN1CC3=CC=CC=C3CC1)C=CC2 | Br[CH2:7][CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:28][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:18]1.[NH:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH2:17]2)[c... | BrCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2 | c1cc(OCCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7901d50fadd7b2205ca48bcd0c91a7ce2a4caa7c5b18385de4e67176215faa6e | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 | 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 | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 1,2,3,4-tetrahydroisoquinoline and acetonitrile essentially as described above in example 48 except that the crude product is dissolve in DCM and purified by using a step gradient of 50% ethyl acetate in hept... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CC[NH]C2 | c1ccccc1.c1ccc2c(c1)CC[NH]C2.c1cc2oncc2s1 | HBr | C(Cl)Cl | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.c1ccc2c(c1)CCNC2>C(Cl)Cl>c1cc(OCCCN2CCc3ccccc3C2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b4bedc2459741bd84e5d05b7da325ca | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2>>c1cc(OCCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].C12(CC3CC(CC(C1)C3)C2)N>>C12(CC3CC(CC(C1)C3)C2)NCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3 | Br[CH2:7][CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:29][c:20](-[c:21]2[n:22][o:23][c:24]3[cH:25][cH:26][s:27][c:28]23)[cH:19]1.[NH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2 | c1cc(OCCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(OCCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[NH2;D1;+0:6])(-[C:7])-[C:8]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3])(-[C:7])-[C:8] | 44 | [{"value": 44.0, "product": "C12(CC3CC(CC(C1)C3)C2)NCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "C12(CC3CC(CC(C1)C3)C2)NCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Mix 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.739 mmol), potassium carbonate (0.205 g, 1.48 mmol), 1-adamantanamine (0.560 g, 3.70 mmol) and acetonitrile (4.0 mL) and heat at 75° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak (1 g) silica gel cartridge (ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cc2oncc2s1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HBr | C(C)#N | 75 | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NC12CC3CC(CC(C3)C1)C2>C(C)#N>c1cc(OCCCNC23CC4CC(CC(C4)C2)C3)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45cf6f3746e741df926ead511858ece5 | BrCCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1>>c1cc(OCCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].N1CCCCC1>>N1(CCCCC1)CCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2 | Br[CH2:7][CH2:6][CH2:5][O:4][c:3]1[cH:2][cH:1][cH:24][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21][s:22][c:23]23)[cH:14]1.[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15](-[c:16]2[n:17][o:18][c:19]3[cH:20][cH:21... | BrCCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1 | c1cc(OCCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCCN2CCCCC2)cc(-c2noc3ccsc23)c1 | 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 | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, piperidine, and acetonitrile essentially as described above in example 56. Purity by LC/MS (APCI)=98%, [M+H]+=343.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.C1CCNCC1>C(C)#N>c1cc(OCCCN2CCCCC2)cc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54b7f7e31bf245bfadb9639c6db33c29 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F>>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=C(CN)C=CC(=C1)F>>FC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C=CC(=C1)F | Br[CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[n:18][o:19][c:20]3[cH:21][cH:22][s:23][c:24]23)[cH:25]1.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[c:26]([F:27])[cH:28]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[n:18][o:... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F | Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2,4-difluorobenzylamine, and acetonitrile essentially as described above in example 56. Purity by LC/MS (APCI)=95%, [M+H]+=401.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(F)cc1F>C(C)#N>Fc1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a546c28eafb14f55b692c780d429b8ea | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F>>Fc1cccc(F)c1CNCCCOc1cccc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC1=C(CN)C(=CC=C1)F>>FC1=C(CNCCCOC2=CC(=CC=C2)C2=NOC3=C2SC=C3)C(=CC=C1)F | Br[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:28]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH2:10]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[CH2:9][NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F | Fc1cccc(F)c1CNCCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2,6-difluorobenzylamine, and acetonitrile essentially as described above in example 56. Purity by LC/MS (APCI)=97%, [M+H]+=401.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1c(F)cccc1F>C(C)#N>Fc1cccc(F)c1CNCCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9d83a9e59e349d98ce7aa61afd34897 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F>>FC(F)(F)c1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC(C1=C(CN)C=CC=C1)(F)F>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC1=C(C=CC=C1)C(F)(F)F)C=CC2 | Br[CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[n:23][o:24][c:25]3[cH:26][cH:27][s:28][c:29]23)[cH:30]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][NH2:12]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][O:16][c:... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F | FC(F)(F)c1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 2-(trifluoromethyl)benzylamine, and acetonitrile essentially as described above in example 56. Purity by LC/MS (APCI)=98%, [M+H]+=433.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccccc1C(F)(F)F>C(C)#N>FC(F)(F)c1ccccc1CNCCCOc1cccc(-c2noc3ccsc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c63dad3018c463d88f3710272719526 | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1>>FC(F)(F)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | BrCCCOC=1C=C(C=CC1)C1=NOC2=C1SC=C2.C([O-])([O-])=O.[K+].[K+].FC(C1=CC=C(CN)C=C1)(F)F>>O1N=C(C2=C1C=CS2)C=2C=C(OCCCNCC1=CC=C(C=C1)C(F)(F)F)C=CC2 | Br[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19](-[c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][s:26][c:27]23)[cH:28]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:29][cH:30]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][... | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound is prepared from 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 4-(trifluoromethyl)benzylamine, and acetonitrile essentially as described above in example 56. Purity by LC/MS (APCI)=98%, [M+H]+=433.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1cc2oncc2s1 | HBr | C(C)#N | null | null | BrCCCOc1cccc(-c2noc3ccsc23)c1.NCc1ccc(C(F)(F)F)cc1>C(C)#N>FC(F)(F)c1ccc(CNCCCOc2cccc(-c3noc4ccsc34)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87d3e58ebd044febb2246a63639c98ea | CC(=N)N.CCOC(=O)CC(=O)c1ccc(F)cc1>>Cc1nc(O)cc(-c2ccc(F)cc2)n1 | FC1=CC=C(C=C1)C(CC(=O)OCC)=O.Cl.C(C)(=N)N.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(C=C1)C1=NC(=NC(=C1)O)C | [CH3:1][C:2](=[NH:3])[NH2:15].CCO[C:4](=[O:5])[CH2:6][C:7](=O)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[n:3][c:4]([OH:5])[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]1 | CC(=N)N.CCOC(=O)CC(=O)c1ccc(F)cc1 | Cc1nc(O)cc(-c2ccc(F)cc2)n1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | fc5f300b5457abe603bff74deaeb6f1e6fee00cab2975ee0ea2f56154ceba1d8 | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc(-c2ccncn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C;D1;H3:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[C;D1;H3:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[cH;D2;+0:3]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):... | 87.6 | [{"value": 87.6, "product": "FC1=CC=C(C=C1)C1=NC(=NC(=C1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8.7 kg of ethyl 3-(4-fluorophenyl)-3-oxopropionate, 11.7 kg of acetoamidine hydrochloride and 28.6 kg of potassium carbonate were stirred for 5 hours at about 50° C. in 34.5 kg of methanol. Insolubles were separated from the reaction mixture and washed with methanol, and the mother liquor and the washing were combined ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | null | CC(=N)N.CCOC(=O)CC(=O)c1ccc(F)cc1>CO>Cc1nc(O)cc(-c2ccc(F)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-566f636694d74e4bbcaca894597ef315 | Cc1nc(O)cc(-c2ccc(F)cc2)n1.O=P(Cl)(Cl)Cl>>Cc1nc(Cl)cc(-c2ccc(F)cc2)n1 | FC1=CC=C(C=C1)C1=NC(=NC(=C1)O)C.P(=O)(Cl)(Cl)Cl.O>>ClC1=NC(=NC(=C1)C1=CC=C(C=C1)F)C | O[c:4]1[n:3][c:2]([CH3:1])[n:15][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:6]1.O=P(Cl)(Cl)[Cl:5]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15]1 | Cc1nc(O)cc(-c2ccc(F)cc2)n1.O=P(Cl)(Cl)Cl | Cc1nc(Cl)cc(-c2ccc(F)cc2)n1 | null | null | C(C)#N | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccncn2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[c:7]):[c:8]:1 | 97 | [{"value": 97.0, "product": "ClC1=NC(=NC(=C1)C1=CC=C(C=C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 13.8 kg of 4-(4-fluorophenyl)-6-hydroxy-2-methylpyrimidine and 11.5 kg of phosphorus oxychloride were refluxed in acetonitrile, and stirred for 4 hours. The reaction solution was combined with water, and the precipitated crystal was separated, and the resultant crystal was washed and dried to obtain 14.6 kg of the targ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | C(C)#N | null | 4 | Cc1nc(O)cc(-c2ccc(F)cc2)n1.O=P(Cl)(Cl)Cl>C(C)#N>Cc1nc(Cl)cc(-c2ccc(F)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c97fb92d3a6490490f59178d44b102c | Cc1nc(Cl)cc(-c2ccc(F)cc2)n1.OCCCCCN1CCCCC1>>Cc1nc(OCCCCCN2CCCCC2)cc(-c2ccc(F)cc2)n1 | ClC1=NC(=NC(=C1)C1=CC=C(C=C1)F)C.[H-].[Na+].N1(CCCCC1)CCCCCO>>FC1=CC=C(C=C1)C1=NC(=NC(=C1)OCCCCCN1CCCCC1)C | Cl[c:4]1[n:3][c:2]([CH3:1])[n:26][c:18](-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[cH:17]1.[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][c:2]1[n:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17][c:18]... | Cc1nc(Cl)cc(-c2ccc(F)cc2)n1.OCCCCCN1CCCCC1 | Cc1nc(OCCCCCN2CCCCC2)cc(-c2ccc(F)cc2)n1 | null | null | C1CCCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cc(OCCCCCN3CCCCC3)ncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[c:6]):[c:7]:1.[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[c:6]):[c:7]:1 | null | [] | null | null | null | null | 13.8 kg of 4-chloro-6-(4-fluorophenyl)-2-methylpyrimidine, 4.8 kg of 60% sodium hydride, 130 kg of cyclohexane and 10.6 kg of 5-piperidino-1-pentanol were stirred under reflux for 4 hours.
Conditions: See reaction.notes.procedure_details.
Workup: under reflux for 4 hours | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HCl | C1CCCCC1 | null | null | Cc1nc(Cl)cc(-c2ccc(F)cc2)n1.OCCCCCN1CCCCC1>C1CCCCC1>Cc1nc(OCCCCCN2CCCCC2)cc(-c2ccc(F)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8210397d84ee46a398b1d1f423bf0696 | CC1CCN(Cc2ccccc2)CC1=O.CN>>CNC1CN(Cc2ccccc2)CCC1C | C(C1=CC=CC=C1)N1CC(C(CC1)C)=O.CO.CN.C(C)(=O)O>>C(C1=CC=CC=C1)N1CC(C(CC1)C)NC | O=[C:3]1[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][CH:15]1[CH3:16].[CH3:1][NH2:2]>>[CH3:1][NH:2][CH:3]1[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][CH:15]1[CH3:16] | CC1CCN(Cc2ccccc2)CC1=O.CN | CNC1CN(Cc2ccccc2)CCC1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CN2CCCCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-[C:6]-[C:7]-1-[C;D1;H3:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C:4]-[#7:3]1-[C:5]-[C:6]-[C:7](-[C;D1;H3:8])-[CH;D3;+0:1](-[NH;D2;+0:10]-[C;D1;H3:9])-[C:2]-1 | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)N1CC(C(CC1)C)NC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a stirred solution of 1-benzyl-4-methyl-piperidin-3-one (2.3 grams, 11.5 mmol), prepared by the methods of Iorio, M. A. and Damia, G., Tetrahedron, 26, 5519 (1970) and Grieco et al., Journal of the American Chemical Society, 107, 1768 (1985), (modified using 5% methanol as a co-solvent), both references are incorpor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | 16 | CC1CCN(Cc2ccccc2)CC1=O.CN>O1CCCC1>CNC1CN(Cc2ccccc2)CCC1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3867a2cb80c486397e66b825750f7a8 | CNC1CN(Cc2ccccc2)CCC1C.Clc1nc[nH]c2nccc1-2>>CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12 | ClC1=C2C(NC=N1)=NC=C2.C(C1=CC=CC=C1)N1CC(C(CC1)C)NC.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1CC(C(CC1)C)N(C=1C2=C(N=CN1)NC=C2)C | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH:14]1[NH:15][CH3:16].Cl[c:17]1[n:18][cH:19][nH:20][c:21]2[n:22][cH:23][cH:24][c:25]1-2>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH:14]1[N:15]([CH3:16])[c:17]1[n:18][cH:19][n:20... | CNC1CN(Cc2ccccc2)CCC1C.Clc1nc[nH]c2nccc1-2 | CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8e944c34490dc9ec97b6cf7570fb7a14f0ef783a0068714fe92ecf3f3ce8f274 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCCC(Nc3ncnc4[nH]ccc34)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[nH;D2;+0:4]:[c;H0;D3;+0:5]2:[n;H0;D2;+0:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-2.[#7:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[C;D1;H3:14])-[C:15]>>[#7:10]-[C:11]-[C:12](-[N;H0;D3;+0:13](-[C;D1;H3:14])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]2:[nH;D2;+0:6]:[c:7]:[c:8]:[c;H0;D3;+0... | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)N1CC(C(CC1)C)N(C=1C2=C(N=CN1)NC=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "C(C1=CC=CC=C1)N1CC(C(CC1)C)N(C=1C2=C(N=CN1)NC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 4-chloropyrrolo[2,3-d]pyrimidine (2.4 grams, 15.9 mmol), prepared by the method of Davoll, J. Am. Chem. Soc., 82, 131 (1960), which is incorporated by reference in its entirety, and the product from Method A (1.7 grams, 7.95 mmol) dissolved in 2 equivalents of triethylamine was heated in a sealed tube at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | C1CC[NH]CC1.c1ccccc1.c1ncc2cc[nH]c2n1 | HCl | null | 100 | null | CNC1CN(Cc2ccccc2)CCC1C.Clc1nc[nH]c2nccc1-2>>CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38d0f49d1c3346b3aa2e2230f8263347 | CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12>>CC1CCNCC1N(C)c1ncnc2[nH]ccc12 | C(C1=CC=CC=C1)N1CC(C(CC1)C)N(C=1C2=C(N=CN1)NC=C2)C.Cl>>CN(C=1C2=C(N=CN1)NC=C2)C2CNCCC2C | c1ccc(C[N:5]2[CH2:4][CH2:3][CH:2]([CH3:1])[CH:7]([N:8]([CH3:9])[c:10]3[n:11][cH:12][n:13][c:14]4[nH:15][cH:16][cH:17][c:18]34)[CH2:6]2)cc1>>[CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH:7]1[N:8]([CH3:9])[c:10]1[n:11][cH:12][n:13][c:14]2[nH:15][cH:16][cH:17][c:18]12 | CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12 | CC1CCNCC1N(C)c1ncnc2[nH]ccc12 | null | null | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1nc(NC2CCCNC2)c2cc[nH]c2n1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 90 | [{"value": 90.0, "product": "CN(C=1C2=C(N=CN1)NC=C2)C2CNCCC2C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "CN(C=1C2=C(N=CN1)NC=C2)C2CNCCC2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To the product from Method B (0.7 grams, 2.19 mmol) dissolved in 15 mL of ethanol was added 1.5 mL of 2 N hydrochloric acid and the reaction mixture degassed by nitrogen purge. To the reaction mixture was then added 0.5 grams of 20% palladium hydroxide on carbon (50% water) (Aldrich) and the resulting mixture shaken (P... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ncc2cc[nH]c2n1 | Other | C(C)O | null | 48 | CC1CCN(Cc2ccccc2)CC1N(C)c1ncnc2[nH]ccc12>C(C)O>CC1CCNCC1N(C)c1ncnc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dedaa27fb1e14f76bacb2c6dcc3a01b4 | CC(=O)Cl.CC1CCNCC1N(C)c1ncnc2[nH]ccc12>>CC(=O)N1CCC(C)C(N(C)c2ncnc3[nH]ccc23)C1 | CN(C=1C2=C(N=CN1)NC=C2)C2CNCCC2C.C(C)(=O)Cl>>CC1C(CN(CC1)C(C)=O)N(C=1C2=C(N=CN1)NC=C2)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][CH:7]([CH3:8])[CH:9]([N:10]([CH3:11])[c:12]2[n:13][cH:14][n:15][c:16]3[nH:17][cH:18][cH:19][c:20]23)[CH2:21]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH3:8])[CH:9]([N:10]([CH3:11])[c:12]2[n:13][cH:14][n:15][c:16]3[nH:17][cH:18][cH:19][c:20]23)[CH2:21]1 | CC(=O)Cl.CC1CCNCC1N(C)c1ncnc2[nH]ccc12 | CC(=O)N1CCC(C)C(N(C)c2ncnc3[nH]ccc23)C1 | null | null | ClCCl.N1=CC=CC=C1 | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1nc(NC2CCCNC2)c2cc[nH]c2n1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7]-[C:8] | 15 | [{"value": 15.0, "product": "CC1C(CN(CC1)C(C)=O)N(C=1C2=C(N=CN1)NC=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "CC1C(CN(CC1)C(C)=O)N(C=1C2=C(N=CN1)NC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of the product from Method C (0.03 grams, 0.114 mmol) dissolved in 5 mL of 10:1 dichloromethane/pyridine was added (0.018 grams, 0.228 mmol) of acetylchloride and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was then partitioned between dichloromethane and s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ncc2cc[nH]c2n1 | HCl | ClCCl.N1=CC=CC=C1 | null | 18 | CC(=O)Cl.CC1CCNCC1N(C)c1ncnc2[nH]ccc12>ClCCl.N1=CC=CC=C1>CC(=O)N1CCC(C)C(N(C)c2ncnc3[nH]ccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77375cbffc264118ad52dfc40e2b8c47 | NC(=O)c1sccc1[N+](=O)[O-]>>N#Cc1sccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(SC=C1)C(=O)N.C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>C(#N)C=1SC=CC1[N+](=O)[O-] | O=[C:2]([NH2:1])[c:3]1[s:4][cH:5][cH:6][c:7]1[N+:8](=[O:9])[O-:10]>>[N:1]#[C:2][c:3]1[s:4][cH:5][cH:6][c:7]1[N+:8](=[O:9])[O-:10] | NC(=O)c1sccc1[N+](=O)[O-] | N#Cc1sccc1[N+](=O)[O-] | null | null | ClCCl | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccsc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[#16;a:5]:[c:6] | 96.6 | [{"value": 96.5, "product": "C(#N)C=1SC=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "C(#N)C=1SC=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | The amide 30 (15.5 g, 90 mmol), prepared as described above, was dissolved in dichloromethane (700 ml). Triethylamine (27.2 g, 37.6 ml, 270 mmol) was added and the solution cooled to 0° C. After dropwise addition of neat trifluoroacetic anhydride (24.6 g, 16.5 ml, 117 mmol), the reaction was allowed to warm to room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccsc1 | HO- | ClCCl | 0 | 1 | NC(=O)c1sccc1[N+](=O)[O-]>ClCCl>N#Cc1sccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb34e2e93aa14e95ac75809f33844761 | COC(=O)c1nc(-c2cscc2NC(=O)OC(C)(C)C)nc(O)c1O>>COC(=O)c1nc(-c2cscc2N)nc(O)c1O | C(C)(C)(C)OC(=O)NC1=CSC=C1C1=NC(=C(C(=N1)O)O)C(=O)OC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.NC1=CSC=C1C1=NC(=C(C(=N1)O)O)C(=O)OC | CC(C)(C)OC(=O)[NH:13][c:12]1[c:8](-[c:7]2[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:17]([OH:18])[c:15]([OH:16])[n:14]2)[cH:9][s:10][cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][s:10][cH:11][c:12]2[NH2:13])[n:14][c:15]([OH:16])[c:17]1[OH:18] | COC(=O)c1nc(-c2cscc2NC(=O)OC(C)(C)C)nc(O)c1O | COC(=O)c1nc(-c2cscc2N)nc(O)c1O | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cnc(-c2ccsc2)nc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1 | 99 | [{"value": 99.0, "product": "FC(C(=O)O)(F)F.NC1=CSC=C1C1=NC(=C(C(=N1)O)O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Ester 40 (828 mg, 2.25 mmol), prepared as described above, was treated with a 6:4 mixture of methylene chloride:trifluoroacetic acid (8 ml). The solution was stirred for 20 min then concentrated in vacuo and the residue dried to give methyl 2-(3-amino-4-thienyl)-4,5-dihydroxy-pyrimidine-6-carboxylate trifluoroacetate (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cncnc1.c1ccsc1 | HO- | C(Cl)Cl | null | 0.333333 | COC(=O)c1nc(-c2cscc2NC(=O)OC(C)(C)C)nc(O)c1O>C(Cl)Cl>COC(=O)c1nc(-c2cscc2N)nc(O)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16b875041d6e42ef88af956f49470849 | CCOC(=O)Cl.NS(=O)(=O)c1cccc2ccccc12>>CCOC(=O)NS(=O)(=O)c1cccc2ccccc12 | C1(=CC=CC2=CC=CC=C12)S(=O)(=O)N.C([O-])([O-])=O.[K+].[K+].ClC(=O)OCC>>C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NC(OCC)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CCOC(=O)Cl.NS(=O)(=O)c1cccc2ccccc12 | CCOC(=O)NS(=O)(=O)c1cccc2ccccc12 | null | null | CC(CC)=O.CCOC(=O)C.O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 2f2696288009d2012d9ec2995f8be43c58fdee99389b7d218ed77c4bafda7b17 | 60493cac785f670383c62b059214a5eb4def232e11814f271849329f2f6b7966 | c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9] | 67 | [{"value": 67.0, "product": "C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NC(OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NC(OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-naphthalene sulfonamide (769 mg, 3.67 mmol) and potassium carbonate (563 mg, 4.07 mmol) in 2-butanone (9 ml) was heated under reflux for 30 min. Ethyl chloroformate (430 mg, 3.96 mmol) was added dropwise and the resulting solution was heated under reflux for 3 h. The mixture was cooled and diluted with H... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Carbamic ester | null | null | c1ccc2ccccc2c1 | HCl | CC(CC)=O.CCOC(=O)C.O | null | null | CCOC(=O)Cl.NS(=O)(=O)c1cccc2ccccc12>CC(CC)=O.CCOC(=O)C.O>CCOC(=O)NS(=O)(=O)c1cccc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40b3fdf101234a18a130f74ed6480c31 | NO.O=Cc1sccc1C1OCCO1>>ON=Cc1sccc1C1OCCO1 | O1C(OCC1)C1=C(SC=C1)C=O.Cl.NO.C(O)([O-])=O.[Na+]>>O1C(OCC1)C1=C(SC=C1)C=NO | [OH:1][NH2:2].O=[CH:3][c:4]1[s:5][cH:6][cH:7][c:8]1[CH:9]1[O:10][CH2:11][CH2:12][O:13]1>>[OH:1][N:2]=[CH:3][c:4]1[s:5][cH:6][cH:7][c:8]1[CH:9]1[O:10][CH2:11][CH2:12][O:13]1 | NO.O=Cc1sccc1C1OCCO1 | ON=Cc1sccc1C1OCCO1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | c1cc(C2OCCO2)cs1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[O;D1;H1:7]-[N;H0;D2;+0:6]=[CH;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5] | null | [] | null | null | null | null | 3-(1,3-Dioxolan-2-yl)thiophene-2-carbaldehyde (13.1 g, 71.11 mmol), prepared by a method described by Hibino (S. Hibino et al., J. Org. Chem. 1984, 49, 5006), was dissolved in ethanol (80 ml). At room temperature a solution of hydroxylamine hydrochloride (two equivalents) and sodium hydrogencarbonate (one equivalent) i... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccsc1.C1COCO1 | HO- | O.C(C)O | null | null | NO.O=Cc1sccc1C1OCCO1>O.C(C)O>ON=Cc1sccc1C1OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b618b7543ade454d9f721a3b5599266c | N#Cc1sccc1C1OCCO1.NO>>NC(=NO)c1sccc1C1OCCO1 | O1C(OCC1)C1=C(SC=C1)C#N.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>O1C(OCC1)C1=C(SC=C1)C(N)=NO | [N:1]#[C:2][c:5]1[s:6][cH:7][cH:8][c:9]1[CH:10]1[O:11][CH2:12][CH2:13][O:14]1.[NH2:3][OH:4]>>[NH2:1][C:2](=[N:3][OH:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[CH:10]1[O:11][CH2:12][CH2:13][O:14]1 | N#Cc1sccc1C1OCCO1.NO | NC(=NO)c1sccc1C1OCCO1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | Amidoxime from nitrile and hydroxylamine | 5f2123b5002b6939ec57e4f55921371a47c78c3ff253c724d87881638fedcd4f | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | c1cc(C2OCCO2)cs1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | 40 | CELSIUS | null | null | To a solution of the foregoing nitrile (5.0 g, 27.59 mmol) in ethanol (20 ml) was added a solution of hydroxylamine hydrochloride (3.7 equivalents) and sodium carbonate (1.7 equivalents) in water (50 ml). The resulting mixture was heated to 40° C. for 5 h, then cooled to room temperature. The colourless precipitate was... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | null | null | c1ccsc1.C1COCO1 | null | O.C(C)O | 40 | null | N#Cc1sccc1C1OCCO1.NO>O.C(C)O>NC(=NO)c1sccc1C1OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9469d6f4a4846c6b2874fbf0254c2dd | BrBr.c1ccc2cnccc2c1>>Brc1cccc2cnccc12 | [OH-].[Na+].[Al].O=[Al-]=O.[Na+].C1=NC=CC2=CC=CC=C12.[Al+3].[Cl-].[Cl-].[Cl-].BrBr>>BrC1=C2C=CN=CC2=CC=C1 | Br[Br:1].[cH:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | BrBr.c1ccc2cnccc2c1 | Brc1cccc2cnccc12 | null | null | null | Functional Group Interconversion | Bromination | dd766f53887400b5e199d60af04f01509e5613a22375639572626e4514c9ae8d | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2cnccc2c1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 26 | [{"value": 26.0, "product": "BrC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.0, "product": "BrC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 1 | HOUR | The apparatus was a 500 mL three-necked flask equipped with a condenser, dropping funnel, and a stirrer terminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle. To the isoquinoline (57.6 g, 447 mmol) in the flask was added AlCl3 (123 g, 920 mmol). The mixture was heated to 75–85° C. Bromine (48.0 g... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | null | 75 | 1 | BrBr.c1ccc2cnccc2c1>>Brc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7ba93572fa64fddbb46271e8f729e27 | Brc1ccc2c(c1)OCO2.O=Cc1cccc2cnccc12>>OC(c1c(Br)ccc2c1OCO2)c1cccc2cnccc12 | CCOC(=O)C.C1=NC=CC=2C(=CC=CC12)C=O.BrC1=CC2=C(C=C1)OCO2.C(C)(C)[N-]C(C)C.[Li+]>>BrC1=C(C2=C(OCO2)C=C1)C(O)C=1C=2C=CN=CC2C=CC1 | [cH:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]2[c:9]1[O:10][CH2:11][O:12]2.[O:1]=[CH:2][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][n:19][cH:20][cH:21][c:22]12>>[OH:1][CH:2]([c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]2[c:9]1[O:10][CH2:11][O:12]2)[c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][n:19][cH:20][cH:21][c:22]12 | Brc1ccc2c(c1)OCO2.O=Cc1cccc2cnccc12 | OC(c1c(Br)ccc2c1OCO2)c1cccc2cnccc12 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7dcb49beac9ea90aaa893087c06f90aa7f0531c120766aa39be5fadb3a836333 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1cc(Cc2cccc3cnccc23)c2c(c1)OCO2 | [Br;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]1:[c:6]-[#8:7]-[C:8]-[#8:9]-1.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[Br;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:5]1:[c:6]-[#8:7]-[C:8]-[#8:9]-1 | 65 | [{"value": 65.0, "product": "BrC1=C(C2=C(OCO2)C=C1)C(O)C=1C=2C=CN=CC2C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "BrC1=C(C2=C(OCO2)C=C1)C(O)C=1C=2C=CN=CC2C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | To a solution of 4-bromo-1,2-(methylendioxy)benzene (3.01 g, 15 mmol) in THF (20 mL) at −78° C. was added dropwise lithium diisopropylamide (10.6 mL of 1.5 M in cyclohexane, 16 mmol). The reaction mixture was stirred at −78° C. under argon for 20 minutes. A brown solution was formed. A solution of 5-isoquinolinecarboxa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2cnccc2c1 | null | C1CCOC1 | -78 | 0.333333 | Brc1ccc2c(c1)OCO2.O=Cc1cccc2cnccc12>C1CCOC1>OC(c1c(Br)ccc2c1OCO2)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2690e096c09541e2a352479b05e1cb9b | c1cc2c3c(c1)Cc1c(ccc4c1OCO4)C3CNC2>>Oc1ccc2c(c1O)Cc1cccc3c1[C@@H]2CNC3 | C([C@@H](O)[C@H](O)C(=O)O)(=O)O.C1OC2=C3CC=4C=5C(CNCC5C=CC4)C3=CC=C2O1.C(C1=CC=CC=C1)(=O)[C@@]([C@@](C(=O)O)(O)C(C1=CC=CC=C1)=O)(O)C(=O)O.[OH-].[K+]>>OC1=C2CC=3C=4[C@H](CNCC4C=CC3)C2=CC=C1O | C1[O:1][c:2]2[cH:3][cH:4][c:5]3[c:6]([c:7]2[O:8]1)[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[CH:16]3[CH2:17][NH:18][CH2:19]2>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[OH:8])[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]3[c:15]1[C@@H:16]2[CH2:17][NH:18][CH2:19]3 | c1cc2c3c(c1)Cc1c(ccc4c1OCO4)C3CNC2 | Oc1ccc2c(c1O)Cc1cccc3c1[C@@H]2CNC3 | null | null | CO.C(C)O | Deprotection | OtherReaction | d0bc6792c42b9100c63f37f4f0c0210e906914205abf19346f1341546fd40726 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc2c(c1)Cc1cccc3c1[C@@H]2CNC3 | [c:1]:[c:2]1:[c:3](:[c:4])-[O;H0;D2;+0:5]-C-[O;H0;D2;+0:6]-1>>[OH;D1;+0:6]-[c:2](:[c:1]):[c:3](-[OH;D1;+0:5]):[c:4] | null | [] | null | null | 4 | HOUR | A solution of racemic (±)-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-napth[1,2,3-de]isoquinoline (3.0 gm, 11.3 mmol) in 100 mL of 95% ethyl alcohol at room temperature was mixed with a warm solution of (+)-dibenzoyl-D-tartaric acid in 40 mL of 95% ethyl alcohol. The solution was allowed to stand at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | c1cc2c3c(c1)Cc1c(ccc4c1OCO4)C3CNC2 | null | c1ccc2c(c1)Cc1cccc3c1[C@@H]2CNC3 | Other | CO.C(C)O | null | 4 | c1cc2c3c(c1)Cc1c(ccc4c1OCO4)C3CNC2>CO.C(C)O>Oc1ccc2c(c1O)Cc1cccc3c1[C@@H]2CNC3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ea103740d49442d947174854bfe2809 | COc1cc2c(cc1OC)CNCC2.COc1cc2c(cc1OC)S(=O)(=O)NC(Cl)=N2>>COc1cc2c(cc1OC)CN(C1=Nc3cc(OC)c(OC)cc3S(=O)(=O)N1)CC2 | ClC=1NS(C2=C(N1)C=C(C(=C2)OC)OC)(=O)=O.COC=1C=C2CCNCC2=CC1OC>>COC=1C=C2CCN(CC2=CC1OC)C=1NS(C2=C(N1)C=C(C(=C2)OC)OC)(=O)=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][CH2:29][CH2:30]2.Cl[C:13]1=[N:14][c:15]2[cH:16][c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23][c:24]2[S:25](=[O:26])(=[O:27])[NH:28]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:12]([C:13]1=[N:14][c:15]3[cH:1... | COc1cc2c(cc1OC)CNCC2.COc1cc2c(cc1OC)S(=O)(=O)NC(Cl)=N2 | COc1cc2c(cc1OC)CN(C1=Nc3cc(OC)c(OC)cc3S(=O)(=O)N1)CC2 | null | null | COC(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 022e6b4a628350be588645f2ff64c69be4f6dc88a4aaeff800053ed5f767d62a | 7a3faccadd4f72d41bdefa782cb4f0da18fb74d78f8a6abeeac897da8f291713 | O=S1(=O)NC(N2CCc3ccccc3C2)=Nc2ccccc21 | Cl-[C;H0;D3;+0:1](=[#7:2]-[c:3])-[#7:4]-[#16:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[#16:5]-[#7:4]-[C;H0;D3;+0:1](-[N;H0;D3;+0:8](-[C:9]-[c:10])-[C:7]-[C:6])=[#7:2]-[c:3] | 50.3 | [{"value": 50.3, "product": "COC=1C=C2CCN(CC2=CC1OC)C=1NS(C2=C(N1)C=C(C(=C2)OC)OC)(=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Chloro-6,7-dimethoxy-2H-benzo[1,2,4]thiadiazine-1,1-dioxide 1a (154 mg, 0.55 mmol) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 2a (wherein R1 and R4 are hydrogen, and R2 and R3 are methoxy) (138 mg, 0.6 mmol) were dissolved in 20 ml of methoxyethanol and heated at reflux for 72 h. The solvent was removed under r... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC2.C1=Nc2ccccc2SN1 | c1ccc2c(c1)CC[NH]C2.C1=Nc2ccccc2SN1 | c1ccc2c(c1)CC[NH]C2.C1=Nc2ccccc2SN1 | HCl | COC(C)O | null | null | COc1cc2c(cc1OC)CNCC2.COc1cc2c(cc1OC)S(=O)(=O)NC(Cl)=N2>COC(C)O>COc1cc2c(cc1OC)CN(C1=Nc3cc(OC)c(OC)cc3S(=O)(=O)N1)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8649f47a7b846b880d52e1adecdf85c | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2c1CCN(Cc1ccccc1)C2>>Clc1ncnc2c1CCN(Cc1ccccc1)C2 | C(C1=CC=CC=C1)N1CC=2N=CNC(C2CC1)=O.C(C)N(C1=CC=CC=C1)CC.O=P(Cl)(Cl)Cl>>C(C1=CC=CC=C1)N1CC=2N=CN=C(C2CC1)Cl | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[c:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:18]2>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:18]2 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2c1CCN(Cc1ccccc1)C2 | Clc1ncnc2c1CCN(Cc1ccccc1)C2 | null | null | null | Functional Group Interconversion | OtherReaction | 6230f0031bbc299153e9e4d2cd6d8946d9b38b76cdc43d4a750aadc0ce3c878e | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(CN2CCc3cncnc3C2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]:1-[C:8])-[C:9]-[#7:10]>>[#7:10]-[C:9]-[c:6]1:[#7;a:5]:[c:4]:[n;H0;D2;+0:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:7]:1-[C:8] | null | [] | 80 | CELSIUS | null | null | To a mixture of 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one 3a (1.0 g, 4.14 mmol) and N,N-diethylaniline (0.37 g, 2.48 mmol) was slowly added POCl3 (12 mL). The mixture was heated to 80° C. for 20 h. After evaporation of the excess of POCl3, the residue was poured into ice, dichloromethane was added and... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ncnc2c1CCNC2 | c1ncc2c(n1)C[NH]CC2 | c1ncc2c(n1)C[NH]CC2.c1ccccc1 | HCl | null | 80 | null | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2c1CCN(Cc1ccccc1)C2>>Clc1ncnc2c1CCN(Cc1ccccc1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-519e79bd4d7445b0b453c00c46cc063d | C1COCCN1.Clc1ncnc2c1CCN(Cc1ccccc1)C2>>c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1 | C(C1=CC=CC=C1)N1CC=2N=CN=C(C2CC1)Cl.N1CCOCC1>>C(C1=CC=CC=C1)N1CC=2N=CN=C(C2CC1)N1CCOCC1 | [NH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.Cl[c:14]1[c:9]2[c:10]([n:11][cH:12][n:13]1)[CH2:21][N:6]([CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:23][cH:22]1)[CH2:7][CH2:8]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][c:9]3[c:10]([n:11][cH:12][n:13][c:14]3[N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH2:21]2)[cH... | C1COCCN1.Clc1ncnc2c1CCN(Cc1ccccc1)C2 | c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8f92036b5a5964bdd4ef7c1a78f08e385ffd8bcaa7103ed46cdd32e1af892fef | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:1-[C:7])-[C:8]-[#7:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7:9]-[C:8]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:6]:1-[C:7] | 100.1 | [{"value": 100.1, "product": "C(C1=CC=CC=C1)N1CC=2N=CN=C(C2CC1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 4a (0.46 g, 1.77 mmol) in isopropanol (20 mL) was added morpholine (0.38 g, 4.42 mmol), and the reaction mixture was heated to reflux for 18 h. The solvent was removed in vacuo, and the residue was suspended in a saturated solution of NaHCO3,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ncc2c(n1)C[NH]CC2 | c1ncc2c(n1)C[NH]CC2.C1COCC[NH]1 | c1ccccc1.c1ncc2c(n1)C[NH]CC2.C1COCC[NH]1 | HCl | C(C)(C)O | null | null | C1COCCN1.Clc1ncnc2c1CCN(Cc1ccccc1)C2>C(C)(C)O>c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4369f92349b7406ebd1712953537ed2e | c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1>>c1nc2c(c(N3CCOCC3)n1)CCNC2 | C(C1=CC=CC=C1)N1CC=2N=CN=C(C2CC1)N1CCOCC1.C(=O)[O-].[NH4+]>>N1(CCOCC1)C=1C2=C(N=CN1)CNCC2 | c1ccc(C[N:15]2[CH2:14][CH2:13][c:4]3[c:3]([n:2][cH:1][n:12][c:5]3[N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[CH2:16]2)cc1>>[cH:1]1[n:2][c:3]2[c:4]([c:5]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)[n:12]1)[CH2:13][CH2:14][NH:15][CH2:16]2 | c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1 | c1nc2c(c(N3CCOCC3)n1)CCNC2 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 9fe3d5d4eb2d7e06fe7cfa86b71cfb910a291164877b53362cd5ff8238fb0ffa | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1nc2c(c(N3CCOCC3)n1)CCNC2 | [#7;a:1]:[c:2]-[C:3]-[N;H0;D3;+0:4](-C-c1:c:c:c:c:c:1)-[C:5]-[C:6]>>[#7;a:1]:[c:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6] | 69.3 | [{"value": 69.3, "product": "N1(CCOCC1)C=1C2=C(N=CN1)CNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Benzyl-4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 5a (0.55 g, 1.77 mmol) was dissolved in methanol (35 mL) under nitrogen. 10% Pd/C (0.55 g) was added under nitrogen followed by ammonium formate (1.12 g, 17.72 mmol) and the mixture was heated to reflux for 12 h. The catalyst was removed by filtration... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ncc2c(n1)C[NH]CC2 | c1ncc2c(n1)CNCC2 | C1COCC[NH]1.c1ncc2c(n1)CNCC2 | Other | [Pd].CO | null | null | c1ccc(CN2CCc3c(ncnc3N3CCOCC3)C2)cc1>[Pd].CO>c1nc2c(c(N3CCOCC3)n1)CCNC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2cf3ec24bb5345429b949a4874f9286b | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1nc2c(c(N3CCOCC3)n1)CCNC2>>COc1cc2nc(N3CCc4c(ncnc4N4CCOCC4)C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.N1(CCOCC1)C=1C2=C(N=CN1)CNCC2>>COC=1C=C2C(NC(=NC2=CC1OC)N1CC=2N=CN=C(C2CC1)N1CCOCC1)=O | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]2[c:25](=[O:26])[nH:24]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([n:13][cH:14][n:15][c:16]2[N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([n:13][cH:14][n:15][... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1nc2c(c(N3CCOCC3)n1)CCNC2 | COc1cc2nc(N3CCc4c(ncnc4N4CCOCC4)C3)[nH]c(=O)c2cc1OC | null | null | COC(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | abd48091fecd9894ccd7541ef02b01838d0e59761e0712f85229bb4c1056e336 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3c(ncnc3N3CCOCC3)C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:10]-[C:11] | 61.9 | [{"value": 61.9, "product": "COC=1C=C2C(NC(=NC2=CC1OC)N1CC=2N=CN=C(C2CC1)N1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (0.28 g, 1.18 mmol) and 4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 6a (0.26 g, 1.20 mmol) in methoxyethanol (10 mL) was heated to 100° C. with stirring for 18 h. After cooling to room temperature, the precipitated solid was separated by filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1ncc2c(n1)CNCC2 | c1ccc2ncncc2c1.c1ncc2c(n1)C[NH]CC2 | c1ccc2ncncc2c1.c1ncc2c(n1)C[NH]CC2.C1COCC[NH]1 | HCl | COC(C)O | 100 | 18 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1nc2c(c(N3CCOCC3)n1)CCNC2>COC(C)O>COc1cc2nc(N3CCc4c(ncnc4N4CCOCC4)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c854fda8c814904b2a39cc1640404a8 | c1cn2c(C3CCCCC3)ncc2cn1>>c1nc(C2CCCCC2)n2c1CNCC2 | C1(CCCCC1)C1=NC=C2N1C=CN=C2.[H][H]>>C1(CCCCC1)C1=NC=C2N1CCNC2 | [cH:1]1[n:2][c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[n:10]2[c:11]1[cH:12][n:13][cH:14][cH:15]2>>[cH:1]1[n:2][c:3]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[n:10]2[c:11]1[CH2:12][NH:13][CH2:14][CH2:15]2 | c1cn2c(C3CCCCC3)ncc2cn1 | c1nc(C2CCCCC2)n2c1CNCC2 | null | O=[Pt]=O | C(C)O | Reduction | OtherReaction | 23d078c54d7da04a52271893296a4ea67f63798d6703ea2ffa724dfcc0169732 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1nc(C2CCCCC2)n2c1CNCC2 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[#7;a:10]:2:1>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]2:[#7;a:10]:1-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[NH;D2;+0:7]-[CH2;D2;+0:6]-2 | 87.5 | [{"value": 87.5, "product": "C1(CCCCC1)C1=NC=C2N1CCNC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-cyclohexyl-imidazo[1,5-a]pyrazine 8a (960 mg, 4.4 mmol) in 25 ml ethanol was treated with 100 mg Adam's catalyst and stirred vigorously under one atmosphere of hydrogen for 18 hr. The mixture was filtered through a pad of Celite®. The filtrate was concentrated in vacuo to yield 790 mg of 3-cyclohexyl-5,... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1cn2cncc2cn1 | c1ncn2c1CNCC2 | C1CCCCC1.c1ncn2c1CNCC2 | null | O=[Pt]=O.C(C)O | null | null | c1cn2c(C3CCCCC3)ncc2cn1>O=[Pt]=O.C(C)O>c1nc(C2CCCCC2)n2c1CNCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e40ebc98c10d4b63a935db49375dcd88 | CN1CCN(S(=O)(=O)c2cccc3cnccc23)CC1>>CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1 | CN1CCN(CC1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1>>CN1CCN(CC1)S(=O)(=O)C1=C2CCNCC2=CC=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[cH:15][cH:16][n:17][cH:18]3)[CH2:19][CH2:20]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[CH2:15][CH2:16][NH:17][CH2:18]3)[CH2:19][CH2:20]1 | CN1CCN(S(=O)(=O)c2cccc3cnccc23)CC1 | CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1 | null | O=[Pt]=O | CO.Cl | Reduction | OtherReaction | 613e5f968714cd0571e472149e77c06133dbd9224fea04a239b625fe26e540e1 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | O=S(=O)(c1cccc2c1CCNC2)N1CCNCC1 | [c:1]:[c:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7]:1:[c:8]>>[c:1]:[c:2]1:[c:7](:[c:8])-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[NH;D2;+0:4]-[CH2;D2;+0:3]-1 | 124.1 | [{"value": 124.1, "product": "CN1CCN(CC1)S(=O)(=O)C1=C2CCNCC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | 5-(4-Methyl-piperazine-1-sulfonyl)-isoquinoline 10a (0.99 g, 3.41 mmol) was dissolved in a solution 2% of HCl in methanol (100 mL) under nitrogen. PtO2 (250 mg) was added under nitrogen and the mixture was hydrogenated in a Parr apparatus at 45 psi for 3.5 h. The catalyst was removed by filtration, rinsed with MeOH, an... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2cnccc2c1 | c1ccc2c(c1)CCNC2 | C1C[NH]CC[NH]1.c1ccc2c(c1)CCNC2 | null | O=[Pt]=O.CO.Cl | null | 3.5 | CN1CCN(S(=O)(=O)c2cccc3cnccc23)CC1>O=[Pt]=O.CO.Cl>CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b5833061e994ba492232cab6c831781 | CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>>COc1cc2nc(N3CCc4c(cccc4S(=O)(=O)N4CCN(C)CC4)C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.CN1CCN(CC1)S(=O)(=O)C1=C2CCNCC2=CC=C1.C(C)N(CC)CC>>COC=1C=C2C(NC(=NC2=CC1OC)N1CC2=CC=CC(=C2CC1)S(=O)(=O)N1CCN(CC1)C)=O | [NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][cH:14][cH:15][c:16]2[S:17](=[O:18])(=[O:19])[N:20]2[CH2:21][CH2:22][N:23]([CH3:24])[CH2:25][CH2:26]2)[CH2:27]1.Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][c:31]2[c:29](=[O:30])[nH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:1... | CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC | COc1cc2nc(N3CCc4c(cccc4S(=O)(=O)N4CCN(C)CC4)C3)[nH]c(=O)c2cc1OC | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1ff4e7e247e9c5784772ca9bff631974543ef5b92189117ec9f9de2907d7e038 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3c(cccc3S(=O)(=O)N3CCNCC3)C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9]-[c:10] | 37.2 | [{"value": 37.2, "product": "COC=1C=C2C(NC(=NC2=CC1OC)N1CC2=CC=CC(=C2CC1)S(=O)(=O)N1CCN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b, (0.77 g, 3.23 mmol), 5-(4-methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 11a (1.25 g, 3.41 mmol) and triethylamine (0.75 g, 1.04 mL, 7.46 mmol) in DMSO (15 mL) was heated at 80° C. with stirring for 18 h. After cooling to room temperature the re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC2.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2.C1C[NH]CC[NH]1 | HCl | CS(=O)C.O | 80 | 18 | CN1CCN(S(=O)(=O)c2cccc3c2CCNC3)CC1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>CS(=O)C.O>COc1cc2nc(N3CCc4c(cccc4S(=O)(=O)N4CCN(C)CC4)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1072292ad8ec44c99727818e337ae56f | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1ccc(Cn2cnc3c2CCNC3)cc1>>COc1cc2nc(N3CCc4c(ncn4Cc4ccccc4)C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.Cl.Cl.C(C1=CC=CC=C1)N1C=NC=2CNCCC21.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)N1C=NC=2CN(CCC21)C2=NC1=CC(=C(C=C1C(N2)=O)OC)OC | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]2[c:25](=[O:26])[nH:24]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([n:13][cH:14][n:15]2[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([n:13][cH:14][n:15]4[... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1ccc(Cn2cnc3c2CCNC3)cc1 | COc1cc2nc(N3CCc4c(ncn4Cc4ccccc4)C3)[nH]c(=O)c2cc1OC | null | null | O.COCCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3311afbd07f332ac7995590774c6354aa8f5e90a24b463f964b7af8133f0252c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3c(ncn3Cc3ccccc3)C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-1>>[#7;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:13]-1 | 29.9 | [{"value": 29.9, "product": "C(C1=CC=CC=C1)N1C=NC=2CN(CCC21)C2=NC1=CC(=C(C=C1C(N2)=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 6 | HOUR | A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1 (wherein R is methyl and Z is —C(O)—, 296 mg, 1.24 mmol), 1-benzyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine dihydrochloride 15a (440 mg, 1.54 mmol)) and diisopropylethylamine (1.2 g, 9.26 mmol) in 2-methoxyethanol (10 mL) was stirred at 120° C. for 6 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2 | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2 | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2.c1ccccc1 | HCl | O.COCCO | 120 | 6 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.c1ccc(Cn2cnc3c2CCNC3)cc1>O.COCCO>COc1cc2nc(N3CCc4c(ncn4Cc4ccccc4)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43a2b6c9e1a140b48fd022c4ada43800 | CCOC1(OCC)CCN(Cc2ccccc2)CC1N.Cc1cccc(N=C=S)c1>>Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1 | C(C1=CC=CC=C1)N1CC(C(CC1)(OCC)OCC)N.C1(=CC(=CC=C1)N=C=S)C>>C(C1=CC=CC=C1)N1CC2=C(CC1)N(C=N2)C=2C=C(C=CC2)C | CCO[C:11]1(OCC)[CH:10]([NH2:9])[CH2:22][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:13][CH2:12]1.S=[C:8]=[N:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2... | CCOC1(OCC)CCN(Cc2ccccc2)CC1N.Cc1cccc(N=C=S)c1 | Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ed278620f95c2efbdc16a499ee8fcaf07a4a0160d013f86b093183abd613fb1f | 1a32a4806b500e20dcc9d9b774d5d133de4f13903adf9dcc3a46113880d0c233 | c1ccc(CN2CCc3c(ncn3-c3ccccc3)C2)cc1 | C-C-O-[C;H0;D4;+0:1]1(-O-C-C)-[C:2]-[C:3]-[#7:4](-[C:5])-[C:6]-[CH;D3;+0:7]-1-[NH2;D1;+0:8].S=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:5]-[#7:4]1-[C:3]-[C:2]-[c;H0;D3;+0:1]2:[c;H0;D3;+0:7](:[n;H0;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D3;+0:10]:2-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15... | 74.9 | [{"value": 74.9, "product": "C(C1=CC=CC=C1)N1CC2=C(CC1)N(C=N2)C=2C=C(C=CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-benzyl-4,4-diethoxy-piperidin-3-ylamine 16 (600 mg, 2.2 mmol), and m-tolyl isothiocyanate (328 mg, 2.2 mmol) in 10 mL chloroform was heated at 60° C. for 2 hr. The solvent was removed in vacuo, and the residue was treated with 10 mL each of 10% hydrochloric acid and dioxane and heated at reflux for 1 h.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Isothiocyanate | null | C1CC[NH]CC1 | c1nc2c([nH]1)CCNC2 | c1ccccc1.c1nc2c([nH]1)CCNC2.c1ccccc1 | Other | C(Cl)(Cl)Cl | null | null | CCOC1(OCC)CCN(Cc2ccccc2)CC1N.Cc1cccc(N=C=S)c1>C(Cl)(Cl)Cl>Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8fb1c319e5948b89f7e69697197210e | Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1>>Cc1cccc(-n2cnc3c2CCNC3)c1 | C(C1=CC=CC=C1)N1CC2=C(CC1)N(C=N2)C=2C=C(C=CC2)C.C(=O)[O-].[NH4+]>>C1(=CC(=CC=C1)N1C=NC=2CNCCC21)C | c1ccc(C[N:14]2[CH2:13][CH2:12][c:11]3[n:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:16]4)[cH:8][n:9][c:10]3[CH2:15]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]2[CH2:12][CH2:13][NH:14][CH2:15]3)[cH:16]1 | Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1 | Cc1cccc(-n2cnc3c2CCNC3)c1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 95f82a72138b22cacaa3205bfe11b7cf593e1e6f06783aa60e3b8cbdb2677263 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(-n2cnc3c2CCNC3)cc1 | [#7;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[N;H0;D3;+0:6](-C-c2:c:c:c:c:c:2)-[C:7]-[C:8]-1>>[#7;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1 | 32.2 | [{"value": 32.2, "product": "C1(=CC(=CC=C1)N1C=NC=2CNCCC21)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 17a (500 mg, 1.6 mmol), ammonium formate (1.0 g), and 700 mg 5% Pd/C (50% with water) in 80% aqueous methanol was heated at reflux for 12 hr, and then allowed to reach ambient temperature. The catalyst was removed by filtration through Celite®... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1nc2c(n1)CNCC2 | c1nc2c([nH]1)CCNC2 | c1ccccc1.c1nc2c([nH]1)CCNC2 | Other | [Pd].CO | null | null | Cc1cccc(-n2cnc3c2CCN(Cc2ccccc2)C3)c1>[Pd].CO>Cc1cccc(-n2cnc3c2CCNC3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c8bf22c88d141f18e9c170291be32b9 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Cc1cccc(-n2cnc3c2CCNC3)c1>>COc1cc2nc(N3CCc4c(ncn4-c4cccc(C)c4)C3)[nH]c(=O)c2cc1OC | C(C)O.C1(=CC(=CC=C1)N1C=NC=2CNCCC21)C.ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.C(C)N(CC)CC>>COC=1C=C2C(NC(=NC2=CC1OC)N1CC2=C(CC1)N(C=N2)C=2C=C(C=CC2)C)=O | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]2[c:25](=[O:26])[nH:24]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([n:13][cH:14][n:15]2-[c:16]2[cH:17][cH:18][cH:19][c:20]([CH3:21])[cH:22]2)[CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([n:13][cH:14][n:15]... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Cc1cccc(-n2cnc3c2CCNC3)c1 | COc1cc2nc(N3CCc4c(ncn4-c4cccc(C)c4)C3)[nH]c(=O)c2cc1OC | null | null | COC(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3311afbd07f332ac7995590774c6354aa8f5e90a24b463f964b7af8133f0252c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3c(ncn3-c3ccccc3)C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-1>>[#7;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:13]-1 | 56.9 | [{"value": 56.9, "product": "COC=1C=C2C(NC(=NC2=CC1OC)N1CC2=C(CC1)N(C=N2)C=2C=C(C=CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 18a (100 mg, 0.5 mmol), 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (100 mg, 0.4 mmol), and triethylamine (140 μL, 1.0 mmol) in 10 mL methoxyethanol was heated at 100° C. under nitrogen for 12 hr. The mixture was pumped to constant weight. The result... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2 | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2 | c1ccc2ncncc2c1.c1nc2c(n1)CNCC2.c1ccccc1 | HCl | COC(C)O | 100 | null | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Cc1cccc(-n2cnc3c2CCNC3)c1>COC(C)O>COc1cc2nc(N3CCc4c(ncn4-c4cccc(C)c4)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bc234eebe6d4b799fd9189d98124c56 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1>>CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1 | C(C)(C)(C)[Li].C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)Br.C(=O)N1CCOCC1.[Cl-].[NH4+]>>C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=O | Br[c:12]1[c:11]2[c:18]([cH:17][cH:16][cH:15]1)[CH2:19][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([CH:13]=[O:14])[cH:15][cH:16][cH:17][c:18]2[CH2:19]1 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1 | CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1 | null | null | C(C)OCC | Oxidation | OtherReaction | 8af97f706bbbcd5819591de005a520e471e6793297b389dc496648e77f674dc6 | c25c3c47812a3895da25740aba48490812213ba83ecb1b4955751c5b0488c20c | c1ccc2c(c1)CCNC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[C:7]=[O;D1;H0:8]):[c:2]:[c:3] | 13.6 | [{"value": 13.6, "product": "C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 19a (3.87 g, 12.39 mmol) in diethyl ether (60 mL) was cooled to −100° C. A solution of 1.7 M tert-butyllithium in hexanes (16.04 mL, 27.27 mmol) was added dropwise. After the addition, stirring was continued for 30 min to −100° C. 4-Fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aldehyde | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | Br- | C(C)OCC | null | null | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1>C(C)OCC>CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8ea807d82c04522b1c9cb4cd3a35d20 | CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1>>CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1 | [Cl-].[NH4+].O.C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=O.[BH4-].[Na+]>>C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)CO | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([CH:13]=[O:14])[cH:15][cH:16][cH:17][c:18]2[CH2:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([CH2:13][OH:14])[cH:15][cH:16][cH:17][c:18]2[CH2:19]1 | CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1 | CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1 | null | null | CO.O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc2c(c1)CCNC2 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 68.8 | [{"value": 68.8, "product": "C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To solution of 5-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 20a (0.44 g, 1.71 mmol) in 40 mL of methanol:tetrahydrofuran (1:1) at room temperature was added sodium borohydride (0.072 g, 1.88 mmol), and the mixture was stirred to room temperature for 3 h. Water (30 mL) was added followed by am... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2c(c1)CC[NH]C2 | null | CO.O1CCCC1 | null | 3 | CC(C)(C)OC(=O)N1CCc2c(C=O)cccc2C1>CO.O1CCCC1>CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e091e38504240cf8d9c4b35fff48911 | CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>>COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)CO.O>>OCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC | CC(C)(C)OC(=O)[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([CH2:13][OH:14])[cH:15][cH:16][cH:17][c:18]2[CH2:19]1.Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]2[c:21](=[O:22])[nH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([CH2:13][OH:14])[cH:15][cH:16][cH:17... | CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC | COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC | null | null | ClCCl.CS(=O)C.FC(C(=O)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | d8508fbf0df3f9944b9a3264c49fae455b02e0e7017d931f736be1954f394f61 | a3c10143aa973a08115e889684e6f4517b7b8ca98c2e86f00b66594b81b483ed | O=c1[nH]c(N2CCc3ccccc3C2)nc2ccccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[C:5].Cl-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10]>>[C:5]-[C:4]-[N;H0;D3;+0:1](-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10])-[C:2]-[c:3] | 49 | [{"value": 49.0, "product": "OCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 2 | HOUR | 5-Hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 21a (0.31 g, 1.17 mmol) was dissolved at room temperature in 10 mL of 10% trifluoroacetic acid in dichloromethane and stirred for 2 h. The volatiles were evaporated, the residue was suspended in toluene, evaporated again and dried under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Tertiary amine | c1ccc2c(c1)CC[NH]C2.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | HCl | ClCCl.CS(=O)C.FC(C(=O)O)(F)F | 85 | 2 | CC(C)(C)OC(=O)N1CCc2c(CO)cccc2C1.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>ClCCl.CS(=O)C.FC(C(=O)O)(F)F>COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-317689f8948d406fac788d164b7bfba0 | Br.COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC>>COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC | OCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.Br>>BrCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC | [BrH:14].O[CH2:13][c:12]1[c:11]2[c:18]([cH:17][cH:16][cH:15]1)[CH2:19][N:8]([c:7]1[n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]3[c:21](=[O:22])[nH:20]1)[CH2:9][CH2:10]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([CH2:13][Br:14])[cH:15][cH:16][cH:17][c:18]4[CH2... | Br.COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC | COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC | null | null | null | Miscellaneous | OtherReaction | cd3478bc4d4e901afd9352e983cdb4ff4c2fc601772cf0af2f0553c983f9121c | 9b4091cd4cf205a0767d592c748f58d9aed076d9567056ed2bfdc4af71bd7267 | O=c1[nH]c(N2CCc3ccccc3C2)nc2ccccc12 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "BrCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 2-(5-Hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-1H-quinazolin-4-one 22a (0.2 g, 0.54 mmol) was dissolved to room temperature in 5 mL of 48% hydrobromic acid and stirred to room temperature for 24 h. The precipitated product was separated by filtration, rinsed with water, dried to yield 0.21 g (91%) 2-... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | HO- | null | null | 24 | Br.COc1cc2nc(N3CCc4c(CO)cccc4C3)[nH]c(=O)c2cc1OC>>COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0069b677ce942f195f1c19229813036 | C1COCCN1.COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC>>COc1cc2nc(N3CCc4c(CN5CCOCC5)cccc4C3)[nH]c(=O)c2cc1OC | O.BrCC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.N1CCOCC1.C([O-])(O)=O.[Na+]>>COC=1C=C2C(NC(=NC2=CC1OC)N1CC2=CC=CC(=C2CC1)CN1CCOCC1)=O | [NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.Br[CH2:13][c:12]1[c:11]2[c:23]([cH:22][cH:21][cH:20]1)[CH2:24][N:8]([c:7]1[n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][c:28]3[c:26](=[O:27])[nH:25]1)[CH2:9][CH2:10]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([CH2:13]... | C1COCCN1.COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC | COc1cc2nc(N3CCc4c(CN5CCOCC5)cccc4C3)[nH]c(=O)c2cc1OC | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]c(N2CCc3c(CN4CCOCC4)cccc3C2)nc2ccccc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1):[c:4] | null | [] | 80 | CELSIUS | 18 | HOUR | A mixture of 2-(5-bromomethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-3H-quinazolin-4-one 23a (54 mg, 0.12 mmol), morpholine (12 mg, 0.13 mmol) and sodium bicarbonate (16 mg, 0.18 mmol) in dimethyl sulfoxide (0.5 mL) was heated to 80° C. with stirring for 18 h. After cooling to room temperature, water (2 mL) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)CC[NH]C2 | HBr | CS(=O)C | 80 | 18 | C1COCCN1.COc1cc2nc(N3CCc4c(CBr)cccc4C3)[nH]c(=O)c2cc1OC>CS(=O)C>COc1cc2nc(N3CCc4c(CN5CCOCC5)cccc4C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ceeddba39e0c466fa26fb10a6049ce5d | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1cccc2c1CCNC2>>COc1cc2nc(N3CCc4c(N)cccc4C3)[nH]c(=O)c2cc1OC | C1NCCC2=C(C=CC=C12)N.ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC>>NC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23][c:22]2[c:20](=[O:21])[nH:19]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([NH2:13])[cH:14][cH:15][cH:16][c:17]2[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([NH2:13])[cH:14][cH:15][cH:16][c:17]4[CH2:18]3)[nH:19][c... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1cccc2c1CCNC2 | COc1cc2nc(N3CCc4c(N)cccc4C3)[nH]c(=O)c2cc1OC | null | null | COC(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1ff4e7e247e9c5784772ca9bff631974543ef5b92189117ec9f9de2907d7e038 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3ccccc3C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9]-[c:10] | 49.7 | [{"value": 49.7, "product": "NC1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 48 | HOUR | A mixture of 1,2,3,4-tetrahydro-isoquinolin-5-ylamine 24a (3.83 g, 25.84 mmol) and 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (5.9 g, 24.54 mmol) in methoxyethanol (60 mL) was heated to 60° C. with stirring for 48 h. The volatiles were evaporated and the residue was purified by flash column chromatography eluting wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1ccc2c(c1)CCNC2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | HCl | COC(C)O | 60 | 48 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1cccc2c1CCNC2>COC(C)O>COc1cc2nc(N3CCc4c(N)cccc4C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8a4a9cfb4e24026804bd3e8127fe6d1 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.N#CN1CCOCC1>>CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1 | N1(CCOCC1)C#N.[OH-].[NH4+].C(CCC)[Li].[Cl-].[NH4+].C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)Br>>C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C(N1CCOCC1)=N | Br[c:16]1[c:11]2[c:12]([cH:13][cH:14][cH:15]1)[CH2:25][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2.[C:17](#[N:18])[N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][cH:14][cH:15][c:16]2[C:17](=[NH:18])[N:1... | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.N#CN1CCOCC1 | CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 15346732c69d7492878389a728b15a5fe22266a12e3b38783a2d42cc26af5dbb | ba2ab38364cf2db116b4f899e50082ce53deaab9b1c45da9b81342ede92f81bf | N=C(c1cccc2c1CCNC2)N1CCOCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6].[C:7]-[#7:8](-[C;H0;D2;+0:9]#[N;H0;D1;+0:10])-[C:11]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[#7:8](-[C:7])-[C:11]):[c:2]:[c:3] | 54.3 | [{"value": 54.3, "product": "C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C(N1CCOCC1)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 26a (0.4 g, 1.28 mmol) in tetrahydrofuran (10 mL) under argon, was cooled to −78° C. A solution of 2.5 M n-butyllithium in hexanes (0.61 mL, 1.53 mmol) was added dropwise over 5 min. After the addition, stirring was continued for 15 mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Cyanamide | null | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2.C1COCC[NH]1 | Br- | O1CCCC1 | null | 0.25 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.N#CN1CCOCC1>O1CCCC1>CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0008c02400784d04915e7583d17b8539 | CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1>>N=C(c1cccc2c1CCNC2)N1CCOCC1 | C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C(N1CCOCC1)=N>>N=C(C1=C2CCNCC2=CC=C1)N1CCOCC1 | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][c:8]2[c:3]([C:2](=[NH:1])[N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[cH:4][cH:5][cH:6][c:7]2[CH2:12]1>>[NH:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][CH2:10][NH:11][CH2:12]2)[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1 | N=C(c1cccc2c1CCNC2)N1CCOCC1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | acbecc2fe3298c7b9fe71052b8ac801d3dd977be469b0445320e26e414cad87c | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | N=C(c1cccc2c1CCNC2)N1CCOCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[c:5] | 105.7 | [{"value": 105.7, "product": "N=C(C1=C2CCNCC2=CC=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 5-(Imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 27a (0.24 g, 0.69 mmol) was dissolved to room temperature in 10 mL of 10% trifluoroacetic acid in dichloromethane and stirred to room temperature for 18 h. The volatiles were evaporated, the residue was suspended in toluene a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.C1COCC[NH]1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 18 | CC(C)(C)OC(=O)N1CCc2c(cccc2C(=N)N2CCOCC2)C1>ClCCl.FC(C(=O)O)(F)F>N=C(c1cccc2c1CCNC2)N1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-75d4b318f11f4445b2f0c64e9eaf1b7a | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.N=C(c1cccc2c1CCNC2)N1CCOCC1>>COc1cc2nc(N3CCc4c(cccc4C(=N)N4CCOCC4)C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.N=C(C1=C2CCNCC2=CC=C1)N1CCOCC1>>N=C(C1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC)N1CCOCC1 | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][c:29]2[c:27](=[O:28])[nH:26]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][cH:14][cH:15][c:16]2[C:17](=[NH:18])[N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([c... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.N=C(c1cccc2c1CCNC2)N1CCOCC1 | COc1cc2nc(N3CCc4c(cccc4C(=N)N4CCOCC4)C3)[nH]c(=O)c2cc1OC | null | null | COC(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1ff4e7e247e9c5784772ca9bff631974543ef5b92189117ec9f9de2907d7e038 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | N=C(c1cccc2c1CCN(c1nc3ccccc3c(=O)[nH]1)C2)N1CCOCC1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9]-[c:10] | 17.9 | [{"value": 17.9, "product": "N=C(C1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 18 | HOUR | A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b(0.159 g, 0.62 mmol) and 5-(imino-morpholin-4-yl-methyl)-3,4-dihydro-1H-isoquinoline 28a (0.179 g, 0.69 mmol) in methoxyethanol (10 mL) was heated to 95° C. with stirring for 18 h. the volatiles were evaporated and the residue was purified by flash column elutin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1ccc2c(c1)CCNC2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2.C1COCC[NH]1 | HCl | COC(C)O | 95 | 18 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.N=C(c1cccc2c1CCNC2)N1CCOCC1>COC(C)O>COc1cc2nc(N3CCc4c(cccc4C(=N)N4CCOCC4)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fa2eca5f3db433194f7dea595645644 | CC(C)(C)OC(=O)Nc1ccncc1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C | C(CCC)[Sn](CCCC)(CCCC)Cl.C(C)(C)(C)[Li].C(C)(C)(C)OC(NC1=CC=NC=C1)=O.[Cl-].[NH4+]>>C(C)(C)(C)OC(NC1=C(C=NC=C1)[Sn](CCCC)(CCCC)CCCC)=O | [cH:14]1[cH:15][n:16][cH:17][cH:18][c:19]1[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].[Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15... | CC(C)(C)OC(=O)Nc1ccncc1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 157ed86a47fdc4e2a8a8cbaf40c9e8c836526372fc356d6404550bda901a11a9 | 8ed099106fd03cd2d2d78800a2ee5fc34a9ebd85fa643ab7cdafec1855cc2f69 | c1ccncc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[cH;D2;+0:14]:1.[C:15]-[C:16]-[Sn;H0;D4;+0:17](-[Cl])(-[C:18]-[C:19])-[C:20]-[C:21]>>[C:15]-[C:16]-[Sn;H0;D4;+0:17](-[C:18]-[C:19])(-[C:20]-[C:21])-[c;H0;D3;+0:14]1:[c:13]:[#7;a:12]:[c:11]:[c:10]:[c:9]:... | 49 | [{"value": 49.0, "product": "C(C)(C)(C)OC(NC1=C(C=NC=C1)[Sn](CCCC)(CCCC)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 3 | HOUR | Pyridin-4-yl-carbamic acid tert-butyl ester (1.74 g, 8.95 mmol) (prepared as described in Venuti et al, J. Med. Chem. 1988, 31(11), 2136–45) dissolved in THF (150 mL) was cooled to −78° C. and a solution of 1.7M tert-butyllithium in hexanes (11.6 mL, 19.70 mmol) was added dropwise. After the addition, the stirring was ... | 10.6084/m9.figshare.5104873.v1 | null | Tin | Tin | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C1CCOC1 | -78 | 3 | CC(C)(C)OC(=O)Nc1ccncc1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3790869c00564abb9c3ed13443381966 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2 | C(C)(C)(C)OC(NC1=C(C=NC=C1)[Sn](CCCC)(CCCC)CCCC)=O.C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)Br.C1(CCCCC1)PC1=C(C=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=1C=NC=CC1NC(=O)OC(C)(C)C | Br[c:15]1[cH:16][cH:17][cH:18][c:19]2[c:20]1[CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:14]1[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:10][cH:11][n:12][cH:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:... | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 5a6c2e45db0aab3d9b0014f047324801e5a8a5f70d13509dc622ce00409128b5 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1cncc(-c2cccc3c2CCNC3)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:1-[#7:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]... | 29.4 | [{"value": 29.4, "product": "C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=1C=NC=CC1NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 24 | HOUR | A mixture of (3-tributylstannyl-pyridin-4-yl)-carbamic acid tert-butyl ester (0.7 g, 1.44 mmol), 5-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.45 g, 1.44 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.066 g, 0.072 mmol) and 2-(cyclohexylphosphino)biphenyl (0.075 g, 0.216 mmol), in toluen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CC[NH]C2 | c1ccncc1.c1ccc2c(c1)CC[NH]C2 | HBr.Sn | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 100 | 24 | CC(C)(C)OC(=O)N1CCc2c(Br)cccc2C1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnccc1NC(=O)OC(C)(C)C>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22d804a479bd47db9e903fb2062703f6 | CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2>>Nc1ccncc1-c1cccc2c1CCNC2 | C(C)(C)(C)OC(=O)N1CC2=CC=CC(=C2CC1)C=1C=NC=CC1NC(=O)OC(C)(C)C>>C1NCCC2=C(C=CC=C12)C=1C=NC=CC1N | CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][CH2:15][N:16](C(=O)OC(C)(C)C)[CH2:17]2>>[NH2:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][CH2:15][NH:16][CH2:17]2 | CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2 | Nc1ccncc1-c1cccc2c1CCNC2 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | OtherReaction | f34fce985f62899a32b2c49d2ba1de62640ed24c67a7e9a574e7958834d5ed29 | 68165f9baedb06aa1415877b4a52e24af10dfeedf018f215590ed608ec495114 | c1cncc(-c2cccc3c2CCNC3)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[c:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | 79.3 | [{"value": 79.3, "product": "C1NCCC2=C(C=CC=C12)C=1C=NC=CC1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 5-(4-tert-Butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.18 g, 0.42 mmol) was dissolved at room temperature in 20 mL of 10% trifluoroacetic acid in dichloromethane and stirred to room temperature for 18 h. The volatiles were evaporated, the residue was suspended in t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Primary amine.Secondary amine | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1ccncc1.c1ccc2c(c1)CCNC2 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 18 | CC(C)(C)OC(=O)Nc1ccncc1-c1cccc2c1CCN(C(=O)OC(C)(C)C)C2>ClCCl.FC(C(=O)O)(F)F>Nc1ccncc1-c1cccc2c1CCNC2 |
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