dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a33f3b286a854755b162b6197f8b9f3f | CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O.CNC1CCNC1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(N3CCC(CNS(C)(=O)=O)C3)c(Cl)c2n(C2CC2)c1=O | C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C=C2C1=O)F)F)Cl)C1CC1)=O)=O.N1CC(CC1)NC.C(C)N(CC)CC.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)CNS(=O)(=O)C)Cl)C1CC1)=O)=O | F[c:16]1[c:14]([F:15])[cH:13][c:12]2[c:10](=[O:11])[n:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:35](=[O:36])[n:31]([CH:32]3[CH2:33][CH2:34]3)[c:30]2[c:28]1[Cl:29].[NH:17]1[CH2:18][CH2:19][CH:20]([NH:22][CH3:21])[CH2:27]1.Cl[S:23]([CH3:24])(=[O:25])=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O... | CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O.CNC1CCNC1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(N3CCC(CNS(C)(=O)=O)C3)c(Cl)c2n(C2CC2)c1=O | null | null | C(C)(=O)OCC.C(C)#N | Acylation | OtherReaction | e8dcfd63826a349914b82e06ab88b34ebbfb0ac921b034f582f6984393e34140 | 619e998b2d3a1fadc60f9908b52a775399d64f49a596f029e05a5589de6f1026 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].F-[c;H0;D3;+0:5]1:[c:6](-[F;D1;H0:7]):[c:8]:[c:9]2:[c:10]:[#7;a:11]:[c:12]:[#7;a:13](-[C:14]):[c:15]:2:[c:16]:1-[Cl;D1;H0:17].[CH3;D1;+0:18]-[NH;D2;+0:19]-[CH;D3;+0:20]1-[C:21]-[C:22]-[NH;D2;+0:23]-[C:24]-1>>[C:14]-[#7;a:13]1:[c:12]:[#7;a:11]:[c:10]:[c:9]2:[c:8]... | 8.4 | [{"value": 8.4, "product": "C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)CNS(=O)(=O)C)Cl)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of (8-chloro-1-cyclopropyl-6,7-difluoro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)carbamic acid tert-butyl ester (Example 14, 0.37 g, 0.97 mmol) in acetonitrile (20 mL) is added pyrrolidin-3-yl-methylamine (0.115 g, 1.16 mmol) and triethylamine (2.7 mL, 19.3 mmol). After refluxing for 20 hours, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine.Sulfonyl halide | Sulfonamide.Tertiary amine | c1ccc2ncncc2c1.C1CCNC1 | c1ccc2ncncc2c1.C1CC[NH]C1 | c1ccc2ncncc2c1.C1CC[NH]C1.C1CC1 | HF | C(C)(=O)OCC.C(C)#N | null | 2 | CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O.CNC1CCNC1.CS(=O)(=O)Cl>C(C)(=O)OCC.C(C)#N>CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(N3CCC(CNS(C)(=O)=O)C3)c(Cl)c2n(C2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a920b8fb152448dab5ca2e70769c5b9 | CCOC(=O)C1CN(Cc2ccccc2)CC12CC2>>CC(=O)C1CN(Cc2ccccc2)CC12CC2 | C(C)OC(=O)C1CN(CC12CC2)CC2=CC=CC=C2.C[Li]>>C(C1=CC=CC=C1)N1CC2(CC2)C(C1)C(C)=O | CCO[C:2](=[O:3])[CH:4]1[CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][C:15]12[CH2:16][CH2:17]2>>[CH3:1][C:2](=[O:3])[CH:4]1[CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][C:15]12[CH2:16][CH2:17]2 | CCOC(=O)C1CN(Cc2ccccc2)CC12CC2 | CC(=O)C1CN(Cc2ccccc2)CC12CC2 | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | 600d91131af1bb1ee8c20c567e56234839eb0602aa06d3adc0666216769f9a6a | ebe855e3c62a5d82c9c1d005e3b3e8a9e3b63aca37bc8a601a136cf86007489d | c1ccc(CN2CCC3(CC3)C2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:3](-[C;H0;D3;+0:1](-[C;D1;H3:7])=[O;D1;H0:2])-[C:4] | 54.6 | [{"value": 54.6, "product": "C(C1=CC=CC=C1)N1CC2(CC2)C(C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | A solution (−78° C.) of 5-benzyl-5-azaspiro[2.4]heptane-7-carboxylic acid ethyl ester (Example A1a, 8.15 g, 31.4 mmol) in diethyl ether (200 mL) under a nitrogen atmosphere is treated with methyllithium (1.4 M in diethyl ether, 22.4 mL, 31.4 mmol) over a period of 10 minutes. After 1 hour, reaction mixture is warmed to... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccccc1.C1CC2(CC2)C[NH]1 | HO- | C(C)OCC | -10 | 1 | CCOC(=O)C1CN(Cc2ccccc2)CC12CC2>C(C)OCC>CC(=O)C1CN(Cc2ccccc2)CC12CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eebca15bfe1a40339125a48548988faa | CC(=O)C1CN(Cc2ccccc2)CC12CC2.NO>>CC(=NO)C1CN(Cc2ccccc2)CC12CC2 | C(C1=CC=CC=C1)N1CC2(CC2)C(C1)C(C)=O.Cl.NO>>C(C1=CC=CC=C1)N1CC2(CC2)C(C1)C(C)=NO | O=[C:2]([CH3:1])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C:16]12[CH2:17][CH2:18]2.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C:16]12[CH2:17][CH2:18]2 | CC(=O)C1CN(Cc2ccccc2)CC12CC2.NO | CC(=NO)C1CN(Cc2ccccc2)CC12CC2 | null | null | C(C)(=O)OCC.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc(CN2CCC3(CC3)C2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](-[C:4])-[C:5]-[#7:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[#7:6]-[C:5]-[C:3](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:7]-[O;D1;H1:8])-[C:4] | 73.5 | [{"value": 73.5, "product": "C(C1=CC=CC=C1)N1CC2(CC2)C(C1)C(C)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 1-(5-benzyl-5-azaspiro[2.4]hept-7-yl)ethanone (Example A2a, 3.93 g, 17.1 mmol) and hydroxylamine hydrochloride (1.78 g, 25.7 mmol) are stirred in pyridine (10 mL) at 90° C. After 20 hours, the reaction mixture is diluted with ethyl acetate and the organic layer is washed with saturated NaHCO3, water, and brine. The org... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.C1CC2(CC2)C[NH]1 | HO- | C(C)(=O)OCC.N1=CC=CC=C1 | null | 20 | CC(=O)C1CN(Cc2ccccc2)CC12CC2.NO>C(C)(=O)OCC.N1=CC=CC=C1>CC(=NO)C1CN(Cc2ccccc2)CC12CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c97a1145efa84e81865b68656041089c | CC(NC(=O)OC(C)(C)C)C1CN(Cc2ccccc2)CC12CC2>>CC(NC(=O)OC(C)(C)C)C1CNCC12CC2 | C(C)(C)(C)OC(NC(C)C1CN(CC12CC2)CC2=CC=CC=C2)=O.[H][H]>>C(C)(C)(C)OC(NC(C)C1CNCC12CC2)=O | c1ccc(C[N:13]2[CH2:12][CH:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C:15]3([CH2:14]2)[CH2:16][CH2:17]3)cc1>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:11]1[CH2:12][NH:13][CH2:14][C:15]12[CH2:16][CH2:17]2 | CC(NC(=O)OC(C)(C)C)C1CN(Cc2ccccc2)CC12CC2 | CC(NC(=O)OC(C)(C)C)C1CNCC12CC2 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 9cf6addfef11f51b635125d0004c52838eb3e9b3bdcfd23e0798327b9efabf21 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CC2(CC2)CN1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | null | [] | null | null | null | null | A solution of [1-(5-benzyl-5-azaspiro[2.4]hept-7-yl)ethyl]carbamic acid tert-butyl ester (Example A4a, 1.47 g) in methanol (30 mL) in a Parr shaker is treated with 10% palladium on carbon (0.5 g) and hydrogen introduced (50 psi) for 24 hours. The reaction mixture is filtered through celite, washed with methanol, and th... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC2(CC2)C[NH]1 | C1CC2(CC2)CN1 | C1CC2(CC2)CN1 | Other | [Pd].CO | null | null | CC(NC(=O)OC(C)(C)C)C1CN(Cc2ccccc2)CC12CC2>[Pd].CO>CC(NC(=O)OC(C)(C)C)C1CNCC12CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03179abb6e0a461e9c57bc862974a3e0 | NO.O=C1CCN(Cc2ccccc2)C1>>ON=C1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)=O.Cl.NO>>C(C1=CC=CC=C1)N1CC(CC1)=NO | [OH:1][NH2:2].O=[C:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1>>[OH:1][N:2]=[C:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1 | NO.O=C1CCN(Cc2ccccc2)C1 | ON=C1CCN(Cc2ccccc2)C1 | null | null | C(C)(=O)OCC.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 916d29c6e2842769ff58df57caef65bf8c6f49de29ec4bf15f1f69069996ca57 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1CCN(Cc2ccccc2)C1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[O;D1;H1:8]>>[C:4]-[#7:3]1-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[C:6]-[C:5]-1 | 102.2 | [{"value": 102.2, "product": "C(C1=CC=CC=C1)N1CC(CC1)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | To a solution of 1-benzylpyrrolidin-3-one (1.0 g, 5.71 mmol) in pyridine (5 mL) is added hydroxylamine hydrochloride (0.59 g, 8.57 mmol). After stirring at 90° C. for 5 hours, the reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate, water, and brine. The organic layer is dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | C(C)(=O)OCC.N1=CC=CC=C1 | 90 | 5 | NO.O=C1CCN(Cc2ccccc2)C1>C(C)(=O)OCC.N1=CC=CC=C1>ON=C1CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c40f5f2214f4dffa7218b5f4c2a3986 | CC=C1CCN(C(=O)OCc2ccccc2)C1>>CC1OC12CCN(C(=O)OCc1ccccc1)C2 | C(C1=CC=CC=C1)OC(=O)N1CC(CC1)=CC.ClC=1C=C(C(=O)OO)C=CC1.S(=O)([O-])[O-].[Na+].[Na+]>>C(C1=CC=CC=C1)OC(=O)N1CC2(C(O2)C)CC1 | [CH3:1][CH:2]=[C:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1>>[CH3:1][CH:2]1[O:3][C:4]12[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:18]2 | CC=C1CCN(C(=O)OCc2ccccc2)C1 | CC1OC12CCN(C(=O)OCc1ccccc1)C2 | null | null | ClCCl | Oxidation | OtherReaction | 9e5cb6df82d89bae604c84d21c7e428abe38ca213049c31d702e54f4902a8523 | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=C(OCc1ccccc1)N1CCC2(CO2)C1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D3;+0:6](=[CH;D2;+0:7]-[C;D1;H3:8])-[C:9]-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D4;+0:6]2(-[#8:11]-[CH;D3;+0:7]-2-[C;D1;H3:8])-[C:9]-[C:10]-1 | 44.8 | [{"value": 44.8, "product": "C(C1=CC=CC=C1)OC(=O)N1CC2(C(O2)C)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-ethylidenepyrrolidine-1-carboxylic acid benzyl ester (Example A8, 0.65 g, 2.8 mmol) and 3-chloroperoxybenzoic acid (0.86 g, 5 mmol) in dichloromethane (15 mL) is stirred at room temperature for 3 hours. The excess peracid is decomposed by the addition of 10% sodium sulfite. The organic layer is washed w... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1CC[NH]C1 | C1CC2(C[NH]1)CO2 | C1CC2(C[NH]1)CO2.c1ccccc1 | Other | ClCCl | null | null | CC=C1CCN(C(=O)OCc2ccccc2)C1>ClCCl>CC1OC12CCN(C(=O)OCc1ccccc1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25d841ff62cf41b6862babb19ab9536f | CC1OC12CCN(C(=O)OCc1ccccc1)C2.[NH4+]>>CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC2(C(O2)C)CC1.[OH-].[NH4+].C(C)(=O)OCC>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(O)C(C)N | [CH3:1][CH:2]1[C:4]2([O:5]1)[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19]2.[NH4+:3]>>[CH3:1][CH:2]([NH2:3])[C:4]1([OH:5])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | CC1OC12CCN(C(=O)OCc1ccccc1)C2.[NH4+] | CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1 | null | null | CO | Functional Group Addition | OtherReaction | db10b7eb178b687892f63f334d8ed428ad001438c623c5a2f88419bcba1448e4 | 139012d3a263c64bc0bc696a4ebabf621f4b634824ee35698a4e4d48832c8397 | O=C(OCc1ccccc1)N1CCCC1 | [#7:1]-[C:2]-[C:3]1(-[C:4])-[O;H0;D2;+0:5]-[CH;D3;+0:6]-1-[C;D1;H3:7].[NH4+;D0:8]>>[#7:1]-[C:2]-[C:3](-[OH;D1;+0:5])(-[CH;D3;+0:6](-[C;D1;H3:7])-[NH2;D1;+0:8])-[C:4] | null | [] | null | null | null | null | A solution of 2-methyl-1-oxa-5-azaspiro[2,4]heptane-5-carboxylic acid benzyl ester (Example A9, 0.31 g, 1.25 mmol) in methanol (10 mL) and ammonium hydroxide (7 mL) is heated in a sealed tube at 100° C. for 16 hours. After cooling, the reaction mixture is dissolved ethyl acetate, washed with water, dried over Na2SO4 an... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol.Primary amine | C1CC2(C[NH]1)CO2 | null | C1CC[NH]C1.c1ccccc1 | null | CO | null | null | CC1OC12CCN(C(=O)OCc1ccccc1)C2.[NH4+]>CO>CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59aeace69c524501960f8f1eb266305a | CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1.O=Cc1ccccc1O>>CC(N=Cc1ccccc1O)C1(O)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(O)C(C)N.C(C=1C(O)=CC=CC1)=O>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)N=CC1=C(C=CC=C1)O)O | [CH3:1][CH:2]([NH2:3])[C:12]1([OH:13])[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH:2]([N:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11])[C:12]1([OH:13])[CH2:14][CH2:15][N:16]([C:17](=[O:1... | CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1.O=Cc1ccccc1O | CC(N=Cc1ccccc1O)C1(O)CCN(C(=O)OCc2ccccc2)C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | O=C(OCc1ccccc1)N1CCC(CN=Cc2ccccc2)C1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C;D1;H3:7])-[N;H0;D2;+0:8]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 35 | [{"value": 35.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)N=CC1=C(C=CC=C1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(1-aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester (Example A10, 0.34 g, 0.93 mmol) and salicylaldehyde (0.147 g, 1.2 mmol) in dry ethanol (5 mL) is refluxed for 3 hours. After evaporation of the solvent, the residue is purified by column chromatography (30:70:0.01 ethyl acetate/hexanes/... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | C(C)O | null | null | CC(N)C1(O)CCN(C(=O)OCc2ccccc2)C1.O=Cc1ccccc1O>C(C)O>CC(N=Cc1ccccc1O)C1(O)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2fa500ca7b4944fca84a3d33e9d249ba | CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1>>CC(N)C1(F)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(F)C(C)N=[N+]=[N-].[H][H]>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(F)C(C)N | [N-]=[N+]=[N:3][CH:2]([CH3:1])[C:4]1([F:5])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>>[CH3:1][CH:2]([NH2:3])[C:4]1([F:5])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1 | CC(N)C1(F)CCN(C(=O)OCc2ccccc2)C1 | null | [Ni] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCC1 | [C:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[N+]=[N-]>>[C:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4] | 90.1 | [{"value": 90.1, "product": "C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(F)C(C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(1-azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl ester (Example A16, 0.16 g, 0.5 mmol) in methanol (10 mL) is treated with Raney nickel (100 mg, wet weight) and shaken in a hydrogen atmosphere at room temperature and at 55 psi for 17 hours. The catalyst is removed by filtration through Celite... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CC[NH]C1.c1ccccc1 | Other | [Ni].CO | null | null | CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1>[Ni].CO>CC(N)C1(F)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb473ca2021b44e6ad238522ab891e1c | COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1>>COCC1(CN)CCN(Cc2ccccc2)C1 | O.NN.C(C1=CC=CC=C1)N1CC(CC1)(COC)CN1C(C2=CC=CC=C2C1=O)=O.Cl>>C(C1=CC=CC=C1)N1CC(CC1)(COC)CN | O=C1c2ccccc2C(=O)[N:6]1[CH2:5][C:4]1([CH2:3][O:2][CH3:1])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1>>[CH3:1][O:2][CH2:3][C:4]1([CH2:5][NH2:6])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1 | COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1 | COCC1(CN)CCN(Cc2ccccc2)C1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccc(CN2CCCC2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 89.5 | [{"value": 89.5, "product": "C(C1=CC=CC=C1)N1CC(CC1)(COC)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrazine hydrate (85% solution in water, 0.372 g, 6.32 mmol) is added to a solution of 2-(1-benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione (Example A20, 1.581 g, 4.34 mmol) in ethanol (50 mL). The resulting mixture is refluxed for 4.5 hours, cooled and acidified with concentrated hydrochloric acid. Th... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC[NH]C1.c1ccccc1 | HO- | C(C)O | null | null | COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1>C(C)O>COCC1(CN)CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99e603ae99de436a99dec9c803eff8bd | CC1OC12CCN(C(=O)OCc1ccccc1)C2.F>>CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC2(C(O2)C)CC1.N1=CC=CC=C1.F>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)O)F | [CH3:1][CH:2]1[O:3][C:4]12[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19]2.[FH:5]>>[CH3:1][CH:2]([OH:3])[C:4]1([F:5])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | CC1OC12CCN(C(=O)OCc1ccccc1)C2.F | CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1 | null | null | ClCCl | Miscellaneous | OtherReaction | 104f13bbcfd8fe847bc8f50c2882a7ad8914446786de7a041173f811193dc35d | 3308376c1af9182795876175318589d58f2494c98ab8c1da1abbbdb180da2297 | O=C(OCc1ccccc1)N1CCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D4;+0:6]2(-[C:7]-[C:8]-1)-[O;H0;D2;+0:9]-[C:10]-2-[C;D1;H3:11].[FH;D0;+0:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D4;+0:6](-[F;H0;D1;+0:12])(-[C:10](-[C;D1;H3:11])-[OH;D1;+0:9])-[C:7]-[C:8]-1 | null | [] | null | null | 3 | HOUR | A solution of 0.247 g, (1 mmol) of 2-methyl-1-oxa-5-azaspiro[2,4]-heptane-5-carboxylic acid benzyl ester (Example A9) in dichloromethane (3 mL) is added to a polypropylene flask containing 0.5 mL of hydrogen fluoride-pyridine at −40° C. The reaction is allowed to come to room temperature and stirring is continued for 3... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary halide.Secondary alcohol | C1CC2(C[NH]1)CO2 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | null | ClCCl | null | 3 | CC1OC12CCN(C(=O)OCc1ccccc1)C2.F>ClCCl>CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f78574fb405d489d91af7e5ae9751dd2 | CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1.CS(=O)(=O)Cl>>CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)O)F.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)OS(=O)(=O)C)F | [CH3:1][CH:2]([OH:3])[C:8]1([F:9])[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1.Cl[S:4]([CH3:5])(=[O:6])=[O:7]>>[CH3:1][CH:2]([O:3][S:4]([CH3:5])(=[O:6])=[O:7])[C:8]1([F:9])[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21]... | CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1.CS(=O)(=O)Cl | CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | O=C(OCc1ccccc1)N1CCCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[C;D1;H3:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C;D1;H3:7])-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 95.5 | [{"value": 95.5, "product": "C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)OS(=O)(=O)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a −10° C. solution of 3-fluoro-3-(1-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester (Example A14, 0.267 g, 1.00 mmol), triethylamine (0.4 g, 4 mmol) and dichloromethane (10 mL) is added methanesulfonyl chloride (0.229 g, 2.00 mmol). The mixture is stirred at room temperature for 2 hours and concentrated in v... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1.c1ccccc1 | HCl | ClCCl | null | 2 | CC(O)C1(F)CCN(C(=O)OCc2ccccc2)C1.CS(=O)(=O)Cl>ClCCl>CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28a8f740c3c44d56886c2f08e9774695 | CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-]>>CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(C(C)OS(=O)(=O)C)F.[N-]=[N+]=[N-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(F)C(C)N=[N+]=[N-] | CS(=O)(=O)O[CH:2]([CH3:1])[C:6]1([F:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1.[N-:3]=[N+:4]=[N-:5]>>[CH3:1][CH:2]([N:3]=[N+:4]=[N-:5])[C:6]1([F:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1 | CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-] | CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 341eb24906c58cd9cfdeec13febaf0724780d7854e6b6d7ec703218c4bcbe27b | 5f2cb2b9819a73a6855f5277f7fe9d5ce3871340baaebb59d42e38e1ca145c0a | O=C(OCc1ccccc1)N1CCCC1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](-[F;D1;H0:4])(-[C:5])-[C:6]-[#7:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[#7:7]-[C:6]-[C:3](-[F;D1;H0:4])(-[CH;D3;+0:1](-[C;D1;H3:2])-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10])-[C:5] | 76 | [{"value": 76.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CC(CC1)(F)C(C)N=[N+]=[N-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a solution of 3-fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester (Example A15, 0.25 g, 0.72 mmol) in N,N-dimethylformamide (5 mL) is added sodium azide (0.13 g, 2 mmol). The reaction mixture is heated at 120° C. overnight. The mixture is diluted with water and extracted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Azide | null | null | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | O.CN(C=O)C | 120 | null | CC(OS(C)(=O)=O)C1(F)CCN(C(=O)OCc2ccccc2)C1.[N-]=[N+]=[N-]>O.CN(C=O)C>CC(N=[N+]=[N-])C1(F)CCN(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bda05e49b0404071a41e804aec975155 | C=C(CBr)C(=O)OCC.C[O-]>>C=C(COC)C(=O)OCC | BrCC(C(=O)OCC)=C.C[O-].[Na+]>>C(C)OC(C(=C)COC)=O | Br[CH2:3][C:2](=[CH2:1])[C:6](=[O:7])[O:8][CH2:9][CH3:10].[O-:4][CH3:5]>>[CH2:1]=[C:2]([CH2:3][O:4][CH3:5])[C:6](=[O:7])[O:8][CH2:9][CH3:10] | C=C(CBr)C(=O)OCC.C[O-] | C=C(COC)C(=O)OCC | null | null | CO.O | Heteroatom Alkylation and Arylation | OtherReaction | 3dd6ea90858eede84ece2f60931b760bd509d5f421f2feb2b0fe7a2c006d84f0 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | null | Br-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[C;D1;H3:8]-[O-;H0;D1:9]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](=[C;D1;H2:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C;D1;H3:8] | 28.7 | [{"value": 28.7, "product": "C(C)OC(C(=C)COC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl α-(bromomethyl)acrylate (0.99 g, 5.1 mmol [Villieras J., Rambaud M., Synthesis, 1982:924–926]) in methanol (10 mL) is added to an ice-cold solution of sodium methoxide (0.33 g, 6.1 mmol) in methanol (50 mL). The suspension is refluxed for 21 hours, cooled, diluted with water and extracted with dichl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | null | null | null | Br- | CO.O | null | null | C=C(CBr)C(=O)OCC.C[O-]>CO.O>C=C(COC)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e346e5323871419b8510bb1982209d01 | CCOC(=O)C1(COC)CCN(Cc2ccccc2)C1>>COCC1(CO)CCN(Cc2ccccc2)C1 | C(C)OC(=O)C1(CN(CC1)CC1=CC=CC=C1)COC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)N1CC(CC1)(COC)CO | CCO[C:5]([C:4]1([CH2:3][O:2][CH3:1])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1)=[O:6]>>[CH3:1][O:2][CH2:3][C:4]1([CH2:5][OH:6])[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1 | CCOC(=O)C1(COC)CCN(Cc2ccccc2)C1 | COCC1(CO)CCN(Cc2ccccc2)C1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(CN2CCCC2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:3](-[C:4])(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 87.5 | [{"value": 87.5, "product": "C(C1=CC=CC=C1)N1CC(CC1)(COC)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 1-benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester (Example A18a, 2.30 g, 8.3 mmol) in anhydrous tetrahydrofuran (10 mL) is added dropwise to an ice-cold suspension of lithium aluminum hydride (0.821 g, 22 mmol) in tetrahydrofuran (50 mL). The resulting mixture is stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | 18 | CCOC(=O)C1(COC)CCN(Cc2ccccc2)C1>O1CCCC1>COCC1(CO)CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7817712f962644f282f5a64037189394 | COCC1(CO)CCN(Cc2ccccc2)C1.O=C1NC(=O)c2ccccc21>>COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1 | N(=NC(=O)OCC)C(=O)OCC.C(C1=CC=CC=C1)N1CC(CC1)(COC)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O>>C(C1=CC=CC=C1)N1CC(CC1)(COC)CN1C(C2=CC=CC=C2C1=O)=O | O[CH2:5][C:4]1([CH2:3][O:2][CH3:1])[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1.[NH:6]1[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][O:2][CH2:3][C:4]1([CH2:5][N:6]2[C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[C:15]2=[O:16])[CH2:17][CH2:18... | COCC1(CO)CCN(Cc2ccccc2)C1.O=C1NC(=O)c2ccccc21 | COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu_imide | 16aabf490ad1bd0cd53a985dff922c76188147a3ad5bf7d09c4c1e93a9e46a19 | 8a66434962da2945c8a8685e3bd4f60c7955241df224c95aa14ead6db9d240f9 | O=C1c2ccccc2C(=O)N1CC1CCN(Cc2ccccc2)C1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[C:5]-[#7:6].[O;D1;H0:7]=[C:8]1-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-1>>[#7:6]-[C:5]-[C:2](-[C:3])(-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8](=[O;D1;H0:7])-[c:13]:[c:12]-[C:10]-1=[O;D1;H0:11])-[C:4] | 21.9 | [{"value": 21.9, "product": "C(C1=CC=CC=C1)N1CC(CC1)(COC)CN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of (1-benzyl-3-methoxymethylpyrrolidin-3-yl)methanol (Example A19, 1.71 g, 7.27 mmol), triphenylphosphine (2.16 g, 8.22 mmol), phthalimide (1.14 g, 7.73 mmol), and anhydrous tetrahydrofuran is cooled to 0° C. and treated with diethyl azodicarboxylate (1.62 g, 9.31 mmol). The resulting mixture is stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | 18 | COCC1(CO)CCN(Cc2ccccc2)C1.O=C1NC(=O)c2ccccc21>O1CCCC1>COCC1(CN2C(=O)c3ccccc3C2=O)CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2eb413225c145a683f8e6c5e0750cba | BrCc1ccccc1.O=C(O)C1CCCNC1>>O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1 | N1CC(C(=O)O)CCC1.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC(=O)C1CN(CCC1)CC1=CC=CC=C1 | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[C:2]([OH:3])[CH:11]1[CH2:12][CH2:13][CH2:14][NH:15][CH2:23]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1 | BrCc1ccccc1.O=C(O)C1CCCNC1 | O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1 | null | null | C(C)(=O)OCC.O.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 5ae533ced5e169e93e6b08a630ab609c527b470a1c1cbce279f0db2c2352f95a | 2fa0f0da58593fdbf30a4a755d6a9f73d3447f670f3350f46ceac20cd57d879f | O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[C:13]-[c:14] | 44.9 | [{"value": 44.9, "product": "C(C1=CC=CC=C1)OC(=O)C1CN(CCC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution added of nipecotic acid (8.0 g, 61.9 mmol) in N,N-dimethylformamide (80 mL) is benzyl bromide (31.8 g, 186 mmol) and potassium carbonate (42.8 g, 310 mmol). The mixture is heated at 70° C. for 18 hours and diluted with ethyl acetate and water. The organic extract is washed with 1.0 M hydrochloric acid, wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Secondary amine | Ester.Tertiary amine | C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Br- | C(C)(=O)OCC.O.CN(C=O)C | 70 | null | BrCc1ccccc1.O=C(O)C1CCCNC1>C(C)(=O)OCC.O.CN(C=O)C>O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97eef82bec22448db417033565e432c7 | O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1>>O=C(O)C1CCCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)OC(=O)C1CN(CCC1)CC1=CC=CC=C1.[OH-].[Na+]>>C(C1=CC=CC=C1)N1CC(CCC1)C(=O)O | c1ccc(C[O:3][C:2](=[O:1])[CH:4]2[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:16]2)cc1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1 | O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1 | O=C(O)C1CCCN(Cc2ccccc2)C1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CN2CCCCC2)cc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 94 | [{"value": 94.0, "product": "C(C1=CC=CC=C1)N1CC(CCC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution 3.0 g (9.7 mmol) of 1-benzylpiperidine-3-carboxylic acid benzyl ester (Example A21) in methanol (20 mL) was added 1N sodium hydroxide (20 mL), and the reaction is stirred at room temperature for 18 hours. The methanol is removed in vacuo and the basic aqueous solution is acidified to pH 4 with 1.0 M hydro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CC[NH]CC1.c1ccccc1 | Other | CO | null | 18 | O=C(OCc1ccccc1)C1CCCN(Cc2ccccc2)C1>CO>O=C(O)C1CCCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-043784f2e57d4bdc9a6caa9b5a21c527 | CC(C)(C)OC(=O)N1CCC2CN(Cc3ccccc3)CC2C1>>CC(C)(C)OC(=O)N1CCC2CNCC2C1 | C(C)(C)(C)OC(=O)N1CC2C(CC1)CN(C2)CC2=CC=CC=C2.[H][H]>>C(C)(C)(C)OC(=O)N1CC2C(CC1)CNC2 | c1ccc(C[N:13]2[CH2:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:16][CH:15]3[CH2:14]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][NH:13][CH2:14][CH:15]2[CH2:16]1 | CC(C)(C)OC(=O)N1CCC2CN(Cc3ccccc3)CC2C1 | CC(C)(C)OC(=O)N1CCC2CNCC2C1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 9251f3ece1810ac4ff2e2dcb7d0b77a547db13ef1851b4999cec798870900a19 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CC2CNCC2CN1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | 99.8 | [{"value": 99.8, "product": "C(C)(C)(C)OC(=O)N1CC2C(CC1)CNC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Benzyloctahydropyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester (Example A26, 24.98 g, 78.8 mmol) in 400 mL of methanol is treated with 2.5 g of 20% Pd/C and shaken for 20.5 hours under 50 PSI of hydrogen. The solution is filtered and concentrated to afford 17.8 g of the title compound as a solid. MS APCI: m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC2C[NH]CC2C[NH]1 | C1CC2CNCC2C[NH]1 | C1CC2CNCC2C[NH]1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CCC2CN(Cc3ccccc3)CC2C1>[Pd].CO>CC(C)(C)OC(=O)N1CCC2CNCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9a5e5f0de004235805830ca3e08b53b | CCOC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1>>O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 | C(C)OC(=O)C1(CN(CC1)CC1=CC=CC=C1)CC1=CC=CC=C1.[OH-].[Na+]>>C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)CC1=CC=CC=C1 | CC[O:3][C:2](=[O:1])[C:4]1([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]1>>[O:1]=[C:2]([OH:3])[C:4]1([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]1 | CCOC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 | O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CC2CCN(Cc3ccccc3)C2)cc1 | 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] | 76.8 | [{"value": 76.8, "product": "C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,3-dibenzylpyrrolidine-3-carboxylic acid ethyl ester (Example A18e, 13.1 g, 41 mmol) in 250 mL of methanol is added 2N NaOH (46 mL, 92 mmol) and the reaction is heated to reflux for 24 hours. The solution is cooled, concentrated, redissolved in water and extracted with ether. The pH of the aqueous lay... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | CO | null | null | CCOC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1>CO>O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02ad2852ead94e6593b17d452a0bcb4b | O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1.[NH4+]>>NC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 | [NH4+].[OH-].C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)CC1=CC=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1CC(CC1)(C(=O)N)CC1=CC=CC=C1 | O[C:2](=[O:3])[C:4]1([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[C:4]1([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]... | O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1.[NH4+] | NC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccc(CC2CCN(Cc3ccccc3)C2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7].[NH4+;D0:8]>>[#7:7]-[C:6]-[C:3](-[C:4])(-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2])-[C:5] | 103.9 | [{"value": 103.9, "product": "C(C1=CC=CC=C1)N1CC(CC1)(C(=O)N)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 1,3-dibenzylpyrrolidine-3-carboxylic acid (Example A28, 4.0 g, 13.5 mmol), 1,1′-carbonyldiimidazole (2.42 g, 14.9 mmol), and triethylamine (2.08 mL, 14.9 mmol) in tetrahydrofuran (100 mL) is heated at reflux for 1.5 hours. The solution is cooled, poured into NH4OH (300 mL), and stirred for 18 hours. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | 18 | O=C(O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1.[NH4+]>O1CCCC1>NC(=O)C1(Cc2ccccc2)CCN(Cc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07031ad2da014fb091396545797a8366 | CC(C)(C)OC(=O)NC1(c2ccccc2)CCN(Cc2ccccc2)C1>>CC(C)(C)OC(=O)NC1(c2ccccc2)CCNC1 | C(C)(C)(C)OC(NC1(CN(CC1)CC1=CC=CC=C1)C1=CC=CC=C1)=O.[H][H]>>C(C)(C)(C)OC(NC1(CNCC1)C1=CC=CC=C1)=O | c1ccc(C[N:18]2[CH2:17][CH2:16][C:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:19]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][NH:18][CH2:19]1 | CC(C)(C)OC(=O)NC1(c2ccccc2)CCN(Cc2ccccc2)C1 | CC(C)(C)OC(=O)NC1(c2ccccc2)CCNC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 846a35f8c83fa58d2c714915319a8bc96745602a4dd9ac20dbad14bc1e16a470 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C2CCNC2)cc1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | 99.9 | [{"value": 99.9, "product": "C(C)(C)(C)OC(NC1(CNCC1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (1-Benzyl-3-phenylpyrrolidin-3-yl)carbamic acid tert-butyl ester (Hagen S. E., Domagala J. M., Heifetz C. L., Sanchez J. P., Solomon M., J. Med. Chem., 1990; 33(2):849–854) (2.79 g, 7.9 mmol) in 100 mL of methanol is treated with 1.0 g of 20% Pd/C and shaken for 17 hours under 50 psi of hydrogen. The solution is filter... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1CCNC1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)NC1(c2ccccc2)CCN(Cc2ccccc2)C1>[Pd].CO>CC(C)(C)OC(=O)NC1(c2ccccc2)CCNC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4019104aa7ff436fb7ae8cac196a3a8a | CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](COCc5ccccc5)[C@@H](OCc5ccccc5)[C@H](OCc5ccccc5)[C@H]4OCc4ccccc4)cc23)cc1>>CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc23)cc1 | C(C)C1=CC=C(CC2=CNC3=CC=C(C=C23)[C@H]2[C@H](OCC3=CC=CC=C3)[C@@H](OCC3=CC=CC=C3)[C@H](OCC3=CC=CC=C3)[C@H](O2)COCC2=CC=CC=C2)C=C1.[OH-].[Na+]>>C(C)C1=CC=C(CC2=CNC3=CC=C(C=C23)[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)C=C1 | c1ccc(C[O:19][CH2:18][C@H:17]2[O:16][C@@H:15]([c:14]3[cH:13][cH:12][c:11]4[nH:10][cH:9][c:8]([CH2:7][c:6]5[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:29][cH:28]5)[c:27]4[cH:26]3)[C@H:24]([O:25]Cc3ccccc3)[C@@H:22]([O:23]Cc3ccccc3)[C@@H:20]2[O:21]Cc2ccccc2)cc1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][nH:10][c:... | CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](COCc5ccccc5)[C@@H](OCc5ccccc5)[C@H](OCc5ccccc5)[C@H]4OCc4ccccc4)cc23)cc1 | CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc23)cc1 | null | null | C1CCOC1.O | Deprotection | OtherReaction | 9622096468e29231a13a0af4bb02cbbbed6ada9c44b575de6d474da0d432309d | 73dfd818b2d879aa8bc6aaeea5cb523f7f4f5ff62317dd7cb2c99f1b31ec455c | c1ccc(Cc2c[nH]c3ccc([C@H]4CCCCO4)cc23)cc1 | C(-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2)-[C:8](-[O;H0;D2;+0:9]-C-c2:c:c:c:c:c:2)-[C:10]-1-[O;H0;D2;+0:11]-C-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](-[OH;D1;+0:9])-[C:10]-1-[OH;D1;+0:11] | 85 | [{"value": 85.0, "product": "C(C)C1=CC=C(CC2=CNC3=CC=C(C=C23)[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Ethylbenzyl)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1H-indole: Part E (0.68 g, 0.78 mmol) was dissolved in THF (15 mL) and 25% aqueous sodium hydroxide (5 mL) and the resulting solution was brought to reflux for 3 h. After cooling to room temperature, the mixture was diluted with water (30 mL), and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2[nH]ccc2c1.C1CCOCC1 | Other | C1CCOC1.O | null | null | CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](COCc5ccccc5)[C@@H](OCc5ccccc5)[C@H](OCc5ccccc5)[C@H]4OCc4ccccc4)cc23)cc1>C1CCOC1.O>CCc1ccc(Cc2c[nH]c3ccc([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e53689819a44ea5b6020ddf049fe8f2 | CCN.NC(=O)CC[C@H](N)C(=O)O>>CCNC(=O)CC[C@H](N)C(=O)O | N[C@@H](CCC(N)=O)C(=O)O.C(C)N>>N[C@@H](CCC(=O)NCC)C(=O)O | [CH3:1][CH2:2][NH2:3].N[C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH2:9])[C:10](=[O:11])[OH:12]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH2:9])[C:10](=[O:11])[OH:12] | CCN.NC(=O)CC[C@H](N)C(=O)O | CCNC(=O)CC[C@H](N)C(=O)O | null | null | B([O-])([O-])[O-] | Acylation | OtherReaction | e6b65aa2cf0415dec90d7472d3f0bc6b9ee4b3e1f07ac8a90a77f65444307f4a | cbe2f1d5a907138095943f49f081313fbf3c1706d27fd317bb9c4ee07b790834 | null | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C;D1;H3:5] | null | [] | null | null | null | null | 0.3 M glutamine and 1.5 M ethylamine were allowed to react at 30° C. for 22 hours in borate buffer (Na2B4O7—NaOH, pH 11) in the presence of 0.3 U glutaminase, to give 225 nmol of L-theanine. In addition, a by-product glutamic acid was 20 nmol. The purification of theanine from the reaction mixture was carried out by su... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Secondary amide | null | null | null | Other | B([O-])([O-])[O-] | null | null | CCN.NC(=O)CC[C@H](N)C(=O)O>B([O-])([O-])[O-]>CCNC(=O)CC[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15d92f3715f741f0bf46d9dec45f38a3 | O=C(O)C1(O)c2ccccc2-c2ccccc21>>COC(=O)C1(O)c2ccccc2-c2ccccc21 | OC1(C2=CC=CC=C2C=2C=CC=CC12)C(=O)O.S(O)(O)(=O)=O.C(O)([O-])=O.[Na+]>>OC1(C2=CC=CC=C2C=2C=CC=CC12)C(=O)OC | [OH:2][C:3](=[O:4])[C:5]1([OH:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([OH:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | O=C(O)C1(O)c2ccccc2-c2ccccc21 | COC(=O)C1(O)c2ccccc2-c2ccccc21 | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | null | [] | null | null | null | null | 50.4 g (0.223 mol) 9-hydroxy-9-fluorenecarboxylic acid are dissolved in 500 ml of methanol, combined with 5 ml (0.089 mol) conc. sulphuric acid and refluxed for 1 hour. After cooling 100 ml sodium hydrogen carbonate solution (about pH 8) are added, and the methanol is largely distilled off under reduced pressure. The r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2c(c1)Cc1ccccc12 | Other | CO | null | null | O=C(O)C1(O)c2ccccc2-c2ccccc21>CO>COC(=O)C1(O)c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad6c840f68ba450a9407247c4d813150 | COC(=O)CC(Br)C=O.Cc1c(Cl)cccc1S(=O)(=O)NC(N)=S>>COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1 | NC(=S)NS(=O)(=O)C1=C(C(=CC=C1)Cl)C.BrC(CC(=O)OC)C=O>>ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)OC)C | O=[CH:7][CH:6](Br)[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:8][C:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[c:20]1[CH3:21])=[S:22]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][n:8][c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][cH:17][c:18]([Cl:19])[c:20]2[CH3:21])[s:22]1 | COC(=O)CC(Br)C=O.Cc1c(Cl)cccc1S(=O)(=O)NC(N)=S | COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 1e98d56449369ed49a01def2ba436800fc8285b6f16adfb3ff0f1aaf7f34bbac | 1467150cea192c09dd35541b6f6ddef57af2b0cb933fc1eb5dedd0a587a7e1db | O=S(=O)(Nc1nccs1)c1ccccc1 | Br-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[CH;D2;+0:7]=O.[#16:8]-[#7:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[S;H0;D1;+0:12]>>[#16:8]-[#7:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:7]:[c;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[s;H0;D2;+0:12]:1 | null | [] | null | null | null | null | N-(aminocarbonothioyl)-3-chloro-2-methylbenzenesulfonamide (0.4 g, 1.5 mmol) and methyl 3-bromo-4-oxobutanoate (0.3 g, 1.5 mmol), dissolved in pyridine (5 mL), were irradiated in a microwave oven for 2.5 min at 130° C. The solvent was removed under reduced pressure and the product separated from the starting materials ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Thiourea | null | null | c1cscn1 | c1cscn1.c1ccccc1 | HBr | N1=CC=CC=C1 | null | null | COC(=O)CC(Br)C=O.Cc1c(Cl)cccc1S(=O)(=O)NC(N)=S>N1=CC=CC=C1>COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83947141fcc74f808a1a2bc552757fcf | COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1>>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1 | ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)OC)C.[OH-].[K+]>>ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)O)C | C[O:20][C:18]([CH2:17][c:16]1[cH:15][n:14][c:13]([NH:12][S:9]([c:8]2[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]2)(=[O:10])=[O:11])[s:21]1)=[O:19]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[NH:12][c:13]1[n:14][cH:15][c:16]([CH2:17][C:18](=[O:19])[OH:20])[s:21]1 | COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1 | Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1 | null | null | CCO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(Nc1nccs1)c1ccccc1 | 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] | 104.9 | [{"value": 97.0, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.9, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To methyl (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetate (Example 2) (0.2 g, 0.55 mmol) dissolved in EtOH (5.5 mL) was added aqueous KOH (0.6 mL, 5.5 M). The reaction mixture was stirred at room temperature for 1 h. The solvent was then removed under reduced pressure and the crude product dissol... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cscn1 | Other | CCO | null | 1 | COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1>CCO>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8b72c473c3d4b2989a2714c082313d6 | C1COCCN1.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1>>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N2CCOCC2)s1 | ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)O)C.CCN=C=NCCCN(C)C.C(C)N(CC)CC.N1CCOCC1>>ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N1CCOCC1)C | [NH:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1.O[C:18]([CH2:17][c:16]1[cH:15][n:14][c:13]([NH:12][S:9]([c:8]2[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]2)(=[O:10])=[O:11])[s:26]1)=[O:19]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[NH:12][c:13]1[n:14][cH:15][c:16]([CH2:17][C:18](=[O:19]... | C1COCCN1.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1 | Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N2CCOCC2)s1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1cnc(NS(=O)(=O)c2ccccc2)s1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[#16;a:5]):[c:6]:[#7;a:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#16;a:5]:[c:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1):[c:6]:[#7;a:7] | 10 | [{"value": 10.0, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N1CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.6, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N1CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetic acid (Example 3) (0.09 g, 0.25 mmol) in CH2Cl2 (5.0 mL) and DMF (0.5 mL) were added EDCI (0.05 g, 0.27 mmol), DMAP (0.02 g, 0.12 mmol), triethylamine (0.1 mL, 0.75 mmol) and morpholine (0.03 mL, 0.30 mmol). The reaction mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1cscn1.C1COCC[NH]1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl | null | 8 | C1COCCN1.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1>CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N2CCOCC2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38f1803929514a51a269f2c4ed9d2e97 | CC(C)NC(C)C.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1>>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N(C(C)C)C(C)C)s1 | ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)O)C.CCN=C=NCCCN(C)C.C(C)N(CC)CC.C(C)(C)NC(C)C>>ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N(C(C)C)C(C)C)C | [NH:20]([CH:21]([CH3:22])[CH3:23])[CH:24]([CH3:25])[CH3:26].O[C:18]([CH2:17][c:16]1[cH:15][n:14][c:13]([NH:12][S:9]([c:8]2[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]2)(=[O:10])=[O:11])[s:27]1)=[O:19]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[NH:12][c:13]1[n:14][cH:15][c:16]([CH2:17][C... | CC(C)NC(C)C.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1 | Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N(C(C)C)C(C)C)s1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=S(=O)(Nc1nccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[#16;a:5]):[c:6]:[#7;a:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])-[C;D1;H3:14]>>[#16;a:5]:[c:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11](-[C:9](-[C;D1;H3:8])-[C;D1;H3:10])-[C:12](-[C;D1;H3:13])-[C;D1;H3:14]):[c:6]:[#7;a:7] | 9.3 | [{"value": 9.0, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N(C(C)C)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.3, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC=1SC(=CN1)CC(=O)N(C(C)C)C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetic acid (Example 3) (0.09 g, 0.25 mmol) in CH2Cl2 (5.0 mL) and DMF (0.5 mL) were added EDCI (0.05 g, 0.27 mmol), DMAP (0.02 g, 0.12 mmol), triethylamine (0.1 mL, 0.75 mmol) and diisopropylamine (0.04 mL, 0.30 mmol). The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1cscn1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl | null | 8 | CC(C)NC(C)C.Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1>CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl>Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)N(C(C)C)C(C)C)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80a2de2b1a184d3f92e129ddd5a674a8 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | BrCC1=C(C(=O)Br)C(=CC=C1)C.[C@H]1(C[C@@H](CCC1)O)O.CC(C)([O-])C.[K+].CC1=C(C(=O)OC)C(=CC=C1)C.BrCC1=C(C(=O)OC)C(=CC=C1)C>>O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C | Br[CH2:12][c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([CH3:7])[cH:8][cH:9][cH:10]1.[OH:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | null | null | CN1CCCC1=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(COC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:3] | 60 | [{"value": 60.0, "product": "O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 30 | MINUTE | 500 g (4.3 mol) of cis-1,3-cyclohexanediol were dissolved in 5 l of NMP and admixed with 336 g (3.0 mol) of potassium tert-butoxide (KOtBu). The internal temperature rose to 28° C. The mixture was stirred for 30 min, then cooled to −5° C. and admixed dropwise with 370 g (approx. 94%, approx. 1.4 mol) of methyl 2-bromom... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCCCC1 | HBr | CN1CCCC1=O.O | -5 | 0.5 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>CN1CCCC1=O.O>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77fb5b5bec6a4685847a43aba0b3d881 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1>>COC(=O)c1c(C)cccc1CO[C@@H]1CCC[C@H](O)C1 | O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C>>O[C@@H]1C[C@@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@@H:14]1[CH2:15][CH2:16][CH2:17][C@H:18]([OH:19])[CH2:20]1 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | COC(=O)c1c(C)cccc1CO[C@@H]1CCC[C@H](O)C1 | null | null | C(C)(=O)OC=C.C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(COC2CCCCC2)cc1 | null | null | [] | null | null | 28 | HOUR | 490 g of the crude, racemic methyl cis-2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoate (see Example 1) were dissolved in 3.1 l of methylene chloride and 850 ml of vinyl acetate, admixed with 18 g of Novozym 435 and stirred at 21–24° C. After 28 h, a further 2 g of Novozym 435 were added. After a total of 44 h, the re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CCCCC1 | null | C(C)(=O)OC=C.C(Cl)Cl | null | 28 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1>C(C)(=O)OC=C.C(Cl)Cl>COC(=O)c1c(C)cccc1CO[C@@H]1CCC[C@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbf07741bcdc4e359660bcd6b271e077 | Cc1ccc(-c2nc(COC3CCCC(O)C3)c(C)o2)cc1>>Cc1ccc(-c2nc(CO[C@@H]3CCC[C@H](O)C3)c(C)o2)cc1 | CC1=CC=C(C=C1)C=1OC(=C(N1)COC1CC(CCC1)O)C>>CC1=CC=C(C=C1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)O)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH2:9][O:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH:15]([OH:16])[CH2:17]3)[c:18]([CH3:19])[o:20]2)[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH2:9][O:10][C@@H:11]3[CH2:12][CH2:13][CH2:14][C@H:15]([OH:16])[CH2:17]3)[c:18]([CH3:19])[o:20]2)[cH:21][cH:2... | Cc1ccc(-c2nc(COC3CCCC(O)C3)c(C)o2)cc1 | Cc1ccc(-c2nc(CO[C@@H]3CCC[C@H](O)C3)c(C)o2)cc1 | null | null | C(C)(=O)OC=C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2nc(COC3CCCCC3)co2)cc1 | null | 52.8 | [{"value": 52.8, "product": "CC1=CC=C(C=C1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 16.3 g of the racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol were dissolved in 100 ml of vinyl acetate, admixed with 1.9 g of Chirazyme L-2, lyo., and stirred at 20–23° C. After about 30 minutes, the enzyme was filtered off and the solution concentrated under reduced pressure, crude product: ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cocn1.C1CCCCC1 | null | C(C)(=O)OC=C | null | 0.5 | Cc1ccc(-c2nc(COC3CCCC(O)C3)c(C)o2)cc1>C(C)(=O)OC=C>Cc1ccc(-c2nc(CO[C@@H]3CCC[C@H](O)C3)c(C)o2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28284bcf97824fbea3f17da5d93ed400 | Cc1oc(-c2ccccc2)nc1CO[C@@H]1CCC[C@H](O)C1>>Cc1oc(-c2ccccc2)nc1CO[C@H]1CCC[C@@H](O)C1 | C1(=CC=CC=C1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)O)C.C[O-].[Na+].C(C)(=O)O>>C1(=CC=CC=C1)C=1OC(=C(N1)CO[C@@H]1C[C@@H](CCC1)O)C | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][C@@H:15]1[CH2:16][CH2:17][CH2:18][C@H:19]([OH:20])[CH2:21]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][C@H:15]1[CH2:16][CH2:17][CH2:18][C@@H:19]([OH:20])[CH2:21]1 | Cc1oc(-c2ccccc2)nc1CO[C@@H]1CCC[C@H](O)C1 | Cc1oc(-c2ccccc2)nc1CO[C@H]1CCC[C@@H](O)C1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2nc(COC3CCCCC3)co2)cc1 | null | 87.5 | [{"value": 87.5, "product": "C1(=CC=CC=C1)C=1OC(=C(N1)CO[C@@H]1C[C@@H](CCC1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 0.96 g of the (1R,3S)-acetyl compound from Example 20 was dissolved in approx. 5–10 ml of MeOH, admixed with 0.1 ml of NaOMe (30%) and stirred at 20–23° C. After 3 h, the mixture was neutralized with acetic acid and concentrated under reduced pressure, taken up with ethyl acetate, washed with saturated NaHCO3, dried (M... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cocn1.c1ccccc1.C1CCCCC1 | null | CO | null | 3 | Cc1oc(-c2ccccc2)nc1CO[C@@H]1CCC[C@H](O)C1>CO>Cc1oc(-c2ccccc2)nc1CO[C@H]1CCC[C@@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdea85ef300d4da788573db5b896a3b8 | CC(=O)OC1CCCC(OCc2coc(-c3ccc(F)cc3)n2)C1>>O[C@@H]1CCC[C@H](OCc2coc(-c3ccc(F)cc3)n2)C1 | C(C)(=O)OC(C)=O.C(C)(=O)OC1CC(CCC1)OCC=1N=C(OC1)C1=CC=C(C=C1)F.C(CCCC(=O)[O-])(=O)OC1CC(CCC1)OCC1=CC=CC=C1.C(C1=CC=CC=C1)OC1CC(CCC1)O>>FC1=CC=C(C=C1)C=1OC=C(N1)CO[C@@H]1C[C@@H](CCC1)O | CC(=O)[O:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([O:7][CH2:8][c:9]2[cH:10][o:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[n:20]2)[CH2:21]1>>[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:6]([O:7][CH2:8][c:9]2[cH:10][o:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[n:20]2)[CH2:21]1 | CC(=O)OC1CCCC(OCc2coc(-c3ccc(F)cc3)n2)C1 | O[C@@H]1CCC[C@H](OCc2coc(-c3ccc(F)cc3)n2)C1 | null | null | P(=O)([O-])([O-])[O-].COCCOC | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | c1ccc(-c2nc(COC3CCCCC3)co2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:6]-[C:5]-[C@H;D3;+0:2](-[OH;D1;+0:1])-[C:3]-[C:4] | 0.1 | [{"value": 0.1, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Approx. 10 mg of 3-[2-(4-fluorophenyl)oxazol-4-ylmethoxyl]cyclohexyl acetate (prepared by reacting 3-benzyloxycyclohexan-1-ol with acetic anhydride, in a similar manner to the synthesis of mono(3-benzyloxycyclohexyl) glutarate see Example 39) were taken up in 2 ml of phosphate buffer (0.1 M, pH=7.0) and 2 ml of DME and... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | C1CCCCC1.c1cocn1.c1ccccc1 | HO- | P(=O)([O-])([O-])[O-].COCCOC | null | null | CC(=O)OC1CCCC(OCc2coc(-c3ccc(F)cc3)n2)C1>P(=O)([O-])([O-])[O-].COCCOC>O[C@@H]1CCC[C@H](OCc2coc(-c3ccc(F)cc3)n2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d65e1d4080f4e729f2a92a415415146 | BrCc1ccccc1.O[C@@H]1CCC[C@H](O)C1>>O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | O.CC(C)([O-])C.[K+].[C@H]1(C[C@@H](CCC1)O)O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[OH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])[CH2:15]1>>[OH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | BrCc1ccccc1.O[C@@H]1CCC[C@H](O)C1 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(COC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | 50.6 | [{"value": 50.6, "product": "C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 150.0 g (1.29 mol) of cis-1,3-cyclohexanediol were dissolved in 1.5 l of NMP, admixed with 111.6 g (0.99 mol) of potassium tert-butoxide (KOtBu) and stirred at 25–27° C. After about 30 minutes, the mixture was cooled to 0° C. and admixed dropwise with 78.1 g (0.46 mol) of benzyl bromide. The mixture was stirred at appr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | C1CCCCC1.c1ccccc1 | HBr | CN1CCCC1=O | 0 | 0.5 | BrCc1ccccc1.O[C@@H]1CCC[C@H](O)C1>CN1CCCC1=O>O[C@H]1CCC[C@@H](OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b466e2935dd142b8a4e2dfd6e267d75d | O[C@H]1CCC[C@@H](OCc2ccccc2)C1>>OC1CCCC(OCc2ccccc2)C1 | C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O>>C(C1=CC=CC=C1)OC1CC(CCC1)O | [OH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>>[OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | OC1CCCC(OCc2ccccc2)C1 | null | null | C(C)(=O)OC=C.C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(COC2CCCCC2)cc1 | null | null | [] | null | null | 6 | HOUR | 20.3 g of cis-3-benzyloxycyclohexan-1-ol were dissolved in 35 ml of vinyl acetate and 125 ml of methylene chloride, admixed with 2.0 g of Novozym 435 and stirred at 20–23° C. for 6 h. After leaving to stand overnight, the enzyme was filtered off. A sample was withdrawn and concentrated by evaporation under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCCC1.c1ccccc1 | null | C(C)(=O)OC=C.C(Cl)Cl | null | 6 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1>C(C)(=O)OC=C.C(Cl)Cl>OC1CCCC(OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b59f332d78f46dc86667879760bad0b | O[C@H]1CCC[C@@H](OCc2ccccc2)C1>>OC1CCCC(OCc2ccccc2)C1 | C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O>>C(C1=CC=CC=C1)OC1CC(CCC1)O | [OH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>>[OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | OC1CCCC(OCc2ccccc2)C1 | null | null | C(C)(=O)OC=C.C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(COC2CCCCC2)cc1 | null | null | [] | null | null | 26 | HOUR | 100.0 g of cis-3-benzyloxycyclohexan-1-ol were dissolved in 170 ml of vinyl acetate and 630 ml of methylene chloride, admixed with 5.0 g of Novozym 435 and stirred at 20–23° C. for 26 h. The enzyme was filtered off, and a sample was withdrawn and concentrated by evaporation under reduced pressure. The enantiomeric exce... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCCC1.c1ccccc1 | null | C(C)(=O)OC=C.C(Cl)Cl | null | 26 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1>C(C)(=O)OC=C.C(Cl)Cl>OC1CCCC(OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46a2b70cb3774dc384354d92898d7d21 | OC1CCCC(OCc2ccccc2)C1>>O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | C(C1=CC=CC=C1)OC1CC(CCC1)O>>C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O | [OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>>[OH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | OC1CCCC(OCc2ccccc2)C1 | O[C@H]1CCC[C@@H](OCc2ccccc2)C1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(COC2CCCCC2)cc1 | null | 36 | [{"value": 36.0, "product": "C(C1=CC=CC=C1)O[C@H]1C[C@H](CCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10 g of the crude acetate/alcohol mixture from Example 29 were taken up in approx. 90 ml of methanol and approx. 70 ml of water and washed three times with in each case approx. 50 ml of n-heptane. The combined heptane phases (contain predominantly the acetate) are extracted with 50 ml of 1:1 methanol/water. The combine... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCCC1.c1ccccc1 | null | CO | null | null | OC1CCCC(OCc2ccccc2)C1>CO>O[C@H]1CCC[C@@H](OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39f6c4bd24b6470583618751582d3aed | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | [C@H]1(C[C@@H](CCC1)O)O.CC(C)([O-])C.[K+].CC1=C(C(=O)OC)C(=CC=C1)C.BrCC1=C(C(=O)OC)C(=CC=C1)C>>O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C | Br[CH2:12][c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([CH3:7])[cH:8][cH:9][cH:10]1.[OH:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | null | null | C(C)(C)(C)OC.O.C(OC)COC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(COC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:3] | 14.2 | [{"value": 14.2, "product": "O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | 5 g (42.8 mmol) of cis-1,3-cyclohexanediol were dissolved in 50 ml of dimethoxyethane (DME), admixed at 20–23° C. with 3.36 g (30 mmol) of potassium tert-butoxide (KOtBu) and stirred. After about 30 minutes, the mixture is cooled to 5° C. and 3.7 g (approx. 50%) of methyl 2-bromomethyl-6-methylbenzoate, which may be pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCCCC1 | HBr | C(C)(C)(C)OC.O.C(OC)COC | 5 | 0.5 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>C(C)(C)(C)OC.O.C(OC)COC>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34aac6db739c484d8d628fa15ea117fa | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | [C@H]1(C[C@@H](CCC1)O)O.CC1=C(C(=O)OC)C(=CC=C1)C.BrCC1=C(C(=O)OC)C(=CC=C1)C.BrCC1=C(C(=O)Br)C(=CC=C1)C.CC(C)([O-])C.[K+]>>O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C | Br[CH2:12][c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([CH3:7])[cH:8][cH:9][cH:10]1.[OH:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | null | null | C(C)(C)(C)OC.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(COC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:3] | 14.2 | [{"value": 14.2, "product": "O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | 10.0 g (86 mmol) of cis-1,3-cyclohexanediol were taken up in 150 ml of methyl tert-butyl ether (MTBE), admixed at approx. 20° C. with 6.72 g (59.9 mmol) of potassium tert-butoxide (KOtBu) and stirred. After about 30 minutes, the suspension was cooled to 5° C. and admixed dropwise with 7.4 g (approx. 50%) of methyl 2-br... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCCCC1 | HBr | C(C)(C)(C)OC.O | 5 | 0.5 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>C(C)(C)(C)OC.O>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65ef42f140954425a031aa8adb08d3a5 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | O.CC(C)([O-])C.[K+].[C@H]1(C[C@@H](CCC1)O)O.BrCC1=C(C(=O)OC)C(=CC=C1)C>>O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C | Br[CH2:12][c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([CH3:7])[cH:8][cH:9][cH:10]1.[OH:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][cH:9][cH:10][c:11]1[CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][CH2:17][C@@H:18]([OH:19])[CH2:20]1 | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1 | COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 | null | null | CN1C(N(CCC1)C)=O.ClC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccc(COC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:3] | 13.7 | [{"value": 13.7, "product": "O[C@H]1C[C@H](CCC1)OCC1=C(C(=O)OC)C(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5 g (42.8 mmol) of cis-1,3-cyclohexanediol were dissolved in 40 ml of chlorobenzene and 10 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, dimethylpropyleneurea), admixed at 20–23° C. with 3.36 g (30 mmol) of potassium tert-butoxide (KOtBu) and stirred. After 10–15 minutes, the mixture was cooled to 15–... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1ccccc1.C1CCCCC1 | HBr | CN1C(N(CCC1)C)=O.ClC1=CC=CC=C1 | null | null | COC(=O)c1c(C)cccc1CBr.O[C@@H]1CCC[C@H](O)C1>CN1C(N(CCC1)C)=O.ClC1=CC=CC=C1>COC(=O)c1c(C)cccc1CO[C@H]1CCC[C@@H](O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47a6823fceb64ef4b003a8a5ae160266 | Cc1ccc(C=O)cc1.O.O>>Cc1ccc(C(O)C(=O)O)cc1 | C(Cl)(Cl)Cl.C1(=CC=C(C=C1)C=O)C.[OH-].[Na+].O.[OH-].[Na+].O>>CC1=CC=C(C(C(=O)O)O)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[cH:11][cH:12]1.[OH2:9].[OH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[C:8](=[O:9])[OH:10])[cH:11][cH:12]1 | Cc1ccc(C=O)cc1.O.O | Cc1ccc(C(O)C(=O)O)cc1 | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | null | Acylation | OtherReaction | e4754e3793ba0362af7cd262e2f320471fced6da69cfa59aaf69349f987b0106 | 7b79ddb9582ae558ef0424125dcd16c236a764b78e4d8d3057436676b03c02cd | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH2;D0;+0:6].[OH2;D0;+0:7]>>[O;H0;D1;+0:6]=[C:8](-[OH;D1;+0:7])-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | null | [] | 10 | CELSIUS | 6 | HOUR | A 300 gal reactor was charged with water (150 L) and sodium hydroxide (100 kg) and the solution was cooled to 10±5° C. A second 300 gal reactor was charged with chloroform (203 kg), benzyltriethylammonium chloride (8.2 kg) and 4-tolualdehyde (99 kg). The reaction mixture was heated to gentle reflux and the sodium hydro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid.Secondary alcohol | null | null | c1ccccc1 | Other | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | 10 | 6 | Cc1ccc(C=O)cc1.O.O>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC>Cc1ccc(C(O)C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a5375979fb5402d8fe980b291f4b317 | Cc1ccc(C2(C(=O)O)CC2C(=O)O)cc1.NC(N)=O>>Cc1ccc(C23CC2C(=O)NC3=O)cc1 | CC1=CC=C(C=C1)C1(C(C1)C(=O)O)C(=O)O.NC(=O)N>>CC1=CC=C(C=C1)C12C(NC(C2C1)=O)=O | O[C:9]([CH:8]1[C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:15][cH:14]2)([C:12](O)=[O:13])[CH2:7]1)=[O:10].NC(=O)[NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]23[CH2:7][CH:8]2[C:9](=[O:10])[NH:11][C:12]3=[O:13])[cH:14][cH:15]1 | Cc1ccc(C2(C(=O)O)CC2C(=O)O)cc1.NC(N)=O | Cc1ccc(C23CC2C(=O)NC3=O)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | f102f31968cec5a5cce8a63f187e2c2787ad6463f06ec6d023228eecad5281ab | 5eb28b4134086b781d00fd84897bce5d880f3b8a3f2763256df6a2d491a6f5b2 | O=C1NC(=O)C2(c3ccccc3)CC12 | N-C(=O)-[NH2;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]1(-[c:5])-[C:6]-[C:7]-1-[C;H0;D3;+0:8](-O)=[O;D1;H0:9]>>[O;D1;H0:9]=[C;H0;D3;+0:8]1-[NH;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]2(-[c:5])-[C:6]-[C:7]-1-2 | null | [] | null | null | null | null | A mixture of purified 1-(4-methylphenyl)-1,2-cyclopropanedicarboxylic acid (58 kg), toluene (465 kg) and urea (23.8 kg) was heated to reflux and the mixture held at reflux until the reaction was complete. On completion of the reaction period, the solution was cooled to 80–90° C. and washed with water (69 L). The lower ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Urea | Unsubstituted dicarboximide | null | C1NCC2CC12 | c1ccccc1.C1NCC2CC12 | HO- | C1(=CC=CC=C1)C | null | null | Cc1ccc(C2(C(=O)O)CC2C(=O)O)cc1.NC(N)=O>C1(=CC=CC=C1)C>Cc1ccc(C23CC2C(=O)NC3=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c509486ce7d542aeba24813fa375ce8e | CCOC(=O)CC(=O)Cl.Nc1ccc(Br)cc1S.O=S1C=Nc2ccc(Br)cc21.O=S1C=Nc2ccc(Br)cc21.[OH-]>>CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1.CCOC(=O)Cc1nc2ccc(Br)cc2s1 | NC1=C(C=C(C=C1)Br)S.C(C)OC(CC(=O)Cl)=O.BrC1=CC2=C(N=CS2=O)C=C1.BrC1=CC2=C(N=CS2=O)C=C1.[OH-].[Na+]>>C(C)OC(CC=1SC2=C(N1)C=CC(=C2)Br)=O.C(C)OC(=O)C=1SC2=C(NC1O)C=CC(=C2)Br | Cl[C:21](=[O:22])[CH2:23][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:25][c:26]1[cH:27][cH:28][c:29]([Br:30])[cH:31][c:32]1[SH:33].[CH:7]1=[N:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[S:17]1=[O:8].O=S1[c:6]2cc(Br)[cH:18][cH:19]c2N=[CH:24]1.[OH-:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([OH:8])[NH:9][c:10]2[... | CCOC(=O)CC(=O)Cl.Nc1ccc(Br)cc1S.O=S1C=Nc2ccc(Br)cc21.O=S1C=Nc2ccc(Br)cc21.[OH-] | CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1.CCOC(=O)Cc1nc2ccc(Br)cc2s1 | null | null | null | C-C Coupling | OtherReaction | bf0ea44699cc37e70c3e03e5bc2ee44e1fc39c23a4fbe8e0f3af1c0cf28c15a5 | c986c860b0f4e047419b8e2b347702ba5635b8e1e85b19f8c1ec6852237aadeb | C1=CSc2ccccc2N1.c1ccc2scnc2c1 | Br-c1:[cH;D2;+0:1]:[cH;D2;+0:2]:c2:[c;H0;D3;+0:3](:c:1)-S(=O)-[CH;D2;+0:4]=N-2.Cl-[C;H0;D3;+0:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15](-[SH;D1;+0:16]):[c:17].[O;H0;D1;+0:18]=[S;H0;D3;+0:19]1-[CH;D2;+0:20]=[N;H0;D2;+0:21]-[c:22](:[c:23]):[c:24]-1:[c... | null | [] | null | null | null | null | Compounds of formula (22) can be prepared from 6-bromobenzothiazolone as shown in Scheme 3. 6-Bromobenzothiazolone is heated in the presence of NaOH base to provide a mixture of 2-amino-5-bromothiophenol (15) and its disulfide (16). The mixture is treated with chlorocarbonyl-acetic acid ethyl ester to provide 6-bromo-b... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Ester.Primary amine.Aromatic thiol.Sulfoxide.Sulfoxide | Enamine.Ester.Ester.Enol.Monosulfide | c1ccccc1.c1ccc2scnc2c1.c1ccc2scnc2c1 | C1=CSc2ccccc2N1.c1ccc2scnc2c1 | C1=CSc2ccccc2N1.c1ccc2scnc2c1 | HCl.Br- | null | null | null | CCOC(=O)CC(=O)Cl.Nc1ccc(Br)cc1S.O=S1C=Nc2ccc(Br)cc21.O=S1C=Nc2ccc(Br)cc21.[OH-]>>CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1.CCOC(=O)Cc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22bb215d286d4b7dacf3111b06283fce | CCOC(=O)Cc1nc2ccc(Br)cc2s1>>OCCc1nc2ccc(Br)cc2s1 | C(C)OC(CC=1SC2=C(N1)C=CC(=C2)Br)=O.[BH4-].[Na+]>>BrC1=CC2=C(N=C(S2)CCO)C=C1 | CCO[C:2](=[O:1])[CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[s:13]1>>[OH:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[s:13]1 | CCOC(=O)Cc1nc2ccc(Br)cc2s1 | OCCc1nc2ccc(Br)cc2s1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2scnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4](:[#16;a:5]):[#7;a:6]>>[#16;a:5]:[c:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[#7;a:6] | null | [] | null | null | null | null | Compounds of formula (22) can be prepared from 6-bromobenzothiazolone as shown in Scheme 3. 6-Bromobenzothiazolone is heated in the presence of NaOH base to provide a mixture of 2-amino-5-bromothiophenol (15) and its disulfide (16). The mixture is treated with chlorocarbonyl-acetic acid ethyl ester to provide 6-bromo-b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2scnc2c1 | HO- | null | null | null | CCOC(=O)Cc1nc2ccc(Br)cc2s1>>OCCc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fbb89cd170e414183553eb3fcd55f41 | CS(=O)(=O)Cl.OCCc1nc2ccc(Br)cc2s1>>CS(=O)(=O)OCCc1nc2ccc(Br)cc2s1 | BrC1=CC2=C(N=C(S2)CCO)C=C1.S(=O)(=O)(C)Cl>>BrC1=CC2=C(N=C(S2)CCOS(=O)(=O)C)C=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[s:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[s:17]1 | CS(=O)(=O)Cl.OCCc1nc2ccc(Br)cc2s1 | CS(=O)(=O)OCCc1nc2ccc(Br)cc2s1 | null | null | C(C)N(CC)CC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2scnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | Compounds of formula (22) can be prepared from 6-bromobenzothiazolone as shown in Scheme 3. 6-Bromobenzothiazolone is heated in the presence of NaOH base to provide a mixture of 2-amino-5-bromothiophenol (15) and its disulfide (16). The mixture is treated with chlorocarbonyl-acetic acid ethyl ester to provide 6-bromo-b... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2scnc2c1 | HCl | C(C)N(CC)CC | null | null | CS(=O)(=O)Cl.OCCc1nc2ccc(Br)cc2s1>C(C)N(CC)CC>CS(=O)(=O)OCCc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a3b06cd55a14560b4976cfed5f06416 | C#CCCN1CCCC1C.Nc1ccc(Br)cc1I>>CC1CCCN1CCC#Cc1cc(Br)ccc1N | C(CC#C)N1C(CCC1)C.BrC1=CC(=C(C=C1)N)I>>BrC1=CC(=C(C=C1)N)C#CCCN1C(CCC1)C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[CH:10].I[c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18] | C#CCCN1CCCC1C.Nc1ccc(Br)cc1I | CC1CCCN1CCC#Cc1cc(Br)ccc1N | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)CCN1CCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6] | null | [] | null | null | null | null | The compound of formula (43) can be prepared from 3-butynyl p-toluenesulfonate (42) and 2(R)-methylpyrrrolidine L-tartrate (40) as shown in Scheme 5. 2(R)-Methylpyrrolidine L-tartrate (40) is treated with potassium carbonate in acetonitrile to provide 2(R)-methylpyrrolidine (41), which is combined with 3-butynyl p-tolu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1 | HI | null | null | null | C#CCCN1CCCC1C.Nc1ccc(Br)cc1I>>CC1CCCN1CCC#Cc1cc(Br)ccc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7024dd9e5254cfbaa00ffa5e9ae3740 | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | BrC1=CC2=C(NC(=N2)CCN2C(CCC2)C)C=C1.BrC1=CC2=C(NC(=N2)CCN2C(CCC2)C)C=C1.C(#N)C1=CC=C(C=C1)B(O)O>>CC1N(CCC1)CCC1=NC2=C(N1)C=CC(=C2)C2=CC=C(C#N)C=C2 | Br[c:13]1[cH:12][c:11]2[n:10][c:9]([CH2:8][CH2:7][N:6]3[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[nH:25][c:24]2[cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[c... | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1 | CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 4c01b75ced48e0c5dbfbda4cb6a596e9d3a1d181f4aef3fbd9604232ef2322c4 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]c(CCN4CCCC4)nc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1):[c:13]:[c:14] | null | [] | null | null | null | null | Compounds of formula (55) and (55a) can be prepared from 2(R)-methylpyrrolidine HCl (50) and ethyl acrylate (51) as shown in Scheme 6. 2(R)-Methylpyrrolidine HCl can be treated with potassium carbonate to provide 2(R)-methylpyrrolidine (41), which is reacted with ethyl acrylate (51) to provide 3-(2-methyl-pyrrolidin-1-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]cnc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HBr.B | null | null | null | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e468895d0537455791117c5aa46e01fd | CC(C)(C)OC(=O)N1CC[C@H]1CO.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O | C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1[C@@H](CC1)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N1[C@@H](CC1)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]1[CH2:12][OH:13].Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]1[CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17] | CC(C)(C)OC(=O)N1CC[C@H]1CO.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#7:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | 0 | CELSIUS | 8 | HOUR | 2-(S)-Hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (prepared as described in Abreo, et al. J. Med. Chem. 1996, 39, 817–825) (9.7 g, 52 mmol) was taken up in dichloromethane (50 mL), treated with triethylamine (8.7 mL, 62 mmol), cooled to 0° C., treated dropwise with methanesulfonyl chloride (4.4 mL, 57 mm... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1C[NH]C1 | HCl | ClCCl | 0 | 8 | CC(C)(C)OC(=O)N1CC[C@H]1CO.CS(=O)(=O)Cl>ClCCl>CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98a2701b80cf40f4b520ee3818c90065 | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O>>C[C@@H]1CCN1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1[C@@H](CC1)COS(=O)(=O)C.C(C)[BH-](CC)CC.[Li+].C(C)(=O)OCC>>C(C)(C)(C)OC(=O)N1[C@@H](CC1)C | CS(=O)(=O)O[CH2:1][C@@H:2]1[CH2:3][CH2:4][N:5]1[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][N:5]1[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12] | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O | C[C@@H]1CCN1C(=O)OC(C)(C)C | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | b912c78cb197e36ec1377256b010930a62c194e425d624f79bd79646c51988b4 | 28e81ae8a7ce8bef7c0a5c5aadad67636bd3c9bf494add5caa6f4f660788ae85 | C1CNC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:5]1-[C:4]-[C:3]-[C:2]-1-[CH3;D1;+0:1] | 30 | [{"value": 30.0, "product": "C(C)(C)(C)OC(=O)N1[C@@H](CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 6 | HOUR | 2-(S)-Methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester was (4.83 g, 18.2 mmol) was taken up in THF (11 mL), cooled to 0° C. under N2, treated drop-wise with a lithium triethylborohydride (1.0 M in THF, 73 mL), stirred at ambient temperature for 6 hours, treated with ethyl acetate (500 mL), washed w... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | null | null | C1C[NH]C1 | MsOH.HO- | C1CCOC1 | 0 | 6 | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O>C1CCOC1>C[C@@H]1CCN1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d77490cfe1ed472b8c43e116c87aa2d2 | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O.[F-]>>CC(C)(C)OC(=O)N1CC[C@H]1CF | C(C)(C)(C)OC(=O)N1[C@@H](CC1)COS(=O)(=O)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)(C)(C)OC(=O)N1[C@@H](CC1)CF | CS(=O)(=O)O[CH2:12][C@H:11]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]1.[F-:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]1[CH2:12][F:13] | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O.[F-] | CC(C)(C)OC(=O)N1CC[C@H]1CF | null | null | null | Functional Group Interconversion | OtherReaction | 119410ad0456baafba3b2935b12d3e44977c506a6dd8cacdd3e4fe37abe9db9f | ddf832dd4937bef392b42ed4281006ae20524cc7fc61b350edeb12d7b5bf783f | C1CNC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[F-;H0;D0:13]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:5]1-[C:4]-[C:3]-[C:2]-1-[CH2;D2;+0:1]-[F;H0;D1;+0:13] | null | [] | null | null | null | null | 2-(S)-Methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (5.62 g, 21.2 mmol) was treated with tetrabutylammonium fluoride (1 M solution in THF, 191 mL) under N2, heated to reflux for 1 hour, cooled to ambient temperature, concentrated to 50 mL, treated with water (100 mL) and extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Primary halide | null | null | C1C[NH]C1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]1COS(C)(=O)=O.[F-]>>CC(C)(C)OC(=O)N1CC[C@H]1CF |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1090695690f74685a1dece36db0314be | C=O.Cc1nc2cc(Br)ccc2s1>>OCCc1nc2cc(Br)ccc2s1 | BrC=1C=CC2=C(N=C(S2)C)C1.[NH4+].[Cl-].[Li]N1C(CCCC1(C)C)(C)C.[Li]CCCC.C=O>>BrC=1C=CC2=C(N=C(S2)CCO)C1 | [O:1]=[CH2:2].[CH3:3][c:4]1[n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[s:13]1>>[OH:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[s:13]1 | C=O.Cc1nc2cc(Br)ccc2s1 | OCCc1nc2cc(Br)ccc2s1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | e09a7c53ddc9875d8ca974c0a8ce2e05d5a94c87ff882117809becd87c4c217b | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | c1ccc2scnc2c1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[CH3;D1;+0:3]-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[#7;a:8]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[#7;a:8]:1 | null | [] | -78 | CELSIUS | 3 | HOUR | To a dry 100 mL flask, 2,2,6′,6′-tetra-methyl piperidine (0.56 g, 4 mmol) and 6 mL of THF was added and cooled to −78° C. Then n-BuLi (1.5 mL, 2.5M) was added rapidly, and the mixture of LiTMP was stirred for 3 hr. 5-Bromo-2-methyl-benzothiazole (0.75 g, 3.3 mmol) was added in solid form in to the reaction at −78° C., ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | null | null | c1ccc2scnc2c1 | null | C1CCOC1 | -78 | 3 | C=O.Cc1nc2cc(Br)ccc2s1>C1CCOC1>OCCc1nc2cc(Br)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab2cc805775c4093bee9592abaf35306 | CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1>>CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1 | CS(=O)(=O)Cl.BrC=1C=CC2=C(N=C(S2)CCO)C1.CCN(CC)CC>>BrC=1C=CC2=C(N=C(S2)CCOS(=O)(=O)C)C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[s:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[s:17]1 | CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1 | CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2scnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | To a mixture of 2-(5-bromo-benzothiazol-2-yl)-ethanol (0.94 g, 3.6 mmol) in 10 mL CH2Cl2, Et3N (0.99 g, 9.8 mmol), was added methanesulfonyl chloride (0.46 g, 4.0 mmol) dropwise at room temperature. The reaction was worked up by concentrating under vacuum and then used in the next step, Example 1C.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2scnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1>C(Cl)Cl>CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a282d85555e47b2bfce6f9522c00967 | CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1.C[C@@H]1CCCN1>>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 | CCN(CC)CC.BrC=1C=CC2=C(N=C(S2)CCOS(=O)(=O)C)C1.C[C@H]1NCCC1>>BrC=1C=CC2=C(N=C(S2)CCN2[C@@H](CCC2)C)C1 | CS(=O)(=O)O[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[s:18]1.[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[s:18]1 | CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1.C[C@@H]1CCCN1 | C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | d27d68bc3d43f6d66a205fa71d9985c3ff34906c317c31aac4632a55b7f79861 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc2sc(CCN3CCCC3)nc2c1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#16;a:4]):[#7;a:5].[C;D1;H3:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#16;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-1-[C;D1;H3:6]):[#7;a:5] | null | [] | 60 | CELSIUS | null | null | The methanesulfonic acid 2-(5-bromo-benzothiazol)-2-yl)-ethyl ester from Example 1B, and 2 equivalents (7.3 mmol) of 2-(R)-methyl pyrrolidine (at a concentration of 10 mg/mL solution in acetonitrile), was combined with excess Et3N (0.99 g, 9.8 mmol), and the resulting mixture was heated to 60° C. for 2 hr. The solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2scnc2c1 | MsOH.HO- | C(C)#N | 60 | null | CS(=O)(=O)OCCc1nc2cc(Br)ccc2s1.C[C@@H]1CCCN1>C(C)#N>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edb4a5288d3a40f7b9ddd0afc3612493 | CC1CCCN1CCc1nc2cc(Br)ccc2s1.N#Cc1ccc(B(O)O)cc1>>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2s1 | C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].C(#N)C1=CC=C(C=C1)B(O)O.C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.BrC=1C=CC2=C(N=C(S2)CCN2C(CCC2)C)C1>>CC1N(CCC1)CCC=1SC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2 | Br[c:13]1[cH:12][c:11]2[n:10][c:9]([CH2:8][CH2:7][N:6]3[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[s:25][c:24]2[cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH... | CC1CCCN1CCc1nc2cc(Br)ccc2s1.N#Cc1ccc(B(O)O)cc1 | CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2s1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | dafc139bc4494937b580450e1f22e20f12d86e297a18c2a2ce8a2d9de753d94b | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3sc(CCN4CCCC4)nc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:2:[c:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:2:[c:8]:[c:9]:1):[c:13]:[c:14] | 31.5 | [{"value": 31.5, "product": "CC1N(CCC1)CCC=1SC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a reaction flask containing K2CO3 (0.326 g, 1.5 mmol), CsF (0.233 g, 1.5 mmol), and (0.19 g, 1.3 mmol) of 4-cyanophenyl boronic acid was added a solution of 5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole (0.25 g, 0.77 mmol) in 3 mL of toluene. The resulting mixture was purged with nitrogen, and then 2-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2scnc2c1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2scnc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 90 | null | CC1CCCN1CCc1nc2cc(Br)ccc2s1.N#Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-047fe1c5f9834cbcb16b3e4e1a1cbfb3 | O=[N+]([O-])c1cc(Br)ccc1S>>Nc1cc(Br)ccc1S | BrC1=CC(=C(C=C1)S)[N+](=O)[O-].BrC1=CC(=C(C=C1)S)[N+](=O)[O-].[H][H]>>NC1=C(C=CC(=C1)Br)S | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[SH:9]>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[SH:9] | O=[N+]([O-])c1cc(Br)ccc1S | Nc1cc(Br)ccc1S | null | [Ni] | C1CCOC1 | 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 | null | null | The mixture of 4-bromo-2-nitro-benzenethiol and its disulfide from Example 2A (14.9 g, 53.5 mmol) in THF (450 mL) was mixed with Raney Ni (30 g, 100% wt). The mixture was hydrogenated in a 1000 mL Paar shaker at a hydrogen pressure of 40 psi at 50° C. for 41 hours. When the reaction was complete, the solids were filter... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C1CCOC1 | null | null | O=[N+]([O-])c1cc(Br)ccc1S>[Ni].C1CCOC1>Nc1cc(Br)ccc1S |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98cc223bf38a4ce9a090aa143a53649e | CCOC(=O)Cc1nc2cc(Br)ccc2s1>>OCCc1nc2cc(Br)ccc2s1 | C(C)OC(CC=1SC2=C(N1)C=C(C=C2)Br)=O.[BH4-].[Na+]>>BrC=1C=CC2=C(N=C(S2)CCO)C1 | CCO[C:2](=[O:1])[CH2:3][c:4]1[n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[s:13]1>>[OH:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[s:13]1 | CCOC(=O)Cc1nc2cc(Br)ccc2s1 | OCCc1nc2cc(Br)ccc2s1 | null | null | C1CCOC1.CCO | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2scnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4](:[#16;a:5]):[#7;a:6]>>[#16;a:5]:[c:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[#7;a:6] | null | [] | null | null | 2 | HOUR | (5-Bromo-benzothiazol-2-yl)-acetic acid ethyl ester (1.25 g, 4.2 mmol) was dissolved in THF (20 mL) and EtOH (5 mL) under N2. Then 0.24 g of NaBH4 was dissolved in EtOH (3 mL) and added to the above solution. The reaction mixture was stirred at room temperature for 2 hours. After the completion the mixture was quenched... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2scnc2c1 | HO- | C1CCOC1.CCO | null | 2 | CCOC(=O)Cc1nc2cc(Br)ccc2s1>C1CCOC1.CCO>OCCc1nc2cc(Br)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-648115ee2be148f0b50d9bf80b823d53 | CC#N.CCN(CC)CC.CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1>>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 | BrC=1C=CC2=C(N=C(S2)CCO)C1.C(C)N(CC)CC.C(C)#N.C(C)N(CC)CC.S(=O)(=O)(C)Cl>>BrC=1C=CC2=C(N=C(S2)CCN2[C@@H](CCC2)C)C1 | [C:2]([CH3:3])#[N:6].CCN(CC)[CH2:5][CH3:4].O=S(=O)(Cl)[CH3:1].O[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[s:18]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[s:18]1 | CC#N.CCN(CC)CC.CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1 | C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | e5920dee39fd4e23ef47b22853f6a079fe3f61b5f6e67d8ed9ea1517aa09b86a | 161a415a813f397cd540024355cb50c7cef50673b6c8766c860bc7e640c38f0d | c1ccc2sc(CCN3CCCC3)nc2c1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].Cl-S(=O)(=O)-[CH3;D1;+0:3].O-[CH2;D2;+0:4]-[C:5]-[c:6](:[#16;a:7]):[#7;a:8].[CH3;D1;+0:9]-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]>>[#16;a:7]:[c:6](-[C:5]-[CH2;D2;+0:4]-[N;H0;D3;+0:11]1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:9]-[C@H;D3;+0:10]-1-[CH3;D1;+0:3]):[#7;a:8] | 100 | [{"value": 100.0, "product": "BrC=1C=CC2=C(N=C(S2)CCN2[C@@H](CCC2)C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2-(5-bromo-benzothiazol-2-yl)-ethanol (1.50 g, 5.8 mmol) and triethylamine (1.33 g, 11.6 mmol) in CH2Cl2 was cooled to 0° C., and mesyl chloride was added dropwise. The mixture was warmed to room temperature and stirred for 1 hr. The solvent was removed under vacuum, and to the residue was added acetonitr... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol.Tertiary amine.Sulfonyl halide | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2scnc2c1 | HCl | C(Cl)Cl | null | 1 | CC#N.CCN(CC)CC.CS(=O)(=O)Cl.OCCc1nc2cc(Br)ccc2s1>C(Cl)Cl>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e0a998deb1f41e6be0b5926a4440d62 | CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1>>CCOC(=O)Cc1nc2ccc(Br)cc2s1 | C(C)OC(=O)C=1SC2=C(NC1O)C=CC(=C2)Br>>C(C)OC(CC=1SC2=C(N1)C=CC(=C2)Br)=O | O[C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[S:16][c:15]2[c:9]([cH:10][cH:11][c:12]([Br:13])[cH:14]2)[NH:8]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[s:16]1 | CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1 | CCOC(=O)Cc1nc2ccc(Br)cc2s1 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | fc649200af8e1ad1b1d9f8e7005a8ae3b629126f30b62ef8211b8ab6436e3821 | 84800cecbc2734529d618fbe9e9bfc0f092a255228f2e6c590042cef943220a2 | c1ccc2scnc2c1 | O-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:11])-[NH;D2;+0:12]-1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:12]:[c:10](:[c:11]):[c:8](:[c:9]):[s;H0;D2;+0:7]:1 | null | [] | 110 | CELSIUS | 2 | HOUR | 7-Bromo-3-hydroxy-4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester (2.47 g, 7.8 mmol) was dissolved in 50 mL of acetic acid and heated to 110° C. under nitrogen. Zinc powder (7.5 g, 114.7 mmol) was added in portions at room temperature over 80 minutes. The mixture was stirred at 110° C. for additional 2 hours and co... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Enol.Monosulfide | Ester | C1=CSc2ccccc2N1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Zn].C(C)(=O)O | 110 | 2 | CCOC(=O)C1=C(O)Nc2ccc(Br)cc2S1>[Zn].C(C)(=O)O>CCOC(=O)Cc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d81361375ed643d0b99a999c148fc8ac | CCOC(=O)Cc1nc2ccc(Br)cc2s1>>OCCc1nc2ccc(Br)cc2s1 | [BH4-].[Na+].C(C)OC(CC=1SC2=C(N1)C=CC(=C2)Br)=O>>BrC1=CC2=C(N=C(S2)CCO)C=C1 | CCO[C:2](=[O:1])[CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[s:13]1>>[OH:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[s:13]1 | CCOC(=O)Cc1nc2ccc(Br)cc2s1 | OCCc1nc2ccc(Br)cc2s1 | null | null | C1CCOC1.C(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2scnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4](:[#16;a:5]):[#7;a:6]>>[#16;a:5]:[c:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[#7;a:6] | null | [] | null | null | 15 | HOUR | To a stirred mixture of sodium borohydride (1.11 g, 29.3 mmol) in ethanol (10 mL) at room temperature was added a solution of the (6-bromo-benzothiazol-2-yl)-acetic acid ethyl ester (2.2 g, 7.3 mmol) in THF (25 mL) at 23–28° C. The mixture was stirred at room temperature for 15 hr, cooled to 3° C. and quenched with 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2scnc2c1 | HO- | C1CCOC1.C(C)O | null | 15 | CCOC(=O)Cc1nc2ccc(Br)cc2s1>C1CCOC1.C(C)O>OCCc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9edf0410addf43d4bed914c8f716366e | C[C@@H]1CCCN1.OCCc1nc2ccc(Br)cc2s1>>CC1CCCN1CCc1nc2ccc(Br)cc2s1 | BrC1=CC2=C(N=C(S2)CCO)C=C1.C(C)N(CC)CC.C([O-])([O-])=O.[K+].[K+].Cl.C[C@H]1NCCC1.S(=O)(=O)(C)Cl>>BrC1=CC2=C(N=C(S2)CCN2C(CCC2)C)C=C1 | [CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6]1.O[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[s:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[s:18]1 | C[C@@H]1CCCN1.OCCc1nc2ccc(Br)cc2s1 | CC1CCCN1CCc1nc2ccc(Br)cc2s1 | null | null | C1CCOC1.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 5b5461e2c999b5ff4ebd02389aabcfa6da1d5461f5b1011870f0b8680e19702d | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc2sc(CCN3CCCC3)nc2c1 | O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#16;a:4]):[#7;a:5].[C;D1;H3:6]-[C@@H;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#16;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[CH;D3;+0:7]-1-[C;D1;H3:6]):[#7;a:5] | 88.7 | [{"value": 88.3, "product": "BrC1=CC2=C(N=C(S2)CCN2C(CCC2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "BrC1=CC2=C(N=C(S2)CCN2C(CCC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 2-(6-bromo-benzothiazol-2-yl)-ethanol (2.23 g, 8.6 mmol) and triethylamine (2.19 g, 21.6 mmol) in THF (45 mL) was cooled to −20° C., and mesyl chloride (1.58 g, 13.8 mmol) was added at −20 to −10° C. The mixture was warmed to room temperature and stirred for 2 hr. Potassium carbonate (1.79 g, 13 mmol), 2-... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2scnc2c1 | HO- | C1CCOC1.C(C)#N | null | 2 | C[C@@H]1CCCN1.OCCc1nc2ccc(Br)cc2s1>C1CCOC1.C(C)#N>CC1CCCN1CCc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7d8686f93f04837b803ce8e0f3a19eb | C[C@@H]1CCCN1CCc1nc2ccc(Br)cc2s1.OB(O)c1cccnc1>>C[C@@H]1CCCN1CCc1nc2ccc(-c3cccnc3)cc2s1 | BrC1=CC2=C(N=C(S2)CCN2[C@@H](CCC2)C)C=C1.N1=CC(=CC=C1)B(O)O.C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>>C[C@H]1N(CCC1)CCC=1SC2=C(N1)C=CC(=C2)C=2C=NC=CC2 | Br[c:14]1[cH:13][cH:12][c:11]2[n:10][c:9]([CH2:8][CH2:7][N:6]3[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[s:23][c:22]2[cH:21]1.OB(O)[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][n:19][cH:20]3)[cH:21]... | C[C@@H]1CCCN1CCc1nc2ccc(Br)cc2s1.OB(O)c1cccnc1 | C[C@@H]1CCCN1CCc1nc2ccc(-c3cccnc3)cc2s1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | O.CC(C)O | C-C Coupling | Suzuki coupling with boronic acids | c70fee0da30dc36b8a4bebab6ea83795444d7fd4b4a174e37bfe6a9f9425b533 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3nc(CCN4CCCC4)sc3c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[#16;a:7]1:[c:6]:[#7;a:5]:[c:4]2:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]3:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:3):[c:9]:[c:8]:1:2 | 68.7 | [{"value": 67.0, "product": "C[C@H]1N(CCC1)CCC=1SC2=C(N1)C=CC(=C2)C=2C=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "C[C@H]1N(CCC1)CCC=1SC2=C(N1)C=CC(=C2)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A mixture of 6-bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole (0.3 g, 0.9 mmol), 3-pyridinyl boronic acid (0.17 g, 1.4 mmol) and 2-(dicyclohexylphosphino)biphenyl (65 mg, 0.2 mmol) in 15 mL of IPA was purged wth nitrogen. Dichlorobis(triphenylphosphine)palladium II (65 mg, 0.1 mmol) was added. Sodium ca... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2scnc2c1.c1ccncc1 | c1ccc2scnc2c1.c1ccncc1 | C1CC[NH]C1.c1ccc2scnc2c1.c1ccncc1 | HBr.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.CC(C)O | 65 | null | C[C@@H]1CCCN1CCc1nc2ccc(Br)cc2s1.OB(O)c1cccnc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.CC(C)O>C[C@@H]1CCCN1CCc1nc2ccc(-c3cccnc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c01067372e44b6680ad32e1a7caf277 | C=CC(=O)O.Nc1cc(Br)ccc1O>>C=Cc1nc2cc(Br)ccc2o1 | C(C=C)(=O)O.NC1=C(C=CC(=C1)Br)O.CS(=O)(=O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.[OH-].[Na+]>>BrC=1C=CC2=C(N=C(O2)C=C)C1 | O=[C:3](O)[CH:2]=[CH2:1].[NH2:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH2:1]=[CH:2][c:3]1[n:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[o:12]1 | C=CC(=O)O.Nc1cc(Br)ccc1O | C=Cc1nc2cc(Br)ccc2o1 | null | null | ClCCl.O.C(C)OCC | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1ccc2ocnc2c1 | O-[C;H0;D3;+0:1](=O)-[C:2]=[C;D1;H2:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H2:3]=[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:1 | 45.1 | [{"value": 45.0, "product": "BrC=1C=CC2=C(N=C(O2)C=C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.1, "product": "BrC=1C=CC2=C(N=C(O2)C=C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 78 | CELSIUS | 12 | HOUR | A mixture of 12 g of methanesulfonic acid and 1.8 g of phosphorus pentoxide (P2O5) was stirred 12 hours. To this well stirred suspension was added 0.346 g (4.8 mmol) of acrylic acid and 0.808 g (4 mmol) of 2-amino-4-bromo-phenol. The reaction was heated at 78° C. for 5 hours, then cooled to room temperature. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | ClCCl.O.C(C)OCC | 78 | 12 | C=CC(=O)O.Nc1cc(Br)ccc1O>ClCCl.O.C(C)OCC>C=Cc1nc2cc(Br)ccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28e2094b51fe4314ac393822d96728b9 | C=Cc1nc2cc(Br)ccc2o1.N#Cc1ccc(B(O)O)cc1>>C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 | BrC=1C=CC2=C(N=C(O2)C=C)C1.C(#N)C1=CC=C(C=C1)B(O)O.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.O1CCCC1>>C(=C)C=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2 | Br[c:7]1[cH:6][c:5]2[n:4][c:3]([CH:2]=[CH2:1])[o:19][c:18]2[cH:17][cH:16]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1>>[CH2:1]=[CH:2][c:3]1[n:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]3)[cH:16][cH:17][c:18]2[o:19]1 | C=Cc1nc2cc(Br)ccc2o1.N#Cc1ccc(B(O)O)cc1 | C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 | null | null | CCCCCC | C-C Coupling | Suzuki coupling with boronic acids | 99bf694f84e9ec22cb82f9819557cd37221283254ff798499273a8b4f21eaca4 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ocnc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#8;a:5]:[c:6](-[C:7]=[C;D1;H2:8]):[#7;a:9]:[c:10]:2:[c:11]:1.O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C;D1;H2:8]=[C:7]-[c:6]1:[#7;a:9]:[c:10]2:[c:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3]:[c:4]:2:[#8;a:5]:1 | 78 | [{"value": 78.0, "product": "C(=C)C=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "C(=C)C=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 24 | HOUR | A mixture of 224 mg (1 mmol) of 5-bromo-2-vinyl-benzooxazole, 191 mg (1.3 mmol) of 4-cyanophenylboronic acid, 55 mg (0.03 mmol) of tris-(dibenzylidineacetone)dipalladium (0) (CAS #52409-22-0), 0.2 mL (0.06 mmol) of a 10% solution of tri-tert-butylphosphine in hexane, and 1.5 mL of tetrahydrofuran was stirred at 23° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1 | HBr.B | CCCCCC | 23 | 24 | C=Cc1nc2cc(Br)ccc2o1.N#Cc1ccc(B(O)O)cc1>CCCCCC>C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-066231d855314bf3955d22c323fbe57e | C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1.CC1CCCN1>>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 | C(=C)C=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2.CC1NCCC1>>CC1N(CCC1)CCC=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2 | [CH2:7]=[CH:8][c:9]1[n:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]3)[cH:22][cH:23][c:24]2[o:25]1.[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH... | C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1.CC1CCCN1 | CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | dd05e02f89f4334a0cbf67e5033d2677d654bbf2f6f7ab2436d63d82eac8e490 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | c1ccc(-c2ccc3oc(CCN4CCCC4)nc3c2)cc1 | [C;D1;H3:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[NH;D2;+0:6]-1.[CH2;D1;+0:7]=[CH;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:1>>[C;D1;H3:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:1 | 100 | [{"value": 100.0, "product": "CC1N(CCC1)CCC=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "CC1N(CCC1)CCC=1OC2=C(N1)C=C(C=C2)C2=CC=C(C#N)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 24.6 mg (0.1 mmol) of 4-(2-vinyl-benzooxazol-5-yl)-benzonitrile and 24 mg of racemic 2-methyl-pyrrolidine (Aldrich, CAS #765-38-8) in 0.25 mL of ethanol was stirred at room temperature for 1 hour, then concentrated in vacuo to a glass to give pure product racemic 4-{2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2ocnc2c1.c1ccccc1 | null | C(C)O | null | null | C=Cc1nc2cc(-c3ccc(C#N)cc3)ccc2o1.CC1CCCN1>C(C)O>CC1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aaf4f21a45734751b2c179840ecdc207 | C#CCCOS(=O)(=O)c1ccc(C)cc1.C[C@@H]1CCCN1>>C#CCCN1CCC[C@H]1C | C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.C[C@H]1NCCC1.C1(=CC=C(C=C1)S(=O)(=O)OCCC#C)C.C([O-])([O-])=O.[K+].[K+]>>C(CC#C)N1[C@@H](CCC1)C | Cc1ccc(S(=O)(=O)O[CH2:4][CH2:3][C:2]#[CH:1])cc1.[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[CH3:10]>>[CH:1]#[C:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[CH3:10] | C#CCCOS(=O)(=O)c1ccc(C)cc1.C[C@@H]1CCCN1 | C#CCCN1CCC[C@H]1C | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | bdf21feb16e238d3a4e1a225eabe2c616c4f3ccb3286bcf173af5a52d353d303 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | C1CCNC1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C;D1;H1:4]):c:c:1.[C;D1;H3:5]-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H1:4]#[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[C:6]-1-[C;D1;H3:5] | null | [] | 85 | CELSIUS | null | null | To a sealed flask was added 2-(R)-methylpyrrolidine L-tartrate (21.1 g, 90 mmol), 3-butynyl p-toluenesulfonate (15.7 mL, 89 mmol), potassium carbonate powder (18.5 g, 134 mmol) and CH3CN (160 mL). The resulting mixture was heated to 85° C. for 24 hours and the reaction was monitored by GC for the complete consumption o... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | TsOH.HO- | CC#N | 85 | null | C#CCCOS(=O)(=O)c1ccc(C)cc1.C[C@@H]1CCCN1>CC#N>C#CCCN1CCC[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e0d8478526940bf83b3ecdefee834a4 | C#CCCN1CCC[C@H]1C.Nc1ccc(Br)cc1I>>C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N | C#CC(C)N1C(CCC1)C.C(CC#C)N1[C@@H](CCC1)C.BrC1=CC(=C(C=C1)N)I.C(C)(C)NC(C)C.BrC1=CC(=C(C=C1)N)I>>BrC1=CC(=C(C=C1)N)C#CCCN1[C@@H](CCC1)C | [CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[CH:10].I[c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18] | C#CCCN1CCC[C@H]1C.Nc1ccc(Br)cc1I | C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N | null | [Cu]I.BrC=1C=CC2=C(N=C(S2)CCO)C1 | null | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)CCN1CCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6] | 97.3 | [{"value": 97.3, "product": "BrC1=CC(=C(C=C1)N)C#CCCN1[C@@H](CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1-butyn-3-yl-2-methyl-pyrrolidine in CH3CN (prepared in Example 65A assuming 100% conversion, 89 mmol) was added 4-bromo-2-iodo-phenylamine (12.0 g, 40 mmol) under nitrogen followed by addition of CuI (0.38 g, 2.0 mmol), PdCl2(PPh3) 2 (0.70 mg, 1.0 mmol) and diisopropylamine (33.6 mL, 240 mmol). The re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1 | HI | [Cu]I.BrC=1C=CC2=C(N=C(S2)CCO)C1 | null | 2 | C#CCCN1CCC[C@H]1C.Nc1ccc(Br)cc1I>[Cu]I.BrC=1C=CC2=C(N=C(S2)CCO)C1>C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20fcc1c0ad4341a8a27727e3d8993f13 | CC1CCCN1CCC#Cc1cc(Br)ccc1N>>C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1 | O([K])C(C)(C)C.BrC1=CC(=C(C=C1)N)C#CCCN1C(CCC1)C>>BrC=1C=C2C=C(NC2=CC1)CCN1[C@@H](CCC1)C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[nH:18]1 | CC1CCCN1CCC#Cc1cc(Br)ccc1N | C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1 | null | null | CN1CCCC1=O | Aromatic Heterocycle Formation | OtherReaction | 3eeece0a35b6fca4def8d3bd74336b0b713b6a44d29870eaf5592e4f702c94e8 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccc2[nH]c(CCN3CCCC3)cc2c1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[nH;D2;+0:8]:1 | 61.2 | [{"value": 61.2, "product": "BrC=1C=C2C=C(NC2=CC1)CCN1[C@@H](CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a cooled (0° C.) suspension of KO-tBu (95%, 7.8 g, 66 mmol) in NMP (150 mL) was added a solution of 4-bromo-2-[4-(2-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine (10 g, 33 mmol) in NMP (50 mL) dropwise keeping the temperature below 5° C. The resulting mixture was then stirred at room temperature for 3 hours under ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | C1CC[NH]C1.c1ccc2[nH]ccc2c1 | null | CN1CCCC1=O | null | 3 | CC1CCCN1CCC#Cc1cc(Br)ccc1N>CN1CCCC1=O>C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6fabe9f122d4790935ad38391ad854e | C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>>C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | BrC=1C=C2C=C(NC2=CC1)CCN1[C@@H](CCC1)C.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+].C(#N)C1=CC=C(C=C1)B(O)O.C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1>>C[C@H]1N(CCC1)CCC=1NC2=CC=C(C=C2C1)C1=CC=C(C#N)C=C1 | Br[c:13]1[cH:12][c:11]2[cH:10][c:9]([CH2:8][CH2:7][N:6]3[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[nH:25][c:24]2[cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:1... | C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1 | C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]c(CCN4CCCC4)cc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 44.9 | [{"value": 44.9, "product": "C[C@H]1N(CCC1)CCC=1NC2=CC=C(C=C2C1)C1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A reaction flask was charged with Cs2CO3 (1.14 g, 3.5 mmol), CsF (0.38 g, 2.5 mmol), 4-cyanophenylboronic acid (425 mg, 2.5 mmol), and H2O (10 mL) followed by a toluene solution (10 mL) of 5-bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-1H-indole (307 mg, 1.0 mmol). The resulting mixture was purged with nitrogen. To... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C | 65 | null | C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C>C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-248bde4b2f92454f832a0d25b1c7fe81 | CI.C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N>>C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2n1C | N1C=CC2=CC=CC=C12.O([K])C(C)(C)C.BrC1=CC(=C(C=C1)N)C#CCCN1[C@@H](CCC1)C.CI>>BrC=1C=C2C=C(N(C2=CC1)C)CCN1[C@@H](CCC1)C | I[CH3:19].[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[n:18]1[CH3:19] | CI.C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N | C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2n1C | null | null | CN1CCCC1=O.O | Aromatic Heterocycle Formation | OtherReaction | 3eeece0a35b6fca4def8d3bd74336b0b713b6a44d29870eaf5592e4f702c94e8 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccc2[nH]c(CCN3CCCC3)cc2c1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[C;H0;D2;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[C:2]-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[n;H0;D3;+0:9]:1-[CH3;D1;+0:1] | 89.8 | [{"value": 89.8, "product": "BrC=1C=C2C=C(N(C2=CC1)C)CCN1[C@@H](CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a cooled (0° C.) suspension of KO-tBu (95%, 6.2 g, 52 mmol) in NMP (120 mL) was added a solution of 4-bromo-2-[4-(2-(R)-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine (8.0 g, 26 mmol) in NMP (50 mL) dropwise keeping the temperature below 5° C. The resulting mixture was then stirred at roan temperature for 3 hours u... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | C1CC[NH]C1.c1ccc2[nH]ccc2c1 | HI | CN1CCCC1=O.O | null | 3 | CI.C[C@@H]1CCCN1CCC#Cc1cc(Br)ccc1N>CN1CCCC1=O.O>C[C@@H]1CCCN1CCc1cc2cc(Br)ccc2n1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e374225418be4187b8abb583b3fe848e | CC1CCCN1CCc1cc2cc(Br)ccc2n1C.N#Cc1ccc(B(O)O)cc1>>C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2n1C | BrC=1C=C2C=C(N(C2=CC1)C)CCN1C(CCC1)C.BrC=1C=C2C=C(N(C2=CC1)C)CCN1C(CCC1)C.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+].C(#N)C1=CC=C(C=C1)B(O)O>>CN1C(=CC2=CC(=CC=C12)C1=CC=C(C#N)C=C1)CCN1[C@@H](CCC1)C | Br[c:13]1[cH:12][c:11]2[cH:10][c:9]([CH2:8][CH2:7][N:6]3[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[n:25]([CH3:26])[c:24]2[cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:... | CC1CCCN1CCc1cc2cc(Br)ccc2n1C.N#Cc1ccc(B(O)O)cc1 | C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2n1C | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]c(CCN4CCCC4)cc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 44.8 | [{"value": 44.8, "product": "CN1C(=CC2=CC(=CC=C12)C1=CC=C(C#N)C=C1)CCN1[C@@H](CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A reaction flask was charged with Cs2CO3 (1.14 g, 3.5 mmol), CsF (0.38 g, 2.5 mmol), 4-cyanophenylboronic acid (425 mg, 2.5 mmol), and H2O (10 mL) followed by a toluene solution (10 mL) of 5-bromo-1-methyl-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-indole (320 mg, 1.0 mmol). The resulting mixture was purged with nitroge... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C | 65 | null | CC1CCCN1CCc1cc2cc(Br)ccc2n1C.N#Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C>C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2n1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fec01abb86294747961ee324773560ef | C=CC(=O)OCC.C[C@@H]1CCCN1>>CCOC(=O)CCN1CCC[C@H]1C | Cl.C[C@H]1NCCC1.C(=O)([O-])[O-].[K+].[K+].C(C=C)(=O)OCC.CCO.C(C=C)(=O)OCC>>C(C)OC(CCN1[C@@H](CCC1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[CH3:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[CH3:13] | C=CC(=O)OCC.C[C@@H]1CCCN1 | CCOC(=O)CCN1CCC[C@H]1C | null | null | CC#N | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 8e7d0268f931cff731a96db8a773eba73ff1401116a985e39d6af747cd29d378 | e6898c28c2a6b7f7f5b5322689c9c6b3b6ad3dd52268b1e45ad4c4843df05f7d | C1CCNC1 | [C;D1;H3:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[NH;D2;+0:6]-1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[C:3]-[C:2]-1-[C;D1;H3:1] | 100.8 | [{"value": 100.8, "product": "C(C)OC(CCN1[C@@H](CCC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In a round-bottom flask, 2-(R)-methylpyrrolidine HCl (5.5 g, 45 mmol) was dissolved in CH3CN (20 mL). To the stirred solution was added milled K2CO3 (8.3 g, 60 mmol). The suspension was stirred at room temperature for approximately 1 h. Ethyl acrylate (3.25 mL, 30 mmol) and EtOH (40 mL) were then added. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ester.Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | null | CC#N | null | 1 | C=CC(=O)OCC.C[C@@H]1CCCN1>CC#N>CCOC(=O)CCN1CCC[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce912197d0244875aab6c2cd6dc5c11e | Nc1ccc(Br)cc1[N+](=O)[O-]>>Nc1ccc(Br)cc1N | BrC1=CC(=C(N)C=C1)[N+](=O)[O-]>>BrC=1C=C(C(=CC1)N)N | O=[N+:1]([O-])[c:2]1[cH:7][c:5]([Br:6])[cH:4][cH:3][c:8]1[NH2:9]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[NH2:9] | Nc1ccc(Br)cc1[N+](=O)[O-] | Nc1ccc(Br)cc1N | null | [Pt] | C1CCOC1 | Functional Group Interconversion | Reduction of nitro groups to amines | 1613b5fba4e86adb9547d5bf6e370cff331bfa463637841d4b06138778df9f24 | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[Br;D1;H0:5]):[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[N;D1;H2:9]>>[Br;D1;H0:5]-[c:4]1:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:2](-[NH2;D1;+0:1]):[c;H0;D3;+0:8](-[N;D1;H2:9]):[cH;D2;+0:3]:1 | 103 | [{"value": 103.0, "product": "BrC=1C=C(C(=CC1)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Bromo-2-nitroaniline (12 g, 55 mmol), 1% Pt/C (1.2 g) and THF (120 mL) were added to a 250 mL bottle. The reaction mixture was hydrogenated at a pressure of approximately 40 psig H2. The hydrogenation reaction mixture was monitored by HPLC until the Area % of 4-bromo-2-nitroaniliine was less than 1%. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Pt].C1CCOC1 | null | null | Nc1ccc(Br)cc1[N+](=O)[O-]>[Pt].C1CCOC1>Nc1ccc(Br)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1314770786e43798d6d10cde0eaf3fd | CCOC(=O)CCN1CCC[C@H]1C.Nc1ccc(Br)cc1N>>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2[nH]1 | C(C)OC(CCN1[C@@H](CCC1)C)=O.BrC=1C=C(C(=CC1)N)N.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>BrC1=CC2=C(NC(=N2)CCN2[C@@H](CCC2)C)C=C1 | CCO[C:9](=O)[CH2:8][CH2:7][N:6]1[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5]1.[NH2:10][c:11]1[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]1[NH2:18]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[nH:18]1 | CCOC(=O)CCN1CCC[C@H]1C.Nc1ccc(Br)cc1N | C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2[nH]1 | null | null | CS(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | ae3a8ae41c7227b9865ca45cfe5b63d35f484ee7158a1d37f47008675ec00c1e | 36efa24579e0043fdba8918e78f1d75cb4504837c08d344d01203f5fa64bfaef | c1ccc2[nH]c(CCN3CCCC3)nc2c1 | C-C-O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[nH;D2;+0:8]:1 | 40 | [{"value": 40.0, "product": "BrC1=CC2=C(NC(=N2)CCN2[C@@H](CCC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | In a round-bottom flask was charged 3-(2-(R)-methyl-pyrrolidin-1-yl)-propionic acid ethyl ester (5.6 g, 30 mmol), 4-bromo-benzene-1,2-diamine (5.6 g, 30 mmol) and 56 mL of 5% P2O5 in CH3SO3H (Eaton's reagent). After briefly stirring, the homogeneous solution was heated to 110° C. for approximately 24–48 h. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | C1CC[NH]C1.c1ccc2[nH]cnc2c1 | HO- | CS(=O)(=O)O | 110 | null | CCOC(=O)CCN1CCC[C@H]1C.Nc1ccc(Br)cc1N>CS(=O)(=O)O>C[C@@H]1CCCN1CCc1nc2cc(Br)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14f696dcbf5a4434a0b46e260bb5ebf6 | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>>C[C@@H]1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC2=C(NC(=N2)CCN2C(CCC2)C)C=C1.C(#N)C1=CC=C(C=C1)B(O)O>>C[C@H]1N(CCC1)CCC1=NC2=C(N1)C=CC(=C2)C2=CC=C(C#N)C=C2 | Br[c:13]1[cH:12][c:11]2[n:10][c:9]([CH2:8][CH2:7][N:6]3[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[nH:25][c:24]2[cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]1[n:10][c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])... | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1 | C[C@@H]1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C(Cl)Cl | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 4c01b75ced48e0c5dbfbda4cb6a596e9d3a1d181f4aef3fbd9604232ef2322c4 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]c(CCN4CCCC4)nc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1):[c:13]:[c:14] | 40.4 | [{"value": 40.4, "product": "C[C@H]1N(CCC1)CCC1=NC2=C(N1)C=CC(=C2)C2=CC=C(C#N)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 24 | HOUR | Nitrogen (N2) gas was bubbled through a solution of 5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazole (0.19 g, 0.6 mmol) and 4-cyanophenylboronic acid (0.13 g, 0.9 mmol) in 1,2-dimethoxyethane (4 mL) and H2O (2 mL). To the mixture was added 2M Na2CO3 (1.2 mL, 2.4 mmol) and Pd(dppf)2Cl2:CH2Cl2 (1:1), and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]cnc2c1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O.COCCOC | 80 | 24 | CC1CCCN1CCc1nc2cc(Br)ccc2[nH]1.N#Cc1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O.COCCOC>C[C@@H]1CCCN1CCc1nc2cc(-c3ccc(C#N)cc3)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d12afd9173344f0ea591ca507c1e1ff0 | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1>>CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 | C(C)(=O)OC(C)(C)C.N1[C@@H](CCC1=O)C(=O)O.Cl(=O)(=O)(=O)O.[OH-].[Na+]>>O=C1CC[C@H](N1)C(=O)OC(C)(C)C | CC(=O)[O:5][C:2]([CH3:1])([CH3:3])[CH3:4].O[C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[NH:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[NH:13]1 | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 | null | null | O | Acylation | OtherReaction | 5eda8161d36467b4dc537f76ab93cf348d82102ac40d865b5fccff23d019462d | 03baa9d39762bbc48d7dd927c5c80fc17976a560c4f5aa44c95e8b810d3c70c8 | O=C1CCCN1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[C:9])-[#7:10]-[C:11]=[O;D1;H0:12]>>[C:9]-[C:8](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5])-[#7:10]-[C:11]=[O;D1;H0:12] | null | [] | null | null | 12 | HOUR | 129 g of L-pyroglutamic acid were suspended in 2 l of tert-butyl acetate. 30 ml of a 70% strength solution of perchloric acid in water were added thereto. The mixture was then stirred at room temperature for 12 h. It was cooled to 0° C. and the pH of the solution was adjusted to 7 by cautious addition of a 2N NaOH solu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester | null | null | C1CCNC1 | HO- | O | null | 12 | CC(=O)OC(C)(C)C.O=C1CC[C@@H](C(=O)O)N1>O>CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36ba26068fa844f5b119a23fefe3f5e6 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@@H]1CCC(O)N1C(=O)OC(C)(C)C | C([O-])(O)=O.[Na+].C(C)[BH-](CC)CC.[Li+].O=C1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.OO>>OC1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[N:13]1[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][CH:11]([OH:12])[N:13]1[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20] | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@@H]1CCC(O)N1C(=O)OC(C)(C)C | null | null | C1CCOC1 | Reduction | OtherReaction | 7a66ad41b54bb485918a759dc010bded0c65a7503d10eee13c33ae0017305eee | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | C1CCNC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[#7:9]-1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-[CH;D3;+0:7](-[OH;D1;+0:8])-[#7:9]-1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C... | null | [] | -78 | CELSIUS | 30 | MINUTE | 93 g of di-tert-butyl (S)-5-oxopyrrolidine-1,2-dicarboxylate were dissolved in 600 ml of THF and cooled to −78° C. 392 ml of a 1N solution of lithium triethylborohydride in THF were added dropwise over the course of 90 min. The mixture was then stirred at −70° C. for 30 min. Subsequently, 240 ml of saturated sodium bic... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1 | null | C1CCOC1 | -78 | 0.5 | CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1C(=O)OC(C)(C)C>C1CCOC1>CC(C)(C)OC(=O)[C@@H]1CCC(O)N1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ee3358ec00f4d3a99109190e3ee13ea | CCOC(=O)C[C@@H]1CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CCO)N1C(=O)OC(C)(C)C | C([O-])(O)=O.[K+].C(C)OC(=O)C[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.[BH4-].[Li+]>>OCC[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CCO[C:13]([CH2:12][C@@H:11]1[CH2:10][CH2:9][C@@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C@@H:11]([CH2:12][CH2:13][OH:14])[N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:2... | CCOC(=O)C[C@@H]1CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CCO)N1C(=O)OC(C)(C)C | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 6 | HOUR | 43 g of the product from 1d were dissolved in 300 ml of diethyl ether. A solution of 3.1 g of lithium borohydride in 300 ml of diethyl ether was added dropwise thereto. The mixture was stirred for 6 h and the reaction was stopped by cautious addition of 300 ml of a saturated potassium bicarbonate solution. The phases w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1 | HO- | C(C)OCC | null | 6 | CCOC(=O)C[C@@H]1CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)OC(C)(C)C>C(C)OCC>CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CCO)N1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eec8fdcdd0e0440fb1b9c9b1ae69362f | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(C#N)NCc2ccccc2)N1C(=O)OC(C)(C)C.OO>>CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C | C(C1=CC=CC=C1)NC(C[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C#N.C([O-])([O-])=O.[K+].[K+].OO>>C(C1=CC=CC=C1)NC(C[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C@@H:11]([CH2:12][CH:13]([NH:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[C:22]#[N:23])[N:25]1[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].O[OH:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][C@@... | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(C#N)NCc2ccccc2)N1C(=O)OC(C)(C)C.OO | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | c1ccc(CNCC[C@@H]2CCCN2)cc1 | O-[OH;D1;+0:1].[#7:2]-[C:3](-[C:4])-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[#7:2]-[C:3](-[C:4])-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;H0;D1;+0:1] | null | [] | null | null | 14 | HOUR | 2.6 g of di-tert-butyl (2S,5S)-5-(2-benzylamino-2-cyanoethyl)pyrrolidine-1,2-dicarboxylate were dissolved in 6.5 ml of dimethyl sulfoxide. 373 mg of finely ground potassium carbonate and 1.08 ml of a 30% strength hydrogen peroxide solution were added thereto. The mixture was stirred at room temperature for 14 h and was... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | C1CC[NH]C1.c1ccccc1 | Other | CS(=O)C.O | null | 14 | CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(C#N)NCc2ccccc2)N1C(=O)OC(C)(C)C.OO>CS(=O)C.O>CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e2f54db65abf48f99044f31ef5758d3e | CC(=O)O.CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O | C(C)(=O)O.[OH-].[Na+].C(C1=CC=CC=C1)NC(C[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(N)=O>>C(C)(C)(C)OC(=O)N1[C@@H](CC[C@H]1CC(C(=O)O)NCC1=CC=CC=C1)C(=O)O | CC(=O)[OH:22].CC(C)(C)[O:28][C:26]([C@H:25]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:9]([CH2:10][CH:11]([NH:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:20](N)=[O:21])[CH2:23][CH2:24]1)=[O:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]([CH2:10][CH:11]([NH:12][CH2:13][... | CC(=O)O.CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O | null | null | O.C(C)O | Acylation | OtherReaction | c189ddade6f073abd1f049c2ff7589d7ef3c92298598276005c6db1a5bca9bfe | 921dee6249f084a5afe68b361e3119014cbca8bae41456f33247d587f86f399e | c1ccc(CNCC[C@@H]2CCCN2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5].N-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[#7:9])-[C:10].C-C(=O)-[OH;D1;+0:11]>>[#7:9]-[C:8](-[C:10])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[OH;D1;+0:11].[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | 2.2 g of di-tert-butyl (2S,5S)-5-(2-benzylamino-2-carbamoylethyl)pyrrolidine-1,2-dicarboxylate were dissolved in 20 ml of ethanol and 5 ml of water. 1.2 g of solid sodium hydroxide were added thereto. The solution was then boiled under reflux for 36 h. For workup, it was cooled to room temperature and neutralized with ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amide.Boc | Carboxylic acid.Carboxylic acid | null | null | C1CC[NH]C1.c1ccccc1 | HO- | O.C(C)O | null | null | CC(=O)O.CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CC(NCc2ccccc2)C(N)=O)N1C(=O)OC(C)(C)C>O.C(C)O>CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0671b17e79594082bfe04925787d737d | CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O>>CC(=O)O.CC(C)(C)OC(=O)N1[C@H](CC(N)C(=O)O)CC[C@H]1C(=O)O | C(C)(C)(C)OC(=O)N1[C@@H](CC[C@H]1CC(C(=O)O)NCC1=CC=CC=C1)C(=O)O.[H][H]>>C(C)(=O)O.C(C)(C)(C)OC(=O)N1[C@@H](CC[C@H]1CC(C(=O)O)N)C(=O)O | c1cc(C[NH:16][CH:15]([CH2:14][C@H:13]2[N:12]([C:10]([O:9][C:6]([CH3:5])([CH3:7])[CH3:8])=[O:11])[C@H:22]([C:23](=[O:24])[OH:25])[CH2:21][CH2:20]2)[C:17](=[O:3])[OH:19])[cH:2][cH:1]c1>>[CH3:1][C:2](=[O:3])[OH:4].[CH3:5][C:6]([CH3:7])([CH3:8])[O:9][C:10](=[O:11])[N:12]1[C@H:13]([CH2:14][CH:15]([NH2:16])[C:17](=[O:18])[OH... | CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O | CC(=O)O.CC(C)(C)OC(=O)N1[C@H](CC(N)C(=O)O)CC[C@H]1C(=O)O | null | [OH-].[OH-].[Pd+2] | C(C)(=O)O | Functional Group Addition | OtherReaction | 7c943473f923398f2f254efe37c2a78ee586499f5f8405c367aad51e852a90f9 | e966341af73f102bbef49d8ca706ff70a257f9f835ed69f2c7c4cc33532963a2 | C1CCNC1 | [C:1]-[C:2](-[NH;D2;+0:3]-C-c1:[cH;D2;+0:4]:[cH;D2;+0:5]:c:c:c:1)-[C;H0;D3;+0:6](-[O;D1;H1:7])=[O;H0;D1;+0:8]>>[CH3;D1;+0:5]-[C;H0;D3;+0:4](-[O;D1;H1:9])=[O;H0;D1;+0:8].[C:1]-[C:2](-[NH2;D1;+0:3])-[C;H0;D3;+0:6](=[O;D1;H0:10])-[O;D1;H1:7] | null | [] | null | null | 10 | MINUTE | 1600 mg of (2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester were dissolved in 30 ml of acetic acid. 100 mg of 20% palladium hydroxide on activated carbon were added thereto, and the mixture was hydrogenated under an atmosphere of 1 bar of hydrogen for 1 h. Ar was then passed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Carboxylic acid.Carboxylic acid.Primary amine | c1ccccc1 | null | C1CC[NH]C1 | Other | [OH-].[OH-].[Pd+2].C(C)(=O)O | null | 0.166667 | CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O>[OH-].[OH-].[Pd+2].C(C)(=O)O>CC(=O)O.CC(C)(C)OC(=O)N1[C@H](CC(N)C(=O)O)CC[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb72a94ce0d34f9d96a25ac130802067 | COC(=O)C(C[C@@H]1CC[C@@H](C(=O)OC)N1C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1>>COC(=O)[C@@H]1CC[C@H]2CC(NC(=O)OCc3ccccc3)C(=O)N21 | C(C1=CC=CC=C1)OC(=O)NC(C[C@@H]1CC[C@H](N1C(=O)OC(C)(C)C)C(=O)OC)C(=O)OC.C1(=CC=CC=C1)SC>>C(C1=CC=CC=C1)OC(=O)NC1C(N2[C@@H](CC[C@H]2C1)C(=O)OC)=O | CO[C:22]([CH:10]([CH2:9][C@@H:8]1[CH2:7][CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[N:24]1C(=O)OC(C)(C)C)[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[O:23]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][C@H:8]2[CH2:9][CH:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]3[cH:17][cH:18... | COC(=O)C(C[C@@H]1CC[C@@H](C(=O)OC)N1C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1 | COC(=O)[C@@H]1CC[C@H]2CC(NC(=O)OCc3ccccc3)C(=O)N21 | null | null | FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | 4418e988074acea71dd24ac14a7ea7a4f3d5446e60376f467c44f429251f5664 | 68b3dbac8e61dda6bb0cc2ed5a0f03fe36b9f9015e9dcb1e6046c632f9edd41f | O=C(NC1C[C@@H]2CCCN2C1=O)OCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7]-[C:8]1-[C:9]-[C:10]-[C:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15])-[N;H0;D3;+0:16]-1-C(=O)-O-C(-C)(-C)-C>>[C;D1;H3:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[C:11]1-[C:10]-[C:9]-[C:8]2-[C:7]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | null | [] | 95 | CELSIUS | 45 | MINUTE | 1500 mg of 1-tert-butyl 2-methyl (2S,5S)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate were mixed with 0.2 ml of thioanisole. Then 10 ml of trifluoroacetic acid were added, and the mixture was stirred for 45 min. The solvents were then removed in vacuo, and the residue was taken up in... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Tertiary amide | C1CC[NH]C1 | C1CC2CCCN2C1 | C1CC2CCCN2C1.c1ccccc1 | HO- | FC(C(=O)O)(F)F | 95 | 0.75 | COC(=O)C(C[C@@H]1CC[C@@H](C(=O)OC)N1C(=O)OC(C)(C)C)NC(=O)OCc1ccccc1>FC(C(=O)O)(F)F>COC(=O)[C@@H]1CC[C@H]2CC(NC(=O)OCc3ccccc3)C(=O)N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93eff2bf0daa450c897e724582f37625 | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C(N)=O)N2C1=O>>CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O | C(N)(=O)[C@H]1N2C([C@@H](C[C@@H]2CC1)NC(OC(C)(C)C)=O)=O.N1=C(Cl)N=C(Cl)N=C1Cl>>C(#N)[C@H]1N2C([C@@H](C[C@@H]2CC1)NC(OC(C)(C)C)=O)=O | O=[C:15]([C@@H:14]1[CH2:13][CH2:12][C@H:11]2[CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:18](=[O:19])[N:17]21)[NH2:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][C@@H:11]2[CH2:12][CH2:13][C@@H:14]([C:15]#[N:16])[N:17]2[C:18]1=[O:19] | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C(N)=O)N2C1=O | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=C1CC[C@@H]2CCCN12 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3](-[C:4])-[#7:5](-[C:6])-[C:7]=[O;D1;H0:8]>>[C:6]-[#7:5](-[C:7]=[O;D1;H0:8])-[C:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2])-[C:4] | null | [] | null | null | 3 | HOUR | 100 mg of tert-butyl ((2R,5S,7aS)-5-carbamoyl-3-oxohexahydropyrrolizin-2-yl)carbamate were dissolved in 2 ml of dimethylformamide, and 65 mg of cyanuric chloride were added. The mixture was stirred for 3 h, and the dimethylformamide was removed in vacuo. The residue was chromatographed on silica gel.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | C1CC2CCCN2C1 | HO- | CN(C=O)C | null | 3 | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C(N)=O)N2C1=O>CN(C=O)C>CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-300496268f1a4ca7a2622d242dab1799 | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O>>N#C[C@@H]1CC[C@H]2C[C@@H](N)C(=O)N21 | C(#N)[C@H]1N2C([C@@H](C[C@@H]2CC1)NC(OC(C)(C)C)=O)=O.C1(=CC=CC=C1)SC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.N[C@H]1C(N2[C@@H](CC[C@H]2C1)C#N)=O | CC(C)(C)OC(=O)[NH:9][C@@H:8]1[CH2:7][C@@H:6]2[CH2:5][CH2:4][C@@H:3]([C:2]#[N:1])[N:12]2[C:10]1=[O:11]>>[N:1]#[C:2][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:7][C@@H:8]([NH2:9])[C:10](=[O:11])[N:12]12 | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O | N#C[C@@H]1CC[C@H]2C[C@@H](N)C(=O)N21 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CC[C@@H]2CCCN12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7]-1=[O;D1;H0:8]>>[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:7]-1=[O;D1;H0:8] | null | [] | null | null | null | null | 80 mg of tert-butyl ((2R,5S,7aS)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate were C reacted with 10% thioanisole in 1 ml of trifluoroacetic acid for 30 min. The solvents were then removed in vacuo, and the residue was stirred with diusopropyl ether.
Conditions: See reaction.notes.procedure_details.
Workup: The solv... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC2CCCN2C1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O>>N#C[C@@H]1CC[C@H]2C[C@@H](N)C(=O)N21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9095f644eb14828b9bed161b97caec1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NCCN1CCCCC1)n1ccnc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCCCC4)nc32)[C@H](O)[C@@H]1O | NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.N1(CCCCC1)CCNC(=O)N1C=NC=C1.C1(=CC=CC=C1)C.C(C)(C)O.N1(CCCCC1)CCNC(=O)N1C=NC=C1>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCCN1CCCCC1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][c:30]([C:31](=[O:32])[NH:33][CH2:34][CH2:35][NH2:36])[n:48][c:49]23)[C@H:50]([OH:51])[C@@H:52]1[OH:53].c1cn([C:37]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NCCN1CCCCC1)n1ccnc1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCCCC4)nc32)[C@H](O)[C@@H]1O | null | null | ClCCl | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NCCN1CCCCC1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | 54.9 | [{"value": 54.9, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCCN1CCCCC1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | N-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S, 5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 10) (90 mg, 0.15 mmol) and N-[2-(1-piperidinyl)ethyl]-1H-imidazole-1-carboxamide (Preparation 18) (36 mg, 0.16 mmol) were dissolved in dichloromethane (3 ml). ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1 | Other | ClCCl | null | 4 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NCCN1CCCCC1)n1ccnc1>ClCCl>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCCCC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69c7055820c24dc2be3109de07647118 | CC(C)C1CCN(CCNC(=O)n2ccnc2)CC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCC(C(C)C)CC4)nc32)[C@H](O)[C@@H]1O | NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)C1CCN(CC1)CCNC(=O)N1C=NC=C1>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCCN1CCC(CC1)C(C)C)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | c1cn([C:37](=[O:38])[NH:39][CH2:40][CH2:41][N:42]2[CH2:43][CH2:44][CH:45]([CH:46]([CH3:47])[CH3:48])[CH2:49][CH2:50]2)cn1.[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4... | CC(C)C1CCN(CCNC(=O)n2ccnc2)CC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCC(C(C)C)CC4)nc32)[C@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NCCN1CCCCC1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | null | [] | null | null | null | null | Prepared from N-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 10) and N-[2-(4-isopropyl-1-piperidinyl)ethyl]-1H-imidazole-1-carboxamide (Preparation 22) by a similar method to Example 1.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1 | Other | null | null | null | CC(C)C1CCN(CCNC(=O)n2ccnc2)CC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN4CCC(C(C)C)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59ce50b918274a759994faec492ad9c0 | CC(C)N(CCNC(=O)n1ccnc1)C1CCCC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN(C(C)C)C4CCCC4)nc32)[C@H](O)[C@@H]1O | NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.C1(CCCC1)N(CCNC(=O)N1C=NC=C1)C(C)C>>C1(CCCC1)N(CCNC(=O)NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C | c1cn([C:37](=[O:38])[NH:39][CH2:40][CH2:41][N:42]([CH:43]([CH3:44])[CH3:45])[CH:46]2[CH2:47][CH2:48][CH2:49][CH2:50]2)cn1.[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4... | CC(C)N(CCNC(=O)n1ccnc1)C1CCCC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN(C(C)C)C4CCCC4)nc32)[C@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NCCNC1CCCC1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | null | [] | null | null | null | null | Prepared from N-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 10) and N-{2-[cyclopentyl(isopropyl)amino]ethyl}-1H-imidazole-1-carboxamide (Preparation 26) by a similar method to Example 1.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CCCC1 | Other | null | null | null | CC(C)N(CCNC(=O)n1ccnc1)C1CCCC1.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCCN(C(C)C)C4CCCC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e37cd6d45bd145b4bd9f02d588d506a7 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCN(c2ccccn2)CC1)n1ccnc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O | NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.N1=C(C=CC=C1)N1CCC(CC1)NC(=O)N1C=NC=C1>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NC1CCN(CC1)C1=NC=CC=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][c:30]([C:31](=[O:32])[NH:33][CH2:34][CH2:35][NH2:36])[n:52][c:53]23)[C@H:54]([OH:55])[C@@H:56]1[OH:57].c1cn([C:37]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCN(c2ccccn2)CC1)n1ccnc1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NC1CCN(c2ccccn2)CC1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | null | [] | null | null | null | null | Prepared from N-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 10) and N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide (Preparation 30) by a similar method to Example 1.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1.c1ccncc1 | Other | null | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCN(c2ccccn2)CC1)n1ccnc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fde1ea0769641d099aecaf4a6f8b926 | CC(C)N(CCNC(=O)NCCN)C(C)C.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(C(=O)NCCNC(=O)NCCN(C(C)C)C(C)C)nc32)[C@H](O)[C@@H]1O | C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC(=CC=C1)C)C1=CC(=CC=C1)C)I.NCCNC(=O)NCCN(C(C)C)C(C)C.C1CCOC1>>CC=1C=C(C=CC1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCCN(C(C)C)C(C)C)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC(=CC=C1)C | [NH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:40])[NH:41][CH2:42][CH2:43][N:44]([CH:45]([CH3:46])[CH3:47])[CH:48]([CH3:49])[CH3:50].O=C(c1ccccc1)[O:56][C@@H:55]1[C@@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][c:21]([CH3:22])[cH:23... | CC(C)N(CCNC(=O)NCCN)C(C)C.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(C(=O)NCCNC(=O)NCCN(C(C)C)C(C)C)nc32)[C@H](O)[C@@H]1O | 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 | null | Acylation | OtherReaction | 2ae826299acf86d14128c62181c55ea7931ee4517720883c75fc6ce1f929a22c | c9ac21fd27fbb51e10283d4cb3296223e3218179c867ce8e9d01fd6be8878238 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]3-[#8:9]-[C:10](-[C:11](-[#7:12])=[O;D1;H0:13])-[C:14](-[O;H0;D2;+0:15]-C(=O)-c4:c:c:c:c:c:4)-[C:16]-3-[O;H0;D2;+0:17]-[C;H0;D3;+0:18](=[O;D1;H0:19])-c3:c:c:c:c:c:3):[c:20]:2:[#7;a:21]:1.[C:22]-[C:23]-[NH2;D1;+0:24]>>[#7:12]-[C:11](=[O;D1;H0:13])-[C:... | null | [] | null | null | 14 | HOUR | A solution of (2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-{[2,2-bis(3-methylphenyl)ethyl]amino}-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (Preparation 48) (200 mg, 0.24 mmol), N-(2-aminoethyl)-N′-[2-(diisopropylamino)ethyl]urea (Preparation 52) (270 mg, 1.18 mmol) and tetrakis(triphenylphosphine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary amide.Secondary alcohol.Secondary alcohol | c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HI | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | 14 | CC(C)N(CCNC(=O)NCCN)C(C)C.CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1>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>CCNC(=O)[C@H... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3667a2bae3747a0957314fe0b87f185 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)O)cc4)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCC1=CC=C(C(=O)OCC2=CC=CC=C2)C=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCC1=CC=C(C(=O)O)C=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | c1ccc(C[O:47][C:45]([c:44]2[cH:43][cH:42][c:41]([CH2:40][NH:39][C:37]([NH:36][CH2:35][CH2:34][NH:33][C:31]([c:30]3[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:12]4[n:11][cH:10][n:9]([C@@H:8]5[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)O)cc4)nc32)[C@H](O)[C@@H]1O | null | [Pd] | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NCc1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 19.2 | [{"value": 19.2, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCC1=CC=C(C(=O)O)C=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzyl 4-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purin-2-yl)carbonyl]amino}ethyl)amino]carbonyl}amino)methyl]benzoate (Preparation 55) (150 mg, 0.18 mmol) in ethanol (10 ml) was hydrogenated at room temperature over 10% w/w pal... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O>[Pd].C(C)O>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)O)cc4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4737901165ba46a4813fc2f285affa0e | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@@H]2OC(C)(C)O[C@@H]21>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O | C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)NCCNC(=O)NC2CCN(CC2)C2=NC=CC=C2.Cl.C([O-])(O)=O.[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NC1CCN(CC1)C1=NC=CC=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | CC1(C)[O:55][C@H:54]2[C@H:8]([n:9]3[cH:10][n:11][c:12]4[c:13]([NH:14][CH2:15][CH:16]([c:17]5[cH:18][cH:19][cH:20][cH:21][cH:22]5)[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[n:29][c:30]([C:31](=[O:32])[NH:33][CH2:34][CH2:35][NH:36][C:37](=[O:38])[NH:39][CH:40]5[CH2:41][CH2:42][N:43]([c:44]6[cH:45][cH:46][cH:47][cH:48][... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O | null | null | C(C)O | Deprotection | Acetal hydrolysis to diol | cd7d99316c4d16a7c810595d0c5705cc11ed3a94563ee4b1b511c64a517d01aa | 3cb0396ca8ad36859ee8d51a67a558871ec1b96bb69d5cbac40dafd7041336b3 | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NC1CCN(c2ccccn2)CC1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2]2-[C:3]-[#8:4]-[C:5](-[C:6](-[#7:7])=[O;D1;H0:8])-[C:9]-2-[O;H0;D2;+0:10]-1>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[#8:4]-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-1-[OH;D1;+0:10] | null | [] | null | null | null | null | To a solution of 9-{(3aR,4R,6S,6aS)-6-[(ethylamino)carbonyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-[(2,2-diphenylethyl)amino]-N-{2-[({[1-(2-pyridinyl)-4-piperidinyl]amino}carbonyl)amino]ethyl}-9H-purine-2-carboxamide (Preparation 71) (20.9 g, 0.0255 moles) in absolute ethanol (200 ml) was added aqueous h... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol.Secondary alcohol | C1O[C@H]2COC[C@H]2O1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1.c1ccncc1 | Other | C(C)O | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@@H]2OC(C)(C)O[C@@H]21>C(C)O>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NC4CCN(c5ccccn5)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69e4a8157db7424a83d31d8e7356ee4a | C1=COCCC1.Clc1nc(Cl)c2nc[nH]c2n1>>Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1 | O1CCCC=C1.ClC1=NC(=C2N=CNC2=N1)Cl.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(O)([O-])=O.[Na+]>>ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)Cl | [CH:10]1=[CH:11][CH2:12][CH2:13][CH2:14][O:15]1.[Cl:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][nH:9][c:16]2[n:17]1>>[Cl:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[c:16]2[n:17]1 | C1=COCCC1.Clc1nc(Cl)c2nc[nH]c2n1 | Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 833f861fd536c4e2067fdcc1a93d2a1e46416364a06b97cd425c149f7dc60f6d | c37c4c64b8e0c6e5b39694c16f8c97245b55f05530ce8b5df4dfb3a695b50244 | c1ncc2ncn(C3CCCCO3)c2n1 | [#7;a:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1:2.[#8:10]1-[C:11]-[C:12]-[C:13]-[CH;D2;+0:14]=[CH;D2;+0:15]-1>>[#7;a:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[n;H0;D3;+0:8](-[CH;D3;+0:15]3-[#8:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-3):[c:9]:1:2 | null | [] | 50 | CELSIUS | null | null | 2,6-Dichloro-9H-purine (20 g, 0.11 mol) and 4-toluenesulphonic acid monohydrate (0.2 g) were dissolved in ethyl acetate (300 ml), the mixture heated to 50° C. and a solution of 3,4-dihydro-2H-pyran (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) added slowly over 30 minutes. The reaction mixture was cooled to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | C1=COCCC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCOCC1 | c1ncc2[nH]cnc2n1.C1CCOCC1 | null | O.C(C)(=O)OCC | 50 | null | C1=COCCC1.Clc1nc(Cl)c2nc[nH]c2n1>O.C(C)(=O)OCC>Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-403b96eddfb546f98e642649c39d1ee0 | Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1.NCC(c1ccccc1)c1ccccc1>>Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)Cl.C(C)N(C(C)C)C(C)C.C1(=CC=CC=C1)C(CN)C1=CC=CC=C1>>ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | Cl[c:4]1[n:3][c:2]([Cl:1])[n:31][c:30]2[c:20]1[n:21][cH:22][n:23]2[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:29]1.[NH2:5][CH2:6][CH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[Cl:1][c:2]1[n:3][c:4]([NH:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15... | Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1.NCC(c1ccccc1)c1ccccc1 | Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 21d996e324b0e5b6b8600e4cdecb831b9110303de341c2f644de0b809c0bfe6c | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C(CNc2ncnc3c2ncn3C2CCCCO2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C:7]-[#8:8]):[c:9]:[#7;a:10]:[c:11]:2:1.[C:12]-[C:13]-[NH2;D1;+0:14]>>[#8:8]-[C:7]-[#7;a:6]1:[c:9]:[#7;a:10]:[c:11]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH;D2;+0:14]-[C:13]-[C:12] | 104.1 | [{"value": 104.1, "product": "ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (Preparation 1) (30.9 g, 0.11 mol) in isopropyl alcohol (600 ml) was treated with N-ethyl-N-isopropyl-2-propanamine (47.5 ml, 0.27 mol) and 2,2-diphenylethylamine (24.8 g, 0.13 mol) and the resulting mixture heated under reflux for 3 hours. The solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOCC1 | HCl | C(C)(C)O | null | null | Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1.NCC(c1ccccc1)c1ccccc1>C(C)(C)O>Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0158caa0433b4a16981a9e69a7155cdb | C[S-].Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>>CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)NCC(C1=CC=CC=C1)C1=CC=CC=C1.C[S-].[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)SC)C1OCCCC1)C1=CC=CC=C1 | [CH3:1][S-:2].Cl[c:3]1[n:4][c:5]([NH:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[n:22][cH:23][n:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:30]3)[c:31]2[n:32]1>>[CH3:1][S:2][c:3]1[n:4][c:5]([NH:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14... | C[S-].Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | fbee7aea651b2476398ef29f4a72310bd225798f2ee7291e155ba0ec2c32e612 | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccc(C(CNc2ncnc3c2ncn3C2CCCCO2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]-[#8:6]):[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[#7;a:11]:1.[C;D1;H3:12]-[S-;H0;D1:13]>>[#8:6]-[C:5]-[#7;a:4]1:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[c;H0;D3;+0:1](-[S;H0;D2;+0:13]-[C;D1;H3:12]):[#7;a:2]:[c:3]:1:2 | 99.8 | [{"value": 99.8, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)SC)C1OCCCC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 72 | HOUR | A solution of 2-chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (Preparation 2) (49.7 g, 0.11 mol) in dry N,N-dimethylformamide (200 ml) was treated with sodium thiomethoxide (10 g, 0.14 mol) and the resulting mixture heated under an atmosphere of nitrogen at 100° C. for 90 minutes. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOCC1 | Other | O.CN(C=O)C | 100 | 72 | C[S-].Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>O.CN(C=O)C>CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6bbeb5096df4e269e3f46d31c8cd773 | CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>>CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | OOS(=O)[O-].[K+].C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)SC)C1OCCCC1)C1=CC=CC=C1.C(O)([O-])=O.[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)S(=O)(=O)C)C1OCCCC1)C1=CC=CC=C1 | [CH3:1][S:2][c:5]1[n:6][c:7]([NH:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[n:24][cH:25][n:26]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][O:32]3)[c:33]2[n:34]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][c:7]([NH:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:... | CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | null | null | CC(=O)C.O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(C(CNc2ncnc3c2ncn3C2CCCCO2)c2ccccc2)cc1 | [#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5](-[S;H0;D2;+0:6]-[C;D1;H3:7]):[#7;a:8]:[c:9]:1:[#7;a:10]>>[#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5](-[S;H0;D4;+0:6](-[C;D1;H3:7])(=[O;D1;H0:11])=[O;D1;H0:12]):[#7;a:8]:[c:9]:1:[#7;a:10] | 75.7 | [{"value": 75.7, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)S(=O)(=O)C)C1OCCCC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of Oxone (trade mark) (potassium peroxymonosulphate) (44 g, 71.7 mmol) in water (200 ml) was added dropwise over 2 hours to a solution of N-(2,2-diphenylethyl)-2-(methylsulfanyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (Preparation 3) (25 g, 56.2 mmol) and sodium hydrogencarbonate (20 g, 238 mmol) in a... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOCC1 | null | CC(=O)C.O | null | null | CSc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>CC(=O)C.O>CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-addae1f9dc0349babc93745e3317e149 | CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1.[C-]#N>>N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | O.C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)S(=O)(=O)C)C1OCCCC1)C1=CC=CC=C1.[C-]#N.[K+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C#N)C1OCCCC1)C1=CC=CC=C1 | CS(=O)(=O)[c:3]1[n:4][c:5]([NH:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[n:22][cH:23][n:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:30]3)[c:31]2[n:32]1.[N:1]#[C-:2]>>[N:1]#[C:2][c:3]1[n:4][c:5]([NH:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13]... | CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1.[C-]#N | N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | b7fae133b98238b2705ae50727cb2f9c40d3e25beef0a49c62600e3dc76cb6ce | afc317b75dc27dd96f8b185a6d88494042f714247ebd3d6ce3b0e647608c4473 | c1ccc(C(CNc2ncnc3c2ncn3C2CCCCO2)c2ccccc2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]-[#8:6]):[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[#7;a:11]:1.[C-;H0;D1:12]#[N;D1;H0:13]>>[#8:6]-[C:5]-[#7;a:4]1:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[c;H0;D3;+0:1](-[C;H0;D2;+0:12]#[N;D1;H0:13]):[#7;a:2]:[c:3]:1:2 | 95.1 | [{"value": 95.1, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C#N)C1OCCCC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1 | HOUR | A solution of N-(2,2-diphenylethyl)-2-(methylsulfonyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (Preparation 4) (20.1 g, 42.1 mmol) in dry N,N-dimethylformamide (100 ml) was treated with potassium cyanide (5.5 g, 84.6 mmol) and the mixture heated at 120° C. for 24 hours under a nitrogen atmosphere. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Nitrile | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOCC1 | HO- | CN(C=O)C | 120 | 1 | CS(=O)(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1.[C-]#N>CN(C=O)C>N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a14d829b1b0f421cb9bd657ac37d643a | N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>>N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C#N)C1OCCCC1)C1=CC=CC=C1.Cl>>C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C#N)C1=CC=CC=C1 | C1CCC([n:24]2[cH:23][n:22][c:21]3[c:5]([NH:6][CH2:7][CH:8]([c:9]4[cH:10][cH:11][cH:12][cH:13][cH:14]4)[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[n:4][c:3]([C:2]#[N:1])[n:26][c:25]32)OC1>>[N:1]#[C:2][c:3]1[n:4][c:5]([NH:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:2... | N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | null | null | C(C)O | Reduction | OtherReaction | 5884540ddb12ce381424fd4d8168e9c573ef97adf4e044c59506f6d05225a030 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1ccc(C(CNc2ncnc3[nH]cnc23)c2ccccc2)cc1 | C1-C-C-C(-[n;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]3:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:3:2)-O-C-1>>[#7;a:3]1:[c:2]:[nH;D2;+0:1]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:[c:4]:1:2 | 99.6 | [{"value": 99.6, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C#N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile (Preparation 5) (17 g, 40.1 mmol) in ethanol (850 ml) was treated with 2 N aqueous hydrochloric acid (50 ml) and the mixture stirred at room temperature for 24 hours. The solvent was removed under reduced pressure, the resi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1CCOCC1.c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | C(C)O | null | 24 | N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>C(C)O>N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6821d444ab2d43739c33dfc175b37f8f | CO.CO.N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | C[O-].[Na+].CO.C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C#N)C1=CC=CC=C1.C[O-].[Na+].CO>>C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C(=O)OC)C1=CC=CC=C1 | [CH3:1][OH:2].C[OH:4].N#[C:3][c:5]1[n:6][c:7]([NH:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[n:24][cH:25][nH:26][c:27]2[n:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([NH:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][... | CO.CO.N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | null | null | null | Acylation | OtherReaction | 632bea7ef0ba9d9c8074dce1accce57a8bc9be8884ed377ae5f21bc270cf078f | 94828388e421b34de4961d7ebd23c2a7025dc4ea4c8196535234f20c82fbf8ae | c1ccc(C(CNc2ncnc3[nH]cnc23)c2ccccc2)cc1 | C-[OH;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]:1.[C;D1;H3:11]-[OH;D1;+0:12]>>[#7;a:8]:[c:7]1:[c:9]:[#7;a:10]:[c:3](-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[O;H0;D2;+0:12]-[C;D1;H3:11]):[#7;a:4]:[c:5]:1:[#7;a:6] | null | [] | null | null | 24 | HOUR | A solution of 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile (Preparation 6) (5.0 g, 14.7 mmol) and sodium methoxide (4.0 g, 74.1 mmol) in methanol (300 ml) was heated under reflux for 24 hours. Further sodium methoxide (2.0 g, 37 mmol) and methanol (100 ml) was added and heating continued for a further 24 hours... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Methanol.Methanol | Ester | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1 | Other | null | null | 24 | CO.CO.N#Cc1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ad4245a898440bbbc97f5b29c144228 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O | C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC.C([O-])([O-])=O.[Na+].[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | O=C(c1ccccc1)[O:38][C@H:37]1[C@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][c:30]([C:31](=[O:32])[O:33][CH3:34])[n:35][c:36]23)[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:39]1[O:40]C(=O)c1ccccc1>>[CH3... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O | null | null | CO | Reduction | OtherReaction | 0d4a8fd544ba3504cf85ce3b470666ee6956214421e280b154aaf1825d3f9d31 | 5d3240d328f37074b617f0f9d19c66c4b6d41381ed0bd925b5261a2dcc33ed48 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | O=C(-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[#8:4]-[C:5](-[C:6](-[#7:7])=[O;D1;H0:8])-[C:9]-1-[O;H0;D2;+0:10]-C(=O)-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[#8:4]-[C:3]-[C:2](-[OH;D1;+0:1])-[C:9]-1-[OH;D1;+0:10] | 98 | [{"value": 98.0, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "CALC... | null | null | null | null | A solution of methyl 9-{(2R,3R,4R,5S)-3,4-bis(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-2-furanyl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 8) (3.4 g, 4.5 mmol) and sodium carbonate (50 mg) in dry methanol (60 ml) was stirred at room temperature for four hours. Solvent was removed under r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Secondary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | CO | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1>CO>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69e9be3268244ec6a9f9871f2e034f0a | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCN>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1.C(CN)N>>NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | CO[C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:41]([OH:42])[C@H:39]3[OH:40])[c:38]2[n:37]1)=[O:32].[NH2:33][CH2:34][CH2:35][NH2:36]>>[CH3:1... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCN | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O | null | null | ClCCl | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;a:7]:[c:6]1:[c:5]:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]-[C:11]):[#7;a:10]:[c:8]:1:[#7;a:9] | 86.1 | [{"value": 86.0, "product": "NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALC... | 105 | CELSIUS | null | null | A mixture of methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate (Preparation 9) (1.1 g, 2 mmol) and 1,2-ethylenediamine (1.1 g, 18.3 mmol) was heated at 105° C. for 2.5 hours. The mixture was dissolved in a little dichloromethane and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | ClCCl | 105 | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCN>ClCCl>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.