dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84ee1e6a9b744bc79c90db211d05d9ac | O=C(OC(=C(F)F)C(F)(F)F)c1ccccc1.O=S([O-])O>>O=C(OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-])c1ccccc1 | C1(=CC=CC=C1)C.C(C1=CC=CC=C1)(=O)OC(=C(F)F)C(F)(F)F.S(=O)(O)[O-].[Na+].C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.[Na+] | [O:1]=[C:2]([O:3][C:4]([C:5]([F:6])([F:7])[F:8])=[C:9]([F:10])[F:11])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[S:12](=[O:13])([O-:14])[OH:15]>>[O:1]=[C:2]([O:3][CH:4]([C:5]([F:6])([F:7])[F:8])[C:9]([F:10])([F:11])[S:12](=[O:13])(=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(OC(=C(F)F)C(F)(F)F)c1ccccc1.O=S([O-])O | O=C(OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-])c1ccccc1 | null | null | O | Oxidation | OtherReaction | b1f7bfda754b564913c1f9e6b260c024a115180a5bc46c540d6b0a998e890b91 | ae6c4bc8dfaf574d2738b3cae60fd320541c663131907e5329598256fee39954 | c1ccccc1 | [F;D1;H0:1]-[C;H0;D3;+0:2](-[F;D1;H0:3])=[C;H0;D3;+0:4](-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12].[O-;H0;D1:13]-[S;H0;D3;+0:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[F;D1;H0:1]-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[CH;D3;+0:4](-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0... | 43 | [{"value": 43.0, "product": "FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.[Na+]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 65 | HOUR | 10.0 g of 1,1,3,3,3-pentafluoropropen-2-yl benzoate which had been synthesized by a conventional technique, was dispersed in 72 g of water, after which 12.0 g of sodium hydrogen sulfite and 1.24 g of benzoyl peroxide were added. Reaction occurred at 85° C. for 65 hours. The reaction solution was allowed to cool, after ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Ester | Tertiary halide.Tertiary halide.Ester.Sulfonic acid | null | null | c1ccccc1 | null | O | null | 65 | O=C(OC(=C(F)F)C(F)(F)F)c1ccccc1.O=S([O-])O>O>O=C(OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-])c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9621656cc7a8465c96016e922cb28b82 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1>>c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | [Cl-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.[Na+]>>FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | [cH:22]1[cH:23][cH:24][c:25]([S+:26]([c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[cH:39][cH:40]1>>[cH:22]1[cH:23][cH:24][c:25]([S+:26]([c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[cH:39][cH:40]1 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | 75 | [{"value": 75.0, "product": "FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To 50 g of dichloromethane were added an amount (corresponding to 0.011 mole) of the triphenylsulfonium chloride aqueous solution of Synthesis Example 1 and 3.6 g (0.01 mole) of sodium 1,1,3,3,3-pentafluoro-2-benzoyloxy-propane-1-sulfonate synthesized in Synthesis Example 9, followed by stirring. The organic layer was ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl | null | null | c1ccc([S+](c2ccccc2)c2ccccc2)cc1>ClCCl>c1ccc([S+](c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b465b6b281246ee8402326ec4889ed5 | CC(C)(C)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1>>Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.C(C)(C)(C)OC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)(=O)O>>FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.OC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)[O:22][c:23]1[cH:24][cH:25][c:26]([S+:27]([c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[cH:40][cH:41]1>>[OH:22][c:23]1[cH:24][cH:25][c:26]([S+:27]([c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[cH:40][cH:41]1 | CC(C)(C)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | ClCCl | Deprotection | OtherReaction | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 40 | CELSIUS | 3 | HOUR | In 60 g of dichloromethane was dissolved 6.7 g of 4-tert-butoxyphenyldiphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate (PAG4) prepared in Synthesis Example 14. Methanesulfonic acid, 0.1 g, was added to the solution, which was heated and stirred at 40° C. for 3 hours. The organic layer was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl | 40 | 3 | CC(C)(C)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1>ClCCl>Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9655de8e3c684ad7ac0f71f73a5f3dc5 | C=C(C)C(=O)Cl.Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1>>C=C(C)C(=O)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | Cl.FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.OC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C(C(=C)C)(=O)Cl.C(C)N(CC)CC>>FC(C(C(F)(F)F)OC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F.C(C(=C)C)(=O)OC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]([S+:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([S+:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20]... | C=C(C)C(=O)Cl.Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | C=C(C)C(=O)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H2:4]=[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | In 15 g of dichloromethane was dissolved 3 g of (4-hydroxyphenyl)diphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate (PAG29) prepared in Synthesis Example 45. Methacryloyl chloride, 1 g, was added to the solution, which was cooled in an ice bath, and 0.9 ml of triethylamine was added dropwise. 30 g ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | C=C(C)C(=O)Cl.Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1>ClCCl>C=C(C)C(=O)Oc1ccc([S+](c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b49d4e785e224d17b74cff95d54c54be | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OC1CN(C(c2ccccc2)c2ccccc2)C1>>CC(C)(C)OC(=O)N1CCN(C2CN(C(c3ccccc3)c3ccccc3)C2)CC1 | CS(=O)(=O)OC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].N1(CCNCC1)C(=O)OC(C)(C)C>>C1(=CC=CC=C1)C(N1CC(C1)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:29][CH2:30]1.CS(=O)(=O)O[CH:12]1[CH2:13][N:14]([CH:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[... | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OC1CN(C(c2ccccc2)c2ccccc2)C1 | CC(C)(C)OC(=O)N1CCN(C2CN(C(c3ccccc3)c3ccccc3)C2)CC1 | null | null | O1CCCC1.C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | 452f4b6a22e737be3056c26c146f414df2540fb6c01938af98034e249e7f90ef | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc(C(c2ccccc2)N2CC(N3CCNCC3)C2)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[N;H0;D3;+0:9]2-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-2)-[C:5]-1 | 69 | [{"value": 69.0, "product": "C1(=CC=CC=C1)C(N1CC(C1)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | Potassium carbonate (26 g) was added to a solution of tert-butyl piperazine-1-carboxylate (7.7 g) in acetonitrile (100 ML), to which a suspension of 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (12.05 g) in tetrahydrofuran (30 mL) was added at room temperature, and the mixture was stirred for 4 hours at 100° C., an... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1.C1C[NH]C1 | C1C[NH]CC[NH]1.C1C[NH]C1 | C1C[NH]CC[NH]1.C1C[NH]C1.c1ccccc1.c1ccccc1 | MsOH.HO- | O1CCCC1.C(C)#N | 100 | 4 | CC(C)(C)OC(=O)N1CCNCC1.CS(=O)(=O)OC1CN(C(c2ccccc2)c2ccccc2)C1>O1CCCC1.C(C)#N>CC(C)(C)OC(=O)N1CCN(C2CN(C(c3ccccc3)c3ccccc3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4559a6888c6b47bd998d55458b50c4ed | CC(C)(C)OC(=O)N1CCN(C2CNC2)CC1.O=C=Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCN(C2CN(C(=O)Nc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C2)CC1 | N1CC(C1)N1CCN(CC1)C(=O)OC(C)(C)C.N(=C=O)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F>>FC(C=1C=C(C=C(C1)C(F)(F)F)NC(=O)N1CC(C1)N1CCN(CC1)C(=O)OC(C)(C)C)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[CH2:13][NH:14][CH2:32]2)[CH2:33][CH2:34]1.[C:15](=[O:16])=[N:17][c:18]1[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10... | CC(C)(C)OC(=O)N1CCN(C2CNC2)CC1.O=C=Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCN(C2CN(C(=O)Nc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C2)CC1 | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(Nc1ccccc1)N1CC(N2CCNCC2)C1 | [C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1.[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[N;H0;D3;+0:3]1-[C:2]-[C:1]-[C:4]-1 | null | [] | null | null | 30 | MINUTE | To a solution of the compound prepared in Example 2 (986 mg) in tetrahydrofuran (12 mL) was dropwise added 1-isocyanato-3,5-bis(trifluoromethyl)benzene (0.85 mL), and the mixture was stirred for 30 minutes. The reaction solution was concentrated. The residue was purified by column chromatography on silica gel (hexane:e... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]CC[NH]1.C1C[NH]C1.c1ccccc1 | null | O1CCCC1 | null | 0.5 | CC(C)(C)OC(=O)N1CCN(C2CNC2)CC1.O=C=Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1>O1CCCC1>CC(C)(C)OC(=O)N1CCN(C2CN(C(=O)Nc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b936bed2c6a04759a2f3f22a97784eeb | C=CC(=O)OC12C(F)(F)C3(OC(=O)C=C)C(F)(F)C(OC(=O)C=C)(C1(F)F)C(F)(F)C(OC(=O)C=C)(C2(F)F)C3(F)F.OC12CC3(O)CC(O)(C1)CC(O)(C2)C3>>C=CC(=O)OC12CC3(OC(=O)C=C)CC(OC(=O)C=C)(C1)C(F)C(OC(=O)C=C)(C2)C3 | FC1C2(CC3CC(CC1(C3)O)(C2)O)O.OC12CC3(CC(CC(C1)(C3)O)(C2)O)O.C(C=C)(=O)OC12C(C3(C(C(C(C(C1(F)F)(C3(F)F)OC(C=C)=O)(F)F)(C2(F)F)OC(C=C)=O)(F)F)OC(C=C)=O)(F)F>>C(C=C)(=O)OC12C(C3(CC(CC(C1)(C3)OC(C=C)=O)(C2)OC(C=C)=O)OC(C=C)=O)F | FC1(F)C2([O:9][C:10](=[O:11])[CH:12]=[CH2:13])C(F)(F)[C:15]3([O:16][C:17](=[O:18])[CH:19]=[CH2:20])[C:21](F)(F)[C:6]1([O:5][C:3]([CH:2]=[CH2:1])=[O:4])[C:30](F)(F)[C:24]([O:25][C:26](=[O:27])[CH:28]=[CH2:29])(C2(F)F)[C:22]3(F)[F:23].OC12CC3(O)CC(O)(C1)[CH2:31][C:8](O)([CH2:7]2)[CH2:14]3>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5... | C=CC(=O)OC12C(F)(F)C3(OC(=O)C=C)C(F)(F)C(OC(=O)C=C)(C1(F)F)C(F)(F)C(OC(=O)C=C)(C2(F)F)C3(F)F.OC12CC3(O)CC(O)(C1)CC(O)(C2)C3 | C=CC(=O)OC12CC3(OC(=O)C=C)CC(OC(=O)C=C)(C1)C(F)C(OC(=O)C=C)(C2)C3 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3f03ef033f2132af8e34535bbb634cf521ca3691cd7f3336593686958c583f8d | a1f03c4554a6ef89185dff801ecc674ba4ec86ccf11faec0345c4e925c59e731 | C1C2CC3CC1CC(C2)C3 | F-C1(-F)-C2(-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C;D1;H2:5])-C(-F)(-F)-[C;H0;D4;+0:6]3(-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[C;D1;H2:11])-[C;H0;D4;+0:12](-F)(-[F;D1;H0:13])-[C;H0;D4;+0:14]-1(-[#8:15]-[C:16](=[O;D1;H0:17])-[C:18]=[C;D1;H2:19])-[C;H0;D4;+0:20](-F)(-F)-[C;H0;D4;+0:21](-[#8:22]-[C:23](=[O;D1;H0:24])-[C... | null | [] | null | null | null | null | The same reactions as in Examples 1-1 to 1-4 are carried out except that 1,3,5-trihydroxyadamantane used in Example 1-1 is changed to 1,3,5,7-tetrahydroxyadamantane, whereupon formation of 1,3,5,7-tetrakisacryloyloxy(perfluoroadamantane) is confirmed. Further, formation of 2-hydro-1,3,5,7-tetrakisacryloyloxy(perfluoroa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ester.Ester.Ester.Ester.Tertiary alcohol.Tertiary alcohol.Tertiary alcohol.Tertiary alcohol | Secondary halide.Ester.Ester.Ester.Ester | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HF | null | null | null | C=CC(=O)OC12C(F)(F)C3(OC(=O)C=C)C(F)(F)C(OC(=O)C=C)(C1(F)F)C(F)(F)C(OC(=O)C=C)(C2(F)F)C3(F)F.OC12CC3(O)CC(O)(C1)CC(O)(C2)C3>>C=CC(=O)OC12CC3(OC(=O)C=C)CC(OC(=O)C=C)(C1)C(F)C(OC(=O)C=C)(C2)C3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61ea217eb45e40da9da272363ff1fda8 | O=S(=O)(O)Cl.Oc1ccc(Cl)cc1>>O=S(=O)(Cl)c1cc(Cl)ccc1O | ClC1=CC=C(C=C1)O.ClS(=O)(=O)O>>OC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl | O[S:2](=[O:1])(=[O:3])[Cl:4].[cH:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12] | O=S(=O)(O)Cl.Oc1ccc(Cl)cc1 | O=S(=O)(Cl)c1cc(Cl)ccc1O | null | null | O | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 04bb0e110ac9bc3104a40572864ecdd042b39019cff0ea96d1a0ad7c9eb6ecf3 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccccc1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[O;D1;H1:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[O;D1;H1:5]):[c:7] | 30.4 | [{"value": 30.4, "product": "OC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 20 | HOUR | 4-Chlorophenol (4 g, 31.25 mmol) was added in portions to chlorosulfonic acid (10.3 mL, 156 mmol) while cooling in an ice bath. The resulting solution was stirred at 25° C. for 20 hrs. This was then added drop-wise to ice and water resulting in an emulsion. This was extracted with CHCl3, dried (Na2SO4) and concentrated... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | 25 | 20 | O=S(=O)(O)Cl.Oc1ccc(Cl)cc1>O>O=S(=O)(Cl)c1cc(Cl)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb2c04385d94409da80ed51508944315 | C1CCNC1.O=S(=O)(Cl)c1cc(Cl)ccc1O>>O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1 | OC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl.N1CCCC1>>OC1=C(C=C(C=C1)Cl)S(=O)(=O)N1CCCC1 | [NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[OH:11]>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[OH:11])[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | C1CCNC1.O=S(=O)(Cl)c1cc(Cl)ccc1O | O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1 | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f3c6fed690e733503a3f0544b78d62f7ee997af455c39a6e6ee11bc2902547ad | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1)-[c:4](:[c:5]):[c:6] | 77.1 | [{"value": 77.1, "product": "OC1=C(C=C(C=C1)Cl)S(=O)(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 2 | HOUR | To a solution of the product of Example 44A (2.16 g, 9.51 mmol) in CHCl3 (8 mL) was added, with ice cooling, pyrrolidine (4.05 g, 57.04 mmol). The mixture was stirred at 25° C. for 2 hrs, then concentrated in vacuo. The residue was dissolved in toluene, washed with HCl and water, dried (Na2SO4) and concentrated. The re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HCl | C(Cl)(Cl)Cl | 25 | 2 | C1CCNC1.O=S(=O)(Cl)c1cc(Cl)ccc1O>C(Cl)(Cl)Cl>O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6310c3b2447f48d09b417e02269609ac | CC(C)(O)C(Cl)(Cl)Cl.O.O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1>>CC(C)(Oc1ccc(Cl)cc1S(=O)(=O)N1CCCC1)C(=O)O | [OH-].[Na+].[OH-].[Na+].OC1=C(C=C(C=C1)Cl)S(=O)(=O)N1CCCC1.O.ClC(C(C)(O)C)(Cl)Cl.[OH-].[Na+]>>ClC1=CC(=C(OC(C(=O)O)(C)C)C=C1)S(=O)(=O)N1CCCC1 | Cl[C:20](Cl)(Cl)[C:2]([CH3:1])([CH3:3])[OH:22].[OH2:21].[OH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[S:12](=[O:13])(=[O:14])[N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[S:12](=[O:13])(=[O:14])[N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20](=[O... | CC(C)(O)C(Cl)(Cl)Cl.O.O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1 | CC(C)(Oc1ccc(Cl)cc1S(=O)(=O)N1CCCC1)C(=O)O | null | null | CC(=O)C | Acylation | OtherReaction | f9e0211230eacba3ecf6f497fabdeac3597582daf98c9e05cf7898765caa3f63 | 5d1d498f693ce6dad1cfa05ea135b3f2c117b86de6eba0d7e7fe25cc06d8fd15 | O=S(=O)(c1ccccc1)N1CCCC1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[OH;D1;+0:5].[OH2;D0;+0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:3]-[C;H0;D4;+0:2](-[C;D1;H3:4])(-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C;H0;D3;+0:1](=[O;H0;D1;+0:6])-[OH;D1;+0:5] | 27 | [{"value": 27.0, "product": "ClC1=CC(=C(OC(C(=O)O)(C)C)C=C1)S(=O)(=O)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "ClC1=CC(=C(OC(C(=O)O)(C)C)C=C1)S(=O)(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1.5 | HOUR | The product of Example 44B (1.0 g, 3.82 mmol) and 1,1,1-trichloro-2-methyl-2-propanol hydrate (1.832 g, 10.32 mmol) were dissolved in acetone (8.5 mL). Powdered NaOH (0.47 g. 11.75 mmol) was added with cooling. The resulting mixture was stirred for 1.5 hr at 25° C. A second batch of powdered NaOH (0.47 g) was added and... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Tertiary alcohol.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]C1 | HCl | CC(=O)C | 25 | 1.5 | CC(C)(O)C(Cl)(Cl)Cl.O.O=S(=O)(c1cc(Cl)ccc1O)N1CCCC1>CC(=O)C>CC(C)(Oc1ccc(Cl)cc1S(=O)(=O)N1CCCC1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1bf00a05ed14ec49459628116391c7d | CCOC(=O)C(C)(C)Br.CSc1ccccc1O>>CCOC(=O)C(C)(C)Oc1ccccc1SC | CSC1=C(C=CC=C1)O.BrC(C(=O)OCC)(C)C.C(=O)([O-])[O-].[K+].[K+].O>>CC(C(=O)OCC)(C)OC1=C(C=CC=C1)SC | Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8].[OH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16][CH3:17] | CCOC(=O)C(C)(C)Br.CSc1ccccc1O | CCOC(=O)C(C)(C)Oc1ccccc1SC | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 657b1e065fabda84e4d6cc80f4d94ce754af0792c9117981e41887a4384f6981 | 2495a256265ef36132d409a6a3e2bd04c3acda5f236d910f184b0a36a846defe | c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 63.3 | [{"value": 63.0, "product": "CC(C(=O)OCC)(C)OC1=C(C=CC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "CC(C(=O)OCC)(C)OC1=C(C=CC=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 8 | HOUR | 2-Methylsulfanyl-phenol (2.00 g, 14.29 mmol), 2-bromo-2-methyl-propionic acid, ethyl ester (28 g, 142.8 mmol) and powdered K2CO3 (4.93 g, 35.7 mmol) were mixed (no solvent) and stirred at 105° C. for 8 hrs. After cooling, water and CHCl3 were added. The CHC13 was separated, dried (MgSO4) and concentrated. Xylene was ad... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(Cl)(Cl)Cl | 105 | 8 | CCOC(=O)C(C)(C)Br.CSc1ccccc1O>C(Cl)(Cl)Cl>CCOC(=O)C(C)(C)Oc1ccccc1SC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c855822450f8460db8a1c3476c0ccddb | CCOC(=O)C(C)(C)Oc1ccccc1S(C)(=O)=O>>CC(C)(Oc1ccccc1S(C)(=O)=O)C(=O)O | C(C)OC(C(C)(OC1=C(C=CC=C1)S(=O)(=O)C)C)=O.[OH-].[Na+].O>>CC(C(=O)O)(C)OC1=C(C=CC=C1)S(=O)(=O)C | CC[O:17][C:15]([C:2]([CH3:1])([CH3:3])[O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11]([CH3:12])(=[O:13])=[O:14])=[O:16]>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11]([CH3:12])(=[O:13])=[O:14])[C:15](=[O:16])[OH:17] | CCOC(=O)C(C)(C)Oc1ccccc1S(C)(=O)=O | CC(C)(Oc1ccccc1S(C)(=O)=O)C(=O)O | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 86.6 | [{"value": 86.6, "product": "CC(C(=O)O)(C)OC1=C(C=CC=C1)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1 | HOUR | The product of Example 46B (1.22 g) was dissolved in MeOH (8 mL) and treated with 50% NaOH (1.75 g, 21.27 mmol) and water (6 mL). The mixture was heated until all was soluble and stirred at 25° C. for 1 hr. The solvents were removed in vacuo, water (6 mL) was added and the solution acidified with HCl. The mixture was e... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | 25 | 1 | CCOC(=O)C(C)(C)Oc1ccccc1S(C)(=O)=O>CO>CC(C)(Oc1ccccc1S(C)(=O)=O)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93f2c6ab1ab14c4ab5215fae305be1ce | C1CCNC1.COc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(S(=O)(=O)N2CCCC2)cc1 | COC1=CC=C(C=C1)S(=O)(=O)Cl.N1CCCC1>>COC1=CC=C(C=C1)S(=O)(=O)N1CCCC1 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][cH:15]1)(=[O:8])=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | C1CCNC1.COc1ccc(S(=O)(=O)Cl)cc1 | COc1ccc(S(=O)(=O)N2CCCC2)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f3c6fed690e733503a3f0544b78d62f7ee997af455c39a6e6ee11bc2902547ad | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1)-[c:4](:[c:5]):[c:6] | 91.6 | [{"value": 91.6, "product": "COC1=CC=C(C=C1)S(=O)(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 4-Methoxy-benzenesulfonyl chloride (3.00 g, 14.52 mmol) was slowly added to a solution of pyrrolidine (5.15 g, 72.6 mmol) in CHCl3 (15 mL) with stirring at 0° C. The reaction mixture was allowed to warm up to room temperature and then stirred for 1 hour. After that the reaction mixture was concentrated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HCl | C(Cl)(Cl)Cl | 0 | null | C1CCNC1.COc1ccc(S(=O)(=O)Cl)cc1>C(Cl)(Cl)Cl>COc1ccc(S(=O)(=O)N2CCCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-557306378b6145e880550f82876e0290 | COc1ccc(S(=O)(=O)N2CCCC2)cc1>>O=S(=O)(c1ccc(O)cc1)N1CCCC1 | COC1=CC=C(C=C1)S(=O)(=O)N1CCCC1.B(Br)(Br)Br.CO>>OC1=CC=C(C=C1)S(=O)(=O)N1CCCC1 | C[O:8][c:7]1[cH:6][cH:5][c:4]([S:2](=[O:1])(=[O:3])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:10][cH:9]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | COc1ccc(S(=O)(=O)N2CCCC2)cc1 | O=S(=O)(c1ccc(O)cc1)N1CCCC1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=S(=O)(c1ccccc1)N1CCCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 35.2 | [{"value": 35.2, "product": "OC1=CC=C(C=C1)S(=O)(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 4 | MINUTE | The product of Example 48A (3.21 g, 13.3 mmol) was dissolved in CH2Cl2 (30 mL), cooled to −78° C. and treated with BBr3 (8.31 g, 3.26 mmol). The resulting dark red solution was stirred at 25° C. for 4 min, then cooled to −78° C. Methanol (100 mL) was added slowly. The solution was concentrated in vacuo. Toluene was add... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]C1 | Other | C(Cl)Cl | -78 | 0.066667 | COc1ccc(S(=O)(=O)N2CCCC2)cc1>C(Cl)Cl>O=S(=O)(c1ccc(O)cc1)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b77db34f2e8491786f47115655075b9 | NS(=O)(=O)C12CC3CC(C1)C1(OCCO1)C(C3)C2>>NS(=O)(=O)C12CC3CC(C1)C(=O)C(C3)C2 | C1COC2(C3CC4(CC(CC2C4)C3)S(=O)(=O)N)O1.Cl>>NS(=O)(=O)C12CC3C(C(CC(C1)C3)C2)=O | C1C[O:12][C:11]2(O1)[CH:9]1[CH2:8][CH:7]3[CH2:6][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])([CH2:10]1)[CH2:15][CH:13]2[CH2:14]3>>[NH2:1][S:2](=[O:3])(=[O:4])[C:5]12[CH2:6][CH:7]3[CH2:8][CH:9]([CH2:10]1)[C:11](=[O:12])[CH:13]([CH2:14]3)[CH2:15]2 | NS(=O)(=O)C12CC3CC(C1)C1(OCCO1)C(C3)C2 | NS(=O)(=O)C12CC3CC(C1)C(=O)C(C3)C2 | null | null | C1CCOC1 | Miscellaneous | Ketal hydrolysis to ketone | 5e47be960d7fbdb207b9b9dbe1fe2b4f63cc30824f7091697d9f1001f9047d54 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1C2CC3CC(C2)CC1C3 | [C:1]-[C:2](-[C:3])-[C;H0;D4;+0:4]1(-O-C-C-[O;H0;D2;+0:5]-1)-[C:6](-[C:7])-[C:8]>>[C:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6](-[C:7])-[C:8] | 82.9 | [{"value": 82.0, "product": "NS(=O)(=O)C12CC3C(C(CC(C1)C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "NS(=O)(=O)C12CC3C(C(CC(C1)C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of the product of Example 54G (1.26 g, 4.63 mmol) in THF (15 mL) at room temperature was treated with 1N hydrochloric acid (14 mL). Reaction heated at 60° C. for 16 hours. Reaction quenched with saturated sodium bicarbonate, and product extracted with 20% methanol in chloroform (2×) and 40% THF in DCM (2×). ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COC2(O1)C1CC3CC(C1)CC2C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HO- | C1CCOC1 | 60 | null | NS(=O)(=O)C12CC3CC(C1)C1(OCCO1)C(C3)C2>C1CCOC1>NS(=O)(=O)C12CC3CC(C1)C(=O)C(C3)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cc48679897047b0bda71072e48bac8f | CCOC(=O)C1(Br)CCC1.Oc1ccc(Cl)cc1>>CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O | ClC1=CC=C(C=C1)O.BrC1(CCC1)C(=O)OCC.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>C(C)C1C(CC1)(C(=O)O)OC1=CC=C(C=C1)Cl | Br[C:6]1([C:15](=[O:16])[O:17][CH2:2][CH3:1])[CH2:3][CH2:4][CH2:5]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][CH:3]1[CH2:4][CH2:5][C:6]1([O:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[C:15](=[O:16])[OH:17] | CCOC(=O)C1(Br)CCC1.Oc1ccc(Cl)cc1 | CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e09aabc05b102a3d84aae77bd288e094aeb3f2953d35502f4395a6ac7548058a | 0467a5c35322759787dd1b958473fb65e33c56f7a3b8b3e943e940fdfc0e4cef | c1ccc(OC2CCC2)cc1 | Br-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:5]-[C;D1;H3:6])-[C:7]-[C:8]-[CH2;D2;+0:9]-1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:6]-[CH2;D2;+0:5]-[CH;D3;+0:9]1-[C:8]-[C:7]-[C;H0;D4;+0:1]-1(-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 26 | [{"value": 26.0, "product": "C(C)C1C(CC1)(C(=O)O)OC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 57.5 | CELSIUS | null | null | A mixture of p-chlorophenol (621 mg, 4.83 mmol), ethyl 1-bromocyclobutanecarboxylate (1.0 g, 4.83 mmol) and potassium carbonate (1.33 g, 9.66 mmol) in DMF (14.5 ml) was stirred and heated to about 55-60° C. under a nitrogen atmosphere for about 18 hours. The solvent was removed under high vacuum, the residue was taken ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | C1CCC1 | C1CCC1 | C1CCC1.c1ccccc1 | HBr | null | 57.5 | null | CCOC(=O)C1(Br)CCC1.Oc1ccc(Cl)cc1>>CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4e0d1e3bbbf4734b60b41d7e0fbd0f7 | CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O>>O=C(O)C1(Oc2ccc(Cl)cc2)CCC1 | C(C)C1C(CC1)(C(=O)O)OC1=CC=C(C=C1)Cl.Cl>>ClC1=CC=C(OC2(CCC2)C(=O)O)C=C1 | CC[CH:15]1[C:4]([C:2](=[O:1])[OH:3])([O:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][CH2:14]1>>[O:1]=[C:2]([OH:3])[C:4]1([O:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][CH2:14][CH2:15]1 | CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O | O=C(O)C1(Oc2ccc(Cl)cc2)CCC1 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | f61ffc391646211cd78b94c95eddfe1e8c8a274f5e8a37324ae1175dc941e5c4 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(OC2CCC2)cc1 | C-C-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1(-[#8:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]>>[#8:5]-[C:4]1(-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | 87.5 | [{"value": 87.0, "product": "ClC1=CC=C(OC2(CCC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "ClC1=CC=C(OC2(CCC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To the product of Example 55A (320 mg, 1.26 mmol) was added glacial acetic acid (10 ml) followed by 5% aqueous hydrochloric acid (2.5 ml) and the mixture was heated to reflux for about 18 hours. The mixture was cooled and was evaporated to dryness. The residue was taken up in toluene and was evaporated to dryness two t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCC1 | C1CCC1 | c1ccccc1.C1CCC1 | Other | C(C)(=O)O | null | null | CCC1CCC1(Oc1ccc(Cl)cc1)C(=O)O>C(C)(=O)O>O=C(O)C1(Oc2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d05dd29f2db04dc4804249e9be8624c8 | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)c2ccccc2n1>>Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1 | O.[OH-].[Na+].Cl.ClCC1=CC(=NC2=CC=CC=C12)C.CS(=O)(=O)C1=CC=C(C=C1)O.[OH-].[Na+]>>CS(=O)(=O)C1=CC=C(OCC2=CC(=NC3=CC=CC=C23)C)C=C1 | [OH:6][c:7]1[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]1.Cl[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:23][c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[... | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)c2ccccc2n1 | Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccnc3ccccc23)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1):[c:11] | 93.5 | [{"value": 93.5, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=NC3=CC=CC=C23)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.5, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=NC3=CC=CC=C23)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 7.23 g (29.6 mmol) of 4-chloromethyl-2-methylquinoline hydrochloride and 5.61 g (32.6 mmol) of 4-methylsulfonylphenol in ethanol (26 mL) was added 17.1 mL (68.1 mmol) of 4 N aqueous sodium hydroxide, followed by heating under reflux for 5 hours. After standing to cool, water (150 mL) and 4 N aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | C(C)O | null | 0.333333 | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)c2ccccc2n1>C(C)O>Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f594dc67e90472b9b1290cb3a5d457c | C=C1CCC(C(=O)OC)CC1.CC(C)[N-]C(C)C.CCCCCC.CCCCCCC.CCc1ccccc1.O=S(=O)(O)O>>C=C1CCC(C(=O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)CC1 | C([O-])(O)=O.[Na+].C(C)(C)[N-]C(C)C.[Li+].CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1.C=C1CCC(CC1)C(=O)OC.S(O)(O)(=O)=O>>C=C1CCC(CC1)C(CS(=O)(=O)C1=CC=C(C=C1)OCC1=CC(=NC2=CC=CC=C12)C)=O | [CH2:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[O:16][CH3:8])[CH2:31][CH2:32]1.CC(C)[N-:22][CH:20]([CH3:19])[CH3:21].[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CCCCC[CH2:17][CH3:18].CC[c:12]1[cH:13][cH:14][cH:15][cH:29][cH:30]1.O[S:9](O)(=[O:10])=[O:11]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[CH2:8][S:... | C=C1CCC(C(=O)OC)CC1.CC(C)[N-]C(C)C.CCCCCC.CCCCCCC.CCc1ccccc1.O=S(=O)(O)O | C=C1CCC(C(=O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)CC1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | b59198bf65b368e8ab806b4314b7375197ed61606e5977cd41831e8debc28244 | d973dcd0b5af8297637ec111ba0c7b494339493ab8c0d7d86d2ddc352e8ddba2 | C=C1CCC(C(=O)CS(=O)(=O)c2ccc(OCc3ccnc4ccccc34)cc2)CC1 | C-C(-C)-[N-;H0;D2:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[CH3;D1;+0:4].C-C-C-C-C-[CH2;D2;+0:5]-[CH3;D1;+0:6].C-C-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:1.O-[S;H0;D4;+0:13](-O)(=[O;D1;H0:14])=[O;D1;H0:15].[CH3;D1;+0:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-[CH2;D2;+0:19]-[CH2;D2;+0:20]-[CH3;D1;+0:21].[C:22]-[C:23](-[C;... | 60 | [{"value": 60.0, "product": "C=C1CCC(CC1)C(CS(=O)(=O)C1=CC=C(C=C1)OCC1=CC(=NC2=CC=CC=C12)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into a solution of 1.95 g (5.94 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline (VI-1) obtained in the above (1-1) in tetrahydrofuran (150 mL) was dropped 3.7 mL (7.43 mmol) of 2 mol/L lithium diisopropylamide solution in hexane-heptane-ethylbenzene (available from Aldrich) at −78° C. under an atmosphere ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Ether.Sulfone | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1 | C1CCCCC1.c1ccccc1.c1ccc2ncccc2c1 | HO- | O1CCCC1 | null | 1 | C=C1CCC(C(=O)OC)CC1.CC(C)[N-]C(C)C.CCCCCC.CCCCCCC.CCc1ccccc1.O=S(=O)(O)O>O1CCCC1>C=C1CCC(C(=O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c339712575dd4559b93b4a15ca21bf5f | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)cc(C)n1>>Cc1cc(COc2ccc(S(C)(=O)=O)cc2)cc(C)n1 | Cl.ClCC1=CC(=NC(=C1)C)C.CS(=O)(=O)C1=CC=C(C=C1)O.[OH-].[Na+]>>CS(=O)(=O)C1=CC=C(OCC2=CC(=NC(=C2)C)C)C=C1 | [OH:6][c:7]1[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]1.Cl[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:20][c:18]([CH3:19])[cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]2)[cH:17][c:18]([CH3:19])[n:20]1 | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)cc(C)n1 | Cc1cc(COc2ccc(S(C)(=O)=O)cc2)cc(C)n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccncc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1):[c:11] | 46.6 | [{"value": 46.6, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=NC(=C2)C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=NC(=C2)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.0 g (5.21 mmol) of 4-chloromethyl-2,6-dimethylpyridine hydrochloride and 1.1 g (6.25 mmol) of 4-methylsulfonylphenol in ethanol (3.5 mL) was added 3.5 mL (14.0 mmol) of 4 N aqueous sodium hydroxide solution, followed by heating under reflux for 90 minutes. After standing to cool, ethanol was evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccccc1 | HCl | C(C)O | null | null | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(CCl)cc(C)n1>C(C)O>Cc1cc(COc2ccc(S(C)(=O)=O)cc2)cc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-640c03154b58417eabd93c299b4e0f58 | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(C)cc(CCl)c1>>Cc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 | O.ClCC1=CC(=CC(=C1)C)C.CS(=O)(=O)C1=CC=C(C=C1)O.[OH-].[Na+]>>CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)C)C=C1 | [OH:9][c:10]1[cH:11][cH:12][c:13]([S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]1.Cl[CH2:8][c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][cH:19]2)[cH:20]1 | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(C)cc(CCl)c1 | Cc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 75.3 | [{"value": 75.3, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.7, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.9 g (18.9 mmol) of 1-chloromethyl-3,5-dimethylbenzene and 3.9 g (22.7 mmol) of 4-methylsulfonylphenol in ethanol (10 mL) was added 10 mL (20.0 mmol) of 2 N aqueous sodium hydroxide solution, followed by heating under reflux for 2 hours. After standing to cool, water was added and the precipitates wer... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)O | null | null | CS(=O)(=O)c1ccc(O)cc1.Cc1cc(C)cc(CCl)c1>C(C)O>Cc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56ab754a640d492095216eb4c3a41332 | COc1cc(C)cc(C)c1.CS(=O)(=O)c1ccc(O)cc1>>COc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 | CC=1C=C(C=C(C1)C)OC.BrN1C(CCC1=O)=O.CS(=O)(=O)C1=CC=C(C=C1)O.[H-].[Na+]>>CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[cH:21]1.[OH:10][c:11]1[cH:12][cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][cH:20]2)[cH:21]1 | COc1cc(C)cc(C)c1.CS(=O)(=O)c1ccc(O)cc1 | COc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | CCCCCC.O.C(Cl)(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(COc2ccccc2)cc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 56.3 | [{"value": 40.4, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "CS(=O)(=O)C1=CC=C(OCC2=CC(=CC(=C2)C)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5.0 g (36.7 mmol) of 3,5-dimethylanisole in carbon tetrachloride (35 mL) was added 5.2 g (29.4 mmol) of N-bromosuccinimide and 0.2 g (0.74 mmol) of benzoyl peroxide at room temperature, followed by heating under reflux for 2 hours. The reaction mixture was left standing to cool and then filtered. The f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCCCCC.O.C(Cl)(Cl)(Cl)Cl | null | null | COc1cc(C)cc(C)c1.CS(=O)(=O)c1ccc(O)cc1>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCCCCC.O.C(Cl)(Cl)(Cl)Cl>COc1cc(C)cc(COc2ccc(S(C)(=O)=O)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c395ebc825df4d51a40a760d2f9d553a | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCSCC3)cc2)c2ccccc2n1.NO>>Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1 | NO.CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)C=CC=C1CCSCC1>>CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(C=C1CCSCC1)NO | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH:14]=[CH:15][CH:16]=[C:17]3[CH2:18][CH2:19][S:20][CH2:21][CH2:22]3)[cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[n:33]1.[NH2:23][OH:24]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O... | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCSCC3)cc2)c2ccccc2n1.NO | Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | aza-Michael addition primary | 898f2b0631574caf0b524d46f1b22d10b11d7b69756dca5de5c24f473c5b1372 | 1934d0d0c902455eece333143400ceea345a3ff6faf610539faa2b8861559fde | O=S(=O)(CCC=C1CCSCC1)c1ccc(OCc2ccnc3ccccc23)cc1 | [C:1]-[C:2](=[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9])-[C:10].[NH2;D1;+0:11]-[O;D1;H1:12]>>[C:1]-[C:2](=[C:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9])-[NH;D2;+0:11]-[O;D1;H1:12])-[C:10] | 63 | [{"value": 63.0, "product": "CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(C=C1CCSCC1)NO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 54 | HOUR | A 50% aqueous solution of hydroxylamine (2 mL) was added to a solution of 0.18 g (0.40 mmol) of 2-methyl-4-{4-[3-(tetrahydrothiopyran-4-ylidene)-1-propene-1-sulfonyl]phenoxymethyl}quinoline obtained in the same manner as Example 9 (9-1) and (9-2) in tetrahydrofuran (5 mL) at room temperature and stirred for 54 hours. A... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Conjugated diene | Secondary amine | null | null | c1ccccc1.C1CCSCC1.c1ccc2ncccc2c1 | null | O1CCCC1 | null | 54 | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCSCC3)cc2)c2ccccc2n1.NO>O1CCCC1>Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18b3ab9748cd4cdf92b31b488066b298 | Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1.O=CO>>Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)N(O)C=O)cc2)c2ccccc2n1 | C(=O)O.C(C)(=O)OC(C)=O.CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(C=C1CCSCC1)NO>>ON(C=O)C(CS(=O)(=O)C1=CC=C(C=C1)OCC1=CC(=NC2=CC=CC=C12)C)C=C1CCSCC1 | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH2:14][CH:15]([CH:16]=[C:17]3[CH2:18][CH2:19][S:20][CH2:21][CH2:22]3)[NH:23][OH:24])[cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[n:35]1.O[CH:25]=[O:26]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:... | Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1.O=CO | Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)N(O)C=O)cc2)c2ccccc2n1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=S(=O)(CCC=C1CCSCC1)c1ccc(OCc2ccnc3ccccc23)cc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[C:5]=[C:6](-[C:7])-[C:8])-[NH;D2;+0:9]-[O;D1;H1:10]>>[C:3]-[C:4](-[C:5]=[C:6](-[C:7])-[C:8])-[N;H0;D3;+0:9](-[O;D1;H1:10])-[CH;D2;+0:1]=[O;D1;H0:2] | 34 | [{"value": 34.0, "product": "ON(C=O)C(CS(=O)(=O)C1=CC=C(C=C1)OCC1=CC(=NC2=CC=CC=C12)C)C=C1CCSCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of formic acid (3.0 mL) and acetic anhydride (0.4 mL) premixed for 30 minutes at 0° C. was added to a solution of 0.28 g (0.58 mmol) of N-{2-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-1-(tetrahydrothiopyran-4-ylidenemethyl)ethyl}hydroxylamine (III-17) in tetrahydrofuran (4 mL) at 0° C., and stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.C1CCSCC1.c1ccc2ncccc2c1 | HO- | O1CCCC1 | null | 2 | Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)NO)cc2)c2ccccc2n1.O=CO>O1CCCC1>Cc1cc(COc2ccc(S(=O)(=O)CC(C=C3CCSCC3)N(O)C=O)cc2)c2ccccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d30caf74ce65475eb4229fe1a75b1cfc | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCN(C(=O)O)CC3)cc2)c2ccccc2n1>>Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCNCC3)cc2)c2ccccc2n1 | Cl.O1CCOCC1.CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)C=CC=C1CCN(CC1)C(=O)O>>CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)C=CC=C1CCNCC1 | O=C(O)[N:20]1[CH2:19][CH2:18][C:17](=[CH:16][CH:15]=[CH:14][S:11]([c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][c:4]3[cH:3][c:2]([CH3:1])[n:31][c:30]4[c:25]3[cH:26][cH:27][cH:28][cH:29]4)[cH:24][cH:23]2)(=[O:12])=[O:13])[CH2:22][CH2:21]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH... | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCN(C(=O)O)CC3)cc2)c2ccccc2n1 | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCNCC3)cc2)c2ccccc2n1 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | 436e8d5d2c9157c077e02a7550caa4fe9ae1ab861962962cb0174cc2f6a18366 | b543b15d89798249e5f91ecb15163955078ae08686dc19063a79a06eb435144b | O=S(=O)(C=CC=C1CCNCC1)c1ccc(OCc2ccnc3ccccc23)cc1 | O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](=[C:5])-[C:6]-[C:7]-1>>[C:5]=[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-1 | null | [] | null | null | 2 | HOUR | To a solution of 0.2 g (0.37 mmol) of tert-butyl ester of 4-{3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]allylidene}piperidine-1-carboxylic acid (II-24a) obtained in Example 12 (12-2) in methanol (2.0 mL) was added 4N hydrochloric acid-dioxane solution (2.0 mL) at 0° C. and stirred for 2 hours at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1.c1ccc2ncccc2c1 | Other | CO | null | 2 | Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCN(C(=O)O)CC3)cc2)c2ccccc2n1>CO>Cc1cc(COc2ccc(S(=O)(=O)C=CC=C3CCNCC3)cc2)c2ccccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97adc6632ffe4899b931aa4034848e5d | CC(=O)c1ccc(C)cc1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1>>Cc1ccc(C(C)(O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)cc1 | CC1=CC=C(C=C1)C(C)=O.CS(=O)(=O)C1=CC=C(OCC2=CC(=NC3=CC=CC=C23)C)C=C1.C(C)(C)[N-]C(C)C.[Li+]>>CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(C)(O)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:32][cH:33]1.[CH3:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][c:21]([CH3:22])[n:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([CH3:7])([OH:8])[CH2:9][S:10](=[O:11])(=[O:12... | CC(=O)c1ccc(C)cc1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1 | Cc1ccc(C(C)(O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)cc1 | null | null | O1CCCC1.[Cl-].[Na+].O | C-C Coupling | OtherReaction | 2fffd6bd6bacb879d7ba2cf29351570d50899c51664d6359aa6c9ef1859cb5dd | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | O=S(=O)(CCc1ccccc1)c1ccc(OCc2ccnc3ccccc23)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[CH3;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[OH;D1;+0:3])(-[CH2;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:4](:[c:5]):[c:6] | 66 | [{"value": 66.0, "product": "CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(C)(O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | null | O1CCCC1.[Cl-].[Na+].O | null | 0.666667 | CC(=O)c1ccc(C)cc1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1>O1CCCC1.[Cl-].[Na+].O>Cc1ccc(C(C)(O)CS(=O)(=O)c2ccc(OCc3cc(C)nc4ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-813382d5a9144c88a46cec519ad33165 | COC(=O)C1(C)CCOCC1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1>>Cc1cc(COc2ccc(S(=O)(=O)CC(O)C3(C)CCOCC3)cc2)c2ccccc2n1 | CC1(CCOCC1)C(=O)OC.[BH4-].[Na+].C(C)(=O)O.C(C)(C)[N-]C(C)C.[Li+].CS(=O)(=O)C1=CC=C(OCC2=CC(=NC3=CC=CC=C23)C)C=C1>>CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(O)C1(CCOCC1)C | CO[C:15](=[O:16])[C:17]1([CH3:18])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1.[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH3:14])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[n:32]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13... | COC(=O)C1(C)CCOCC1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1 | Cc1cc(COc2ccc(S(=O)(=O)CC(O)C3(C)CCOCC3)cc2)c2ccccc2n1 | null | null | O1CCCC1.O.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | C-C Coupling | OtherReaction | 4777847ea7b4b7f1cd37fd22d671f5d2a7ed0d00640e3b8ee085047aa425c0ec | c564a209a349ce54d4e465c396e8767d7bc4e45dc071828f803481faed329d15 | O=S(=O)(CCC1CCOCC1)c1ccc(OCc2ccnc3ccccc23)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6].[CH3;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[C:5]-[C:3](-[C;D1;H3:4])(-[CH;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:6] | 74.2 | [{"value": 74.2, "product": "CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(O)C1(CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "CC1=NC2=CC=CC=C2C(=C1)COC1=CC=C(C=C1)S(=O)(=O)CC(O)C1(CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | Under an atmosphere of argon, 1.7 mL (3.45 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene was dropped, at −78° C., into a solution of 1.03 g (3.14 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline (VI-1) in tetrahydrofuran (40 mL), and then stirred for 50 minutes. Into this solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccccc1.C1CCOCC1.c1ccc2ncccc2c1 | HO- | O1CCCC1.O.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | null | 0.833333 | COC(=O)C1(C)CCOCC1.Cc1cc(COc2ccc(S(C)(=O)=O)cc2)c2ccccc2n1>O1CCCC1.O.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1>Cc1cc(COc2ccc(S(=O)(=O)CC(O)C3(C)CCOCC3)cc2)c2ccccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b370c6950ceb406cb4e529876c96c623 | CO.Cc1ccc2nc(C)ccc2c1>>Cc1ccc2nc(C)cc(CO)c2c1 | CC1=NC2=CC=C(C=C2C=C1)C.[NH4+].[NH4+].[O-]S(=O)(=O)OOS(=O)(=O)[O-].CO.S(O)(O)(=O)=O>>CC1=NC2=CC=C(C=C2C(=C1)CO)C | [CH3:11][OH:12].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([CH3:8])[cH:9][cH:10][c:13]2[cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([CH3:8])[cH:9][c:10]([CH2:11][OH:12])[c:13]2[cH:14]1 | CO.Cc1ccc2nc(C)ccc2c1 | Cc1ccc2nc(C)cc(CO)c2c1 | null | null | O | C-C Coupling | OtherReaction | e7cc5c4c961f1a329921d509903a21b23b4b263e02c3b1d766e4418b79465d59 | e869cbe8a607411cfab69b4e60b9305ec52e29a933c34bd13cb5b3befde9ccd2 | c1ccc2ncccc2c1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:1.[CH3;D1;+0:10]-[O;D1;H1:11]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:10]-[O;D1;H1:11]):[c:9]:1 | 46 | [{"value": 46.0, "product": "CC1=NC2=CC=C(C=C2C(=C1)CO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.0 g (63.6 mmol) of 2,6-dimethylquinoline and 29.1 g (127.5 mmol) of ammonium peroxodisulfate in a mixed solvent of methanol (140 mL)-water (110 mL) was added 4.0 mL of concentrated sulfuric acid and heated under reflux for 24 hours. After the reaction mixture was left to cool, methanol was evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Primary alcohol | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | O | null | null | CO.Cc1ccc2nc(C)ccc2c1>O>Cc1ccc2nc(C)cc(CO)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9425d19cbb9a4f1ab0ccc6c054305a0a | CO.Cc1ccc2cc(F)ccc2n1>>Cc1cc(CO)c2cc(F)ccc2n1 | S(O)(O)(=O)=O.FC=1C=C2C=CC(=NC2=CC1)C.[NH4+].[NH4+].[O-]S(=O)(=O)OOS(=O)(=O)[O-].O.CO>>FC=1C=C2C(=CC(=NC2=CC1)C)CO | [CH3:5][OH:6].[CH3:1][c:2]1[cH:3][cH:4][c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[n:14]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][OH:6])[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[n:14]1 | CO.Cc1ccc2cc(F)ccc2n1 | Cc1cc(CO)c2cc(F)ccc2n1 | null | null | null | C-C Coupling | OtherReaction | e7cc5c4c961f1a329921d509903a21b23b4b263e02c3b1d766e4418b79465d59 | e869cbe8a607411cfab69b4e60b9305ec52e29a933c34bd13cb5b3befde9ccd2 | c1ccc2ncccc2c1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:1.[CH3;D1;+0:10]-[O;D1;H1:11]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:10]-[O;D1;H1:11]):[c:9]:1 | 81 | [{"value": 81.0, "product": "FC=1C=C2C(=CC(=NC2=CC1)C)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.0 g (62.0 mmol) of 6-fluoro-2-methylquinoline and 28.3 g (124.0 mmol) of ammonium peroxodisulfate in a mixture of methanol (140 mL)-water (110 mL) was added 4.0 mL of concentrated sulfuric acid, and heated under reflux for 18 hours. The reaction mixture was left to cool, and methanol was removed und... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Primary alcohol | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | null | null | null | CO.Cc1ccc2cc(F)ccc2n1>>Cc1cc(CO)c2cc(F)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-091889aa753f4cca905df24bfa612e2b | CC(C)(C)[Si](C)(C)Oc1ccc(S(C)(=O)=O)cc1.Cc1ccccc1C=O>>Cc1ccccc1C(O)CS(=O)(=O)c1ccc(O)cc1 | C(C)O.C(C)(C)(C)[Si](C)(C)OC1=CC=C(C=C1)S(=O)(=O)C.C(C)(C)[N-]C(C)C.[Li+].CC1=C(C=O)C=CC=C1>>OC(CS(=O)(=O)C1=CC=C(C=C1)O)C1=C(C=CC=C1)C | CC(C)(C)[Si](C)(C)[O:18][c:17]1[cH:16][cH:15][c:14]([S:11]([CH3:10])(=[O:12])=[O:13])[cH:20][cH:19]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[O:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([OH:9])[CH2:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][cH:20]1 | CC(C)(C)[Si](C)(C)Oc1ccc(S(C)(=O)=O)cc1.Cc1ccccc1C=O | Cc1ccccc1C(O)CS(=O)(=O)c1ccc(O)cc1 | null | null | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | C-C Coupling | OtherReaction | 294b1204742e0a3ef9e7b44d9d0fe7ad0ce19e091a2ffa0c3b594e6e35d7e429 | 6535a4e30111192ce8bdbfa40178a1882cc66575aec404ed9ef46d7a778d1456 | O=S(=O)(CCc1ccccc1)c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:7]=[#16:6](=[O;D1;H0:8])(-[c:9])-[CH2;D2;+0:5]-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 60.8 | [{"value": 60.8, "product": "OC(CS(=O)(=O)C1=CC=C(C=C1)O)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "OC(CS(=O)(=O)C1=CC=C(C=C1)O)C1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Into a solution of 1.50 g (5.24 mmol) of tert-butyl-(4-methanesulfonylphenoxy)dimethylsilane in tetrahydrofuran (30 mL) was dropped, at −78° C. under an atmosphere of argon, 3.1 mL (6.20 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene (available from Aldrich), and stirred for 1 hour. Into this ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.TMS ether protective group | Secondary alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | null | 0.5 | CC(C)(C)[Si](C)(C)Oc1ccc(S(C)(=O)=O)cc1.Cc1ccccc1C=O>O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1>Cc1ccccc1C(O)CS(=O)(=O)c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba2c7cd3b44c474585e7b2cb71dfb5e2 | CI.COC(=O)C1CCOCC1>>COC(=O)C1(C)CCOCC1 | [Cl-].[NH4+].COC(=O)C1CCOCC1.C(C)(C)[N-]C(C)C.[Li+].CI>>COC(=O)C1(CCOCC1)C | I[CH3:6].[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1 | CI.COC(=O)C1CCOCC1 | COC(=O)C1(C)CCOCC1 | null | null | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | C-C Coupling | Methylation with MeI_tertiary | 147983420c87113dac66e5b9f8ce9ef407b0a040fd93372379bbfe3ebcd08c52 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | C1CCOCC1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]1-[C:7]-[C:8]-[#8:9]-[C:10]-[C:11]-1>>[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6]1(-[CH3;D1;+0:1])-[C:7]-[C:8]-[#8:9]-[C:10]-[C:11]-1 | 86.9 | [{"value": 86.4, "product": "COC(=O)C1(CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "COC(=O)C1(CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Into a solution of 6.18 g (42.9 mmol) of tetrahydropyran-4-carboxylic acid methyl ester in tetrahydrofuran (140 mL) was dropped, at −78° C. under an atmosphere of argon, 25.7 mL (51.5 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene (available from Aldrich), and stirred for 90 minutes. To this s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HI | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | null | 4 | CI.COC(=O)C1CCOCC1>O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1>COC(=O)C1(C)CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03531cd306ad45e69b8c314f83c9520d | COC(=O)C1CCOCC1.COCCl>>COCC1(C(=O)OC)CCOCC1 | [Cl-].[NH4+].COC(=O)C1CCOCC1.C(C)(C)[N-]C(C)C.[Li+].COCCl>>COC(=O)C1(CCOCC1)COC | [CH:4]1([C:5](=[O:6])[O:7][CH3:8])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][C:4]1([C:5](=[O:6])[O:7][CH3:8])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | COC(=O)C1CCOCC1.COCCl | COCC1(C(=O)OC)CCOCC1 | null | null | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | C-C Coupling | OtherReaction | 36e55d0be0eb4267487cc9c33ab3be564da77be4afcde7508c12710fdf640b53 | 8ef4a7f3c2aa2c61ba42c1b7d8665a33daf968ae3eb9e2122661626a98ff3349 | C1CCOCC1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8]1-[C:9]-[C:10]-[#8:11]-[C:12]-[C:13]-1>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:8]1(-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4])-[C:9]-[C:10]-[#8:11]-[C:12]-[C:13]-1 | 32.7 | [{"value": 32.4, "product": "COC(=O)C1(CCOCC1)COC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.7, "product": "COC(=O)C1(CCOCC1)COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 30 | MINUTE | Into a solution of 3.0 g (20.8 mmol) of tetrahydropyran-4-carboxylic acid methyl ester (IX-49) in tetrahydrofuran (60 mL) was dropped, at −78° C. under an atmosphere of argon, 12.6 mL (25.2 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene (available from Aldrich), and stirred for 90 minutes. To ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ether | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HCl | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | -10 | 0.5 | COC(=O)C1CCOCC1.COCCl>O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1>COCC1(C(=O)OC)CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74feaf0457f54e15a04898127b057169 | COC(=O)C1(C)CCC(=O)CC1>>COC(=O)C1(C)CCC(O)CC1 | [BH4-].[Na+].COC(=O)C1(CCC(CC1)=O)C.CO.C(C)O>>COC(=O)C1(CCC(CC1)O)C | [CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][CH2:12]1 | COC(=O)C1(C)CCC(=O)CC1 | COC(=O)C1(C)CCC(O)CC1 | null | null | O | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1CCCCC1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | 109.8 | [{"value": 100.0, "product": "COC(=O)C1(CCC(CC1)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.8, "product": "COC(=O)C1(CCC(CC1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 3.7 g (20.1 mmol) of 1-methyl-4-oxocyclohexanecarboxylic acid methyl ester in mixture of methanol and ethanol (6 mL+15 mL) was added 200 mg (5.29 mmol) of sodium borohydride at 0° C., and stirred for 1 hour at 0° C. After addition of water thereto, the reaction mixture was concentrated under a reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | O | 0 | 1 | COC(=O)C1(C)CCC(=O)CC1>O>COC(=O)C1(C)CCC(O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-351862a70b1548c38f668489ed5b4048 | C1CCOC1.O.O=C1CCOCC1>>CCOC(=O)C(C)=C1CCOCC1 | O.CC(C)([O-])C.[K+].O1CCCC1.O1CCC(CC1)=O>>C(C)OC(C(C)=C1CCOCC1)=O | O1[CH2:2][CH2:1][CH2:7][CH2:6]1.[OH2:3].[O:5]=[C:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])=[C:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | C1CCOC1.O.O=C1CCOCC1 | CCOC(=O)C(C)=C1CCOCC1 | null | null | null | Acylation | OtherReaction | 96d16fe8bd2136e1332e1070b2057e8a6632989c55f747cad5d05f2243fbdae9 | 01f45e60fb10950211ce425de5a41b05eedb1a7fdc40f2ace54aa22fbcb5d10b | C=C1CCOCC1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#8:9]-[C:10]-[C:11]-1.[OH2;D0;+0:12]>>[CH3;D1;+0:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[C:13](=[O;H0;D1;+0:5])-[C;H0;D3;+0:4](-[CH3;D1;+0:3])=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#8:9]-[C:10]-[C:11]-1 | 42.1 | [{"value": 42.1, "product": "C(C)OC(C(C)=C1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 5 | HOUR | To a solution of 12.9 g (54.1 mmol) of 2-phosphonopropionic acid triethyl etser in tetrahydrofuran (60 mL) was added, at 25° C. under an atmosphere of argon, 5.52 g (49.2 mmol) of potassium t-butoxide, and stirred for 10 minutes. Into this solution, 5.42 g (54.1 mmol) of tetrahydropyran-4-one was dropped and stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ester | C1CCOC1.C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | null | null | 70 | 5 | C1CCOC1.O.O=C1CCOCC1>>CCOC(=O)C(C)=C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1188d8bcd25241758846be29e41c10d6 | CCOC(=O)C(C)=C1CCOCC1>>CC(CO)=C1CCOCC1 | C(C)OC(C(C)=C1CCOCC1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O1CCC(CC1)=C(CO)C | CCO[C:3]([C:2]([CH3:1])=[C:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]>>[CH3:1][C:2]([CH2:3][OH:4])=[C:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | CCOC(=O)C(C)=C1CCOCC1 | CC(CO)=C1CCOCC1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C=C1CCOCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])=[C:5](-[C:6])-[C:7]>>[C:6]-[C:5](=[C:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:7] | 121.1 | [{"value": 100.0, "product": "O1CCC(CC1)=C(CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 121.1, "product": "O1CCC(CC1)=C(CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a cooled (0° C.) solution of 4.2 g (24.39 mmol) of 2-(tetrahydropyran-4-ylidene)propionic acid ethyl ester obtained in the above 1) in ether (50 mL) was added 1.20 g (31.7 mmol) of lithium aluminum hydride under an atmosphere of argon, and stirred for 1 hour at 0° C., followed by stirring for 2 hours at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCOCC1 | HO- | CCOCC | 0 | 1 | CCOC(=O)C(C)=C1CCOCC1>CCOCC>CC(CO)=C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0debe4fba3324569b97e46435e2ee7e8 | CC(CO)=C1CCOCC1>>CC(C=O)=C1CCOCC1 | O1CCC(CC1)=C(CO)C>>O1CCC(CC1)=C(C=O)C | [CH3:1][C:2]([CH2:3][OH:4])=[C:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1>>[CH3:1][C:2]([CH:3]=[O:4])=[C:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | CC(CO)=C1CCOCC1 | CC(C=O)=C1CCOCC1 | null | [O-2].[O-2].[Mn+4] | ClCCl.CCCCCC.ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C=C1CCOCC1 | [C:1]-[C:2](=[C:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-[OH;D1;+0:6])-[C:7]>>[C:1]-[C:2](=[C:3](-[C;D1;H3:4])-[CH;D2;+0:5]=[O;H0;D1;+0:6])-[C:7] | 101.4 | [{"value": 100.0, "product": "O1CCC(CC1)=C(C=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.4, "product": "O1CCC(CC1)=C(C=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 40 | HOUR | To a suspension of 23 g (0.265 mmol) of activated manganese dioxide in a mixture of hexane-dichloromethane (20 mL+70 mL) was added a solution of 2.0 g (14.07 mmol) of 2-(tetrahydropyran-4-ylidene)propan-1-ol obtained in the above 2) in dichloromethane (4 mL), and stirred for 40 hours at 25° C. Upon filtration of the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCOCC1 | null | [O-2].[O-2].[Mn+4].ClCCl.CCCCCC.ClCCl | 25 | 40 | CC(CO)=C1CCOCC1>[O-2].[O-2].[Mn+4].ClCCl.CCCCCC.ClCCl>CC(C=O)=C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0c4cdd380964b5f8fd335b8114b5110 | CCOC(=O)C(F)P(=O)(OCC)OCC.O=C1CCOCC1>>CCOC(=O)C(F)=C1CCOCC1 | O.CCOC(=O)C(F)P(=O)(OCC)OCC.C(CCC)[Li].O1CCC(CC1)=O>>C(C)OC(C(=C1CCOCC1)F)=O | CCOP(=O)(OCC)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[F:7].O=[C:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([F:7])=[C:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | CCOC(=O)C(F)P(=O)(OCC)OCC.O=C1CCOCC1 | CCOC(=O)C(F)=C1CCOCC1 | null | null | O1CCCC1.CCCCCC | C-C Coupling | OtherReaction | 41282367f53d267b21975e7ea8d04e66034440264df830a19dab20c28f399b46 | 2efd590c84d275da290fb685a0bc5ee93b804bfe1a2f7b92e8e06abd6f6aeaa4 | C=C1CCOCC1 | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[F;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].O=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[#8:10]-[C:11]-[C:12]-1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](-[F;D1;H0:2])=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[#8:10]-[C:11]-[C:12]-1 | 88.8 | [{"value": 88.8, "product": "C(C)OC(C(=C1CCOCC1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)OC(C(=C1CCOCC1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Into a cooled (−10° C.) solution of 5.25 g (21.68 mmol) of 2-fluoro-2-phosphonoacetic acid triethyl ester in tetrahydrofuran (30 mL) under an atmosphere of argon was dropped 13.2 mL (19.87 mmol) of 1.5 mol/L n-butyllithium in hexane (available from KANTO KAGAKU). After stirring for 20 minutes at room temperature, 2.0 g... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester | Alkenyl halide.Ester | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HO- | O1CCCC1.CCCCCC | null | 0.333333 | CCOC(=O)C(F)P(=O)(OCC)OCC.O=C1CCOCC1>O1CCCC1.CCCCCC>CCOC(=O)C(F)=C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d4e138396074abea79a0ccf8f7482a4 | CCOC(=O)CP(=O)(OCC)OCC.OCC1CCCO1>>COC(=O)C=CC1(C)CCOCC1 | C(C)OC(CP(=O)(OCC)OCC)=O.O1C(CCC1)CO.C[O-].[Na+]>>COC(C=CC1(CCOCC1)C)=O | CCOP(=O)(OCC)[CH2:5][C:3]([O:2][CH2:1][CH3:9])=[O:4].O[CH2:6][CH:7]1[CH2:8][CH2:13][CH2:12][O:11]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]1([CH3:8])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | CCOC(=O)CP(=O)(OCC)OCC.OCC1CCCO1 | COC(=O)C=CC1(C)CCOCC1 | null | null | O1CCCC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | e1a18dd822bfc64ba58d50348f7e0fd55cc754151d999c9c6a8dc2789873ac17 | 4f3379985b0b29c640da756ae2b8c8731aeb3a806b0e67cc74a7e12f208693bb | C1CCOCC1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[CH3;D1;+0:6].O-[CH2;D2;+0:7]-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[O;H0;D2;+0:12]-1>>[CH3;D1;+0:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[CH;D2;+0:7]-[C;H0;D4;+0:8]1(-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[C:11]-[O;H0;D2;+0:12]-[C:13]-[C... | 64.7 | [{"value": 64.7, "product": "COC(C=CC1(CCOCC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Into a cooled (0° C.) solution of 1.92 g (8.58 mmol) of diethylphosphonoacetic acid ethyl ester in tetrahydrofuran-methanol (3.5 mL+2.8 mL) was dropped 1.65 mL (8.58 mmol) of 28% sodium methoxide in methanol solution, and stirred for 10 minutes. Into this solution was dropped a solution of 1.0 g (7.80 mmol) of 4-methyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary alcohol | Ester.Ether | C1CCOC1 | C1CCOCC1 | C1CCOCC1 | HO- | O1CCCC1.CO | null | 0.166667 | CCOC(=O)CP(=O)(OCC)OCC.OCC1CCCO1>O1CCCC1.CO>COC(=O)C=CC1(C)CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd7f8e13f7d0487588bb7cf4fccb3afd | COC(=O)C=CC1(C)CCOCC1>>CC1(C=CCO)CCOCC1 | COC(C=CC1(CCOCC1)C)=O.[H-].C(C(C)C)[Al+]CC(C)C.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+]>>CC1(CCOCC1)C=CCO | CO[C:5]([CH:4]=[CH:3][C:2]1([CH3:1])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)=[O:6]>>[CH3:1][C:2]1([CH:3]=[CH:4][CH2:5][OH:6])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1 | COC(=O)C=CC1(C)CCOCC1 | CC1(C=CCO)CCOCC1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCOCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4]-[C:5]>>[C:5]-[C:4]=[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 100.2 | [{"value": 71.0, "product": "CC1(CCOCC1)C=CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "CC1(CCOCC1)C=CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 3 | HOUR | Into a cooled (−78° C.) solution of 640 mg (3.47 mmol) of 3-(4-methyltetrahydropyran-4-yl)acrylic acid methyl ester obtained in the above 3) in THF was dropped 8.0 mL (8.00 mmol) of 1.0 mol/L diisobutylaluminum hydride in toluene at under an atmosphere of argon, and stirred for 3 hours at −78° C. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCOCC1 | Other | C1(=CC=CC=C1)C.C1CCOC1 | -78 | 3 | COC(=O)C=CC1(C)CCOCC1>C1(=CC=CC=C1)C.C1CCOC1>CC1(C=CCO)CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cdadb8e507934b2e8863900d7f05c0be | COC(=O)C=CC1(C)CCOCC1>>COC(=O)CCC1(C)CCOCC1 | COC(C=CC1(CCOCC1)C)=O.[H][H]>>COC(CCC1(CCOCC1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]1([CH3:8])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1([CH3:8])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | COC(=O)C=CC1(C)CCOCC1 | COC(=O)CCC1(C)CCOCC1 | null | [C].[Pd] | CO | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | C1CCOCC1 | [C:1]-[C:2](-[C;D1;H3:3])(-[CH;D2;+0:4]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[C:10]>>[C:1]-[C:2](-[C;D1;H3:3])(-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[C:10] | 100.2 | [{"value": 100.0, "product": "COC(CCC1(CCOCC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "COC(CCC1(CCOCC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 220 g (1.19 mmol) of 3-(4-methyltetrahydropyran-4-yl)acrylic acid methyl ester in methanol (15 mL) was added 40 mg of palladium-carbon, replaced with hydrogen gas, and then stirred for 12 hours at room temperature. After the reaction mixture was filtered through Celite, the solvent was removed under a ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | C1CCOCC1 | null | [C].[Pd].CO | null | 12 | COC(=O)C=CC1(C)CCOCC1>[C].[Pd].CO>COC(=O)CCC1(C)CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5385d5d927784378a0a0b7072ff648a0 | CI.COC(=O)CC1CCOCC1>>COC(=O)C(C)C1CCOCC1 | Cl.C(C)(C)[N-]C(C)C.[Li+].CI.COC(CC1CCOCC1)=O>>COC(C(C)C1CCOCC1)=O | I[CH3:6].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1 | CI.COC(=O)CC1CCOCC1 | COC(=O)C(C)C1CCOCC1 | null | null | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | C-C Coupling | Methylation with MeI_secondary | 4a52ebe9ffae5bdd307b0b4ac6a7069bc533ab8d42293ed2712c32b846010273 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | C1CCOCC1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[C:9]>>[C:2]-[C:3](-[CH;D3;+0:4](-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[C:9] | 85.2 | [{"value": 85.1, "product": "COC(C(C)C1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "COC(C(C)C1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Into a cooled (−78° C.) solution of 1.00 g (6.32 mmol) of (tetrahydropyran-4-yl)acetic acid methyl ester in tetrahydrofuran (20 mL) was dropped, under an atmosphere of argon, a solution of 4.5 mL (9.00 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene (available from Aldrich) and subsequently 0.4... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | C1CCOCC1 | HI | O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1 | null | 48 | CI.COC(=O)CC1CCOCC1>O1CCCC1.CCCCCC.CCCCCCC.C(C)C1=CC=CC=C1>COC(=O)C(C)C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2139e1c3124a41e38d8ac505bc3ba0c8 | CCOC(=O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCOCC1>>CCOC(=O)CCC=C1CCOCC1 | [Br-].C(C)OC(=O)CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Na+].O1CCC(CC1)=O>>C(C)OC(CCC=C1CCOCC1)=O | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[C:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]=[C:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1 | CCOC(=O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCOCC1 | CCOC(=O)CCC=C1CCOCC1 | null | null | CN(C=O)C | C-C Coupling | Wittig with Phosphonium | ce2fed0cbc4035981091c6407c45479c3c9d9bae55fcb8faadfd1ff938e4e2f1 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C1CCOCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-[CH2;D2;+0:12]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-[CH;D2;+0:12]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1 | 6.6 | [{"value": 6.6, "product": "C(C)OC(CCC=C1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.6, "product": "C(C)OC(CCC=C1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | A solution of 11.2 g (24.5 mmol) of [3-(ethoxycarbonyl)propyl]triphenylphosphonium bromide in dimethylformamide (19 mL) was dropped into a cooled (10° C.) suspension of 1.13 g (28.2 mmol) of a 60% sodium hydride in dimethylformamide (2 mL) under an atmosphere of argon, and stirred for 40 minutes. Into this, 2.5 g (24.5... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HO- | CN(C=O)C | null | 0.666667 | CCOC(=O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCOCC1>CN(C=O)C>CCOC(=O)CCC=C1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef36f3dab449480895fef773192a1f2a | CCOC(=O)C=Cc1cccc(C)n1>>CCOC(=O)CCc1cccc(C)n1 | C(C)OC(C=CC1=NC(=CC=C1)C)=O>>C(C)OC(CCC1=NC(=CC=C1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH3:13])[n:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH3:13])[n:14]1 | CCOC(=O)C=Cc1cccc(C)n1 | CCOC(=O)CCc1cccc(C)n1 | null | [C].[Pd] | CO | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccncc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | 77.6 | [{"value": 77.6, "product": "C(C)OC(CCC1=NC(=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 1.39 g (7.85 mmol) of 3-(6-methylpyridin-2-yl)acrylic acid ethyl ester in methanol (50 mL) was added 200 mg of 10% palladium-carbon, and stirred for 4 hours at room temperature under an atmosphere of hydrogen. The solution was filtered through Celite and the obtained filtrate was concentrated under a r... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1 | null | [C].[Pd].CO | null | 4 | CCOC(=O)C=Cc1cccc(C)n1>[C].[Pd].CO>CCOC(=O)CCc1cccc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cfc68ec8af5428abb6cdc8e74cf36ad | COc1cccc(CCC(=O)O)c1>>COC(=O)CCC1=CCCC(O)C1 | COC=1C=C(C=CC1)CCC(=O)O.N.N.[Na].C[Si](C)(C)C=[N+]=[N-].[BH4-].[Na+].[Cl-].[NH4+]>>COC(CCC1=CCCC(C1)O)=O | [CH3:1][O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([OH:2])=[O:4])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1=[CH:8][CH2:9][CH2:10][CH:11]([OH:12])[CH2:13]1 | COc1cccc(CCC(=O)O)c1 | COC(=O)CCC1=CCCC(O)C1 | null | null | O1CCCC1.C(C)(C)(C)O.C(C)O | Reduction | OtherReaction | 45b26aaccd3b5d5b94db01ab3bb1af5742d1d9e0f566d314780f6aa6df2a8839 | 5feaedb4bd6e37d83def05780340d8102dc68bdc60d88b8dd36264552f8399e8 | C1=CCCCC1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]):[cH;D2;+0:13]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:12]-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-[C;H0;D3;+0:7]1=[CH;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH;D3;+0:3](-[OH;D1;+0:2])-[CH2;... | 35.6 | [{"value": 35.6, "product": "COC(CCC1=CCCC(C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 45 | MINUTE | Under an atmosphere of argon, 2.18 g (12.09 mmol) of 3-(3-methoxyphenyl)propionic acid was put into a three-neck flask, and tetrahydrofuran (20 mL) and tert-butylalcohol (20 mL) were added thereto. After cooling to −78° C., about 150 mL of liquid ammonia was added thereto, and then sodium was added piece by piece. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester.Secondary alcohol | c1ccccc1 | C1=CCCCC1 | C1=CCCCC1 | null | O1CCCC1.C(C)(C)(C)O.C(C)O | -78 | 0.75 | COc1cccc(CCC(=O)O)c1>O1CCCC1.C(C)(C)(C)O.C(C)O>COC(=O)CCC1=CCCC(O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-837679e5d7ae48f7b6381523e1ee1665 | CC(C)(C)OC(=O)N1CCC(=CCO)CC1>>CC(C)(C)OC(=O)N1CCC(=CC=O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)=CCO.C(Cl)(Cl)Cl>>C(C)(C)(C)OC(=O)N1CCC(CC1)=CC=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][CH2:13][OH:14])[CH2:15][CH2:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][CH:13]=[O:14])[CH2:15][CH2:16]1 | CC(C)(C)OC(=O)N1CCC(=CCO)CC1 | CC(C)(C)OC(=O)N1CCC(=CC=O)CC1 | null | [O-2].[O-2].[Mn+4] | CCCCCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | [CH]=C1CCNCC1 | [C:1]-[C:2](=[C:3]-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6]>>[C:1]-[C:2](=[C:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6] | 89 | [{"value": 89.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)=CC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)=CC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a solution of 4-(2-hydroxyethylidene)piperidine-1-carboxylic acid t-butyl ester (10.4 g, 46 mmol) in a mixture of hexane (300 mL)-chloroform (100 mL) was added manganese dioxide (100 g), and stirred for 10 hours. After the reaction was completed, insoluble materials were filtered off through Celite and the filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | [O-2].[O-2].[Mn+4].CCCCCC | null | 10 | CC(C)(C)OC(=O)N1CCC(=CCO)CC1>[O-2].[O-2].[Mn+4].CCCCCC>CC(C)(C)OC(=O)N1CCC(=CC=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b886c25d68fe477190678449243acf3f | CC(C)(C)OC(=O)N1CCCC(=CCO)CC1>>CC(C)(C)OC(=O)N1CCCC(=CC=O)CC1 | C(Cl)(Cl)Cl.C(C)(C)(C)OC(=O)N1CCC(CCC1)=CCO>>C(C)(C)(C)OC(=O)N1CCC(CCC1)=CC=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C:12](=[CH:13][CH2:14][OH:15])[CH2:16][CH2:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C:12](=[CH:13][CH:14]=[O:15])[CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N1CCCC(=CCO)CC1 | CC(C)(C)OC(=O)N1CCCC(=CC=O)CC1 | null | [O-2].[O-2].[Mn+4] | CCCCCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | [CH]=C1CCCNCC1 | [C:1]-[C:2](=[C:3]-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6]>>[C:1]-[C:2](=[C:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6] | 55.5 | [{"value": 55.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CCC1)=CC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.5, "product": "C(C)(C)(C)OC(=O)N1CCC(CCC1)=CC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Manganese dioxide (507 g) was added to a solution of 61 g (0.25 mol) of 4-(2-hydroxyethylidene)azepane-1-carboxylic acid t-butyl ester obtained in the above 2) in a mixture of hexane (1865 ml)-chloroform (624 mL) and stirred for 18 hours. After the reaction was completed, insoluble materials were filtered off through C... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCC[NH]CC1 | null | [O-2].[O-2].[Mn+4].CCCCCC | null | 18 | CC(C)(C)OC(=O)N1CCCC(=CCO)CC1>[O-2].[O-2].[Mn+4].CCCCCC>CC(C)(C)OC(=O)N1CCCC(=CC=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbde1e1a9a2a424bb6d3c71afc2a278f | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1C>>CC1CN(C(=O)OC(C)(C)C)CCC1=CCO | C(C)O.[H-].C(C(C)C)[Al+]CC(C)C.C1(=CC=CC=C1)C.C(C)(C)(C)OC(=O)N1CC(C(CC1)=CC(=O)OC)C>>C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)C | CO[C:16]([CH:15]=[C:14]1[CH:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13]1)=[O:17]>>[CH3:1][CH:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:12][CH2:13][C:14]1=[CH:15][CH2:16][OH:17] | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1C | CC1CN(C(=O)OC(C)(C)C)CCC1=CCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](=[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6] | 89.6 | [{"value": 89.6, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1 M diisobutylaluminum hydride in toluene (13.9 mL, 13.9 mmol) was slowly dropped into a cooled (-78° C.) solution of 4-methoxycarbonylmethylene-3-methylpiperidine-1-carboxylic acid t-butyl ester (1.5 g, 5.6 mmol) obtained in the above 1) in tetrahydrofuran (30 mL) under an atmosphere of argon. After drop... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | Other | O1CCCC1 | null | 2 | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1C>O1CCCC1>CC1CN(C(=O)OC(C)(C)C)CCC1=CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ecabee530a54afaa5a933f5da3d5975 | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1.CCOC(=O)CP(=O)(OCC)OCC.CO>>COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C | C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)(C)C.C(C)OC(CP(=O)(OCC)OCC)=O.C[O-].[Na+].CO>>C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC(=O)OC)(C)C | O=[C:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1([CH3:19])[CH3:20].CCOP(=O)(OCC)[CH2:5][C:3]([O:2]CC)=[O:4].O[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1=[CH:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]1([CH3:19])[CH3:20] | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1.CCOC(=O)CP(=O)(OCC)OCC.CO | COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 926dc31f46180c876033ba1a50a93dddbc7978427f7ca843cf53093610d1f3dd | 05f0d751044690d0e011dcbd06539e29c2dbf8d178db734b13b2048a09b193a4 | C1=CCNCC1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C.O-[CH3;D1;+0:5].O=[C;H0;D3;+0:6]1-[CH2;D2;+0:7]-[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[C:17]-[C:18]-1(-[C;D1;H3:19])-[C;D1;H3:20]>>[C;D1;H3:14]-[C:13](-[C;D1;H3:15])(-[C;D1;H3:16])-[#8:12]-[... | 58.9 | [{"value": 32.1, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC(=O)OC)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC(=O)OC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | To a cooled (0° C.) solution of diethylphosphonoacetic acid ethyl ester (4.4 mL, 24.2 mmol) in tetrahydrofuran (50 mL) under an atmosphere of nitrogen were added a solution of 28% sodium methoxide in methanol (4.6 mL, 26.4 mmol), and then a solution of 3,3-dimethyl-4-oxopiperidine-1-carboxylic acid t-butyl ester (5.0 g... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Methanol | Ester | C1CC[NH]CC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)N1CCC(=O)C(C)(C)C1.CCOC(=O)CP(=O)(OCC)OCC.CO>O1CCCC1>COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5186bd1ffcc24a888a0bb47a8e2cf0c2 | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1(C)C>>CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1 | C(C)O.[H-].C(C(C)C)[Al+]CC(C)C.C(C)(C)(C)OC(=O)N1CC(C(CC1)=CC(=O)OC)(C)C.C1(=CC=CC=C1)C>>C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)(C)C | CO[C:13]([CH:12]=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:18][C:15]1([CH3:16])[CH3:17])=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][CH2:13][OH:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1 | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1(C)C | CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](=[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6] | 58.6 | [{"value": 58.6, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Into a cooled (−78° C.) solution of 4-methoxycarbonylmethylene-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester (1.8 g, 6.4 mmol) in tetrahydrofuran (50 mL) obtained in the above 1) was slowly dropped, under an atmosphere of argon, 1 M diisobutylaluminum hydride in toluene (15.9 mL, 15.9 mmol). After dropping, th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | Other | O1CCCC1 | null | 2 | COC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1(C)C>O1CCCC1>CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be4546298cda49fca703fee5e512e5ba | CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1>>CC(C)(C)OC(=O)N1CCC(=CC=O)C(C)(C)C1 | C(C)(C)(C)OC(=O)N1CC(C(CC1)=CCO)(C)C.C(Cl)(Cl)Cl>>C(C)(C)(C)OC(=O)N1CC(C(CC1)=CC=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][CH2:13][OH:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH:12][CH:13]=[O:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1 | CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1 | CC(C)(C)OC(=O)N1CCC(=CC=O)C(C)(C)C1 | null | [O-2].[O-2].[Mn+4] | CCCCCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | [CH]=C1CCNCC1 | [C:1]-[C:2](=[C:3]-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6]>>[C:1]-[C:2](=[C:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6] | 71.1 | [{"value": 70.8, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CC=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "C(C)(C)(C)OC(=O)N1CC(C(CC1)=CC=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | Manganese dioxide (10 g) was added to a solution of 4-(2-hydroxyethylidene)-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester (0.9 g, 3.5 mmol) in a mixture of hexane (30 mL)-chloroform (10 mL) and stirred for 10 hours. After the reaction was completed, insoluble materials were filtered off through Celite, and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | [O-2].[O-2].[Mn+4].CCCCCC | null | 10 | CC(C)(C)OC(=O)N1CCC(=CCO)C(C)(C)C1>[O-2].[O-2].[Mn+4].CCCCCC>CC(C)(C)OC(=O)N1CCC(=CC=O)C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7263ca15bd0a461da290b2fd55b38647 | COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C>>CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1 | C(C)O.[H-].C(C(C)C)[Al+]CC(C)C.C1(=CC=CC=C1)C.C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC(=O)OC)(C)C>>C(C)(C)(C)OC(=O)N1CC(C(=CC1)CCO)(C)C | CO[C:13]([CH2:12][C:11]1=[CH:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:18][C:15]1([CH3:16])[CH3:17])=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1 | COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C | CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4](=[C:5]-[C:6]-[#7:7])-[C:8]>>[#7:7]-[C:6]-[C:5]=[C:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:8] | 76.4 | [{"value": 76.4, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CCO)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CCO)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1 M diisobutylaluminum hydride in toluene (14.0 mL, 14.1 mmol) was slowly dropped into a cooled (−78° C.) solution of 1.6 g (5.7 mmol) of 4-methoxycarbonylmethyl-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester obtained in the above 1) of PREPARATION EXAMPLE 20 in tetrahydrofuran (70 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=CC[NH]CC1 | Other | O1CCCC1 | null | 2 | COC(=O)CC1=CCN(C(=O)OC(C)(C)C)CC1(C)C>O1CCCC1>CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c235919f9e6f457b9518331e938ac7b5 | CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1>>CC(C)(C)OC(=O)N1CC=C(CC=O)C(C)(C)C1 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)(C)(C)OC(=O)N1CC(C(=CC1)CCO)(C)C.[Cl-].[NH4+]>>C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([CH2:12][CH:13]=[O:14])[C:15]([CH3:16])([CH3:17])[CH2:18]1 | CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1 | CC(C)(C)OC(=O)N1CC=C(CC=O)C(C)(C)C1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1=CCNCC1 | [#7:1]-[C:2]-[C:3]=[C:4](-[C:5]-[CH2;D2;+0:6]-[OH;D1;+0:7])-[C:8]>>[#7:1]-[C:2]-[C:3]=[C:4](-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7])-[C:8] | 41.6 | [{"value": 41.1, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.6, "product": "C(C)(C)(C)OC(=O)N1CC(C(=CC1)CC=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of dimethylsulfoxide (1.1 mL, 15 mmol) in dichloromethane (5ml) was added to a cooled (−78° C.) solution of oxalyl chloride (0.67 mL, 7.5 mmol) in dichloromethane (50 mL) under an atmosphere of argon, and stirred for 10 minutes. Then a solution of 4-(2-hydroxyethyl)-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-car... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1=CC[NH]CC1 | null | ClCCl | null | 0.166667 | CC(C)(C)OC(=O)N1CC=C(CCO)C(C)(C)C1>ClCCl>CC(C)(C)OC(=O)N1CC=C(CC=O)C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7c66406cc374ffb8b548acd13078612 | CC(C)(C)OC(=O)N1CCC(=CC(=O)O)CC1.CNOC>>COCNC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)=CC(=O)O.ON1N=NC2=C1C=CC=C2.Cl.CNOC.O>>C(C)(C)(C)OC(=O)N1CCC(CC1)=CC(NCOC)=O | O[C:5](=[O:6])[CH:7]=[C:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][O:2][NH:4][CH3:3]>>[CH3:1][O:2][CH2:3][NH:4][C:5](=[O:6])[CH:7]=[C:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCC(=CC(=O)O)CC1.CNOC | COCNC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C=O)C | Acylation | OtherReaction | f3d2102ab258a9aea40e3ec5161d0ef98ae3e1c9854f05889d24fc814a3fd1bd | 139b4c4e666d3283f3777133e40f462e31f0a86a17ece5a1ded1ce02355aaaa8 | [CH]=C1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4](-[C:5])-[C:6].[C;D1;H3:7]-[O;H0;D2;+0:8]-[NH;D2;+0:9]-[CH3;D1;+0:10]>>[C:5]-[C:4](=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[CH2;D2;+0:10]-[O;H0;D2;+0:8]-[C;D1;H3:7])-[C:6] | 60.8 | [{"value": 60.8, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)=CC(NCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | An aqueous solution of 1 M sodium hydroxide (15 mL) was added to a solution of 3.02 g (11.8 mmol) of tert-butyl ester of 4-metoxycarbonylmethylenepiperidine-1-carboxylic acid in THF (15 mL) and stirred for 2 hours. Then an aqueous solution of 1 M sodium hydroxide (another 10 mL) was added thereto, and stirred for 18 ho... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Ether.Secondary amide | null | null | C1CC[NH]CC1 | HO- | CN(C=O)C | null | 20 | CC(C)(C)OC(=O)N1CCC(=CC(=O)O)CC1.CNOC>CN(C=O)C>COCNC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b407a8250b7486dbbb86d1adc1d85a8 | CO.Cc1ccc2cccc(F)c2n1>>Cc1cc(CO)c2cccc(F)c2n1 | S(O)(O)(=O)=O.FC=1C=CC=C2C=CC(=NC12)C.[NH4+].[NH4+].[O-]S(=O)(=O)OOS(=O)(=O)[O-].O.CO>>FC=1C=CC=C2C(=CC(=NC12)C)CO | [CH3:5][OH:6].[CH3:1][c:2]1[cH:3][cH:4][c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[n:14]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][OH:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[n:14]1 | CO.Cc1ccc2cccc(F)c2n1 | Cc1cc(CO)c2cccc(F)c2n1 | null | null | null | C-C Coupling | OtherReaction | e7cc5c4c961f1a329921d509903a21b23b4b263e02c3b1d766e4418b79465d59 | e869cbe8a607411cfab69b4e60b9305ec52e29a933c34bd13cb5b3befde9ccd2 | c1ccc2ncccc2c1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:1.[CH3;D1;+0:10]-[O;D1;H1:11]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:10]-[O;D1;H1:11]):[c:9]:1 | 32 | [{"value": 32.0, "product": "FC=1C=CC=C2C(=CC(=NC12)C)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated sulfuric acid (1.2 mL) was added to a solution of 2.70 g (16.8 mmol) of 8-fluoro-2-methylquinoline and 7.70 g (33.7 mmol) of ammonium peroxodisulfate in a mixture of methanol (35 mL)-water (25 mL) and heated under reflux for 15 hours. The reaction mixture was left to cool, followed by a removal of methanol... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Primary alcohol | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | null | null | null | CO.Cc1ccc2cccc(F)c2n1>>Cc1cc(CO)c2cccc(F)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4a0988fa12e4acb83ea520bc0e7ed4c | Cc1cc(CO)c2cccc(F)c2n1.O=S(Cl)Cl>>Cc1cc(CCl)c2cccc(F)c2n1.Cl | S(=O)(Cl)Cl.FC=1C=CC=C2C(=CC(=NC12)C)CO>>Cl.ClCC1=CC(=NC2=C(C=CC=C12)F)C | O[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[n:14][c:13]2[c:7]1[cH:8][cH:9][cH:10][c:11]2[F:12].O=S([Cl:6])[Cl:15]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][Cl:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[n:14]1.[ClH:15] | Cc1cc(CO)c2cccc(F)c2n1.O=S(Cl)Cl | Cc1cc(CCl)c2cccc(F)c2n1.Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc2ncccc2c1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[Cl;H0;D1;+0:9]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[ClH;D0;+0:8] | 100.8 | [{"value": 100.0, "product": "Cl.ClCC1=CC(=NC2=C(C=CC=C12)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.8, "product": "Cl.ClCC1=CC(=NC2=C(C=CC=C12)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | At 0° C., 0.75 mL (10.4 mmol) of thionyl chloride was dropped into a solution of 1.00 g (5.23 mmol) of (8-fluoro-2-methylquinolin-4-yl)methanol obtained in the above 1) in chloroform (12 mL) and stirred for 15 hours at room temperature. The reaction mixture was removed under a reduced pressure and then, the residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2ncccc2c1 | Other | C(Cl)(Cl)Cl | null | 15 | Cc1cc(CO)c2cccc(F)c2n1.O=S(Cl)Cl>C(Cl)(Cl)Cl>Cc1cc(CCl)c2cccc(F)c2n1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a07b8de8d7f84159844f991ff4e74e5f | COC(=O)c1ccc([N+](=O)[O-])c(/C=C/N(C)C)c1.O>>COC(=O)c1ccc([N+](=O)[O-])c(C=O)c1 | COC(C1=CC(=C(C=C1)[N+](=O)[O-])\C=C\N(C)C)=O.C1CCOC1.O>>COC(C1=CC(=C(C=C1)[N+](=O)[O-])C=O)=O | CN(C)/C=[CH:13]/[c:12]1[c:8]([N+:9](=[O:10])[O-:11])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15]1.[OH2:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([CH:13]=[O:14])[cH:15]1 | COC(=O)c1ccc([N+](=O)[O-])c(/C=C/N(C)C)c1.O | COC(=O)c1ccc([N+](=O)[O-])c(C=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1bc53144aaaadfebb6804333b37b20e33a34fa620575111a961d81231c604008 | ee34f37ac54cbb3add9bb610747eeab45d01320a19fe84bf63f0866779dc68a8 | c1ccccc1 | C-N(-C)/C=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4].[OH2;D0;+0:5]>>[O;H0;D1;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 40 | CELSIUS | null | null | Compound 3 (11.81 g 47.2 mmol) and NaIO4 (30.3 g 141.6 mmol) was dissolved in 250 mL THF/H2O 1:1 at room temperature. The dark red solution was warmed to about 40° C. while heavy precipitation occurred and the color changed to light brown. After 1 h the precipitate was removed by filtration and washed with 200 mL ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Aldehyde | null | null | c1ccccc1 | Other | null | 40 | null | COC(=O)c1ccc([N+](=O)[O-])c(/C=C/N(C)C)c1.O>>COC(=O)c1ccc([N+](=O)[O-])c(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8abe8252512649bcaa209f9c32202d50 | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1>>COC(=O)c1ccc(N)c(C(OC)OC)c1 | COC(C1=CC(=C(C=C1)[N+](=O)[O-])C(OC)OC)=O>>COC(C1=CC(=C(C=C1)N)C(OC)OC)=O | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16][c:10]1[CH:11]([O:12][CH3:13])[O:14][CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([CH:11]([O:12][CH3:13])[O:14][CH3:15])[cH:16]1 | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1 | COC(=O)c1ccc(N)c(C(OC)OC)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | MINUTE | 100 mg 10% Pd/C and 1 g Mg2SO4 were suspended in 20 mL methanol and were hydrogenated in a Parr apparatus at 30 psi for 15 minutes. The apparatus was opened, and 1.22 g (4.78 mmol) of Compound 5 dissolved in 40 mL methanol was added, followed by 2 mL TEA. The mixture was hydrogenated at 30 psi for 30 minutes, the catal... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 0.25 | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1>[Pd].CO>COC(=O)c1ccc(N)c(C(OC)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f88972134c84ff88bec872e5ace47db | COC(=O)c1ccc(N)c(C(OC)OC)c1>>COC(=O)c1ccc(N)c(C=O)c1 | COC(C1=CC(=C(C=C1)N)C(OC)OC)=O>>COC(C1=CC(=C(C=C1)N)C=O)=O | CO[CH:11]([c:10]1[c:8]([NH2:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13]1)[O:12]C>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([CH:11]=[O:12])[cH:13]1 | COC(=O)c1ccc(N)c(C(OC)OC)c1 | COC(=O)c1ccc(N)c(C=O)c1 | null | null | CCO.C(C)(=O)O.O | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccccc1 | C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C)-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | MINUTE | Compound 6 (0.95 g, 4.2 mmol) was dissolved at room temperature in 15 mL of a solvent mixture composed of EtOH-acetic acid-water 2:2:1. The strongly colored yellow solution became pale yellow in 5 minutes. The mixture was let stand for an additional 15 minutes before it was evaporated to dryness and further dried in hi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccccc1 | HO- | CCO.C(C)(=O)O.O | null | 0.083333 | COC(=O)c1ccc(N)c(C(OC)OC)c1>CCO.C(C)(=O)O.O>COC(=O)c1ccc(N)c(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2ede4b4f4be459a9770a97f6390fb5a | CCO.O=C(O)c1ccc(Cl)c([N+](=O)[O-])c1>>CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | ClC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].C(C)O.S(O)(O)(=O)=O>>C(C)OC(C1=CC(=C(C=C1)Cl)[N+](=O)[O-])=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | CCO.O=C(O)c1ccc(Cl)c([N+](=O)[O-])c1 | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4-chloro-3-nitrobenzoic acid (100 g) was dissolved in 500 mL anhydrous ethanol and 35 mL concentrated sulfuric acid was added dropwise over a period of 5 minutes. The mixture was refluxed overnight then poured on 1 L ice. The precipitate was separated by filtration, washed four times with water and was then air dried. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)c1ccc(Cl)c([N+](=O)[O-])c1>>CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5e0bd8ff69a4e21abafde0eae58e9a5 | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1>>CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | O.C(C)OC(C1=CC(=C(C=C1)Cl)[N+](=O)[O-])=O.C1(CCCCC1)N>>C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)[N+](=O)[O-])=O | Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:21][c:17]1[N+:18](=[O:19])[O-:20].[NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]([N+:18](=[O:19])[O-:20])[cH:21]1 | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1 | CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10]):[c:2]:[c:3] | null | [] | null | null | null | null | A solution of Compound 9 (22.96 g, 100 mmol), cyclohexylamine (15.31 g, 154 mmol) and TEA (13.57 g, 134 mmol) in 100 mL acetonitrile was refluxed overnight. The reaction mixture was poured into icy water and the precipitated crystals were collected by means of filtration, washed three times with water then was dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HCl | C(C)#N | null | null | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.NC1CCCCC1>C(C)#N>CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29174407198c49d7a92d8befd421f1d3 | CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1>>CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)[N+](=O)[O-])=O>>C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O | O=[N+:18]([O-])[c:17]1[c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]([NH2:18])[cH:19]1 | CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1 | null | [Pd] | CO.C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NC2CCCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | To a solution of 5.84 g (20 mmol) of Compound 10 in 50 mL ethyl acetate and 30 mL methanol, 100 mg of 10% Pd/C was added, and the mixture was hydrogenated at 30 psi for 6 h. The catalyst was removed by filtration through a pad of Celite, the solvent was evaporated to dryness resulting in a dark purple solid which was r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCCCC1 | Other | [Pd].CO.C(C)(=O)OCC | null | 6 | CCOC(=O)c1ccc(NC2CCCCC2)c([N+](=O)[O-])c1>[Pd].CO.C(C)(=O)OCC>CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-281bf03bd1aa4c5aae79f22617d8f70f | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@H]1CC[C@H](O)CC1>>CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c([N+](=O)[O-])c1 | CO.C(C)OC(C1=CC(=C(C=C1)Cl)[N+](=O)[O-])=O.C(C)N(CC)CC.Cl.N[C@@H]1CC[C@H](CC1)O>>C(C)OC(C1=CC(=C(C=C1)N[C@@H]1CC[C@H](CC1)O)[N+](=O)[O-])=O | Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22][c:18]1[N+:19](=[O:20])[O-:21].[NH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:16][CH2:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:16][CH2:17]2)[c:18]([N+:19](=[O:20])[O-:21])... | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@H]1CC[C@H](O)CC1 | CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c([N+](=O)[O-])c1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCCCC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound 9 (689 mg, 3 mmol) was suspended in acetonitrile (5 mL) and then triethylamine was added (1.3 mL, 9 mmol). trans-4-aminocyclohexanol hydrochloride (682 mg, 4.5 mmol) was then added and the reaction refluxed for 12 hours, 2 mL methanol was then added and the reaction further refluxed for another 24 hours. Water... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HCl | O.C(C)#N | null | null | CCOC(=O)c1ccc(Cl)c([N+](=O)[O-])c1.N[C@H]1CC[C@H](O)CC1>O.C(C)#N>CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28c8ed27750a429a900e0c2e79d0c12a | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CC[C@@H](O)CC1 | C(C)OC(C1=CC(=C(C=C1)N[C@@H]1CC[C@H](CC1)O)N)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>O[C@@H]1CC[C@H](CC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | CC(C)N(C(C)C)[CH2:21][CH3:20].[O:1]=[C:2]([O:3][CH2:23][CH3:22])[c:4]1[cH:5][cH:6][c:7]([NH:28][C@H:29]2[CH2:30][CH2:31][C@H:32]([OH:33])[CH2:34][CH2:35]2)[c:8]([NH2:10])[cH:9]1.CN([C:17](O[n:25]1n[n:16][c:15]2[cH:14][cH:13][cH:12][cH:27][c:26]21)=[N+](C)C)[CH3:24].O=[CH:11]N([CH3:18])[CH3:19]>>[O:1]=[C:2]([OH:3])[c:4]... | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CC[C@@H](O)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d5224d3e39b5ea5e36ea115d5bbd42cdeb988ae706ebd58627c54fe64a28c596 | 477f657131ca4589b743a8a28b6796d63976298e2013be05ff0fa3589cec1ea5 | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C(-C)-N(-[CH2;D2;+0:1]-[CH3;D1;+0:2])-C(-C)-C.C-N(-[CH3;D1;+0:3])-[C;H0;D3;+0:4](-O-[n;H0;D3;+0:5]1:n:[n;H0;D2;+0:6]:[c:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:2:1)=[N+](-C)-C.O=[CH;D2;+0:13]-N(-[CH3;D1;+0:14])-[CH3;D1;+0:15].[C:16]-[C:17](-[NH;D2;+0:18]-[c:19](:[c:20]):[c:21](-[NH2;D1;+0:22]):[c:23]:[c:24]-[C:25... | null | [] | null | null | 20 | HOUR | Compound 36A Y=Phenyl, (200 mg, 0.8 mmol) was activated in 8 mL DMF with TBTU (282 mg, 0.88 mmol) and DIEA (0.285 mL, 1.6 mmol) for 30 minutes at room temperature. This solution was then added to Compound 579b (265 mg, 0.95 mmol) and stirred at ambient temperature for 20 hours. The reaction was concentrated to a residu... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Ester.Tertiary amide.Primary amine.Secondary amine.Tertiary amine | Carboxylic acid | c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | 20 | CCN(C(C)C)C(C)C.CCOC(=O)c1ccc(N[C@@H]2CC[C@@H](O)CC2)c(N)c1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2[C@@H]1CC[C@@H](O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9acaf5e7aee4f5993ef2b0b1bcf0fa7 | N[C@@H](CO)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1>>O=C(NC(CO)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2.N[C@@H](CO)C(=O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CO)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2 | [NH2:3][C@@H:4]([CH2:5][OH:6])[C:7](=[O:8])[OH:9].O[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[n:16][c:17](-[c:18]1[cH:19][cH:20][c:21]3[n:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31][c:32]3[cH:33]1)[n:34]2[CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1>>[O:1]=[C:2]([NH:3][CH:4]... | N[C@@H](CO)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | O=C(NC(CO)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[NH2;D1;+0:8]-[C@@H;D3;+0:9](-[C:10]-[O;D1;H1:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[CH;D3;+0:9](-[C:10]-[O;D1;H1:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]):[c:4] | 36 | [{"value": 36.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CO)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 231 was synthesized from Compound 201 as described for Compound 235, except L-serine was used instead of L-5-hydroxytryptophane. Yield: 36%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | N[C@@H](CO)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1>>O=C(NC(CO)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fd0395e750240669fd42f7dddee8699 | O=C(O)[C@@H]1CCCN1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1>>O=C(O)C1CCCN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2.N1[C@H](C(=O)O)CCC1>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2C(CCC2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2 | [O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[n:17][c:18](-[c:19]1[cH:20][cH:21][c:22]3[n:23][c:24](-[c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[cH:31][cH:32][c:33]3[cH:34]1)[n:35]2[CH:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1>>[O:1]=[C:2]([OH:... | O=C(O)[C@@H]1CCCN1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | O=C(O)C1CCCN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[C@@H;D3;+0:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:15]1-[C:14]-[C:13]-[C:12]-[CH;D3;+0:11]-1-[C:9](=[O;D1;H0:8])-[O;D1;H1:10]):[c:4] | 15 | [{"value": 15.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2C(CCC2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 233 was synthesized from Compound 201 as described for Compound 235, except L-proline was used instead of L-5-hydroxytryptophane. Yield: 15%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(O)[C@@H]1CCCN1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1>>O=C(O)C1CCCN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ecc5e60d49c4375b81517015a6752e1 | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.OC1=CC=C2NC=C(C[C@H](N)C(=O)O)C2=C1.CCN(C(C)C)C(C)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CNC1=CC=C(C=C21)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | [NH2:3][C@@H:4]([CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][c:15]12)[C:16](=[O:17])[OH:18].O[C:2](=[O:1])[c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[n:25][c:26](-[c:27]1[cH:28][cH:29][c:30]3[n:31][c:32](-[c:33]4[cH:34][cH:35][cH:36][cH:37][cH:38]4)[cH:39][n:40][c:41]3[cH:42]1)[n:43]2[CH:44]1[CH... | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1c[nH]c2ccccc12)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[#7;a:8]:[c:9]:[c:10]-[C:11]-[C@H;D3;+0:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[CH;D3;+0:12](-[C:11]-[c:10]:[c:9]:[#7;a:8])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]):[c:4] | null | [] | null | null | 1 | HOUR | Compound 203 (100 mg, 0.22 mmol) was activated in 2 mL DMF with 92 mg (0.24 mmol) HBTU and 85 μL DIEA for 10 minutes at room temperature. 56 mg 5-hydroxy-L-tryptophane, dissolved in 1 mL DMF was added followed by 44 μL DIEA. The mixture was stirred at room temperature for 1 h, then evaporated to dryness. The oil was pu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=O | null | 1 | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>CN(C)C=O>O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-909554a9c9e143c28f84455eeb665bc7 | C1CCNC1.CC(=O)c1cc(C(=O)O)ccc1O>>CC(=O)c1cc(C(=O)N2CCCC2)ccc1O | N1CCCC1.C(C)(=O)C=1C=C(C(=O)O)C=CC1O.CCN(C(C)C)C(C)C>>OC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.O[C:7]([c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:16]([OH:17])[cH:15][cH:14]1)=[O:8]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15][c:16]1[OH:17] | C1CCNC1.CC(=O)c1cc(C(=O)O)ccc1O | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | 62.8 | [{"value": 51.0, "product": "OC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.8, "product": "OC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 500 mg (2.8 mmol) of 3-acetyl-4-hydroxy-benzoic acid in 5 mL of DMF, 721.6 μL (4.2 mmol) of TFA-OPfp and 731.5 μL (4.2 mmol) of DIEA were added. The clear solution was stirred at room temperature for 15 minutes, then 467.5 μL (5.6 mmol) of pyrrolidine was added. The mixture was stirred for another hour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 0.25 | C1CCNC1.CC(=O)c1cc(C(=O)O)ccc1O>CN(C)C=O>CC(=O)c1cc(C(=O)N2CCCC2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a50cb176a218444796fa053ada1da08f | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O.COC(=O)c1ccc(N)c(C=O)c1>>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 | OC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O.COC(C1=CC(=C(C=C1)N)C=O)=O.[OH-].[K+].C(C)O>>OC1=C(C=C(C=C1)C(=O)N1CCCC1)C1=NC2=CC=C(C=C2C=C1)C(=O)O | O=[C:9]([c:10]1[cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20][cH:21][c:22]1[OH:23])[CH3:24].C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:26]([CH:25]=O)[cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][c:12]([C:13](=[O:14])[N:15]4[CH2:16][CH2:17][CH2:... | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O.COC(=O)c1ccc(N)c(C=O)c1 | O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 787f3948029cf179e86dce49d8fd4f56f7e959c161a049f67df1ad4098021aec | 29de9b43cd722ca10570b285d85bb37daead64f0fed7c96c040dae8d2e821222 | O=C(c1cccc(-c2ccc3ccccc3n2)c1)N1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[CH;D2;+0:7]=O):[c:8](-[NH2;D1;+0:9]):[c:10].O=[C;H0;D3;+0:11](-[CH3;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]-[C:16](-[#7:17])=[O;D1;H0:18]):[c:19](-[O;D1;H1:20]):[c:21]>>[#7:17]-[C:16](=[O;D1;H0:18])-[c:15]:[c:14]:[c;H0;D3;+0:13](-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:... | null | [] | null | null | null | null | Compound 18 (410 mg, 1.75 mmol) and Compound 7 (315 mg, 1.75 mmol) were dissolved in 30 mL of ethanol, 2.45 mL of a 10% KOH/ethanol solution was added and the mixture was refluxed overnight under argon. The ethanol was evaporated, the residue dissolved in water, and acidified with 3 mL of 1M HCl. The formed gel was sol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Carboxylic acid | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1 | HO- | C(C)O | null | null | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O.COC(=O)c1ccc(N)c(C=O)c1>C(C)O>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57391e0ab296494086ca597e54799ab9 | CO.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1>>COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 | OC1=C(C=C(C=C1)C(=O)N1CCCC1)C1=NC2=CC=C(C=C2C=C1)C(=O)O.CO>>COC(=O)C=1C=C2C=CC(=NC2=CC1)C1=C(C=CC(=C1)C(=O)N1CCCC1)O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][CH2:19][CH2:20]4)[cH:21][cH:22][c:23]3[OH:24])[cH:25][cH:26][c:27]2[cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:... | CO.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 | null | null | Cl.O1CCOCC1 | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(c1cccc(-c2ccc3ccccc3n2)c1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | null | null | To the solution of 295 mg (0.81 mmol) of Compound 19 in 3 mL of methanol, 1 mL of 4M HCl/dioxane was added, and the mixture was heated at 60° C. overnight. The reaction mixture was then evaporated to dryness to give Compound 20 in quantitative yield. MS: 377.18 (M+H+).
Conditions: See reaction.notes.procedure_details.
... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1 | HO- | Cl.O1CCOCC1 | 60 | null | CO.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1>Cl.O1CCOCC1>COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3O)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bd090c8f47e4c028b7d041b07d55119 | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3OS(=O)(=O)C(F)(F)F)ccc2c1.OB(O)c1ccc(Cl)cc1>>COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | COC(=O)C=1C=C2C=CC(=NC2=CC1)C1=C(C=CC(=C1)C(=O)N1CCCC1)OS(=O)(=O)C(F)(F)F.ClC1=CC=C(C=C1)B(O)O.ClC1=CC=C(C=C1)B(O)O.[O-]P(=O)([O-])[O-].[K+].[K+].[K+].[Li+].[Cl-]>>COC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1 | O=S(=O)(O[c:23]1[c:11](-[c:10]2[n:9][c:8]3[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:34][c:33]3[cH:32][cH:31]2)[cH:12][c:13]([C:14](=[O:15])[N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1)C(F)(F)F.OB(O)[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[n... | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3OS(=O)(=O)C(F)(F)F)ccc2c1.OB(O)c1ccc(Cl)cc1 | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids OTf | 3fcd38cd143accaacc097756f175627a8a766b312949d1dc56f9f30bda1e5856 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3ccccc3n2)c1)N1CCCC1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound 21 (320 mg, 0.63 mmol), 4-chloro-phenylboronic acid (Compound 22, 148 mg, 0.94 mmol), 500 mg (2.35 mmol) of K3PO4, 27 mg (0.63 mmol) of LiCl and 36.5 mg (0.031 mmol) of Pd(PPh3)4 were dissolved in 30 mL dioxane (degassed). The mixture was refluxed under argon overnight. The black solution was filtered through ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | TfOH.HO-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3OS(=O)(=O)C(F)(F)F)ccc2c1.OB(O)c1ccc(Cl)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bb067aa9e124cfba1b76803ee35be69 | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | COC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1.[OH-].[Na+]>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][c:12]([C:13](=[O:14])[N:15]4[CH2:16][CH2:17][CH2:18][CH2:19]4)[cH:20][cH:21][c:22]3-[c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]3)[cH:30][cH:31][c:32]2[cH:33]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][c:12]([C:13](... | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccccc2)c(-c2ccc3ccccc3n2)c1)N1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 96 | [{"value": 96.0, "product": "ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 23 from the previous step (0.63 mmol) was dissolved in 15 mL methanol, and 5 mL of 1M NaOH were added. The solution was refluxed for 2 hours, then evaporated. The residue was then dissolved in water, acidified with 5 mL of 1M HCl, and the precipitate was filtered off, washed three times with water and dried to... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | CO | null | null | COC(=O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>CO>O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc2f37d7126f464e98b6500b96223c44 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>>CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)N)=O.ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C(=O)N2CCCC2)C=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]([NH2:18])[cH:51]1.O[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]2[n:25][c:26](-[c:27]3[cH:28][c:29]([C:30](=[O:31])[N:32]4[CH2:33][CH2:34][CH2:35][CH2:36]4)[cH:37][cH:38][c:39]3-[c:40]3[cH:41][cH:42][c:4... | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1 | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1NC1CCCCC1)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccccc3)ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | Compound 24 (270 mg, 0.59 mmol) in 4 mL of DMF was activated with 246.6 mg (0.65 mmol) of HATU and 226 μL (1.30 mmol) of DIEA at room temperature for 15 minutes. Compound 11 (170 mg, 0.65 mmol) was added as solid and the mixture was stirred overnight. The DMF was evaporated; the remaining oil was solidified by triturat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | CN(C)C=O | null | 8 | CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1.O=C(O)c1ccc2nc(-c3cc(C(=O)N4CCCC4)ccc3-c3ccc(Cl)cc3)ccc2c1>CN(C)C=O>CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7044bea1cd14d9da16f302f9bea6c67 | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3ncc(-c4ccccc4)nc3c2)c1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2N=C(C=NC2=CC1)C1=CC=CC=C1)=O>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=C(C=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1 | O=[C:13]([NH:12][c:10]1[c:9]([NH:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]1)[c:14]1[cH:15][cH:16][c:17]2[n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[n:27][c:28]2[cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c... | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3ncc(-c4ccccc4)nc3c2)c1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | ebf150ea69999a65f3ea0fceee53a6530bfdd5940c707365f6a84450104b494b | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ccc(-c2cnc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3n2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C:7](-[C:8])-[C:9]):[c:10])-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]2:[#7;a:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:2:[c:20]:1>>[C:8]-[C:7](-[n;H0;D3;+0:6]1:[c:5](:[c:10]):[c:3](:[c:4]):[n;H0;D2;+0:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]2:[#7;a... | null | [] | null | null | null | null | Compound 41 (0.95 mmol) from the previous step was refluxed in 80 mL acetic acid for 3.5 h. The mixture was then evaporated to dryness and dried overnight under high vacuum to yield Compound 42 in quantitative yield. It was not further purified before saponification.
Conditions: See reaction.notes.procedure_details.
Wo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | C(C)(=O)O | null | null | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3ncc(-c4ccccc4)nc3c2)c1>C(C)(=O)O>CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ebc40419c924cbbbc229da2d37904ee | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | C(C)OC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=C(C=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C=NC1=CC2)C2=CC=CC=C2 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:12]1[cH:13][cH:14][c:15]3[n:16][cH:17][c:18](-[c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[n:25][c:26]3[cH:27]1)[n:28]2[CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[n:10][c:11](-[c:1... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cnc3ccc(-c4nc5ccccc5n4C4CCCCC4)cc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 81 | [{"value": 81.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C=NC1=CC2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To the solution of Compound 42 (0.95 mmol) in 25 mL ethanol 5 mL, 1 M NaOH was added and the mixture was refluxed for 1 h. It was then cooled and evaporated to dryness. The residue was dissolved in 50 mL water, acidified with 1M HCl to pH 4. The precipitate was filtered off, washed with water (4×) and dried to give 345... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | Other | C(C)O | null | null | CCOC(=O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1>C(C)O>O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0105d45447284ad8ba813b9a863a705c | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1>>O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1N=C(C=NC1=CC2)C2=CC=CC=C2.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.OC1=CC=C2NC=C(C[C@H](N)C(=O)O)C2=C1.CCN(C(C)C)C(C)C>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CNC1=CC=C(C=C21)O)C=2C=C1N=C(C=NC1=CC2)C2=CC=CC=C2 | [NH2:3][C@@H:4]([CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([OH:13])[cH:14][c:15]12)[C:16](=[O:17])[OH:18].O[C:2](=[O:1])[c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[n:25][c:26](-[c:27]1[cH:28][cH:29][c:30]3[n:31][cH:32][c:33](-[c:34]4[cH:35][cH:36][cH:37][cH:38][cH:39]4)[n:40][c:41]3[cH:42]1)[n:43]2[CH:44]1[CH... | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1c[nH]c2ccccc12)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[#7;a:8]:[c:9]:[c:10]-[C:11]-[C@H;D3;+0:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[CH;D3;+0:12](-[C:11]-[c:10]:[c:9]:[#7;a:8])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]):[c:4] | null | [] | null | null | 1 | HOUR | Compound 205 (100 mg, 0.22 mmol) was activated in 2 mL of DMF with 92 mg (0.24 mmol) of HBTU and 85 μL of DIEA for 10 minutes at room temperature. 5-hydroxy-L-tryptophane (56 mg) dissolved in 1 mL DMF was added, followed by 44 μL of DIEA. The mixture was stirred at room temperature for 1 h, then was evaporated to dryne... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | CN(C)C=O | null | 1 | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1>CN(C)C=O>O=C(NC(Cc1c[nH]c2ccc(O)cc12)C(=O)O)c1ccc2c(c1)nc(-c1ccc3ncc(-c4ccccc4)nc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3f42ab515274d48aa98ec9b3327df67 | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(NC(C(=O)O)C1CCCCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.N([C@@H](CC1CCCCC1)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C1(CCCCC1)C(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1 | C1([CH2:8][CH:4]([NH:3][C:2](=[O:1])[c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[n:20][c:21](-[c:22]2[cH:23][cH:24][c:25]4[n:26][c:27](-[c:28]5[cH:29][cH:30][cH:31][cH:32][cH:33]5)[cH:34][n:35][c:36]4[cH:37]2)[n:38]3[CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)[C:5](=[O:6])[OH:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(NC(C(=O)O)C1CCCCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 497ed6fa2fecc89bd99211bb234d91811e03f385203fb438fe023970267815cc | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(NCC1CCCCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4](-[CH2;D2;+0:5]-C1-[CH2;D2;+0:6]-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[O;D1;H0:1]=[C:2]-[#7:3]-[C:4](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1 | 48 | [{"value": 48.0, "product": "C1(CCCCC1)C(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Cha Wang resin (250 mg, 0.4 mmol/g), producing 29 mg of the title compound (48% yield). MS: 586.27 (M−H+) HPLC Procedure A, retention time=14.94 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | Other | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(NC(C(=O)O)C1CCCCC1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15200b5071cc425b84d0e423c16c6a4f | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(NC(Cc1ccccc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.C1=CC=C(C=C1)C[C@@H](C=O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CC=CC=C2)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | [O:1]=[C:2]([NH:3][CH:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[C:12](=[O:13])[OH:14])[c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[n:21][c:22](-[c:23]1[cH:24][cH:25][c:26]3[n:27][c:28](-[c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[cH:35][n:36][c:37]3[cH:38]1)[n:39]2[CH:40]1[CH2:41][CH2:42][CH2:43][CH2:44... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(NC(Cc1ccccc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Oxidation | OtherReaction | 2ff58657929e5a22525dda14a0665f3839e925138d262abe75106950487d7414 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C(NCCc1ccccc1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[CH;D3;+0:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1 | 44 | [{"value": 44.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CC=CC=C2)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Phe Wang resin (167 mg, 0.6 mmol/g), producing 26 mg of the title compound (44% yield). MS: 594.24 (M−H+) HPLC Procedure A, retention time=14.58 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | c1ccccc1 | c1ccccc1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | null | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(NC(Cc1ccccc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a38c25b623e4a459694e3d4280799ad | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(O)CNC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCC=O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NCC(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | C1CCC(C[CH:4]([C:2](=[O:1])[OH:3])[NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]4[n:20][c:21](-[c:22]5[cH:23][cH:24][cH:25][cH:26][cH:27]5)[cH:28][n:29][c:30]4[cH:31]2)[n:32]3[CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)CC1>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][C... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O=C(O)CNC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | bb65fc67218684cc396a8ffe8ad7da2888aff205a97ffc45cd6633318feea9bc | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-C-C1-C-C-C-C-C-1)-[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[c:8] | 55 | [{"value": 55.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NCC(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Gly Wang resin (125 mg, 0.8 mmol/g), producing 30 mg of the title compound (55% yield). MS: 504.21 (M−H+) HPLC Procedure A, retention time=12.32 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | null | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | Other | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>O=C(O)CNC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-006655b3886d4335a617177cf96948e5 | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1c[nH]cn1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(NC(Cc1c[nH]cn1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.N([C@@H](CC1=CNC=N1)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC=2N=CNC2)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | C1CC[CH:6]([CH2:5][CH:4]([NH:3][C:2](=[O:1])[c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[n:20][c:21](-[c:22]2[cH:23][cH:24][c:25]4[n:26][c:27](-[c:28]5[cH:29][cH:30][cH:31][cH:32][cH:33]5)[cH:34][n:35][c:36]4[cH:37]2)[n:38]3[CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)[C:11](=[O:12])[OH:13])CC1.O=C(N[C@@H](Cc1[cH:... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1c[nH]cn1)C(=O)O)OCC1c2ccccc2-c2ccccc21 | O=C(NC(Cc1c[nH]cn1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 2956083794072489de438a0326b4f67a31b280fb2d0829b0c1c14f475a5388af | ca4b05253b0321c0bf8530f65cf5bcc07978b7ca6833810686f19f4e97a4e6c0 | O=C(NCCc1c[nH]cn1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O-C(=O)-[C@@H](-C-c1:[cH;D2;+0:1]:[#7;a:2]:[c:3]:[n;H0;D2;+0:4]:1)-N-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[C:8]-[C:9]-[CH;D3;+0:10]1-C-C-C-C-C-1>>[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[C:8]-[C:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:1]:[#7;a:2]:[c:3]:[n;H0;D2;+0:4]:1 | 51 | [{"value": 51.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC=2N=CNC2)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-His Wang resin (250 mg, 0.4 mmol/g), producing 30 mg of the title compound (51% yield). MS: 584.24 (M−H+) HPLC Procedure A, retention time=11.16 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether | null | C1CCCCC1.c1c[nH]cn1.c1ccc2c(c1)Cc1ccccc12 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1c[nH]cn1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(NC(Cc1c[nH]cn1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c49fcd2ea8941769c8e93158e59cf9b | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCC1c2ccccc2-c2ccccc21>>O=C(O)C1CC(O)CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.N1([C@H](C(=O)O)C[C@@H](O)C1)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2C(CC(C2)O)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | O=C(O)C(CC1CCCCC1)N[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[n:18][c:19](-[c:20]1[cH:21][cH:22][c:23]3[n:24][c:25](-[c:26]4[cH:27][cH:28][cH:29][cH:30][cH:31]4)[cH:32][n:33][c:34]3[cH:35]1)[n:36]2[CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1.O=C(OCC1c2ccccc2-c2ccccc21)[N:9]1[C@H:4]([C:2](=[O:1])[O... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCC1c2ccccc2-c2ccccc21 | O=C(O)C1CC(O)CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Acylation | OtherReaction | 187c726284ca2e0d1dc94c639e880f34f14d4b60f1523bbaf901e6ff56daa757 | fbbe73966b830a999bbe31d7b1af379c7f7f39b5667cba8e3ef0abff4d98fc39 | O=C(c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)N1CCCC1 | O-C(=O)-C(-C-C1-C-C-C-C-C-1)-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:11]-[C@H;D3;+0:12]-1-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:11... | 50 | [{"value": 50.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2C(CC(C2)O)C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Hyp Wang resin (143 mg, 0.7 mmol/g), producing 23 mg of the title compound (50% yield). MS: 560.23 (M−H+) HPLC Procedure A, retention time=11.58 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amide | Tertiary amide | C1CCCCC1.C1CC[NH]C1.c1ccc2c(c1)Cc1ccccc12 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCC1c2ccccc2-c2ccccc21>>O=C(O)C1CC(O)CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db075497cce64b28aa3e5dd774cdb991 | CC[C@H](C)[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>CCC(C)C(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.CC[C@H](C)[C@@H](C=O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)C(CC)C)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | O=C[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)[C@H:3]([CH2:2][CH3:1])[CH3:4].C1CCC(C[CH:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[n:15][c:16](-[c:17]2[cH:18][cH:19][c:20]4[n:21][c:22](-[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29][n:30][c:31]4[cH:32]2)[n:33]3[CH:34]2[CH2:35][CH2:36][CH2:37][CH2:3... | CC[C@H](C)[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | CCC(C)C(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O | null | null | null | C-C Coupling | OtherReaction | e5069954d2c8d0dd8a2b4fc6a2c37b04c6b94c0fbf82757f348bbbed65492b59 | ea5719a3397984907dc224fc4ac4d86177efd84a5f65e660515ff9567dbfb68c | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | O=C-[C@@H](-N-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[CH;D3;+0:8](-C-C1-C-C-C-C-C-1)-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C;D1;H3:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:8](-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12])-[C:6](=[O;D1;H0:... | 54 | [{"value": 54.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)C(CC)C)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Ile Wang resin (250 mg, 0.4 mmol/g), producing 23 mg of the title compound (54% yield). MS: 560.26 (M−H+) HPLC Procedure A, retention time=14.34 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether | null | c1ccc2c(c1)Cc1ccccc12.C1CCCCC1 | null | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC[C@H](C)[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>CCC(C)C(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16acc94d2e88466fa25743098ed6bc7b | CC(C)C[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>CC(C)CC(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.CC(C)C[C@@H](C=O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC(C)C)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | O=C[C@H](C[CH:2]([CH3:1])[CH3:3])NC(=O)OCC1c2ccccc2-c2ccccc21.C1CCC([CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[n:15][c:16](-[c:17]2[cH:18][cH:19][c:20]4[n:21][c:22](-[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29][n:30][c:31]4[cH:32]2)[n:33]3[CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38]... | CC(C)C[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | CC(C)CC(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O | null | null | null | C-C Coupling | OtherReaction | e5069954d2c8d0dd8a2b4fc6a2c37b04c6b94c0fbf82757f348bbbed65492b59 | ea5719a3397984907dc224fc4ac4d86177efd84a5f65e660515ff9567dbfb68c | c1ccc(-c2cnc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | O=C-[C@H](-C-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-N-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[CH2;D2;+0:11]-C1-C-C-C-C-C-1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[CH2;D2;+0:11]-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:5](=[O;D1;H0:4])-[O;D1;H1:6] | 14 | [{"value": 14.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC(C)C)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Leu Wang resin (111 mg, 0.9 mmol/g), producing 8.1 mg of the title compound (14% yield). MS: 560.25 (M−H+) HPLC Procedure A, retention time=17.17 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether | null | c1ccc2c(c1)Cc1ccccc12.C1CCCCC1 | null | c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)C[C@@H](C=O)NC(=O)OCC1c2ccccc2-c2ccccc21.O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1>>CC(C)CC(NC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f0029f5f5a74f9fb2c53ce9bc2035db | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1Cc2ccccc2CN1C(=O)OCC1c2ccccc2-c2ccccc21>>O=C(O)C1Cc2ccccc2CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.N1([C@@H](CC2=CC=CC=C2C1)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2CC1=CC=CC=C1CC2C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | C1CCC(C[CH:4]([C:2](=[O:1])[OH:3])[NH:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[n:22][c:23](-[c:24]2[cH:25][cH:26][c:27]4[n:28][c:29](-[c:30]5[cH:31][cH:32][cH:33][cH:34][cH:35]5)[cH:36][n:37][c:38]4[cH:39]2)[n:40]3[CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]2)CC1.O=C(O)[C@H]1N(C(=O)OCC2c3ccccc... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1Cc2ccccc2CN1C(=O)OCC1c2ccccc2-c2ccccc21 | O=C(O)C1Cc2ccccc2CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 71fe47c6bdd77e344dbc1e5f712017b58b087ff739f51dc4b8098e9bf2ed7123 | baf54976ffa7e0ea08d57fbd34ec949a9ec7f9c72964ed32f1e463f505a20c91 | O=C(c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1)N1CCc2ccccc2C1 | O-C(=O)-[C@@H]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:5])-[CH2;D2;+0:6]-N-1-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[O;D1;H0:7]=[C:8](-[c:9])-[NH;D2;+0:10]-[CH;D3;+0:11](-C-C1-C-C-C-C-C-1)-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[O;D1;H0:7]=[C:8](-[c:9])-[N;H0;D3;+0:10]1-[CH2;D2;+0:6]-[c:4](:[c:5]):[c:2](:[c:3])-[CH2;... | 41 | [{"value": 41.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)N2CC1=CC=CC=C1CC2C(=O)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Tic Wang resin (143 mg, 0.7 mmol/g), producing 25 mg of the title compound (41% yield). MS: 606.22 (M−H+) HPLC Procedure A, retention time=17.18 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amide | Tertiary amide | C1CCCCC1.c1ccc2c(c1)CCNC2.c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(O)[C@@H]1Cc2ccccc2CN1C(=O)OCC1c2ccccc2-c2ccccc21>>O=C(O)C1Cc2ccccc2CN1C(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb5c027e03e6415d968c993d4dbb6529 | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(NC(Cc1ccc(O)cc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | C1(CCCCC1)CC(C(=O)O)NC(=O)C1=CC2=C(N(C(=N2)C=2C=C3N=CC(=NC3=CC2)C2=CC=CC=C2)C2CCCCC2)C=C1.N([C@@H](CC1=CC=C(C=C1)O)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CC=C(C=C2)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2 | C1CCC([CH2:5][CH:4]([NH:3][C:2](=[O:1])[c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[n:22][c:23](-[c:24]2[cH:25][cH:26][c:27]4[n:28][c:29](-[c:30]5[cH:31][cH:32][cH:33][cH:34][cH:35]5)[cH:36][n:37][c:38]4[cH:39]2)[n:40]3[CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]2)[C:13](=[O:14])[OH:15])CC1.O=C(N[C@@H](C[c:6]1[cH:7... | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCC1c2ccccc2-c2ccccc21 | O=C(NC(Cc1ccc(O)cc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 68a2829aa2fe4f5af6c50b9bc44b3303d73f8833bee9b17764cf3d3ec8dff6f3 | c63297b1799aa3266bafffeda5390b0ca608e1cecf8d555809cf48439c00d4a6 | O=C(NCCc1ccccc1)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 | O-C(=O)-[C@@H](-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-N-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[O;D1;H0:6]=[C:7](-[O;D1;H1:8])-[C:9](-[#7:10]-[C:11]=[O;D1;H0:12])-[CH2;D2;+0:13]-C1-C-C-C-C-C-1>>[O;D1;H0:6]=[C:7](-[O;D1;H1:8])-[C:9](-[#7:10]-[C:11]=[O;D1;H0:12])-[CH2;D2;+0:13]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c... | 36 | [{"value": 36.0, "product": "C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)NC(C(=O)O)CC2=CC=C(C=C2)O)C=2C=C1N=CC(=NC1=CC2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The general procedure described for Compound 242 was used with Fmoc-Tyr Wang resin (125 mg, 0.8 mmol/g), producing 22 mg of the title compound (36% yield). MS: 610.22 (M−H+) HPLC Procedure A, retention time=16.14 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether | null | C1CCCCC1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1 | c1ccccc1.c1ccc2nc[nH]c2c1.c1ccc2nccnc2c1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | O=C(NC(CC1CCCCC1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1.O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(NC(Cc1ccc(O)cc1)C(=O)O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4)cnc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e17b79c8d794eb18eacc939146659d4 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.OB(O)c1ccncc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccncc4)ccc3c1)n2C1CCCCC1 | ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C=C1.N1=CC=C(C=C1)B(O)O>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=C(C=CC=C2)C2=CC=NC=C2 | Clc1ccc(-[c:23]2[c:18](-[c:17]3[n:16][c:15]4[cH:14][cH:13][c:12](-[c:11]5[n:10][c:8]6[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]6)[n:34]5[CH:35]5[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]5)[cH:33][c:32]4[cH:31][cH:30]3)[cH:19][cH:20][cH:21][cH:22]2)cc1.OB(O)[c:24]1[cH:25][cH:26][n:27][cH:28][cH:29]1>>[O:1]=[C:2]([... | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.OB(O)c1ccncc1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccncc4)ccc3c1)n2C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 16f54d157237efebdb53d22fd611e71a39585c4a0bebef4efcc4595aa8b81cf2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c(-c2ccncc2)c1 | Cl-c1:c:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:1.O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:2]:[c:3] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 387 except pyridine-4-boronic acid was used instead of 4-chlorophenyl-boronic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccncc1.C1CCCCC1 | HCl.B | null | null | null | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.OB(O)c1ccncc1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccncc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-646d0f843ba64899b93369d2fcf73691 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O>>CC(=O)c1cccc(C(=O)N2CCCC2)c1 | OC1=C(C=C(C=C1)C(=O)N1CCCC1)C(C)=O.C(C)(=O)C=1C=C(C(=O)O)C=CC1>>N1(CCCC1)C(=O)C=1C=C(C=CC1)C(C)=O | O[c:5]1[c:4]([C:2]([CH3:1])=[O:3])[cH:16][c:8]([C:9](=[O:10])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:7][cH:6]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:16]1 | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O | CC(=O)c1cccc(C(=O)N2CCCC2)c1 | null | null | null | Reduction | OtherReaction | 0b15258bc3b0efb75716a15093f26f3ade1fb35d0d50493dcb65925b9449d16a | 27ebe27a5e17883303ac9a42d30f2cb918c0044de7ff3c79776e1ddb80cc53d9 | O=C(c1ccccc1)N1CCCC1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | The title intermediate was synthesized as described for Compound 18 except 3-acetylbenzoic acid was used instead of 3-acetyl-4-hydroxy benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1 | Other | null | null | null | CC(=O)c1cc(C(=O)N2CCCC2)ccc1O>>CC(=O)c1cccc(C(=O)N2CCCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b3431549d244b98a38fd0c4ff8b8882 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(C(=O)N5CCCC5)c4)ccc3c1)n2C1CCCCC1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C(=O)N3CCCC3)C=C1.C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1)=O.C(C)(=O)C1=CC=CC=C1>>C1(CCCCC1)N1C(=NC2=C1C=CC(=C2)C(=O)O)C=2C=C1C=CC(=NC1=CC2)C2=CC(=CC=C2)C(=O)N2CCCC2 | Clc1ccc(-[c:19]2[c:18](-[c:17]3[n:16][c:15]4[cH:14][cH:13][c:12](-[c:11]5[n:10][c:8]6[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]6)[n:35]5[CH:36]5[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]5)[cH:34][c:33]4[cH:32][cH:31]3)[cH:30][c:22]([C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[cH:21][cH:20]2)cc1>>[O:1]... | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(C(=O)N5CCCC5)c4)ccc3c1)n2C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 37126fe409d177b10098697f84f460c144cc4ba4154e21f8875ccf680fa3140f | f004e58a958e83ed69c0f163c54d2c11d46ff03ec9dbfbb5a519e7e4cb2f94a4 | O=C(c1cccc(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | Cl-c1:c:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]):c:c:1>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | The title compound was synthesized in four steps as described for Compound 13, Compound 25, Compound 27 Q=ethyl and Compound 204, respectively, except the product of the previous step was used in the first step, instead of acetophenone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.C1CCCCC1 | HCl | null | null | null | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cccc(C(=O)N5CCCC5)c4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b497d444bf14705a74cc22daed94216 | COC(=O)c1ccc(N)cc1.O=Cc1ccccc1Br>>COC(=O)c1ccc(/N=C/c2ccccc2Br)cc1 | COC(C1=CC=C(C=C1)N)=O.BrC1=C(C=O)C=CC=C1>>COC(C1=CC=C(C=C1)/N=C/C1=C(C=CC=C1)Br)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:18][cH:19]1.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[Br:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](/[N:9]=[CH:10]/[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Br:17])[cH:18][cH:19]1 | COC(=O)c1ccc(N)cc1.O=Cc1ccccc1Br | COC(=O)c1ccc(/N=C/c2ccccc2Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=N/c1ccccc1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](/[CH;D2;+0:1]=[N;H0;D2;+0:5]/[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 8 | HOUR | 4-aminobenzoic acid methyl ester (1.51 g, 10 mmol) and 2-bromobenzaldehyde (1.45 mL, 12.5 mmol) were dissolved in 15 mL of methanol. The mixture was let stand overnight. A white precipitate formed and the crystals were filtered off, washed with cold methanol (2×) and dried.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1ccccc1.c1ccccc1 | HO- | CO | null | 8 | COC(=O)c1ccc(N)cc1.O=Cc1ccccc1Br>CO>COC(=O)c1ccc(/N=C/c2ccccc2Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c1876e49ccd4ba6b93659497178e00f | COC(=O)c1ccc2nc(-c3ccccc3Br)cc(C)c2c1>>Cc1cc(-c2ccccc2Br)nc2ccc(C(=O)O)cc12 | COC(=O)C=1C=C2C(=CC(=NC2=CC1)C1=C(C=CC=C1)Br)C>>BrC1=C(C=CC=C1)C1=NC2=CC=C(C=C2C(=C1)C)C(=O)O | C[O:19][C:17]([c:16]1[cH:15][cH:14][c:13]2[n:12][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[Br:11])[cH:3][c:2]([CH3:1])[c:21]2[cH:20]1)=[O:18]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[Br:11])[n:12][c:13]2[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][c:21]12 | COC(=O)c1ccc2nc(-c3ccccc3Br)cc(C)c2c1 | Cc1cc(-c2ccccc2Br)nc2ccc(C(=O)O)cc12 | null | null | O1CCOCC1.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc3ccccc3n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Compound 471b (500 mg, 1.4 mmol) was refluxed in a mixture of 15 mL dioxane and 15 mL 1M aqueous NaOH for 1 h then it was evaporated to dryness, the residue dissolved in 50 mL water and acidified with 1M HCl solution to pH 4. The precipitate was filtered off, washed four times with water and dried. Yield: 361 mg (75%).... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | O1CCOCC1.[OH-].[Na+] | null | null | COC(=O)c1ccc2nc(-c3ccccc3Br)cc(C)c2c1>O1CCOCC1.[OH-].[Na+]>Cc1cc(-c2ccccc2Br)nc2ccc(C(=O)O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f413cfc3b0141ebacd5e8fccda73064 | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1.O=C(O)c1ccc2nc(-c3ccccc3-c3ccc(Cl)cc3)ccc2c1>>O=C(O)c1ccc2[nH]c(-c3ccc4nc(-c5ccccc5-c5ccc(Cl)cc5)ccc4c3)nc2c1 | C(C)OC(C1=CC(=C(C=C1)NC1CCCCC1)NC(=O)C=1C=C2C=CC(=NC2=CC1)C1=CC(=CC=C1C1=CC=C(C=C1)Cl)C(=O)N1CCCC1)=O.ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2)C(=O)O)C=C1>>ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2)C=CC(=C3)C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8]C2CCCCC2)[c:34]([NH:33][C:9](=O)[c:10]2[cH:11][cH:12][c:13]3[n:14][c:15](-[c:16]4c(-c5ccc(Cl)cc5)ccc(C(=O)N5CCCC5)[cH:17]4)[cH:29][cH:30][c:31]3[cH:32]2)[cH:35]1.O=C(O)c1ccc2nc(-c3c[cH:18][cH:19][cH:20][c:21]3-[c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)ccc2c1>>... | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1.O=C(O)c1ccc2nc(-c3ccccc3-c3ccc(Cl)cc3)ccc2c1 | O=C(O)c1ccc2[nH]c(-c3ccc4nc(-c5ccccc5-c5ccc(Cl)cc5)ccc4c3)nc2c1 | null | null | null | Miscellaneous | OtherReaction | 7844f5673d3fec6ca368b245d17ba7505082dda8d78106abab9d94d0d5d6d2da | 3cd5bfc5b8b0f02a7f1c5888e0aaef43804d43e748574d0e4cf9deb9505606d0 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5[nH]4)ccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[NH;D2;+0:7]-[C;H0;D3;+0:8](=O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](:[#7;a:13]:[c:14](-[c;H0;D3;+0:15]2:[cH;D2;+0:16]:c(-C(=O)-N3-C-C-C-C-3):c:c:c:2-c2:c:c:c(-Cl):c:c:2):[c:17]):[c:18]:[c:19]:1):[c:20](-[NH;D2;+0:21]-C1-C-C-C-C-C-1):[c:22].O-C(=O)-c1:c:c:c2:n:c... | null | [] | null | null | null | null | The title compound was synthesized from Compound 353b in two steps as described for Compound 25 and 27 Q=ethyl, respectively.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Ester.Secondary amide.Tertiary amide.Secondary amine | Carboxylic acid | c1ccccc1.C1CCCCC1.c1ccccc1.c1ccccc1.C1CCNC1.c1ccc2ncccc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1ccc(NC2CCCCC2)c(NC(=O)c2ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c2)c1.O=C(O)c1ccc2nc(-c3ccccc3-c3ccc(Cl)cc3)ccc2c1>>O=C(O)c1ccc2[nH]c(-c3ccc4nc(-c5ccccc5-c5ccc(Cl)cc5)ccc4c3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-417b95c144e346c1a204a500c786e324 | O=C(O)c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1.OC1CCNCC1>>O=C(c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1)N1CCC(O)CC1 | ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC(=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)F)C=C1.OC1CCNCC1>>ClC1=CC=C(C2=CC=CC=C2C2=NC3=CC(=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)N3CCC(CC3)O)F)C=C1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10](-[c:11]1[cH:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4-[c:23]4[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]4)[n:30][c:31]3[cH:32][c:33]1[F:34])[n:35]2[CH:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1.[NH:42]1[CH2:43][CH2:44][C... | O=C(O)c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1.OC1CCNCC1 | O=C(c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1)N1CCC(O)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc2c(c1)nc(-c1ccc3nc(-c4ccccc4-c4ccccc4)ccc3c1)n2C1CCCCC1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C:9]-[C:8])-[C:11]-[C:12]):[c:4] | null | [] | null | null | null | null | The title compound was synthesized from Compound 408 and 4-hydroxypiperidine using standard HBTU activation.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1.C1CC[NH]CC1 | HO- | null | null | null | O=C(O)c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1.OC1CCNCC1>>O=C(c1ccc2c(c1)nc(-c1cc3ccc(-c4ccccc4-c4ccc(Cl)cc4)nc3cc1F)n2C1CCCCC1)N1CCC(O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28d046793373421aa5344a8501d964e6 | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1>>COC(OC)c1cc(C(=O)O)ccc1[N+](=O)[O-] | COC(C1=CC(=C(C=C1)[N+](=O)[O-])C(OC)OC)=O>>COC(C=1C=C(C(=O)O)C=CC1[N+](=O)[O-])OC | C[O:11][C:9]([c:8]1[cH:7][c:6]([CH:3]([O:2][CH3:1])[O:4][CH3:5])[c:14]([N+:15](=[O:16])[O-:17])[cH:13][cH:12]1)=[O:10]>>[CH3:1][O:2][CH:3]([O:4][CH3:5])[c:6]1[cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17] | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1 | COC(OC)c1cc(C(=O)O)ccc1[N+](=O)[O-] | null | null | CO.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 2 | HOUR | To a solution of 5.49 g (21.5 mmol) of Compound 5 in 200 mL of methanol, 50 mL of 1M NaOH were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was then evaporated to dryness, the residue was dissolved in 100 mL water, acidified with 1 M HCl to pH 3-4. The precipitate was then filtere... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.[OH-].[Na+] | null | 2 | COC(=O)c1ccc([N+](=O)[O-])c(C(OC)OC)c1>CO.[OH-].[Na+]>COC(OC)c1cc(C(=O)O)ccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99c1c52090f74667854cb9244b549d2b | CCOC(=O)c1ccc2c(c1)nc(-c1ccc([N+](=O)[O-])c(C(OC)OC)c1)n2C1CCCCC1>>CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C(OC)OC)c1)n2C1CCCCC1 | [O-]S(=O)(=O)[O-].[Mg+2].C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)[N+](=O)[O-])C(OC)OC)C2CCCCC2)C=C1>>C(C)OC(=O)C1=CC2=C(N(C(=N2)C2=CC(=C(C=C2)N)C(OC)OC)C2CCCCC2)C=C1 | O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14](-[c:13]2[n:12][c:10]3[c:9]([cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]3)[n:26]2[CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:25][c:19]1[CH:20]([O:21][CH3:22])[O:23][CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12][c... | CCOC(=O)c1ccc2c(c1)nc(-c1ccc([N+](=O)[O-])c(C(OC)OC)c1)n2C1CCCCC1 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C(OC)OC)c1)n2C1CCCCC1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2nc3ccccc3n2C2CCCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | In 20 mL methanol 100 mg of 10% Pd-C was pre-hydrogenated in the presence of 1 g MgSO4 at 30 psi for 15 minutes. Compound 354c (100 mg) dissolved in a solution of 20 mL of methanol containing 2 mL triethylamine, was added to the catalyst and the hydrogenation was continued for 30 minutes. The catalyst and the magnesium... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2nc[nH]c2c1.c1ccccc1.C1CCCCC1 | Other | [Pd].CO | null | 0.5 | CCOC(=O)c1ccc2c(c1)nc(-c1ccc([N+](=O)[O-])c(C(OC)OC)c1)n2C1CCCCC1>[Pd].CO>CCOC(=O)c1ccc2c(c1)nc(-c1ccc(N)c(C(OC)OC)c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b35501ea7ea84326a3153ec3757cfa04 | COc1ccc(O)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)C(=O)N3CCCC3)C=C1.CC(=O)C1=C(C=CC(=C1)OC)O>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OC)C=C1 | CC(=O)[c:14]1[c:6](O)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43]1.O=C(c1ccc(-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)c(-[c:15]2[cH:16][cH:17][c:18]3[cH:19][c:20](-[c:21]4[n:22][c:23]5[cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30][c:31]5[n:32]4[CH:33]4[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]4)[cH:39][cH:40][c:4... | COc1ccc(O)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 497bfe732398c4a738c6e77bf0e42de389d231b4f3b47174ddda27fc01db72a7 | f0941aa72c1052eaf5962addba6315ee54aa4f9cbd7f3d35c596c5c7cca3a39d | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-O.O=C(-N1-C-C-C-C-1)-c1:c:c:c(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):c(-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]):c:1>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c... | null | [] | null | null | null | null | The title compound was synthesized in seven steps as described for Compound 204 except 2-hydroxy-5-methoxy acetophenone was used instead of Compound 18.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.C1CCNC1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | null | null | null | COc1ccc(O)c(C(C)=O)c1.O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(C(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1>>COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e214870f98549bea9cf3f9e96546682 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.COCCBr>>COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)O)C2CCCCC2)C=C1.[H-].[Na+].BrCCOC>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOC)C=C1 | C[O:31][C:29]([c:28]1[cH:27][c:26]2[n:25][c:24](-[c:23]3[cH:22][c:21]4[cH:20][cH:19][c:18](-[c:17]5[c:9](-[c:10]6[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]6)[cH:8][cH:7][c:6]([OH:5])[cH:46]5)[n:45][c:44]4[cH:43][cH:42]3)[n:35]([CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[c:34]2[cH:33][cH:32]1)=[O:30].Br[CH2:4][C... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.COCCBr | COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | null | [] | null | null | 8 | HOUR | Compound 475a (100 mg, 0.162 mmol) was dissolved in 2 mL of DMF and treated with 16.8 mg (0.7 mmol) of NaH for 30 min. 1-bromo-2-methoxy ethane (30.5 μL) was added and the mixture was agitated overnight. The next day the reaction mixture was evaporated to dryness, the oily residue dissolved in 3 mL methanol followed by... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | CN(C)C=O | null | 8 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.COCCBr>CN(C)C=O>COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-929375494e55402ca20484b819b4d3e3 | CCOCCBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>CCOCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOC)C=C1.BrCCOCC.BrCCOC>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOCC)C=C1 | BrC[CH2:4][O:3][CH2:2][CH3:1].COC[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24](-[c:25]4[n:26][c:27]5[cH:28][c:29]([C:30](=[O:31])[OH:32])[cH:33][cH:34][c:35]5[n:36]4[CH:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[cH:43][cH:... | CCOCCBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | CCOCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | C-methylation | 3d8e6ce3d88f34a35f7f0c9de676fefcf97c38df6c98620e3ce85e4603c2ec5c | 030ff2f3688fbc135f4b0801cdaaff8955dd15fbd4acb1840524f3277bf69aa0 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-C-[CH2;D2;+0:1]-[#8:2]-[C:3].C-O-C-[CH2;D2;+0:4]-[#8:5]-[c:6]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[#8:5]-[c:6] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 475, except 1-bromo-2-ethoxy ethane was used for alkylation instead of 1-bromo-2-methoxy ethane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Ether | Ether.Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | null | null | null | CCOCCBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>CCOCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e80f65a9c90345988fb63d7efb2f68f4 | CC(C)(C)OC(=O)CBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>O=C(O)COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOC)C=C1.BrCC(=O)OC(C)(C)C.BrCCOC>>C(=O)(O)COC=1C=C(C(=CC1)C1=CC=C(C=C1)Cl)C1=NC2=CC=C(C=C2C=C1)C1=NC2=C(N1C1CCCCC1)C=CC(=C2)C(=O)O | CC(C)(C)[O:3][C:2](CBr)=[O:1].COC[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][c:21]3[cH:22][c:23](-[c:24]4[n:25][c:26]5[cH:27][c:28]([C:29](=[O:30])[OH:31])[cH:32][cH:33][c:34]5[n:35]4[CH:36]4[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]4)[cH:42][cH:4... | CC(C)(C)OC(=O)CBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | O=C(O)COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | null | null | null | C-C Coupling | OtherReaction | 1cad33f62a425797bcc7907e5cff31512c9018692fde58f55ac0dee551b87c87 | 11077438a76dc5116e5f60f7283a036db68c0f3b20dd2558ae18f44c1dd17562 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | Br-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:3]-C(-C)(-C)-C.C-O-C-[CH2;D2;+0:4]-[#8:5]-[c:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:3])-[CH2;D2;+0:4]-[#8:5]-[c:6] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 475, except tert-butyl bromoacetate was used for alkylation instead of 1-bromo-2-methoxy ethane. The tert-butyl group was removed in a separate step before saponification by a 1 h treatment with TFA.
Conditions: See reaction.notes.procedure_details.
Workup: T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Ether.Boc | Carboxylic acid.Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1.c1ccc2nc[nH]c2c1.C1CCCCC1 | HBr | null | null | null | CC(C)(C)OC(=O)CBr.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>O=C(O)COc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a662eb771b9d4c87905f3eacaa250c08 | C1CCNC1.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCCCN5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOC)C=C1.BrCCCBr.N1CCCC1.BrCCOC>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCCN3CCCC3)C=C1 | [NH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1.CO[CH2:23][CH2:22][O:21][c:20]1[cH:19][c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:44]4[CH:45]4[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]4)[cH:43][c:42]3[cH:41][cH:40]2)[c:32](-[c:33]2[cH:34][cH:35][c:... | C1CCNC1.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCCCN5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4b0f97014035cf0d99b32a42bcb79ab87c0cd49b39ff30f05a7ff00b27a74c06 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | c1ccc(-c2ccc(OCCCN3CCCC3)cc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[C:9]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 475, except 1,3-dibromopropane was used for alkylation instead of 1-bromo-2-methoxy ethane. The resulting 3-bromopropyl derivative was treated in situ with an excess of pyrrolidine to give the final product.
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | C1CCNC1.COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCCCN5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-201e1ca4bfb84b008c056857988a2b0e | COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=C(CBr)N1CCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCC(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCCOC)C=C1.BrCC(=O)N1CCCC1.BrCCOC>>ClC1=CC=C(C2=CC=C(C=C2C2=NC3=CC=C(C=C3C=C2)C2=NC3=C(N2C2CCCCC2)C=CC(=C3)C(=O)O)OCC(N3CCCC3)=O)C=C1 | COCC[O:21][c:20]1[cH:19][c:18](-[c:17]2[n:16][c:15]3[cH:14][cH:13][c:12](-[c:11]4[n:10][c:8]5[c:7]([cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9]5)[n:44]4[CH:45]4[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]4)[cH:43][c:42]3[cH:41][cH:40]2)[c:32](-[c:33]2[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]2)[cH:31][cH:30]1.Br[CH2:22][C... | COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=C(CBr)N1CCCC1 | O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCC(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | accc2cc81d8ac122c6ee715cc3f5bd64541ff5865eb86e6ef0288225381cd9b8 | 4c4576f42ee87cfd2aa61a9c0f26fb46862a977051ffac86867860dac238a6aa | O=C(COc1ccc(-c2ccccc2)c(-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)c1)N1CCCC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].C-O-C-C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | null | [] | null | null | null | null | The title compound was synthesized as described for Compound 475, except 2-bromo-1-pyrrolidin-1-yl-ethanone was used for alkylation instead of 1-bromo-2-methoxy ethane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether | Ether | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.C1CC[NH]C1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | COCCOc1ccc(-c2ccc(Cl)cc2)c(-c2ccc3cc(-c4nc5cc(C(=O)O)ccc5n4C4CCCCC4)ccc3n2)c1.O=C(CBr)N1CCCC1>>O=C(O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OCC(=O)N5CCCC5)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-836801a6af724cc5b6f5ef38e88bef22 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OS(=O)(=O)C(F)(F)F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)O)C2CCCCC2)C=C1.N1=CC=CC=C1.O(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F>>COC(=O)C1=CC2=C(N(C(=N2)C=2C=C3C=CC(=NC3=CC2)C2=CC(=CC=C2C2=CC=C(C=C2)Cl)OS(=O)(=O)C(F)(F)F)C2CCCCC2)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[n:11][c:12](-[c:13]1[cH:14][cH:15][c:16]3[n:17][c:18](-[c:19]4[cH:20][c:21]([OH:22])[cH:30][cH:31][c:32]4-[c:33]4[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]4)[cH:40][cH:41][c:42]3[cH:43]1)[n:44]2[CH:45]1[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]1.O=S(=O)(O[... | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OS(=O)(=O)C(F)(F)F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Functional Group Interconversion | Alcohol to triflate conversion | 934d625c86d5da305dd43240eee33b5e46f4d298c87ccdc218e9e2eb60c650b5 | 13e8f5cec02bd6a2d12ae535029c405c270682596231c5c8422ac50b2cb1ec74 | c1ccc(-c2ccccc2-c2ccc3cc(-c4nc5ccccc5n4C4CCCCC4)ccc3n2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of 1 g (1.7 mmol) of Compound 475a in 20 mL of DCM, 550 μL (6.8 mmol) of pyridine, and 21 mg (0.17 mmol) of DMAP were added and the entire mixture was cooled to 0° C. Dropwise, 860 μL of Tf2O was added. The reaction was then stirred at room temperature for 1 h. Finally the reaction mixture was evaporated,... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Aromatic alcohol | Triflate | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | HF | CN(C)C=1C=CN=CC1.C(Cl)Cl | 0 | 1 | COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(O)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)c1ccc2c(c1)nc(-c1ccc3nc(-c4cc(OS(=O)(=O)C(F)(F)F)ccc4-c4ccc(Cl)cc4)ccc3c1)n2C1CCCCC1 |
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