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-f83e86f633f84f5f9939b049f416c75f | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1ccncc1-c1cccc2c1CCNC2>>COc1cc2nc(N3CCc4c(cccc4-c4cnccc4N)C3)[nH]c(=O)c2cc1OC | ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.C1NCCC2=C(C=CC=C12)C=1C=NC=CC1N>>NC1=C(C=NC=C1)C1=C2CCN(CC2=CC=C1)C1=NC2=CC(=C(C=C2C(N1)=O)OC)OC | Cl[c:7]1[n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][c:28]2[c:26](=[O:27])[nH:25]1.[NH:8]1[CH2:9][CH2:10][c:11]2[c:12]([cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][n:19][cH:20][cH:21][c:22]2[NH2:23])[CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][c:11]4[c:12]([cH:13][cH:14]... | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1ccncc1-c1cccc2c1CCNC2 | COc1cc2nc(N3CCc4c(cccc4-c4cnccc4N)C3)[nH]c(=O)c2cc1OC | null | null | COC(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1ff4e7e247e9c5784772ca9bff631974543ef5b92189117ec9f9de2907d7e038 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(N2CCc3c(cccc3-c3cccnc3)C2)nc2ccccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9]-[c:10] | null | [] | 95 | CELSIUS | 18 | HOUR | A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (0.076 g, 0.31 mmol) and 3-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine (0.075 g, 0.33 mmol) in methoxyethanol (5 mL) was heated to 95° C. with stirring for 18 h the volatiles were evaporated and the residue was purified by flash column eluting with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.c1ccc2c(c1)CCNC2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2 | c1ccc2ncncc2c1.c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HCl | COC(C)O | 95 | 18 | COc1cc2nc(Cl)[nH]c(=O)c2cc1OC.Nc1ccncc1-c1cccc2c1CCNC2>COC(C)O>COc1cc2nc(N3CCc4c(cccc4-c4cnccc4N)C3)[nH]c(=O)c2cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-617f60e42998408eb2d6587c55676ac9 | C1COCCN1.Clc1nccc2cnccc12>>c1cc2c(N3CCOCC3)nccc2cn1 | ClC1=NC=CC2=CN=CC=C12.N1CCOCC1>>N1(CCOCC1)C1=NC=CC2=CN=CC=C12 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Cl[c:4]1[c:3]2[cH:2][cH:1][n:16][cH:15][c:14]2[cH:13][cH:12][n:11]1>>[cH:1]1[cH:2][c:3]2[c:4]([N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[n:11][cH:12][cH:13][c:14]2[cH:15][n:16]1 | C1COCCN1.Clc1nccc2cnccc12 | c1cc2c(N3CCOCC3)nccc2cn1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | efb89a7fae314945df61cc249e6c54046a4ce960df3b95d10c9da0114efd0e05 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2c(N3CCOCC3)nccc2cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#8:10]-[C:11]-[C:12]-1):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | null | [] | null | null | null | null | To 1-chloro-2,6-naphthyridine (164.3 mg, 0.998 mmol) (prepared as described in Van den Haak et al, J. Org. Chem 1982, 47 (9), 1673–7) was added morpholine (15 mL) and the mixture was heated at reflux for 4 h. Removal of the volatile components gave 216.6 mg of 1-morpholin-4-yl-[2,6]naphthyridine as a beige solid.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cc2cnccc2cn1 | C1COCC[NH]1.c1cc2cnccc2cn1 | C1COCC[NH]1.c1cc2cnccc2cn1 | HCl | null | null | null | C1COCCN1.Clc1nccc2cnccc12>>c1cc2c(N3CCOCC3)nccc2cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6647c4f09b6c419a9d4dc6d55a619a4e | Brc1ccccc1.COc1cc2[nH]c(N3CCn4ccnc4C3)nc(=O)c2cc1OC.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>>COc1cc2[nH]c(N3CCn4c(-c5ccccc5)cnc4C3)nc(=O)c2cc1OC.[NH4+].[OH-] | BrC1=CC=CC=C1.ClC1=NC2=CC(=C(C=C2C(N1)=O)OC)OC.N=1C=CN2C1CN(CC2)C=2NC1=CC(=C(C=C1C(N2)=O)OC)OC.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N=1C=CN2C1CNCC2>>[NH4+].[OH-].COC=1C=C2C(N=C(NC2=CC1OC)N1CC=2N(CC1)C(=CN2)C2=CC=CC=C2)=O | Br[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[nH:6][c:7]([N:8]3[CH2:9][CH2:10][n:11]4[cH:12][cH:19][n:20][c:21]4[CH2:22]3)[n:23][c:24](=[O:25])[c:26]2[cH:27][c:28]1[O:29][CH3:30].COc1cc2nc(Cl)[nH:31]c(=O)c2cc1OC>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[nH:6][c:7]([N:8]3[CH2:9][CH2:10][n:11]4[c:12]... | Brc1ccccc1.COc1cc2[nH]c(N3CCn4ccnc4C3)nc(=O)c2cc1OC.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC | COc1cc2[nH]c(N3CCn4c(-c5ccccc5)cnc4C3)nc(=O)c2cc1OC.[NH4+].[OH-] | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | C-C Coupling | OtherReaction | 51f174b122b4148efe85294a56b64d149a95665eefd585d6934ae86691193038 | 96400e5d57c3fc3e239eb6559ef444ea690c3a427f5529d3d28176dd4529b3cf | O=c1nc(N2CCn3c(-c4ccccc4)cnc3C2)[nH]c2ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-O-c1:c:c2:n:c(-Cl):[nH;D2;+0:6]:c(=O):c:2:c:c:1-O-C.[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[cH;D2;+0:12]:1>>[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH4+;D0:6] | null | [] | 140 | CELSIUS | null | null | 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine, prepared as described in PCT Application WO 01/44250, was coupled with 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b, as described herein. 2-(5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-6,7-dimethoxy-1H-quinazolin-4-one (150 mg, 0.46 mmol) was combined with bromobezene (97 μL, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether | null | c1ccccc1.c1cn2c(n1)C[NH]CC2.c1ccc2ncncc2c1 | c1ccccc1.c1cn2c(n1)C[NH]CC2 | c1ccc2ncncc2c1.c1ccccc1.c1cn2c(n1)C[NH]CC2 | HCl.Br- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | 140 | null | Brc1ccccc1.COc1cc2[nH]c(N3CCn4ccnc4C3)nc(=O)c2cc1OC.COc1cc2nc(Cl)[nH]c(=O)c2cc1OC>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>COc1cc2[nH]c(N3CCn4c(-c5ccccc5)cnc4C3)nc(=O)c2cc1OC.[NH4+].[OH-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ba65496943c421e8ec262612b95b609 | CCCCO.CP(=O)(Cl)Cl>>CCCCOP(C)(=O)O | C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC.C(=O)(O)[O-].[Na+].CP(=O)(Cl)Cl.N1=CC(=CC(=C1)C)C.N1=CC(=CC(=C1)C)C.C(CCC)O>>C(CCC)OP(O)(=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[P:6](Cl)([CH3:7])=[O:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6]([CH3:7])(=[O:8])[OH:9] | CCCCO.CP(=O)(Cl)Cl | CCCCOP(C)(=O)O | null | N1N=NN=C1 | CCOC(=O)C.C(Cl)Cl | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | null | Cl-[P;H0;D4;+0:1](-Cl)(-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[P;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])-[O;D1;H1:7] | 376.5 | [{"value": 376.5, "product": "C(CCC)OP(O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | To a flask containing 1H-tetrazole (˜0.002 g, 0.028 mmol) was added a solution of n-butanol (0.041 g, 0.55 mmol) in 0.33 mL of DCM, followed by a solution of 3,5-lutidine (0.090 g, 0.84 mmol) in 0.33 mL of DCM. The resulting clear solution was cooled to 0° C. then added, under an atmosphere of N2, a solution of methylp... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | null | Other | N1N=NN=C1.CCOC(=O)C.C(Cl)Cl | 0 | 8 | CCCCO.CP(=O)(Cl)Cl>N1N=NN=C1.CCOC(=O)C.C(Cl)Cl>CCCCOP(C)(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6397b187f4af46799fe266abba7004ed | CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CO[C@@]12[C@H](COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1C[C@@H]1N[C@@H]12.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H... | CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4)N.N(=NC(=O)OC(C)C)C(=O)OC(C)C.CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C=5C=CC=CC5)NC(=O)C=6C=CC=CC6)O)O)OC(=O)C=7C=CC=CC7)(CO4)OC(=O)C)O)C)OC(=O)C.C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC=3C2... | CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H:16]([O:15]C(C)=O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)[c:19]4ccccc4)c4ccccc4)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C.C[C:7]1=[C:8](N)[C:9](=O)[C:4]2=[C:5](N3C[C@@H]4N[C@@H:21]4[C@:22]3([O:23]C)[C@@H:3]2COC(N)=O)[C:6]1=O.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C... | CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CO[C@@]12[C@H](COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1C[C@@H]1N[C@@H]12.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H... | COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a952d9c4cc02b540039f414cf22e48b597111dabf9a7e1389b29e740894644a1 | 98bcab2161137fee6bc0c4c66a26addfdcdd3e2f18092d3d98c96ef4b51f0aff | C(=C\c1ccccc1)\c1ccccc1 | null | null | [] | null | null | null | null | Commercially available reagents and solvents were obtained as follows: HPLC-grade solvents, Fisher; anhydrous solvents, Aldrich; diisopropyl azodicarboxylate (DIAD, 95%), Lancaster; 4-aminobenzyl alcohol, Alfa Aesar; Z-val-OSu, Advanced ChemTech; L-citrulline, Novabiochem; (1S, 2R)-(+)-norephedrine and other commercial... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Carbamic ester.Carboxylic acid.Ketone.Ketone.Ketone.Ketone.Ketone.Ketone.Ketone.Ketone.Ketone.Ester.Ester.Ester.Ester.Ether.Ether.Ether.Ether.Ether.Ether.Ether.Ether.Ether.Urea.Secondary amide.Primary alcohol.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary... | Ether.Ether.Ether.Ether.Aromatic alcohol | C1=C2CC[C@@H]3CC[C@H]4OC[C@@H]4[C@H]3C[C@H](CC1)C2.c1ccccc1.c1ccccc1.c1ccccc1.C1=CCC2=C(C1)C[C@H]1[C@H]3N[C@H]3CN21.c1ccc2c(c1)Cc1cc3c(cc1C2)CCCC3.C1CCOCC1.C1CCOCC1.c1ccc2c(c1)Cc1cc3c(cc1C2)CCCC3.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CO[C@@]12[C@H](COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1C[C@@H]1N[C@@H]12.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5062c37bf9ad4880a95eebcce007759c | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)(C)OC(=O)C1(N)CCCC1>>CC(C)(C)OC(=O)C1(N)C=COC=C1 | C(#N)[BH3-].[Na+].C(C)(C)(C)OC(=O)C1(CCCC1)N.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)(C)(C)OC(=O)C1(C=COC=C1)N | CC(=O)O[BH-](OC(C)=O)OC(C)=[O:12].C1[CH2:10][C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([NH2:9])[CH2:14][CH2:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C:8]1([NH2:9])[CH:10]=[CH:11][O:12][CH:13]=[CH:14]1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)(C)OC(=O)C1(N)CCCC1 | CC(C)(C)OC(=O)C1(N)C=COC=C1 | null | null | null | Acylation | OtherReaction | bd4e55b9a1806502487f17e5bc91d7ce55cfe35462a744004bb4316beb890800 | 94fdff9f10c6953a5a157a0a3d842c4d1e483ed489aa0d9d85a68c42c68923d0 | C1=COC=CC1 | C-C(=O)-O-[BH-](-O-C(-C)=O)-O-C(-C)=[O;H0;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1(-[N;D1;H2:10])-[CH2;D2;+0:11]-C-[CH2;D2;+0:12]-[CH2;D2;+0:13]-1>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1(-[N;D1;H2:10])-[CH;D2;+0:11]=[C:14]-[O;H0;D2... | null | [] | null | null | null | null | An alternative route for the preparation of some 1,3,4-trisubstituted cyclopentanes within the scope of the instant invention is given in Scheme 11. Reductive alkylation, using for example sodium triacetoxyborohydride or sodium cyanoborohydride, of a cycloalkyl amino-acid 11-2, such as 1-aminocyclopentane carboxylic ac... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1CCCC1 | C1=COC=CC1 | C1=COC=CC1 | HO-.B | null | null | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)(C)OC(=O)C1(N)CCCC1>>CC(C)(C)OC(=O)C1(N)C=COC=C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2d23674e1954e95b0862e72fba9eb4a | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | C(=O)(OC(C)(C)C)N1CCC(C(=O)O)CC1.C[Si](C)(C)C=[N+]=[N-]>>C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)OC | [OH:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1.C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.C[Si](C)(C)C=[N+]=[N-] | COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | ClCCl.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | C1CCNCC1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 96.6 | [{"value": 96.6, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of BOC-isonipecotic acid (45.0 g, 0.20 mol) dissolved in a 3:1 solution of dichloromethane/methanol (1200 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (147 mL, 0.29 mol, 2.0M in hexane) over 30 min via an addition funnel. The reaction mixture was then concentrated to afford the title co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | C1CC[NH]CC1 | Other | ClCCl.CO | null | null | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.C[Si](C)(C)C=[N+]=[N-]>ClCCl.CO>COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-292d55b0aa854c219dbd269febe9a838 | C=CCCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>>C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 | C([O-])(O)=O.[Na+].C[Si](C)(C)[N-][Si](C)(C)C.[K+].C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)OC.BrCCCC=C>>C(CCC=C)C1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC | Br[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[CH:6]1([C:7](=[O:8])[O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]1([C:7](=[O:8])[O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[... | C=CCCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | cc17dfd0def644ca87e815e637357310f207eb90d8b3273b51858e3602d79eca | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10]1-[C:11]-[C:12]-[#7:13]-[C:14]-[C:15]-1>>[C;D1;H2:5]=[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:10]1(-[C:8](=[O;D1;H0:9])-[#8:7]-[C;D1;H3:6])-[C:11]-[C:12]-[#7:13]-[C:14]-[C:15]-1 | 99.2 | [{"value": 99.2, "product": "C(CCC=C)C1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of potassium bis(trimethylsilyl)amide (30.7 g, 0.15 mol) in tetrahydrofuran (750 mL) at 0° C. was added a solution of methyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate (25 g, 0.10 mol) from Step A in tetrahydrofuran (250 mL) and the reaction mixture was stirred for 1 h. 5-Bromo-1-pentene (19.4 mL, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | O1CCCC1 | null | 1 | C=CCCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-093ff50ed82045c98be5e1147b0de0d3 | C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1.CO>>COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1 | C(CCC=C)C1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC.CO.CSC>>O=CCCCC1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC | C=[CH:9][CH2:8][CH2:7][CH2:6][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.C[OH:10]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:... | C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1.CO | COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 819cc56f1de0795ade47bb88544c1667e77ababe1a9f8886b0ab43d7fc61baf3 | d60fee5fdd239063d17d89701ffcf20659b907d096a729f7ffeb7d37370ddb04 | C1CCNCC1 | C-[OH;D1;+0:1].C=[CH;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1] | null | [] | null | null | null | null | A solution of methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (29.4 g, 0.0945 mol) from Step B in methanol (1000 mL) was cooled to −78° C. in a dry ice/methanol bath and ozone was bubbled into the solution until a blue color persisted. The excess ozone was removed with a stream of nitrogen and... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Methanol | Aldehyde | null | null | C1CC[NH]CC1 | Other | null | null | null | C=CCCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1.CO>>COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-190dcd50c65c412eb9c6458f3623a7b2 | COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1 | O=CCCCC1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)OC)CCCC(=O)O | [CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11])[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[... | COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1 | COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1 | null | null | CC(=O)C | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | C1CCNCC1 | [C:1]-[C:2]-[CH;D2;+0:3]=[O;D1;H0:4]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;D1;H1:5] | null | [] | null | null | 5 | MINUTE | To a solution of methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (23.0 g, 0.0734 mol) from Step C in acetone (775 mL) at room temperature was added Jones reagent (28.2 mL, 2.6M) via syringe. After 5 min, the reaction mixture was concentrated. The residue was taken up in water and diethyl ether ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | C1CC[NH]CC1 | Other | CC(=O)C | null | 0.083333 | COC(=O)C1(CCCC=O)CCN(C(=O)OC(C)(C)C)CC1>CC(=O)C>COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b2aefe82fc74fb8a87e403b637a98cc | COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)OC)CCCC(=O)O.C[Si](C)(C)C=[N+]=[N-]>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)OC)CCCC(=O)OC | [OH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]1([C:9](=[O:10])[O:11][CH3:12])[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1.C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]1([C:9](=[O:10])[O:11][CH3:12])[CH2:13][CH2:14][N:15]([C:16](=[O:17... | COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1.C[Si](C)(C)C=[N+]=[N-] | COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 | null | null | ClCCl.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | C1CCNCC1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 82.4 | [{"value": 82.4, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)OC)CCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 4-(1-(tert-butoxycarbonyl)-4-(methoxy-carbonyl)piperidin-4-yl)butanoic acid (23.4 g, 0.071 mol) from Step D in 3:1 dichloromethane/methanol (480 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (53 mL, 0.11 mol, 2.0M in hexane). The reaction mixture was stirred for 15 min and then concen... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | C1CC[NH]CC1 | Other | ClCCl.CO | null | 0.25 | COC(=O)C1(CCCC(=O)O)CCN(C(=O)OC(C)(C)C)CC1.C[Si](C)(C)C=[N+]=[N-]>ClCCl.CO>COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2199290325e045e6997c103221fdd023 | COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | O1CCCC1.C(C)(C)[N-]C(C)C.[Li+].C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)OC)CCCC(=O)OC.O1CCCC1.C(C)(C)[N-]C(C)C.[Li+].[Cl-].[NH4+].C(C)(=O)OCC>>COC(=O)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O | CO[C:21]([C:8]1([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)=[O:22]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[C:... | COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | fdbcf46d25defdaa148ed0cf50374ec5c2675fb6f93e6d5b812ee842c73dfa8d | 6f130a746a78d10ca37f94948711de2b0c76f45052ca887b0e681c66276a7764 | O=C1CCCC12CCNCC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])(-[C:11])-[C:12]>>[C:11]-[C:3]1(-[C:12])-[C:4]-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 110.2 | [{"value": 110.2, "product": "COC(=O)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 25 | MINUTE | To a solution of methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate (20.1 g, 0.058 mol) from Step E in tetrahydrofuran (600 mL) at −78° C. was added lithium diisopropylamide mono(tetrahydrofuran) (47 mL, 0.070 mol, 1.5M solution in cyclohexanes). The reaction mixture was stirred at −78° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | HO- | O1CCCC1 | -78 | 0.416667 | COC(=O)CCCC1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-279bb325608143949a9c5045f8750794 | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O>>CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1 | COC(=O)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O.[OH-].[Li+]>>O=C1CCCC12CCN(CC2)C(=O)OC(C)(C)C | COC(=O)[CH:14]1[CH2:13][CH2:12][C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:18][CH2:17]2)[C:15]1=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13][CH2:14][C:15]2=[O:16])[CH2:17][CH2:18]1 | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1 | null | null | C(C)O.O1CCCC1.O | Reduction | Decarboxylation | 2a633e18f5bcad5f2ae1e8675360a573985c0816d41c2f33a88053978877ccf7 | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | O=C1CCCC12CCNCC2 | C-O-C(=O)-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]1-[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | 67.5 | [{"value": 67.5, "product": "O=C1CCCC12CCN(CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | HO- | C(C)O.O1CCCC1.O | 90 | null | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O>C(C)O.O1CCCC1.O>CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4d34c0f487347f9a801ff3387bd1e3d | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCC=O>>CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | [Cl-].[NH4+].O=C1CCCC12CCN(CC2)C(=O)OC(C)(C)C.O1CCCC1.C(C)(C)[N-]C(C)C.[Li+].C(CC)=O>>OC(CC)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O | [CH2:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[C:21]1=[O:22].[CH3:1][CH2:2][CH:3]=[O:4]>>[CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)... | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCC=O | CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | null | null | C(C)OCC | C-C Coupling | OtherReaction | 0608dea009714d2fb6fc79421f83631a68b8a53e44927021afcf353589bd65c5 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | O=C1CCCC12CCNCC2 | [C;D1;H3:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1>>[C;D1;H3:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[CH;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[C:6]-1=[O;D1;H0:5] | 120.9 | [{"value": 120.9, "product": "OC(CC)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | null | C(C)OCC | -78 | 0.5 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCC=O>C(C)OCC>CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0879ba6ad3742769d2b05b03691ff97 | CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O>>CCC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.OC(CC)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O>>O=C(CC)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[C:21]1=[O:22]>>[CH3:1][CH2:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[... | CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | CCC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCC12CCNCC2 | [C:1]-[C:2](-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[C:9]>>[C:1]-[C:2](-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[C:9] | 84.1 | [{"value": 84.1, "product": "O=C(CC)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a solution of oxalyl chloride (1.6 mL, 18.3 mmol) in dichloromethane (150 mL) at −78° C. was slowly added dimethyl sulfoxide (2.6 mL, 37 mmol). After 5 min, a solution of tert-butyl 2-(1-hydroxyprop-1-yl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (4.75 g, 15.3 mmol) from Step H in dichloromethane (40 mL) was added v... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CCC2(C1)CC[NH]CC2 | null | ClCCl | -78 | 0.083333 | CCC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O>ClCCl>CCC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c06c86d3f3444378259f57ae88f4d91 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CC=O>>CC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | [Cl-].[NH4+].O=C1CCCC12CCN(CC2)C(=O)OC(C)(C)C.O1CCCC1.C(C)(C)[N-]C(C)C.[Li+].C(C)=O>>OC(C)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O | [CH2:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[C:20]1=[O:21].[CH3:1][CH:2]=[O:3]>>[CH3:1][CH:2]([OH:3])[CH:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[C:20]1=[O:21] | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CC=O | CC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | null | null | C(C)OCC | C-C Coupling | OtherReaction | 0608dea009714d2fb6fc79421f83631a68b8a53e44927021afcf353589bd65c5 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | O=C1CCCC12CCNCC2 | [C;D1;H3:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3].[O;D1;H0:4]=[C:5]1-[C:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-1>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH;D3;+0:9]1-[C:8]-[C:7]-[C:6]-[C:5]-1=[O;D1;H0:4] | 479.3 | [{"value": 479.3, "product": "OC(C)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 35 | MINUTE | tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | null | C(C)OCC | -78 | 0.583333 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CC=O>C(C)OCC>CC(O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-01aabc2e796f428ba758c5068521a6d6 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCOC=O>>CC(C)(C)OC(=O)N1CCC2(CCC(CO)C2=O)CC1 | Cl.O=C1CCCC12CCN(CC2)C(=O)OC(C)(C)C.C(=O)OCC.CC(C)([O-])C.[K+]>>OCC1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13][CH2:14][C:17]2=[O:18])[CH2:19][CH2:20]1.CCO[CH:15]=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13][CH:14]([CH2:15][OH:16])[C:17]2=[O:18])[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCOC=O | CC(C)(C)OC(=O)N1CCC2(CCC(CO)C2=O)CC1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | ffec183098c03479e4a94391acf17db5e4f037a4dd9bf7d5e807c1809ed885c2 | 5190634190ddef4dc4ac4507891dca9c66c26991d95954d4514241a45c93ba26 | O=C1CCCC12CCNCC2 | C-C-O-[CH;D2;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[C:4]1-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-1>>[O;D1;H0:3]=[C:4]1-[C:5]-[C:6]-[C:7]-[CH;D3;+0:8]-1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 51.4 | [{"value": 51.4, "product": "OCC1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | DAY | tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-bu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ketone.Primary alcohol | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | HO- | C(C)OCC | -78 | 48 | CC(C)(C)OC(=O)N1CCC2(CCCC2=O)CC1.CCOC=O>C(C)OCC>CC(C)(C)OC(=O)N1CCC2(CCC(CO)C2=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-701f21b2c1d643e889f13cae87e55dcf | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O.NN>>CC(C)(C)OC(=O)N1CCC2(CCc3c2[nH][nH]c3=O)CC1 | COC(=O)C1C(C2(CC1)CCN(CC2)C(=O)OC(C)(C)C)=O.NN>>C(C)(C)(C)OC(=O)N1CCC2(CC1)CCC=1C(NNC12)=O | CO[C:18]([CH:14]1[CH2:13][CH2:12][C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:21][CH2:20]2)[C:15]1=O)=[O:19].[NH2:16][NH2:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13][c:14]3[c:15]2[nH:16][nH:17][c:18]3=[O:19])[CH2:20][CH2:21]1 | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O.NN | CC(C)(C)OC(=O)N1CCC2(CCc3c2[nH][nH]c3=O)CC1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | b2393f5ac303949ae2f8c96993959cb5eae8c5a8c32c1d0f6b02ba97ef7f919b | f32fac81dfdb000dc8678b0df4fe3b0a64c38caab136205f41649f692b09b3bd | O=c1[nH][nH]c2c1CCC21CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5]-[C:6](-[C:7])(-[C:8])-[C;H0;D3;+0:9]-1=O.[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[C:7]-[C:6]1(-[C:8])-[C:5]-[C:4]-[c;H0;D3;+0:3]2:[c;H0;D3;+0:9]-1:[nH;D2;+0:10]:[nH;D2;+0:11]:[c;H0;D3;+0:1]:2=[O;D1;H0:2] | 61.4 | [{"value": 61.4, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC1)CCC=1C(NNC12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxate from Procedure 1, Step F (0.448 g, 1.46 mmol) in toluene (15 mL) was added hydrazine (0.084 mL, 1.72 mmol). The reaction mixture was refluxed for 12 h, concentrated and the residue was purified by flash chromatography eluting with 5... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | null | C1CCC2(C1)CC[NH]CC2 | c1nnc2c1CCC21CCNCC1 | c1nnc2c1CCC21CCNCC1 | HO- | C1(=CC=CC=C1)C | null | null | COC(=O)C1CCC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O.NN>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCC2(CCc3c2[nH][nH]c3=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51623ca6fed2402986932fa772644519 | COC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>>COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C[Si](C)(C)C[Li].[Cl-].[NH4+].C[Si](C)(C)C[Li].COC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC>>C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC | O([C:4]([C:3]1([O:2][CH3:1])[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1)=[O:6])[CH3:5]>>[CH3:1][O:2][C:3]1([C:4]([CH3:5])=[O:6])[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1 | COC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1 | null | null | C(C)(=O)OCC.O.O1CCCC1.C(C)OCC | Miscellaneous | OtherReaction | 3724e934ace06da3205b28d40bd9eba0c9f8214e3431e58c6de85eacba50eaae | 0ffdc15c7ac34be51edf4589ed8aa3f210774f50305a479999afbf21400d0a96 | C1CCNCC1 | [#8:1]-[C:2](-[C;H0;D3;+0:3](=[O;D1;H0:4])-O-[CH3;D1;+0:5])(-[C:6])-[C:7]>>[#8:1]-[C:2](-[C;H0;D3;+0:3](-[CH3;D1;+0:5])=[O;D1;H0:4])(-[C:6])-[C:7] | 37.1 | [{"value": 37.1, "product": "C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-tert-butyl 4-methoxycarbonyl-4-methoxypiperidine-1-carboxylate (2.5 g, 9.05 mmol) dissolved in 100 mL of tetrahydrofuran at −78° C. was added trimethylsilylmethyl lithium (23 mL, 23 mmol). After 30 min additional trimethylsilylmethyl lithium (2.7 mL, 2.7 mmol) was added. The reaction mixture was then... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | C1CC[NH]CC1 | Other | C(C)(=O)OCC.O.O1CCCC1.C(C)OCC | null | 0.5 | COC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>C(C)(=O)OCC.O.O1CCCC1.C(C)OCC>COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b89820f3efd14138aa3a6cb136df92cc | CCC=O.COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1>>CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | [Cl-].[NH4+].C(CC)=O.C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC.C(C)(C)NC(C)C.[Li]>>OC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC)CC | [CH3:1][CH2:2][CH:3]=[O:4].[CH3:5][C:6](=[O:7])[C:8]1([O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][C:6](=[O:7])[C:8]1([O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:2... | CCC=O.COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1 | CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | d08eb7b2615717189cce315501bb2cfa7ee3668e6d8eaa24218b092d1454a850 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | C1CCNCC1 | [C;D1;H3:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH2;D2;+0:7]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:2]-[C;D1;H3:1] | 55.9 | [{"value": 55.9, "product": "OC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of tert-butyl 4-acetyl-4-methoxypiperidine-1-carboxylate (0.589 g, 2.29 mmol) from Step A in tetrahydrofuran (20 mL) at −78° C. was added lithium diisopropylamine (0.650 mL, 0.974 mmol) followed by propionaldehyde (0.266 g, 0.330 mL, 4.58 mmol). After 5 min, the reaction mixture was poured into saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | null | null | C1CC[NH]CC1 | null | O1CCCC1 | null | 0.083333 | CCC=O.COC1(C(C)=O)CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2abda1273cd6457e8d73afd6e5bd1098 | CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>>CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.OC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)OC)CC>>COC1(CCN(CC1)C(=O)OC(C)(C)C)C(CC(CC)=O)=O | [CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][C:6](=[O:7])[C:8]1([O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[C:8]1([O:9][CH3:10])[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:2... | CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | C1CCNCC1 | [C:1]-[C:2](=[O;D1;H0:3])-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[C;D1;H3:8]>>[C:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[C;D1;H3:8] | 56.6 | [{"value": 56.6, "product": "COC1(CCN(CC1)C(=O)OC(C)(C)C)C(CC(CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a solution of oxalyl chloride (0.168 mL, 1.92 mmol) in dichloromethane (10 mL) at −78° C. was slowly added dimethyl sulfoxide (0.272 mL, 3.84 mmol). After 5 min, a solution of tert-butyl 4-(3-hydroxy-1-oxopent-1-yl)-4-methoxypiperidine-1-carboxylate (0.404 g, 1.28 mmol) from Step B in dichloromethane (5 mL) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CC[NH]CC1 | null | ClCCl | -78 | 0.083333 | CCC(O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>ClCCl>CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18eecdd894a74a9f87c65b58f6dc5b31 | CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1.CS(=O)(=O)N=[N+]=[N-]>>CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | S(=O)(=O)(C)N=[N+]=[N-].COC1(CCN(CC1)C(=O)OC(C)(C)C)C(CC(CC)=O)=O.C(C)N(CC)CC.S(=O)(=O)(C)N=[N+]=[N-].[OH-].[Na+]>>COC1(CCN(CC1)C(=O)OC(C)(C)C)C(C(C(CC)=O)=[N+]=[N-])=O | [CH3:1][CH2:2][C:3](=[O:4])[CH2:5][C:8](=[O:9])[C:10]1([O:11][CH3:12])[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1.CS(=O)(=O)N=[N+:6]=[N-:7]>>[CH3:1][CH2:2][C:3](=[O:4])[C:5](=[N+:6]=[N-:7])[C:8](=[O:9])[C:10]1([O:11][CH3:12])[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:1... | CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1.CS(=O)(=O)N=[N+]=[N-] | CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | f358b81561b63628a435536c95a58e24369f7410be3aef157399b9be06e39ab4 | 2b9143c475c316d66255d8905b2d10a18b2a882ea82323797903eb2242ddbe89 | C1CCNCC1 | C-S(=O)(=O)-N=[N+;H0;D2:1]=[N;-;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9]>>[C:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[N+;H0;D2:1]=[N;-;D1;H0:2])-[C:7](-[C:8])=[O;D1;H0:9] | 70.8 | [{"value": 70.8, "product": "COC1(CCN(CC1)C(=O)OC(C)(C)C)C(C(C(CC)=O)=[N+]=[N-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a solution of tert-butyl 4-methoxy-4-(1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.227 g, 0.724 mmol) from Step C in dichloromethane (10 mL) was added triethylamine (0.101 mL, 0.724 mmol). Next, a solution of mesyl azide (0.087 g, 0.724 mmol) in dichloromethane (1 mL) was added. The reaction mixture was stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Azide | Ketone.Ketone.Diazo | null | null | C1CC[NH]CC1 | HO- | ClCCl | null | 3.5 | CCC(=O)CC(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1.CS(=O)(=O)N=[N+]=[N-]>ClCCl>CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-877888e2a7554dd4b0bc69673d1bcb3a | CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>>CCC(=O)C1COC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | COC1(CCN(CC1)C(=O)OC(C)(C)C)C(C(C(CC)=O)=[N+]=[N-])=O>>O=C1C(COC12CCN(CC2)C(=O)OC(C)(C)C)C(CC)=O | [N-]=[N+]=[C:5]([C:3]([CH2:2][CH3:1])=[O:4])[C:21]([C:8]1([O:7][CH3:6])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1)=[O:22]>>[CH3:1][CH2:2][C:3](=[O:4])[CH:5]1[CH2:6][O:7][C:8]2([CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:... | CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1 | CCC(=O)C1COC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O | null | CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+2].[Rh+2] | ClCCl.Cl | C-C Coupling | OtherReaction | b2189da653e23c552f6068c1da0f8f076fd3f7e4bcbb39d3445080dac356b3a3 | 19d22f448f5253959cc773014604735a9b26e6bbe34e776b92a0afbc2264fb46 | O=C1CCOC12CCNCC2 | [C:1]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:4](=[N+]=[N-])-[C:5](=[O;D1;H0:6])-[C:7]-[#8:8]-[CH3;D1;+0:9]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4]1-[CH2;D2;+0:9]-[#8:8]-[C:7]-[C:5]-1=[O;D1;H0:6] | 40.4 | [{"value": 40.4, "product": "O=C1C(COC12CCN(CC2)C(=O)OC(C)(C)C)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of rhodium acetate dimer (0.002 g, 0.005 mmol) in dichloromethane (27 mL) was heated to 81° C. A solution of tert-butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.092 g, 0.270 mmol) from Step D in dichloromethane (7 mL) was added slowly dropwise over 12 min. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Diazo | Ketone.Ketone.Ether | null | C1COC2(C1)CC[NH]CC2 | C1COC2(C1)CC[NH]CC2 | Other | CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+2].[Rh+2].ClCCl.Cl | null | null | CCC(=O)C(=[N+]=[N-])C(=O)C1(OC)CCN(C(=O)OC(C)(C)C)CC1>CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+2].[Rh+2].ClCCl.Cl>CCC(=O)C1COC2(CCN(C(=O)OC(C)(C)C)CC2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fc8772e8a914fc196de9870a1e7a81f | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2>>CC(C)(C)OC(=O)N1CCC2(CCC(=O)C2C=O)CC1 | O=[O+][O-].C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)=O>>C(=O)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)=O | C=[CH:17][CH:16]1[C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:19]2)[CH2:12][CH2:13][C:14]1=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13][C:14](=[O:15])[CH:16]2[CH:17]=[O:18])[CH2:19][CH2:20]1 | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | CC(C)(C)OC(=O)N1CCC2(CCC(=O)C2C=O)CC1 | null | null | CO | Oxidation | Alkene oxidation to aldehyde | d8a9b78d3268b1276aae5339f679b7d52c3239349ff909dd02d119f9b6b6fbf6 | 63e1c45bed9e5e455511d54aa776987c80b93229f60232b32aa30b9f700d26d1 | O=C1CCC2(CCNCC2)C1 | C=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[C:6]>>[C:3]-[C:2](-[CH;D2;+0:1]=[O;D1;H0:7])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | Ozone was bubbled into a solution of tert-butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate (0.168 g, 0.599 mmol) from Step B in methanol (6 mL) at −70° C. until a blue color persisted. Excess ozone was removed with a stream of nitrogen and then dimethyl sulfide (0.5 mL) was added. The mixture was allowed to warm... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Aldehyde | null | null | C1CCC2(C1)CC[NH]CC2 | null | CO | null | null | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2>CO>CC(C)(C)OC(=O)N1CCC2(CCC(=O)C2C=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c841e5b9f76e464caf7e47b43aa62af9 | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2>>C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)=O.[BH4-].[Na+]>>C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O | [CH2:1]=[CH:2][CH:3]1[C:4](=[O:5])[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2>>[CH2:1]=[CH:2][CH:3]1[CH:4]([OH:5])[CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2 | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 436995e4b29546c77ec774184ce22ee76b939a31d8b42f590afcb0d9fcf0ad91 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1CCC2(C1)CCNCC2 | [C;D1;H2:1]=[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8]>>[C;D1;H2:1]=[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[OH;D1;+0:8] | 104.6 | [{"value": 104.6, "product": "C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate (0.59 g, 2.11 mmol) from Procedure 17, Step B in methanol (6 mL) was cooled to −70° C. and sodium borohydride (0.022 g, 0.60 mmol) was added. The reaction was allowed to warm to room temperature for 3 h and was then quenched with the addition of... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | null | CO | null | null | C=CC1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2>CO>C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ec86a96bfa746418eba080ec0d772d5 | C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2.CC(C)(C)[Si](C)(C)Cl>>C=CC1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 | [Si](C)(C)(C(C)(C)C)Cl.C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O.N1C=NC=C1>>C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C | [CH2:1]=[CH:2][CH:3]1[CH:4]([OH:5])[CH2:13][CH2:14][C:15]12[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2.Cl[Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH2:1]=[CH:2][CH:3]1[CH:4]([O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2... | C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2.CC(C)(C)[Si](C)(C)Cl | C=CC1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 | null | null | C([O-])(O)=O.[Na+].CN(C)C=O.CCOCC | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | C1CCC2(C1)CCNCC2 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]-[C:12]=[C;D1;H2:13]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11]-[C:12]=[C;D1;H2:13] | 86.2 | [{"value": 86.2, "product": "C(=C)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.462 g, 1.64 mmoL) from Step A in DMF (8 mL) was added imidazole (0.335 mg, 4.92 mmol) and then tert-butyldimethylsilyl chloride (0.370 g, 2.4 mmol). The reaction was stirred at room temperature for 20 h and then diluted with ether and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | C1CCC2(C1)CC[NH]CC2 | HCl | C([O-])(O)=O.[Na+].CN(C)C=O.CCOCC | null | 20 | C=CC1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2.CC(C)(C)[Si](C)(C)Cl>C([O-])(O)=O.[Na+].CN(C)C=O.CCOCC>C=CC1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6b06fbe021c44f3b8106057062933c8 | CC(C)(C)OC(=O)N1CCC2(CCC(O[Si](C)(C)C(C)(C)C)C2C=O)CC1>>CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 | C([O-])(O)=O.[Na+].C(C)[Mg]Br.C(=O)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C.C(C)[Mg]Br>>OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C | [CH:3](=[O:4])[CH:5]1[CH:6]([O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16][C:17]12[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2>>[CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH:6]([O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14... | CC(C)(C)OC(=O)N1CCC2(CCC(O[Si](C)(C)C(C)(C)C)C2C=O)CC1 | CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 | null | null | C1CCOC1.CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | C1CCC2(C1)CCNCC2 | [C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5]>>[C:1]-[C:2](-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:6]-[C;D1;H3:7])-[C:5] | 81.2 | [{"value": 81.2, "product": "OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of tert-butyl 1-formyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate (0.284 g, 0.714 mmol) from Step C in THF (7 mL) was cooled to −70° C. and ethyl magnesium bromide (3.0M, 0.262 mL, 0.786 mmol) was added. The reaction was stirred for 30 min and then an additional aliquot of ethyl magne... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1CCC2(C1)CC[NH]CC2 | Other | C1CCOC1.CCOCC | null | 0.5 | CC(C)(C)OC(=O)N1CCC2(CCC(O[Si](C)(C)C(C)(C)C)C2C=O)CC1>C1CCOC1.CCOCC>CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93cc11062a204c5dbc59f3d76e2c7a2a | CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2>>CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O[Si](C)(C)C(C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O | CC(C)(C)[Si](C)(C)[O:7][CH:6]1[CH:5]([CH:3]([CH2:2][CH3:1])[OH:4])[C:10]2([CH2:9][CH2:8]1)[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]2>>[CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH:6]([OH:7])[CH2:8][CH2:9][C:10]12[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])(... | CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2 | CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | null | null | C1CCOC1.C(C)(=O)OCC.Cl | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | C1CCC2(C1)CCNCC2 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | 99 | [{"value": 99.0, "product": "OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate (0.248 g, 0.58 mmol) in THF (15 mL) was added 1M tetrabutylammonium fluoride in THF (2.3 mL, 2.3 mmol). The solution was stirred at room temperature for 4 h and was then diluted with ethyl acetate, pour... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | C1CCC2(C1)CC[NH]CC2 | Other | C1CCOC1.C(C)(=O)OCC.Cl | null | 4 | CCC(O)C1C(O[Si](C)(C)C(C)(C)C)CCC12CCN(C(=O)OC(C)(C)C)CC2>C1CCOC1.C(C)(=O)OCC.Cl>CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1ccb3f7a4454efaa02b3ba0424b4745 | CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2>>CCC(=O)C1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | OC(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)O.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>O=C(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH:6]([OH:7])[CH2:8][CH2:9][C:10]12[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]2>>[CH3:1][CH2:2][C:3](=[O:4])[CH:5]1[C:6](=[O:7])[CH2:8][CH2:9][C:10]12[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH... | CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | CCC(=O)C1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2 | null | null | CC(=O)C | Oxidation | OtherReaction | ea7d092d21dc7125486e9b2efcd7f66954cd05df4007b8b9d4fa83bb8b8a9165 | 784b65917ae952abb76a69fc81990586d899be4ce8f5fa5c24fb1cb70b659234 | O=C1CCC2(CCNCC2)C1 | [C;D1;H3:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]1-[C:6]-[C:7]-[C:8]-[CH;D3;+0:9]-1-[OH;D1;+0:10]>>[C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]1-[C:6]-[C:7]-[C:8]-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10] | 66.7 | [{"value": 66.7, "product": "O=C(CC)C1C(CCC12CCN(CC2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.050 g, 0.16 mmol) from Step E in acetone (2 mL) at 0° C. was added 2.6M Jones reagent (0.122 mL, 0.32 mmol). The reaction was stirred at room temperature for 10 min and was then quenched with isopropanol. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ketone.Ketone | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | C1CCC2(C1)CC[NH]CC2 | null | CC(=O)C | null | 0.166667 | CCC(O)C1C(O)CCC12CCN(C(=O)OC(C)(C)C)CC2>CC(=O)C>CCC(=O)C1C(=O)CCC12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0cc87cbef5e40de9f67dab66499498b | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | C([O-])(O)=O.[Na+].C[Si](C)(C)[N-][Si](C)(C)C.[K+].COC(=O)C1CCN(CC1)C(=O)OC(C)(C)C.BrCCO[Si](C)(C)C(C)(C)C>>COC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C | Br[CH2:6][CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15].[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:... | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | cc17dfd0def644ca87e815e637357310f207eb90d8b3273b51858e3602d79eca | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:8]1(-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4])-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1 | null | [] | null | null | 1 | HOUR | To a solution of KHMDS (8.72 g, 44 mmol) in THF (300 mL) at −70° C. was slowly added over 10 min a solution of tert-butyl 4-methoxycarbonylpiperidine-1-carboxylate (7.1 g, 29 mmol) in THF (70 mL). After 1 h, 2-bromo-1-(tert-butyldimethylsilyloxy)ethane (10 g, 47 mmol) was added and the reaction was allowed to warm to r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | C1CCOC1 | null | 1 | CC(C)(C)[Si](C)(C)OCCBr.COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>C1CCOC1>COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0677070e85e2467c947e5de20344088b | COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1 | [BH4-].[Li+].COC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C.[BH4-].[Li+]>>OCC1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C | CO[C:12]([C:11]1([CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH2:14][CH2:15][O:16][Si:17]... | COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]>>[C:5]-[C:3](-[C:4])(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:6] | null | [] | null | null | 2 | DAY | The crude tert-butyl 4-methoxycarbonyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (assumed 44 mmol) from Step A was taken up in THF (200 mL) and 2M lithium borohydride in THF (29 mL, 58 mmol) was added via syringe at room temperature. The reaction was stirred for 2 days at room temperature and t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | Other | C1CCOC1 | null | 48 | COC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bd35abee2ce4dad988436debf719e15 | CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1 | C(C)N(CC)CC.OCC1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([CH2:14][CH2:15][O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH:12]=[O:13])([CH2:14][CH2:15][O:16][Si:17]([C... | CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1 | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCNCC1 | [C:1]-[C:2](-[C:3])(-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6]>>[C:1]-[C:2](-[C:3])(-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6] | 89.2 | [{"value": 89.2, "product": "C(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of oxalyl chloride (3.3 mL, 38 mmol) in methylene chloride (500 mL) at −70° C. was added DMSO (5.4 mL, 76 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-hydroxymethyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (7.1 g, 19 mmol) in methylene chloride (125 mL) was slowly a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | O.C(Cl)Cl | null | 0.25 | CC(C)(C)OC(=O)N1CCC(CO)(CCO[Si](C)(C)C(C)(C)C)CC1>O.C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f72326cb43594b419689d372b0652184 | CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1>>CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | C([O-])(O)=O.[Na+].C[Li].C(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C.C[Li]>>OC(C)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C | [CH:2](=[O:3])[C:4]1([CH2:5][CH2:6][O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1>>[CH3:1][CH:2]([OH:3])[C:4]1([CH2:5][CH2:6][O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16... | CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1 | CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1CCOC1.CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | C1CCNCC1 | [C:1]-[C:2](-[C:3])(-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6]>>[C:1]-[C:2](-[C:3])(-[CH;D3;+0:4](-[C;D1;H3:7])-[OH;D1;+0:5])-[C:6] | null | [] | null | null | 2 | HOUR | To a solution of tert-butyl 4-formyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.3 g, 17 mmol) in THF (170 mL) at −70° C. was added 1.4M methyl lithium in ether (13.3 mL, 19 mmol). After 2 h, an additional amount of 1.4M methyl lithium in ether (2.5 mL) was added. After an additional 30 min, t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1CC[NH]CC1 | Other | C1CCOC1.CCOCC | null | 2 | CC(C)(C)OC(=O)N1CCC(C=O)(CCO[Si](C)(C)C(C)(C)C)CC1>C1CCOC1.CCOCC>CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f33fd77764b4fe7a6059f8325c13e1b | CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1>>CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | C(C)N(CC)CC.OC(C)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C | [CH3:1][CH:2]([OH:3])[C:4]1([CH2:5][CH2:6][O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1>>[CH3:1][C:2](=[O:3])[C:4]1([CH2:5][CH2:6][O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][... | CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | C1CCNCC1 | [C:1]-[C:2](-[C:3])(-[CH;D3;+0:4](-[C;D1;H3:5])-[OH;D1;+0:6])-[C:7]>>[C:1]-[C:2](-[C:3])(-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;H0;D1;+0:6])-[C:7] | 68.6 | [{"value": 68.6, "product": "C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of oxalyl chloride (3.0 mL, 34 mmol) in methylene chloride (400 mL) at −70° C. was added DMSO (4.8 mL, 68 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.6 g, 17 mmol) in methylene chloride (125 mL) was sl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CC[NH]CC1 | null | O.C(Cl)Cl | null | 0.25 | CC(O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1>O.C(Cl)Cl>CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25b347290fcb4197b31ab076516a514a | CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1.O=CCc1ccccc1>>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1 | [Cl-].[NH4+].C1(=CC=CC=C1)CC=O.C(C)(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C.CN(C)P(=O)(N(C)C)N(C)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>C1(=CC=CC=C1)CC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])([C:22](=[O:23])[CH3:24])[CH2:34][CH2:35]1.[CH:25](=[O:26])[CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])... | CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1.O=CCc1ccccc1 | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1 | null | null | C1CCOC1.CCOCC | C-C Coupling | OtherReaction | d08eb7b2615717189cce315501bb2cfa7ee3668e6d8eaa24218b092d1454a850 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | O=C(CCCc1ccccc1)C1CCNCC1 | [C:1]-[C:2](-[CH3;D1;+0:3])=[O;D1;H0:4].[O;H0;D1;+0:5]=[CH;D2;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:3]-[CH;D3;+0:6](-[OH;D1;+0:5])-[C:7]-[c:8] | null | [] | null | null | 1 | HOUR | To a solution of tert-butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (4.6 g, 12 mmol) in THF (120 mL) at −70° C. was added HMPA (20.7 mL, 120 mmol) and 1M LHMDS in THF (12 mL, 12 mmol). After 1 h, phenylacetaldehyde (5.7 g, 48 mmol) was added in THF (80 mL) over 10 min and the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | null | null | C1CC[NH]CC1.c1ccccc1 | null | C1CCOC1.CCOCC | null | 1 | CC(=O)C1(CCO[Si](C)(C)C(C)(C)C)CCN(C(=O)OC(C)(C)C)CC1.O=CCc1ccccc1>C1CCOC1.CCOCC>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ad6df59fec94b07b829b6f097e8956d | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1>>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1 | C1(=CC=CC=C1)CC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C)O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C1(=CC=CC=C1)CC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])([C:22](=[O:23])[CH2:24][CH:25]([OH:26])[CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[CH2:34][CH2:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[... | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1 | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1 | null | null | C(Cl)Cl.CCOCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CC(=O)C1CCNCC1)Cc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[c:8]>>[C:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[c:8] | 69.5 | [{"value": 69.5, "product": "C1(=CC=CC=C1)CC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of tert-butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (494 mg, 0.98 mmol) from Step F in methylene chloride (10 mL) at room temperature was added Dess-Martin reagent (621 mg, 1.5 mmol). After 3 h, the reaction was diluted with ether and quenc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CC[NH]CC1.c1ccccc1 | null | C(Cl)Cl.CCOCC | null | 3 | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(O)Cc2ccccc2)CC1>C(Cl)Cl.CCOCC>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1cbf72bde5741aa9e5793f4199bac7c | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1.NN>>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1 | C1(=CC=CC=C1)CC(CC(=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CCO[Si](C)(C)C(C)(C)C)=O.O.NN>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO[Si](C)(C)C(C)(C)C | O=[C:22]([C:11]1([CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:35][CH2:34]1)[CH2:23][C:24](=O)[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[NH2:32][NH2:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[... | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1.NN | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 96717cf3e91d029570228ab77c24b1373a8a647af1e168bf2ca95f0bd5bf6ad5 | d14f370ee7ee5e4a5c5c7412f191c74a005faab09898998e0db4b3670a6f4f81 | c1ccc(Cc2cc(C3CCNCC3)[nH]n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[C:4]-[c:5])-[C:6](-[C:7])(-[C:8])-[C:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[C:8]-[C:6](-[C:7])(-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[c:5]):[n;H0;D2;+0:10]:[nH;D2;+0:11]:1)-[C:9] | 71.5 | [{"value": 71.5, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of tert-butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (343 mg, 0.68 mmol) from Step G in ethanol (7 mL) was added hydrazine hydrate (0.040 mL, 0.82 mmol). The reaction was heated at 85° C. for 3 h and was then concentrated in vacuo. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ketone | null | null | c1cn[nH]c1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1 | HO- | C(C)O | 85 | null | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(C(=O)CC(=O)Cc2ccccc2)CC1.NN>C(C)O>CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22577971d76249afb71b0146d403c604 | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1>>CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO[Si](C)(C)C(C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO | CC(C)(C)[Si](C)(C)[O:14][CH2:13][CH2:12][C:11]1([c:15]2[cH:16][c:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[n:25][nH:26]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28][CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][CH2:13][OH... | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1 | CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1 | null | null | C1CCOC1.C(C)(=O)OCC | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(Cc2cc(C3CCNCC3)[nH]n2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 66.2 | [{"value": 66.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-(tert-butoxycarbonyl)-4-(2-tert-butyldimethylsilyloxyeth-1-yl)-4-(3-benzyl-(1H)-pyrazol-5-yl)piperidine (243 mg, 0.49 mmol) from Step H in THF (5 mL) was added 1M tetrabutylammonium fluoride in THF (0.63 mL, 0.63 mmol). The reaction was stirred at room temperature for 1 h and was then diluted with et... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1 | Other | C1CCOC1.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N1CCC(CCO[Si](C)(C)C(C)(C)C)(c2cc(Cc3ccccc3)n[nH]2)CC1>C1CCOC1.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23fa4558efeb46a98b4c522d23affa0c | CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1>>CC(C)(C)OC(=O)N1CCC2(CC1)CCn1nc(Cc3ccccc3)cc12 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C1=CC(=NN1)CC1=CC=CC=C1)CCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)/N=N/C(=O)OCC>>C(C)(C)(C)OC(=O)N1CCC2(CCN3N=C(C=C32)CC3=CC=CC=C3)CC1 | O[CH2:15][CH2:14][C:11]1([c:27]2[nH:16][n:17][c:18]([CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[CH2:14][CH2:15][n:16]1... | CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1 | CC(C)(C)OC(=O)N1CCC2(CC1)CCn1nc(Cc3ccccc3)cc12 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 833218c7f4017c2be13a67b7225b7323c9da4df321a97231afa48998818e7315 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | c1ccc(Cc2cc3n(n2)CCC32CCNCC2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[nH;D2;+0:8]:1>>[#7;a:7]1:[c:6]:[c:5]:[c:4]2:[n;H0;D3;+0:8]:1-[CH2;D2;+0:1]-[C:2]-[C:3]-2 | 85 | [{"value": 85.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CCN3N=C(C=C32)CC3=CC=CC=C3)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyeth-1-yl)-4-(3-benzyl-(1H)-pyrazol-5-yl)piperidine (125 mg, 0.32 mmol) from Step I in THF (4 mL) at 0° C. was added triphenylphosphine (85 mg, 0.32 mmol) and DEAD (0.051 mL, 0.32 mmol). The reaction was stirred for 20 min and was then allowed to warm to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1cn[nH]c1 | c1cc2n(n1)CCC21CC[NH]CC1 | c1cc2n(n1)CCC21CC[NH]CC1.c1ccccc1 | HO- | C1CCOC1 | null | 0.333333 | CC(C)(C)OC(=O)N1CCC(CCO)(c2cc(Cc3ccccc3)n[nH]2)CC1>C1CCOC1>CC(C)(C)OC(=O)N1CCC2(CC1)CCn1nc(Cc3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a5cb637174d4ad49a54d0c4b3153ed7 | C=C(COC(C)=O)C[Si](C)(C)C.COC(=O)/C=C/c1cccc(F)c1>>C=C1C[C@@H](C(=O)OC)[C@H](c2cccc(F)c2)C1 | FC=1C=C(/C=C/C(=O)OC)C=CC1.C(C)(=O)OCC(=C)C[Si](C)(C)C>>C=C1C[C@H]([C@@H](C1)C(=O)OC)C1=CC(=CC=C1)F | CC(=O)O[CH2:3][C:2](=[CH2:1])[CH2:17][Si](C)(C)C.[CH:4](\[C:5](=[O:6])[O:7][CH3:8])=[CH:9]/[c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1>>[CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[O:7][CH3:8])[C@H:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]2)[CH2:17]1 | C=C(COC(C)=O)C[Si](C)(C)C.COC(=O)/C=C/c1cccc(F)c1 | C=C1C[C@@H](C(=O)OC)[C@H](c2cccc(F)c2)C1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(CCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | a760b47d5c9f87e43eb85d2a7bf6ac4fc7baa2780167d2a6ed0d04254a77a67a | 2fba473587163766819c8b06dbebd40b4bfa0901fa09bca7745f4d7d9635e563 | C=C1CC[C@H](c2ccccc2)C1 | C-C(=O)-O-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[CH2;D2;+0:4]-[Si](-C)(-C)-C.[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])/[CH;D2;+0:9]=[CH;D2;+0:10]/[c:11](:[c:12]):[c:13]>>[C;D1;H2:3]=[C:2]1-[CH2;D2;+0:4]-[C@@H;D3;+0:10](-[c:11](:[c:12]):[c:13])-[C@H;D3;+0:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C;D1;H3:5])-[CH2;D2;+0:1]-1 | 83.9 | [{"value": 83.9, "product": "C=C1C[C@H]([C@@H](C1)C(=O)OC)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of methyl trans-3-fluorocinnamate (41.25 g, 229 mmol), tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mmol), 1,2-bis(diphenylphosphino)ethane (5.5 g, 13.7 mmol), and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (42.66 g, 229 mmol) in THF (300 mL) under nitrogen was heated to reflux for 6 h and then... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Silyl protective group | Ester | null | C1CCCC1 | C1CCCC1.c1ccccc1 | HO- | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(CCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1.CCCCCC | null | 16 | C=C(COC(C)=O)C[Si](C)(C)C.COC(=O)/C=C/c1cccc(F)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(CCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1.CCCCCC>C=C1C[C@@H](C(=O)OC)[C@H](c2cccc(F)c2)C... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e31142420d854a6b93bb0fdda233b4cb | BrCC1CC1.CCOP(=O)(CC(=O)OCc1ccc(OC)cc1)OCC>>CCOP(=O)(OCC)C(CC1CC1)C(=O)OCc1ccc(OC)cc1 | BrCC1CC1.[H-].[Na+].COC1=CC=C(COC(CP(=O)(OCC)OCC)=O)C=C1.C([O-])(O)=O.[Na+]>>COC1=CC=C(COC(C(CC2CC2)P(=O)(OCC)OCC)=O)C=C1 | Br[CH2:10][CH:11]1[CH2:12][CH2:13]1.[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH2:9][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH:11]1[CH2:12][CH2:13]1)[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:1... | BrCC1CC1.CCOP(=O)(CC(=O)OCc1ccc(OC)cc1)OCC | CCOP(=O)(OCC)C(CC1CC1)C(=O)OCc1ccc(OC)cc1 | null | null | C(C)OCC.CN(C)C=O | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C(CCC1CC1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#8:5]-[#15:6](-[#8:7])(=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[#8:5]-[#15:6](-[#8:7])(=[O;D1;H0:8])-[CH;D3;+0:9](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | 60.9 | [{"value": 60.9, "product": "COC1=CC=C(COC(C(CC2CC2)P(=O)(OCC)OCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of 60% sodium hydride in mineral oil (0.840 g, 21.0 mmol) in DMF (100 mL) was added a solution of 2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester (6.04 g, 19.1 mmol) from Step A in DMF (10 mL). The reaction mixture was stirred for 30 min at room temperature. Bromomethylcyclopropane (2.4 mL, 24.8... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | C1CC1.c1ccccc1 | HBr | C(C)OCC.CN(C)C=O | null | 0.5 | BrCC1CC1.CCOP(=O)(CC(=O)OCc1ccc(OC)cc1)OCC>C(C)OCC.CN(C)C=O>CCOP(=O)(OCC)C(CC1CC1)C(=O)OCc1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4f5c73c0baa450b83cabe4ac2020d77 | BrCc1ccccc1.C=C1C[C@@H](CO)[C@H](c2cccc(F)c2)C1>>C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 | OC[C@H]1[C@@H](CC(C1)=C)C1=CC(=CC=C1)F.C(C1=CC=CC=C1)Br.[H-].[Na+]>>C(C1=CC=CC=C1)OC[C@@H]1[C@H](CC(C1)=C)C1=CC(=CC=C1)F | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH2:1]=[C:2]1[CH2:3][C@@H:4]([CH2:5][OH:6])[C@H:14]([c:15]2[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]2)[CH2:22]1>>[CH2:1]=[C:2]1[CH2:3][C@H:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@@H:14]([c:15]2[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]2)[CH... | BrCc1ccccc1.C=C1C[C@@H](CO)[C@H](c2cccc(F)c2)C1 | C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 | null | null | CN(C)C=O.CCOCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C=C1C[C@H](COCc2ccccc2)[C@@H](c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 90.4 | [{"value": 90.4, "product": "C(C1=CC=CC=C1)OC[C@@H]1[C@H](CC(C1)=C)C1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of (+)-trans-1-hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane (5.0 g, 26.5 mmol) from Example 1, Step C and benzyl bromide (4.7 mL, 40 mmol) in DMF (130 mL) was added 60% sodium hydride in mineral oil (0.77 g, 32 mmol). The reaction was stirred at room temperature for 24 h was then diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CCCC1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O.CCOCC | null | 24 | BrCc1ccccc1.C=C1C[C@@H](CO)[C@H](c2cccc(F)c2)C1>CN(C)C=O.CCOCC>C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36b5e5b058cd4a5891c61b3f493afe55 | C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1.CO>>O=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 | C(C1=CC=CC=C1)OC[C@@H]1[C@H](CC(C1)=C)C1=CC(=CC=C1)F.CO>>C(C1=CC=CC=C1)OC[C@H]1CC(C[C@@H]1C1=CC(=CC=C1)F)=O | C=[C:2]1[CH2:3][C@H:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@@H:14]([c:15]2[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]2)[CH2:22]1.C[OH:1]>>[O:1]=[C:2]1[CH2:3][C@H:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@@H:14]([c:15]2[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]2)[CH2:22... | C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1.CO | O=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 88ae21c3f20673f4bc27c05c339b079cc70654b9dd7997b20f5f5e7ab29d07c2 | b3f3e066e03c3af32b607e16083a7c1c9ca6bb82423de27d41bf12513c20f16d | O=C1C[C@H](COCc2ccccc2)[C@@H](c2ccccc2)C1 | C-[OH;D1;+0:1].C=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1 | null | [] | null | null | 10 | MINUTE | A solution of 1-(S)-benzyloxymethyl-2-(S)-(3-fluorophenyl)-4-methylenecyclopentane from Step A (7.1 g, 25.5 mmol) in methanol (300 mL) was cooled in a dry ice/acetone bath and ozone was bubbled into the solution until the blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethylsulf... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Methanol | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccccc1.c1ccccc1 | Other | null | null | 0.166667 | C=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1.CO>>O=C1C[C@H](COCc2ccccc2)[C@@H](c2cccc(F)c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9a34e53b9a1434693a6a7c389a733f1 | COC(OC)N(C)C.O=C(Cc1ccc(Cl)cc1)c1ccc(Cl)cc1Cl>>CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 | ClC1=C(C=CC(=C1)Cl)C(=O)CC1=CC=C(C=C1)Cl.COC(N(C)C)OC>>CN(C=C(C(=O)C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl)C | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH2:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1 | COC(OC)N(C)C.O=C(Cc1ccc(Cl)cc1)c1ccc(Cl)cc1Cl | CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | [CH]=C(C(=O)c1ccccc1)c1ccccc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:6](=[O;D1;H0:5])-[c:7])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | A solution of 4-chlorobenzyl 2,4-dichlorophenyl ketone (4.5 g, 14.4 mmol) and dimethyl-formamide dimethylacetal (7.7 mL, 58 mmol) in DMF (60 mL) was heated at 75° C. for 20 h. The volatiles were removed in vacuo to provide the crude product which was used directly in the next step. HPLC/MS: 354 (M+1), 356 (M+3); Rt=3.4... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | COC(OC)N(C)C.O=C(Cc1ccc(Cl)cc1)c1ccc(Cl)cc1Cl>CN(C)C=O>CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69b20dddb4ce4c1fbef670bef6b342b4 | CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O | CN(C=C(C(=O)C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl)C.C(#N)CC(=O)N.CO.[H-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=C(C=C(C(N1)=O)C#N)C1=CC=C(C=C1)Cl | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=O)[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]1[Cl:21].[N:1]#[C:2][CH2:3][C:23]([NH2:22])=[O:24]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]2[Cl:21]... | CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 60e6cdceb0baa245fe4412e5afd8e8b3b5ab470991e8279dcbe754fb697cedb2 | 9bf1fd3c6bd3248cd0029464a9f1478a19f5ad042fa396153933395993aab801 | O=c1ccc(-c2ccccc2)c(-c2ccccc2)[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[Cl;D1;H0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[N;D1;H0:15]#[C:16]-[CH2;D2;+0:17]-[C;H0;D3;+0:18](-[NH2;D1;+0:19])=[O;D1;H0:20]>>[Cl;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[nH;D2;+0:19]:[c;H0;... | null | [] | 95 | CELSIUS | null | null | A solution of 3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one (14.4 mmol assumed) from Step A, cyanoacetamide (1.33 g, 15.8 mmol), and methanol (1.3 mL, 32 mmol) in DMF (35 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil) (1.45 g, 36 mmol) in DMF (16 mL) at rt. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 95 | null | CN(C)C=C(C(=O)c1ccc(Cl)cc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O>CN(C)C=O>N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c15f147adfaa4abe825a35be35b3fb8b | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O.O=C(CCl)c1ccccc1>>Nc1c(C(=O)c2ccccc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | ClC1=C(C=CC(=C1)Cl)C1=C(C=C(C(N1)=O)C#N)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[Cs+].[Cs+].ClCC(=O)C1=CC=CC=C1>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)C2=CC=CC=C2 | [N:1]#[C:2][c:33]1[c:13](=[O:12])[nH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]2[Cl:23])[c:24](-[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[cH:32]1.Cl[CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[o:12][c:1... | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O.O=C(CCl)c1ccccc1 | Nc1c(C(=O)c2ccccc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1c3dde6f8fb234f99de372746776db1852e1e639963c229bf01260e389d5e88d | 481fee288c2b1a3101ebae707e584a0e925bd48483299d9da5a41b1420634672 | O=C(c1ccccc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[c:11]):[nH;D2;+0:12]:[c;H0;D3;+0:13]:1=[O;H0;D1;+0:14]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[c:10](-[c:11]):[n;H0;D2;+0:12]:[c;H0;D3;+0:13]:2:[o;H0;D2;+0:14]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | 16 | HOUR | A solution of the product from Step B (0.300 g; 0.8 mmol) in DMP (8 mL) was treated with cesium carbonate (0.521 g; 1.6 mmol), 2-chloroacetophenone (0.124 g; 0.8 mmol), and stirred at room temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Nitrile | Ketone.Primary amine | c1cnccc1 | c1cnc2occc2c1 | c1ccccc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | null | null | 16 | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccc(Cl)cc2Cl)[nH]c1=O.O=C(CCl)c1ccccc1>>Nc1c(C(=O)c2ccccc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e87674c3aba466295873e89f7a3ec9d | CC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | ClC1=CC=C(C=C1)C=1C(=NC(=C(C#N)C1)OCC(C)=O)C1=C(C=C(C=C1)Cl)Cl.[O-]CC.[Na+]>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[Cl:16])[c:17](-[c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[cH:25][c:26]1[C:27]#[N:28]>>[CH3:1][C:2](=[O:3])[c:4]1[o:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]3[Cl:16])[c:17](-[c:18]3[cH... | CC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | afeb9d0652c7b91e28d2fc40e15810604a7053aaa837e966d0d1156989738b30 | 115ab1fe56a5ae93cee071ae15ca2fbb717f63761b06155835b0712a0ef50301 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]):[c:12]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[o;H0;D2;+0:5]:[c:6](:[#7;a:7]:[c:8]):[c:9](:[c:12]):[c;H0;D3;+0:10]:1-[NH2;D1;+0:11] | null | [] | null | null | null | null | A solution of the product from Step A (0.126 g; 0.292 mmol) in ethanol (4 mL) was treated with sodium ethoxide (0.040 g; 0.584 mmol) and stirred at reflux for 1 hour. The reaction was allowed to cool to room temperature and quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Nitrile | Ketone.Primary amine | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | C(C)O | null | null | CC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>C(C)O>CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c635e54935543898c0a9c00395ecef1 | CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCN(CC)CC.CS(=O)(=O)Cl>>CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N(S(C)(=O)=O)S(C)(=O)=O | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C)=O.CS(=O)(=O)Cl.C(C)N(CC)CC>>C(C)(=O)C1=C(C=2C(=NC(=C(C2)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)O1)N(S(=O)(=O)C)S(=O)(=O)C | [CH3:1][C:2](=[O:3])[c:4]1[o:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]3[Cl:16])[c:17](-[c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]3)[cH:25][c:26]2[c:27]1[NH2:28].CCN(CC)C[CH3:34].Cl[S:29]([CH3:30])(=[O:31])=[O:32]>>[CH3:1][C:2](=[O:3])[c:4]1[o:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c... | CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCN(CC)CC.CS(=O)(=O)Cl | CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N(S(C)(=O)=O)S(C)(=O)=O | null | null | C(Cl)Cl | Oxidation | OtherReaction | 28dc40e546c6cce7c71516552b4ad9521de3a79d04e582ba1e6a06d57c835550 | 2bb3125db569d4a0c90efcb3ae96ba2c88b9226c575694149f023fc9ffefbf6e | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;D1;H0:5].[#7;a:6]:[c:7]1:[#8;a:8]:[c:9](-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]):[c:13](-[NH2;D1;+0:14]):[c:15]:1>>[#7;a:6]:[c:7]1:[#8;a:8]:[c:9](-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]):[c:13](-[N;H0;D3;+0:14](-[#16:16](-[CH3;D1;+0:1])(=[O;D1;H0:17])... | null | [] | null | null | 2 | HOUR | A solution of 0.030 g (0.0696 mmol)of the product from Example 5 in CH2Cl2 (1 mL) cooled to 0° C. was treated with methanesulfonyl chloride (5 μL; 0.0696 mmol), followed by triethylamine (30 μL; 0.209 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine.Sulfonyl halide | Tertiary amine | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCN(CC)CC.CS(=O)(=O)Cl>C(Cl)Cl>CC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N(S(C)(=O)=O)S(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e05681d149548b4b3f14d7ef43684ef | CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>>CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)OCC.C(CO)(=O)OCC.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C=1C=C(C(=NC1C1=C(C=C(C=C1)Cl)Cl)OCC(=O)OCC)C#N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[o:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[cH:27][c:28]2[c:29]1[NH2:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:... | CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | c98c0adc09f6bda89fb656a6801ef398ca5e5ec0ef38903eb4c87a6f73f10b53 | d3ecc5cca77061b45721069d4e9a17b24829facb7c096d498f145e2b57bd7226 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[o;H0;D2;+0:6]:[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[c;H0;D3;+0:12]:1-[NH2;D1;+0:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[C;H0;D2;+0:12]#[N;H0;D1;+0:13]):[c:11] | null | [] | 80 | CELSIUS | 6 | HOUR | A solution of 1.55 g (3.93 mmol) of the product from Step A in toluene (20 mL) was treated with ethyl glycolate (0.41 mL; 4.33 mmol) and cesium carbonate (2.54 g; 7.8 mmol). The reaction mixture was heated in a sealed pressure tube at 80° C. and stirred for 6 h. The reaction mixture was cooled to room temperature and p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Ester.Ether.Nitrile | c1cnc2occc2c1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | 80 | 6 | CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>C1(=CC=CC=C1)C>CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18a54a893318434ebd0c2f0f966da44b | CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | C[Si](C)(C)[N-][Si](C)(C)C.[Li+].ClC1=CC=C(C=C1)C=1C=C(C(=NC1C1=C(C=C(C=C1)Cl)Cl)OCC(=O)OCC)C#N>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[c:19](-[c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[cH:27][c:28]1[C:29]#[N:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[o:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17... | CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 59bcb1d0292a9d6aab4c779dc11fad7b9f43062efa223c362ac1ee6a27f4c785 | 9dcfc7fb45090136d7ea5d1e73f2fc7bd6ce09ea58bac801b2d4160abff5cb53 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):[c:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[o;H0;D2;+0:6]:[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:13]):[c;H0;D3;+0:11]:1-[NH2;D1;+0:12] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of the product from Step B (0.130 g; 0.282 mmol) in THF (3 mL) cooled to 0° C. was treated with 1 M solution of lithium bis(trimethylsilyl)amide in THF (0.85 mL; 0.85 mmol) and stirred at 0° C. under nitrogen for 30 minutes. The reaction mixture was quenched at 0° C. with 10% aqueous NaHSO4 solution. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Nitrile | Ester.Primary amine | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | 0 | 0.5 | CCOC(=O)COc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>C1CCOC1>CCOC(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb04649c7f1948398453cc6289ed3098 | O=C(c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F)N1CCCCC1>>Nc1c(C(=O)N2CCCCC2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(C(F)(F)F)=O)C(=O)N2CCCCC2.C(=O)([O-])[O-].[K+].[K+]>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2N)C(=O)N2CCCCC2 | O=C(C(F)(F)F)[NH:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[o:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32][c:33]12>>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C... | O=C(c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F)N1CCCCC1 | Nc1c(C(=O)N2CCCCC2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | O=C(c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1)N1CCCCC1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#7;a:5]):[#8;a:6]:[c:7]:1-[C:8](-[#7:9])=[O;D1;H0:10]>>[#7:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:4](:[#7;a:5]):[c:3]:[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 35 mg of the product of Example 12 dissolved in 1 mL of methanol was treated with 41 mg of K2CO3 at 60° C. for 2 hours. The reaction mixture was then partitioned between EtOAc and water and the organic product was extracted. The extracts were dried (Na2SO4), filtered and evaporated in vacuo to afford to a... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | C1CC[NH]CC1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | Other | CO | null | null | O=C(c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F)N1CCCCC1>CO>Nc1c(C(=O)N2CCCCC2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abf83597ba6e4559a8be72219905d54c | CC(=O)Cl.CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>>CC(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | C(C)N(CC)CC.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O.C(C)(=O)Cl>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(C)=O)C(C(C)(C)C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[o:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]3[Cl:24])[c:25](-[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[cH:33][c:34]12>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([C... | CC(=O)Cl.CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | CC(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[#8;a:6]:[c:7](-[C:8]=[O;D1;H0:9]):[c:10](-[NH2;D1;+0:11]):[c:12]:1>>[#7;a:4]:[c:5]1:[#8;a:6]:[c:7](-[C:8]=[O;D1;H0:9]):[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:12]:1 | null | [] | null | null | 1 | HOUR | A solution of 0.050 g (0.106 mmol) of the product from Example 17 in CH2Cl2 (1 mL) at 0° C. was treated with acetyl chloride (8 μL; 0.106 mmol) followed by triethylamine (15 μL; 0.106 mmol). After the addition, the reaction mixture was warmed to RT and stirred for 1 hour. The reaction was quenched with saturated NaHCO3... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | CC(=O)Cl.CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>C(Cl)Cl>CC(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2815f51ce1f4e4fbbb926016cb5c247 | CC(C)(C)C(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CC(C)(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | C(C)N(CC)CC.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)C=2C=NC=CC2.CC(C(=O)Cl)(C)C>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(C(C)(C)C)=O)C(=O)C=2C=NC=CC2 | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[o:18][c:19]2[n:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]3[Cl:29])[c:30](-[c:31]3[cH:32][cH:33][c:34]([Cl:35])[cH:36][cH:37]3)[cH:38][c:39]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]... | CC(C)(C)C(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CC(C)(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1cccnc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[c:8]1:[#8;a:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13](-[NH2;D1;+0:14]):[c:15]:1>>[#7;a:7]:[c:8]1:[#8;a:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13](-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c... | null | [] | null | null | 16 | HOUR | A solution of 0.200 g (0.405 mmol) of the product from Example 26 in CH2Cl2 (4 mL) at 0° C. was treated with trimethylacetyl chloride (50 μL; 0.405 mmol) followed by triethylamine (113 μL; 0.810 mmol). After the addition, the reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction was que... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 16 | CC(C)(C)C(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>C(Cl)Cl>CC(C)(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b854e7dc2de4f828680e0b9d210b2fe | COC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>COC(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | C(C)(C)N(CC)C(C)C.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)C=2C=NC=CC2.ClC(=O)OC>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(OC)=O)C(=O)C=2C=NC=CC2 | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[o:16][c:17]2[n:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]3[Cl:27])[c:28](-[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[cH:36][c:37]12>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[c:7]([C:8](=[O:9]... | COC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | COC(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1cccnc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH2;D1;+0:12]):[c:13]:1>>[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4]):[c:13]:1 | null | [] | null | null | 16 | HOUR | A solution of 0.030 g (0.0607 mmol) of the product from Example 26 in CH2Cl2 (0.6 mL) at 0° C. was treated with methyl chloroformate (5 μL; 0.0607 mmol) followed by diisopropylethylamine (10 μL; 0.0607 mmol). After the addition, the reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccncc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 16 | COC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>C(Cl)Cl>COC(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-465b85b846ba480ab12263322a36681a | CN(C)S(=O)(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CN(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | [H-].[Na+].C1CCOC1.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)C=2C=NC=CC2.C1CCOC1.CN(S(=O)(=O)Cl)C>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(N(C)C)=O)C(=O)C=2C=NC=CC2 | O=S(Cl)([N:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][c:7]1[c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[o:17][c:18]2[n:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]3[Cl:28])[c:29](-[c:30]3[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]3)[cH:37][c:38]12>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[NH:6][c:7]... | CN(C)S(=O)(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CN(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Acylation | OtherReaction | 6c16e9e6c124c414c1ad4cacebf047406027aae7e5b317e16f63e05e6a23fab2 | 0759a3c95a8b36ced23f0830233262728dd65cae0539873906a2229ea157808c | O=C(c1cccnc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | Cl-S(=O)(=[O;H0;D1;+0:1])-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH2;D1;+0:12]):[c:13]:1>>[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH;D2;+0:12]-[C:14](=[O;H0;D1;+0:1])-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C;D1;H3:4]):[c:13]:1 | null | [] | 0 | CELSIUS | 30 | MINUTE | To a suspension of sodium hydride (0.004 g; 60% dispersion; 0.111 mmol) in THF (0.5 mL) at 0° C. was added a solution of 0.050 g 0.101 mmol) of the product from Example 26 (in THF (0.5 mL) and the reaction mixture was stirred at 0° C. for 30 minutes. Dimethylsulfamoyl chloride (9 μL; 0.101 mmol) was added dropwise and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Urea | null | null | c1ccncc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | null | 0 | 0.5 | CN(C)S(=O)(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CN(C)C(=O)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-670afcfaaaf549ff9091b4ef1486c46e | C1CC2CCC1CN2.CC(=O)Nc1c(C(=O)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CC(=O)Nc1c(C(=O)N2CC3CCC2CC3)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | C(C)(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)O.Cl.C12NCC(CC1)CC2.C(CCl)Cl.CN1CCOCC1>>C12N(CC(CC1)CC2)C(=O)C2=C(C=1C(=NC(=C(C1)C1=CC=C(C=C1)Cl)C1=C(C=C(C=C1)Cl)Cl)O2)NC(C)=O | [NH:9]1[CH2:10][CH:11]2[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]2.O[C:7]([c:6]1[c:5]([NH:4][C:2]([CH3:1])=[O:3])[c:38]2[c:18]([o:17]1)[n:19][c:20](-[c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]1[Cl:28])[c:29](-[c:30]1[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]1)[cH:37]2)=[O:8]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6](... | C1CC2CCC1CN2.CC(=O)Nc1c(C(=O)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CC(=O)Nc1c(C(=O)N2CC3CCC2CC3)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 6a9cf6b8de28dd6c2a4b0ec408de367f03e79e81384ba9bc53d30df5e6067a68 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1)N1CC2CCC1CC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]:[#7;a:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11](-[C:12])-[C:13]>>[#7;a:7]:[c:6]:[#8;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C:9]-[C:8])-[C:11](-[C:12])-[C:13]):[c:4] | null | [] | null | null | 16 | HOUR | A solution of 0.027 g (0.0568 mmol) of the product from Step A in CH2Cl2 (0.6 mL) was treated with 2-azabicyclo[2.2.2]octane hydrochloride (0.009 g; 0.0625 mmol), EDC (0.016 g; 0.0852 mmol), DMAP (0.007 g; 0.0568 mmol), and 1-methylmorpholine (19 μL; 0.170 mmol), then stirred at room temperature for 16 hours. The react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CC2CCC1CN2 | C1CC2CCC1C[NH]2 | c1cnc2occc2c1.c1ccccc1.c1ccccc1.C1CC2CCC1C[NH]2 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 16 | C1CC2CCC1CN2.CC(=O)Nc1c(C(=O)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(=O)Nc1c(C(=O)N2CC3CCC2CC3)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-679402d1219b469b81cbcf32fa23699d | CN(C(=O)C(F)(F)F)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2N(C(C(F)(F)F)=O)C)C(C(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC)C(C(C)(C)C)=O | O=C(C(F)(F)F)[N:2]([CH3:1])[c:3]1[c:4]([C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[o:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[c:23](-[c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[cH:31][c:32]12>>[CH3:1][NH:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[o:1... | CN(C(=O)C(F)(F)F)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | CO.O | Reduction | Hydrogenolysis of tertiary amines | 16961a3d99942c0ab361f2149cf4766848c112f4d4d9e5e515a20194fa44ecb0 | 9d0759623d33e2d41aafe1af3bb1025d4d7a88f20060c872279b889c110cab65 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4]:[c:5](:[#7;a:6]):[#8;a:7]:[c:8]:1-[C:9]=[O;D1;H0:10]>>[#7;a:6]:[c:5]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:3](-[NH;D2;+0:1]-[C;D1;H3:2]):[c:4]:1 | null | [] | null | null | null | null | A solution of the product from Step A (0.0703 mmol) in methanol (2 mL) and water (0.1 mL) was treated with potassium carbonate (0.049 g; 0.351 mmol) at room temperature. The reaction mixture was stirred a room temperature until the reaction was judged complete by TLC analysis. The reaction mixture was then partitioned ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Tertiary amide | Secondary amine | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | Other | CO.O | null | null | CN(C(=O)C(F)(F)F)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>CO.O>CNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3e770690d984187be9a3bc66ad344d0 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CI.CN(C)C=O>>CN(C)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | IC.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O.[H-].[Na+].CN(C)C=O>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2N(C)C)C(C(C)(C)C)=O | [NH2:2][c:4]1[c:5]([C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[o:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32][c:33]12.I[CH3:1].CN(C=O)[CH3:3]>>[CH3:1][N:2]([CH3:3])[c:4]1[c:5]([C:6](=[O:7])[C:8]([CH3:9])([CH3:10]... | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CI.CN(C)C=O | CN(C)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49e97dc5c4663bf1af5b9459b20429dc1c61d967c03ec2264af690226d29471e | 6e9cf66e5c33b8adfc96ab6ca734f2e68e464a4b02d1a8813c05c370f4bc819a | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-N(-[CH3;D1;+0:1])-C=O.I-[CH3;D1;+0:2].[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[NH2;D1;+0:10]):[c:11]:1>>[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[N;H0;D3;+0:10](-[CH3;D1;+0:2])-[CH3;D1;+0:1]):[c:11]:1 | null | [] | 0 | CELSIUS | 20 | MINUTE | A solution of 0.050 g (0.106 mmol) of the product from Example 17 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.010 g; 60% dispersion; 0.232 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (26 μL; 0.424 mmol). The reaction was warmed to ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | Tertiary amine | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HI | null | 0 | 0.333333 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CI.CN(C)C=O>>CN(C)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ab14d756ba14936bc6b2f503da78bc2 | CI.CN(C)C=O.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CN(C)c1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | IC.NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(=O)C=2C=NC=CC2.[H-].[Na+].CN(C)C=O>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2N(C)C)C(=O)C=2C=NC=CC2 | I[CH3:1].CN(C=O)[CH3:3].[NH2:2][c:4]1[c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[o:14][c:15]2[n:16][c:17](-[c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]3[Cl:25])[c:26](-[c:27]3[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]3)[cH:34][c:35]12>>[CH3:1][N:2]([CH3:3])[c:4]1[c:5]([C:6](=[O:7])[c:8]2[cH:9][cH... | CI.CN(C)C=O.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CN(C)c1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49e97dc5c4663bf1af5b9459b20429dc1c61d967c03ec2264af690226d29471e | 6e9cf66e5c33b8adfc96ab6ca734f2e68e464a4b02d1a8813c05c370f4bc819a | O=C(c1cccnc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | C-N(-[CH3;D1;+0:1])-C=O.I-[CH3;D1;+0:2].[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[NH2;D1;+0:10]):[c:11]:1>>[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[N;H0;D3;+0:10](-[CH3;D1;+0:2])-[CH3;D1;+0:1]):[c:11]:1 | null | [] | 0 | CELSIUS | 20 | MINUTE | A solution of 0.050 g (0.101 mmol) of the product from Example 26 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.008 g; 60% dispersion; 0.213 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (19 μL; 0.303 mmol). The reaction was warmed to ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | Tertiary amine | null | null | c1ccncc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HI | null | 0 | 0.333333 | CI.CN(C)C=O.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CN(C)c1c(C(=O)c2cccnc2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-537916f9a3f54e7cb12f121d01c3fc54 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCBr>>CCNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O.C(C)Br>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NCC)C(C(C)(C)C)=O | [NH2:3][c:4]1[c:5]([C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[o:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32][c:33]12.Br[CH2:2][CH3:1]>>[CH3:1][CH2:2][NH:3][c:4]1[c:5]([C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11... | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCBr | CCNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[NH2;D1;+0:10]):[c:11]:1>>[#7;a:3]:[c:4]1:[#8;a:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:11]:1 | null | [] | null | null | null | null | Using the procedure described in Example 39, the product of Example 17 was reacted with one equivalent of ethyl bromide to afford the title compound. HPLC/MS: 500.9 (M+1), 502.9 (M+3); Rt=4.08 min.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.CCBr>>CCNc1c(C(=O)C(C)(C)C)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b22fb182a5a04572853f4b28447fe852 | N#CCOc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>N#Cc1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | ClC1=CC=C(C=C1)C=1C(=NC(=C(C#N)C1)OCC#N)C1=C(C=C(C=C1)Cl)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1CCOC1>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C#N | [N:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[Cl:15])[c:16](-[c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[cH:24][c:25]1[C:26]#[N:27]>>[N:1]#[C:2][c:3]1[o:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[Cl:15])[c:16](-[c:17]3[cH:18][cH:19][c:20]([C... | N#CCOc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | N#Cc1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 310e82a1a04ad8be5cc811c019c822a32b44ad18376ea0176a8296685624b50f | 1840d341887117642bffcff327c44a81dcd63e1f29237a5b99bb06120b967248 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [N;D1;H0:1]#[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[#7;a:6]:[c:7]):[c:8](-[C;H0;D2;+0:9]#[N;H0;D1;+0:10]):[c:11]>>[N;D1;H0:1]#[C:2]-[c;H0;D3;+0:3]1:[o;H0;D2;+0:4]:[c:5](:[#7;a:6]:[c:7]):[c:8](:[c:11]):[c;H0;D3;+0:9]:1-[NH2;D1;+0:10] | null | [] | 0 | CELSIUS | 15 | MINUTE | A solution of the product from Step A (0.132 g; 0.319 mmol) in TB (3 mL) cooled to 0° C. was treated with 1 M solution of lithium bis(trimethylsilyl)amide in THF (701 μL; 0.701 mmol) and stirred at 0° C. under nitrogen for 15 minutes. The reaction mixture was warmed to room temperature and then stirred for an additiona... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Primary amine | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | null | 0 | 0.25 | N#CCOc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>N#Cc1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f47096e8f5d1498496da5e56b2bf7d62 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.O=C(Cl)CCCCl>>CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O.ClCCCC(=O)Cl.C(C)N(CC)CC>>ClCCCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[cH:28][c:29]2[c:30]1[NH2:31].Cl[C:32](=[O:33])[CH2:34][CH2:35][CH2:36][Cl:37]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]... | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.O=C(Cl)CCCCl | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH2;D1;+0:12]):[c:13]:1>>[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:13]:1 | null | [] | null | null | 1.5 | HOUR | To a magnetically stirred solution of 0.300 g (0.63 mmol) of the product of Example 17 in 6 mL of CH2Cl2 at 0° C. was added 70 μL (0.63 mmol) of 4-chlorobutyryl chloride and 96 mg (0.95 mmol) of triethylamine. The reaction was stirred for 1.5 h and allowed to warm to room temperature. The reaction mixture was then part... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1.5 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N.O=C(Cl)CCCCl>C(Cl)Cl>CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06ce1654413a4001b8df472ef7bcb703 | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl>>CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N1CCCC1=O | [H-].[Na+].ClCCCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)C)=O>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2N2C(CCC2)=O)C(C(C)(C)C)=O | Cl[CH2:32][CH2:33][CH2:34][C:35]([NH:31][c:30]1[c:7]([C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[cH:28][c:29]21)=[O:36]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[o:8][... | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N1CCCC1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 62f43057f012567ee0d9bea97538013537b046013f70e56d5406a05691c3dc0d | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCN1c1coc2nc(-c3ccccc3)c(-c3ccccc3)cc12 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9](:[#7;a:10]):[#8;a:11]:[c:12]:1-[C:13]=[O;D1;H0:14]>>[#7;a:10]:[c:9]1:[#8;a:11]:[c:12](-[C:13]=[O;D1;H0:14]):[c:7](-[N;H0;D3;+0:6]2-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-2=[O;D1;H0:5]):[c:8]:1 | null | [] | 60 | CELSIUS | null | null | To a magnetically stirred suspension of 7 mg (0.173 mmol) of sodium hydride in 1 mL THF was slowly added 0.100 g (0.173 mmol) of the product of Example 47 dissolved in 1 mL of THF. After 15 min the addition was complete and the reaction mixture was stirred and heated to 60° C. for 3.5 h. The reaction was then cooled to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | C1CC[NH]C1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | HCl | C1CCOC1 | 60 | null | CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CCCCl>C1CCOC1>CC(C)(C)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N1CCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b9d55aab8b243c5a6fc73781db5ccd2 | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>>CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)O)=O.C(C)(=O)OCC(=O)Cl.C(C)#N>>C(C)(=O)OCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)O)=O | Cl[C:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])=[O:7].[NH2:8][c:9]1[c:10]([C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[OH:16])[o:17][c:18]2[n:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]3[Cl:28])[c:29](-[c:30]3[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]3)[cH:37][c:38]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O... | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[#7;a:8]:[c:9]1:[#8;a:10]:[c:11](-[C:12]=[O;D1;H0:13]):[c:14](-[NH2;D1;+0:15]):[c:16]:1>>[#7;a:8]:[c:9]1:[#8;a:10]:[c:11](-[C:12]=[O;D1;H0:13]):[c:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c... | null | [] | null | null | null | null | The product of Step B (0.120 g; 0.253 mmol) and acetoxyacetyl chloride (0.11 mL; 1.01 mmol) were added to 2 mL of acetonitrile and stirred at room temperature. After 50 minutes the reaction mixture was diluted with ethyl acetate and washed two times with aqueous sodium bicarbonate. The organic layer was dried over sodi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | null | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>C(C)(=O)OCC>CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d44fccaefc041d68a448a30ecfbc9e3 | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>>CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO | [OH-].[Li+].O.C(C)(=O)OCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=C(C=C2)Cl)Cl)C(C(C)(C)O)=O.CO>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2NC(CO)=O)C(C(C)(C)O)=O | CC(=O)[O:35][CH2:34][C:32]([NH:31][c:30]1[c:7]([C:5]([C:2]([CH3:1])([CH3:3])[OH:4])=[O:6])[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[cH:28][c:29]21)=[O:33]>>[CH3:1][C:2]([CH3:3])([OH:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:... | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO | null | null | C1CCOC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]:[c:7]:[#8;a:8]>>[#8;a:8]:[c:7]:[c:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | Lithium hydroxide-H2O (0.004 g; 0.174 mmol), the product of Step C (0.100 g; 0.174 mmol), and methanol (0.3 mL) were combined in 2 mL of THF and stirred at room temperature. The reaction was monitored by TLC until complete at which point the reaction was quenched by addition of 0.50 mL of acetic acid. The reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | null | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12>C1CCOC1>CC(C)(O)C(=O)c1oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56f0e6a441a9460baf2227bb5042856e | COC(=O)C(Oc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N)c1ccc(F)c(F)c1>>COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O | ClC1=CC=C(C=C1)C=1C=C(C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(C(=O)OC)C1=CC(=C(C=C1)F)F)C#N.C1CCOC1.C1CCOC1.C[Si](C)(C)[NH-].C[Si](C)(C)[NH-].[Li+].[Li+]>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(C2=O)(C(=O)OC)C2=CC(=C(C=C2)F)F | N#[C:36][c:35]1[c:15]([O:14][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]2[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[cH:13]2)[n:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]2[Cl:25])[c:26](-[c:27]2[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]2)[cH:34]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([c:6]2[cH:7][cH:8][c:9]([F:10])... | COC(=O)C(Oc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N)c1ccc(F)c(F)c1 | COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0d978b6e4b9400ed54bef533c5e070747a1a63797d169cd81c7d0830df3f18b2 | 6372e17458037521a28318b54428d2d0705ec274dc001be8d214e49aaab58744 | O=C1c2cc(-c3ccccc3)c(-c3ccccc3)nc2OC1c1ccccc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[#8:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[c:11](:[c:12]):[c:13]):[#7;a:14]:[c:15]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:6]1(-[c:11](:[c:12]):[c:13])-[#8:5]-[c:4](:[#7;a:14]:[c:15]):[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[O;D1;H0:16] | null | [] | null | null | 30 | MINUTE | To a magnetically stirred solution of 1.20 g (2.14 mmol) the product of Step A dissolved in 12 mL of THF was slowly added 3.2 mL of a 1.0 N solution (3.2 mmol) of lithium bis(trimethylsilylamide) in THF at 0° C. The reaction mixture was stirred for 30 min and allowed to warm to room temperature. The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Nitrile | Ketone | null | c1cnc2c(c1)CCO2 | c1ccccc1.c1cnc2c(c1)CCO2.c1ccccc1.c1ccccc1 | null | null | null | 0.5 | COC(=O)C(Oc1nc(-c2ccc(Cl)cc2Cl)c(-c2ccc(Cl)cc2)cc1C#N)c1ccc(F)c(F)c1>>COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e1c4faac4c241878ca727421cfe449d | COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O>>Oc1c(-c2ccc(F)c(F)c2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(C2=O)(C(=O)OC)C2=CC(=C(C=C2)F)F.[BH4-].[Na+]>>ClC1=CC=C(C=C1)C=1C=C2C(=NC1C1=C(C=C(C=C1)Cl)Cl)OC(=C2O)C2=CC(=C(C=C2)F)F | COC(=O)[C:3]1([c:4]2[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[cH:11]2)[C:2](=[O:1])[c:33]2[c:13]([n:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32]2)[O:12]1>>[OH:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[cH:11]2)[o:12]... | COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O | Oc1c(-c2ccc(F)c(F)c2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | CCO | Functional Group Interconversion | OtherReaction | 4b4af184adbfc9512d460afa65e86656b8968d40567dc72a215f915700b1b99e | 73948743e2b7cc73319dbdc34494386c440f48774dd498a1deddf56bb0ad34ec | c1ccc(-c2cc3cc(-c4ccccc4)c(-c4ccccc4)nc3o2)cc1 | C-O-C(=O)-[C;H0;D4;+0:1]1(-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6])-[O;H0;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14]>>[OH;D1;+0:14]-[c;H0;D3;+0:13]1:[c:11](:[c:12]):[c:8](:[#7;a:9]:[c:10]):[o;H0;D2;+0:7]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | null | [] | null | null | 5 | MINUTE | To a solution of 80 mg (0.14 mmol) of the product of Step B dissolved in 1 mL EtOH was added 9 mg (0.20 mmol) of sodium borohydride. The reaction mixture was stirred at RT for 5 min then partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether | Aromatic alcohol | c1cnc2c(c1)CCO2 | c1cnc2occc2c1 | c1ccccc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | CCO | null | 0.083333 | COC(=O)C1(c2ccc(F)c(F)c2)Oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc2C1=O>CCO>Oc1c(-c2ccc(F)c(F)c2)oc2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2374f352d7f2478f8a9850727af6b546 | CN(C)C=O.O=C(Cc1ccc(Cl)cc1)c1ccccc1Cl>>CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1 | ClC1=C(C=CC=C1)C(CC1=CC=C(C=C1)Cl)=O.CN(C)C=O>>ClC1=C(C=CC=C1)C(C(=CN(C)C)C1=CC=C(C=C1)Cl)=O | O=[CH:4][N:2]([CH3:1])[CH3:3].[CH2:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14])[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1 | CN(C)C=O.O=C(Cc1ccc(Cl)cc1)c1ccccc1Cl | CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1 | null | null | null | C-C Coupling | Aldol condensation | 0834f5811c64eb07624bb510b1953a99dc97db16ae8dba7bd11fc9475950992e | c44260df9c9577267c7fe93dac0096ae481ad05229440bab62074d975d8d7748 | [CH]=C(C(=O)c1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:6](=[O;D1;H0:5])-[c:7])-[c:9](:[c:10]):[c:11] | null | [] | 75 | CELSIUS | 16 | HOUR | To 13.2 g of 1-(2-chlorophenyl)-2-(4-chlorophenyl)ethanone in 100 mL of DMF was added 23.8 g of N,N-dimethylormamide dimethyl acetal. The mixture was stirred at 75° C. for 16 hours. The solution was then concentrated and used without further purification in the next step.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | Enamine | null | null | c1ccccc1.c1ccccc1 | HO- | null | 75 | 16 | CN(C)C=O.O=C(Cc1ccc(Cl)cc1)c1ccccc1Cl>>CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4bf6cda5e1b41fbb814ac2110f72af8 | CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | ClC1=C(C=CC=C1)C(C(=CN(C)C)C1=CC=C(C=C1)Cl)=O.C(#N)CC(=O)N.[H-].[Na+]>>ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C#N)C1=CC=C(C=C1)Cl | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=O)[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Cl:20].[N:1]#[C:2][CH2:3][C:22]([NH2:21])=[O:23]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[Cl:20])[nH:21][c:22]1=... | CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 60e6cdceb0baa245fe4412e5afd8e8b3b5ab470991e8279dcbe754fb697cedb2 | 9bf1fd3c6bd3248cd0029464a9f1478a19f5ad042fa396153933395993aab801 | O=c1ccc(-c2ccccc2)c(-c2ccccc2)[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[Cl;D1;H0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[N;D1;H0:15]#[C:16]-[CH2;D2;+0:17]-[C;H0;D3;+0:18](-[NH2;D1;+0:19])=[O;D1;H0:20]>>[Cl;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[nH;D2;+0:19]:[c;H0;... | null | [] | 95 | CELSIUS | null | null | A solution of the crude product from step A dissolved in 80 mL of DMF containing 4.4 mL methanol and 4.61 g cyanoacetamide was transferred by cannula into a flask containing a suspension of NaH (4.98 g, 60% dispersion in mineral oil, freed of excess oil by washing with hexane just prior to use) in DMF (40 mL). The solu... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 95 | null | CN(C)C=C(C(=O)c1ccccc1Cl)c1ccc(Cl)cc1.N#CCC(N)=O>CN(C)C=O>N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1947bd8bee374badb21ae13f23022d0b | CC(C)(C)C(=O)CBr.N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C#N)C1=CC=C(C=C1)Cl.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC(C(C)(C)C)=O>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(C(C)(C)C)=O | Br[CH2:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[O:8]=[c:9]1[nH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19](-[c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[cH:27][c:28]1[C:29]#[N:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15... | CC(C)(C)C(=O)CBr.N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | C(C)(=O)OCC.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 1c3dde6f8fb234f99de372746776db1852e1e639963c229bf01260e389d5e88d | 481fee288c2b1a3101ebae707e584a0e925bd48483299d9da5a41b1420634672 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[c:11]):[nH;D2;+0:12]:[c;H0;D3;+0:13]:1=[O;H0;D1;+0:14]>>[C:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[o;H0;D2;+0:14]:[c;H0;D3;+0:13]2:[n;H0;D2;+0:12]:[c:10](-[c:11]):[c:9]:[c:8]:[c:7]:2:[c;H0;D3;+0:6]:1-[NH2;D1;+0:5] | null | [] | null | null | 17 | HOUR | To a solution of 0.5 g (1.46 mmol) of the product of Step B in 10 mL DMF was added 0.954 g Cs2CO3 and 0.197 mL of 1-bromopinacolone. The reaction was stirred 17 hours at room temperature at which point the reaction mixture was diluted with ethyl acetate and washed with saturated NaCl/NaHCO3 solution (1:1). The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Nitrile | Ketone.Primary amine | c1cnccc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HBr | C(C)(=O)OCC.CN(C)C=O | null | 17 | CC(C)(C)C(=O)CBr.N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>C(C)(=O)OCC.CN(C)C=O>CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55de1cf4dad34fd0a88cd397f786f4e7 | CN(CCO)C(=O)C(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>>CN1CCN(c2c(C(=O)C(C)(C)C)oc3nc(-c4ccccc4Cl)c(-c4ccc(Cl)cc4)cc23)C(=O)C1=O | ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(C(=O)N(C)CCO)=O)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2N2C(C(N(CC2)C)=O)=O)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | O[CH2:4][CH2:3][N:2]([CH3:1])[C:37]([C:35]([NH:5][c:6]1[c:7]([C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[o:14][c:15]2[n:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25](-[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[cH:33][c:34]12)=[O:36])=[O:38]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[c... | CN(CCO)C(=O)C(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | CN1CCN(c2c(C(=O)C(C)(C)C)oc3nc(-c4ccccc4Cl)c(-c4ccc(Cl)cc4)cc23)C(=O)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 26d79d8ccb8e97e1e8c40a78dae5e25aa5f79bf63d44c4f52ff9627941de4a23 | 53e9ea6bdc0d22524e13e79960e55c0106a6cc8b9aed21c29c8c6a7e9792ce5b | O=C1NCCN(c2coc3nc(-c4ccccc4)c(-c4ccccc4)cc23)C1=O | O-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10]1:[c:11]:[c:12](:[#7;a:13]):[#8;a:14]:[c:15]:1-[C:16]=[O;D1;H0:17]>>[#7;a:13]:[c:12]1:[#8;a:14]:[c:15](-[C:16]=[O;D1;H0:17]):[c:10](-[N;H0;D3;+0:9]2-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[C:7]-2=... | null | [] | 0 | CELSIUS | null | null | A 10 mL rb flask was charged with a solution of 0.075 g (0.13 mmol) of the product of Step A and 0.052 g (0.2 mmol) triphenylphosphine in 2 mL THF. The reaction mixture was stirred at 0° C. and 39 μL of diisopropylazodicarboxylate was added dropwise. The reaction mixture was stirred an additional 1 h at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol | Tertiary amide | null | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | 0 | null | CN(CCO)C(=O)C(=O)Nc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>C1CCOC1>CN1CCN(c2c(C(=O)C(C)(C)C)oc3nc(-c4ccccc4Cl)c(-c4ccc(Cl)cc4)cc23)C(=O)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29f404ef857d4408835b46d31710774a | CO.O=C(O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C(=O)O)C1=CC=C(C=C1)Cl.S(O)(O)(=O)=O.CO>>ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C(=O)OC)C1=CC=C(C=C1)Cl | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[nH:23][c:24]1=[O:25]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21... | CO.O=C(O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=c1ccc(-c2ccccc2)c(-c2ccccc2)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](=[O;D1;H0:6]):[#7;a:7]:[c:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](=[O;D1;H0:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | A 250 mL rb flask equipped with a magnetic stir bar was charged with 6.68 g (19.0 mmol) of the product of Step A, 100 mL methanol, 3 mL of concentrated sulfuric acid and the suspension was refluxed overnight. The resulting clear solution was then cooled to room temperature and evaporated. The residue was partitioned be... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1cnccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CO.O=C(O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fd2ced16c8e4fd7949b21830373d6d1 | CC(C)(C)C(=O)CBr.COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C(=O)OC)C1=CC=C(C=C1)Cl.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC(C(C)(C)C)=O>>ClC1=C(C=CC=C1)C1=NC(=C(C(=O)OC)C=C1C1=CC=C(C=C1)Cl)OCC(C(C)(C)C)=O | Br[CH2:26][C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[CH3:32].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[nH:23][c:24]1=[O:25]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13]... | CC(C)(C)C(=O)CBr.COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 017f1986ac01103f0525dbacad19524e64453382475ee28a007aff29ee613a92 | ac82728493611c77c7c1994f790cea214315197e0940bdfcb00528b82f40a945 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](-[c:13]):[nH;D2;+0:14]:[c;H0;D3;+0:15]:1=[O;H0;D1;+0:16]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:16]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:14]:[c:12](-[c:13]):[c:11]:[c:10]:[c:9]:1-[C:7](=[O;D1;H0:8])-[#8:6... | null | [] | null | null | 1 | HOUR | A 25 mL rb flask was charged with 1.111 g (2.97 mmol) of the product of Step B, 1.451 g (4.45 mmol) Cs2CO3, 10 mL DMF and finally 0.5 mL (3.71 mmol) of bromopinacolone. The reaction mixture was stirred at room temperature 1 h then partitioned between EtOAc and water. The organic layer was washed with water, brine, then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ether | c1cnccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 1 | CC(C)(C)C(=O)CBr.COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>CN(C)C=O>COC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea6785e61a9d489682d374698133b827 | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O.CC(C)(C)C(=O)CBr>>CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | C(C)(=O)C=1C(NC(=C(C1)C1=CC=C(C=C1)Cl)C1=C(C=CC=C1)Cl)=O.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(C(C)(C)C)=O>>C(C)(=O)C=1C(=NC(=C(C1)C1=CC=C(C=C1)Cl)C1=C(C=CC=C1)Cl)OCC(C(C)(C)C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[nH:22][c:23]1=[O:24].Br[CH2:25][C:26](=[O:27])[C:28]([CH3:29])([CH3:30])[CH3:31]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[c:... | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O.CC(C)(C)C(=O)CBr | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 017f1986ac01103f0525dbacad19524e64453382475ee28a007aff29ee613a92 | ac82728493611c77c7c1994f790cea214315197e0940bdfcb00528b82f40a945 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](-[c:12]):[nH;D2;+0:13]:[c;H0;D3;+0:14]:1=[O;H0;D1;+0:15]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:15]-[c;H0;D3;+0:14]1:[n;H0;D2;+0:13]:[c:11](-[c:12]):[c:10]:[c:9]:[c:8]:1-[C:6](-[C;D1;H3:5])=[O;D1;H0:7] | null | [] | null | null | 1.5 | HOUR | To a 25 mL rb flask equipped with a magnetic stir bar was added 0.309 g(0.86 mmol) of the product of Step A, 0.422 g (1.29 mmol) of cesium carbonate, 3 mL DMF and finally 145 μL of 1-bromopinacolone was added. The reaction mixture was stirred at room temperature for 1.5 h then partitioned between EtOAc and water. The o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ether | c1cnccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 1.5 | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O.CC(C)(C)C(=O)CBr>CN(C)C=O>CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c143f1741694798b05a671e25e7f738 | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C>>Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | C(C)(=O)C=1C(=NC(=C(C1)C1=CC=C(C=C1)Cl)C1=C(C=CC=C1)Cl)OCC(C(C)(C)C)=O.N12CCCCCC2=NCCC1>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | O=[C:2]([CH3:1])[c:30]1[c:11]([O:10][CH2:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[CH3:9])[n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[Cl:20])[c:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29]1>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[CH3:9])[o:10][c:11]2[n:12][c:13](-[c:14]3[c... | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 6658b0feb74b91a7acd0ca4b28442f33718467434cddc811566102deb8a65181 | 17fbc58a598d113342a42a036a912fac83e383e9122994bfeebfa959aeec122c | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-[C:8](-[C:9])=[O;D1;H0:10]):[#7;a:11]:[c:12]>>[C:9]-[C:8](=[O;D1;H0:10])-[c;H0;D3;+0:7]1:[o;H0;D2;+0:6]:[c:5](:[#7;a:11]:[c:12]):[c:3](:[c:4]):[c;H0;D3;+0:1]:1-[C;D1;H3:2] | null | [] | 150 | CELSIUS | null | null | A mixture of 0.432 g (0.95 mmol) of the product of Step B, 250 A (1.67 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 2 mL DMF was placed in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor. The reaction vessel was sealed, placed in the microwave reactor and heated at 150° C. for 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether | Ketone | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 150 | null | CC(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C>CN(C)C=O>Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d4a5433cbe84b68be4d18623d3dc161 | Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>>CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O | C[N+]1(CCOCC1)[O-].ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C=O)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[cH:27][c:28]2[c:29]1[CH3:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH... | Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O | null | null | C(Cl)(Cl)(Cl)Cl | Oxidation | OtherReaction | f82793a7e1ee6561b7709c4a971f65b04fd777875bf3438ec6d6e1a0cf7ef2e4 | 4f1055c03ef3f74f7ecbf5450c9237f5c3ae016780958675e61943dfb81da1e6 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [#7;a:1]:[c:2]1:[#8;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7](-[CH3;D1;+0:8]):[c:9]:1>>[#7;a:1]:[c:2]1:[#8;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7](-[CH;D2;+0:8]=[O;D1;H0:10]):[c:9]:1 | null | [] | null | null | null | null | A 10 mL rb flask equipped with a magnetic stir bar was charged with 0.227 g (0.52 mmol) of the product of Example 89, 0.101 g (0.57 mmol) of N-bromosuccinimide, 3 mL CCl4 and ca. 5 mg of 2,2′-azobisisobutyronitrile (AIBN). The reaction mixture was heated to reflux under a nitrogen atmosphere for 2 h then cooled to room... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)(Cl)Cl | null | null | Cc1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>C(Cl)(Cl)(Cl)Cl>CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d62e65ff015489fb58702512914ae73 | CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O.CO>>COC(=O)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | [C-]#N.[Na+].ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C=O)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl.CO>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C(=O)OC)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | [CH:3](=[O:4])[c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[o:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32][c:33]12.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3... | CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O.CO | COC(=O)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | [O-2].[O-2].[Mn+4] | null | Acylation | Oxidation of alcohol and aldehyde to ester | 6c2cf9780d2b06093c0103c8dd3456912317575c5e7e70f8999846e7a24bbf0c | df63d853b69ab8d080a5e6aeacb0edaa9eaa2dd261e6fc3594fda9a1c296389c | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [#7;a:1]:[c:2]1:[#8;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:10]:1.[C;D1;H3:11]-[OH;D1;+0:12]>>[#7;a:1]:[c:2]1:[#8;a:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[O;H0;D2;+0:12]-[C;D1;H3:11]):[c:10]:1 | null | [] | null | null | 4 | HOUR | A 10 mL rb flask equipped with a magnetic stir bar and a septum was charged with a solution of 50 mg (0.11 mmol) of the product of Example 90, in 2 mL MeOH, 24 mg (0.27 mmol) of manganese dioxide and ca. 5 mg of sodium cyanide was added. The reaction mixture was stirred at room temperature for 4 h, then filtered and ev... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Methanol | Ester | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | [O-2].[O-2].[Mn+4] | null | 4 | CC(C)(C)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1C=O.CO>[O-2].[O-2].[Mn+4]>COC(=O)c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d45f944e0ce54e2692d6389881056355 | CC(C)(C)C(=O)CCl.O=Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>CC(C)(C)C(=O)c1cc2cc(-c3ccc(Cl)cc3)c(-c3ccccc3Cl)nc2o1 | ClCC(C(C)(C)C)=O.ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C=O)C1=CC=C(C=C1)Cl.ClCC(C(C)(C)C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Cs+].[Cs+]>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | Cl[CH2:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].O=[CH:8][c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[nH:27][c:28]1=[O:29]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([... | CC(C)(C)C(=O)CCl.O=Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | CC(C)(C)C(=O)c1cc2cc(-c3ccc(Cl)cc3)c(-c3ccccc3Cl)nc2o1 | null | null | CCOCC | Aromatic Heterocycle Formation | OtherReaction | c7d63de9e2b9aa67c866fcc5b7e8367f6d86730e213054f205bfc771c9800fac | c44055920a7c123f4a11c0861cb7271b9b4758af86c4c5d6f1ec7b42da62d18e | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].O=[CH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12]:1=[O;H0;D1;+0:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[cH;D2;+0:5]:[c:6]2:[c:7]:[c:8]:[c:9](-[c:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:2:[o;H0;D2;+0:13]:1 | null | [] | 60 | CELSIUS | 2 | HOUR | To a solution of 0.38 g of the product of Step A dissolved in 3 mL of DW, was added 0.14 mL (1.07 mmol) of 1-chloropinacolone and 0.65 g of Cs2CO3. After stirring for 2 h, another 0.05 mL (0.38 mmol) of 1-chloropinacolone was added and the stirring was continued for another 1 h. Additional 0.325 g (1 mmol) of Cs2CO3 wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde.Ketone | Ketone | c1cnccc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | CCOCC | 60 | 2 | CC(C)(C)C(=O)CCl.O=Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>CCOCC>CC(C)(C)C(=O)c1cc2cc(-c3ccc(Cl)cc3)c(-c3ccccc3Cl)nc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d705a74c03e9403c99b2e96def32a4aa | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>>CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(C(C)(C)O)=O.C(C)(=O)OCC(=O)Cl>>C(C)(=O)OCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(C(C)(C)O)=O | Cl[C:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])=[O:7].[NH2:8][c:9]1[c:10]([C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[OH:16])[o:17][c:18]2[n:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[Cl:27])[c:28](-[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[cH:36][c:37]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[NH:... | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(C)#N.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[#7;a:8]:[c:9]1:[#8;a:10]:[c:11](-[C:12]=[O;D1;H0:13]):[c:14](-[NH2;D1;+0:15]):[c:16]:1>>[#7;a:8]:[c:9]1:[#8;a:10]:[c:11](-[C:12]=[O;D1;H0:13]):[c:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c... | null | [] | null | null | null | null | To a solution of 4.0 g of the product of Example 100 in 25 mL of acetonitrile was added 7.5 mL acetoxy acetylchloride and the reaction mixture was stirred at room temperature. After 50 min the reaction mixture was diluted with CH2Cl2 and washed two times with aqueous sodium bicarbonate. The organic layer was dried over... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)#N.C(Cl)Cl | null | null | CC(=O)OCC(=O)Cl.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>C(C)#N.C(Cl)Cl>CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2587e99f20af4b9a95cc53879079e3af | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>>CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO | C(C)(=O)O.[OH-].[Li+].O.C(C)(=O)OCC(=O)NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(C(C)(C)O)=O.CO>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(CO)=O)C(C(C)(C)O)=O)C2=CC=C(C=C2)Cl | CC(=O)[O:34][CH2:33][C:31]([NH:30][c:29]1[c:7]([C:5]([C:2]([CH3:1])([CH3:3])[OH:4])=[O:6])[o:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[cH:27][c:28]21)=[O:32]>>[CH3:1][C:2]([CH3:3])([OH:4])[C:5](=[O:6])[c:7]1[o:8][c:9]2[n:10][c:11... | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO | null | null | C1CCOC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]:[c:7]:[#8;a:8]>>[#8;a:8]:[c:7]:[c:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | Lithium hydroxide-H2O (0.293 g), the product of Step A (3.78 g), and methanol (8.4 mL) were combined in 245 mL of THF and stirred at room temperature. After 5 min 0.50 mL of acetic acid was added and the solution concentrated. The residue was diluted with ethyl acetate and this solution washed two times with aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | null | CC(=O)OCC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>C1CCOC1>CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1aac933471c4119887b78fda5452eab | CC(=O)OC(C)=O.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>>CC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(C(C)(C)O)=O.C(C)(=O)OC(C)=O>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(C)=O)C(C(C)(C)O)=O)C2=CC=C(C=C2)Cl | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[OH:12])[o:13][c:14]2[n:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[cH:32][c:33]12>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:1... | CC(=O)OC(C)=O.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | CC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | C(C)(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[#8;a:6]:[c:7](-[C:8]=[O;D1;H0:9]):[c:10](-[NH2;D1;+0:11]):[c:12]:1>>[#7;a:4]:[c:5]1:[#8;a:6]:[c:7](-[C:8]=[O;D1;H0:9]):[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:12]:1 | null | [] | 85 | CELSIUS | null | null | The product of Example 100 (0.200 g), acetic anhydride (1.25 mL) and acetic acid (0.25 mL) were combined and then heated to 85° C. After 3 h the reaction was concentrated and the residue was dissolved in dichloromethane and washed twice with aqueous sodium bicarbonate. The solution was then concentrated and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O | 85 | null | CC(=O)OC(C)=O.CC(C)(O)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N>C(C)(=O)O>CC(=O)Nc1c(C(=O)C(C)(C)O)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c381bed665bb4627a586bfbdff44fdf8 | CC(=O)OCC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>>O=C(CO)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(=O)C=2C=NC=CC2.C(C)(=O)OCC(=O)Cl>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(CO)=O)C(=O)C=2C=NC=CC2)C2=CC=C(C=C2)Cl | CC(=O)[O:4][CH2:3][C:2](Cl)=[O:1].[NH2:5][c:6]1[c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[o:16][c:17]2[n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[Cl:26])[c:27](-[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[cH:35][c:36]12>>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][c:6]1[c:7]([C:8](=[O:9])... | CC(=O)OCC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | O=C(CO)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | null | Acylation | OtherReaction | 8239c8557518ad9a51ed2d39c8a2c37cf919e23e81df767084f341a4c55fccb6 | 85d144b1d3fe1a2e0dfc6c909128903cc17adef9115f74214503f6a8fa9c284a | O=C(c1cccnc1)c1cc2cc(-c3ccccc3)c(-c3ccccc3)nc2o1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH2;D1;+0:12]):[c:13]:1>>[#7;a:5]:[c:6]1:[#8;a:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1]):[c:13]:1 | null | [] | null | null | null | null | Using the general acylating procedure described in Example 18, the product of Example 157 was reacted with acetoxyacetyl chloride and then subjected to the general ester hydrolysis procedure described in Example 25 to afford the title compound. HPLC/MS: 518.0 (M+1), 520.0 (M+3); Rt=3.52 min.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Secondary amide.Primary alcohol | null | null | c1ccncc1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(=O)OCC(=O)Cl.Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12>>O=C(CO)Nc1c(C(=O)c2cccnc2)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8aaed631857a4993a8ca04b643cc93d8 | CC(C)(C)S(=O)(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>CC(C)(C)S(=O)(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | C(C)(C)(C)S(=O)(=O)COC1=C(C#N)C=C(C(=N1)C1=C(C=CC=C1)Cl)C1=CC=C(C=C1)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>C(C)(C)(C)S(=O)(=O)C1=C(C=2C(=NC(=C(C2)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)O1)N | [CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])(=[O:7])[CH2:8][O:9][c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[cH:28][c:29]1[C:30]#[N:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])(=[O:7])[c:8]1[o:9][c:10]2[n:11][c:12](-[c:13]3[cH:14]... | CC(C)(C)S(=O)(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | CC(C)(C)S(=O)(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | C1CCOC1.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 310e82a1a04ad8be5cc811c019c822a32b44ad18376ea0176a8296685624b50f | 1840d341887117642bffcff327c44a81dcd63e1f29237a5b99bb06120b967248 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [C:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):[c:13]>>[C:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[o;H0;D2;+0:6]:[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:13]):[c;H0;D3;+0:11]:1-[NH2;D1;+0:12] | null | [] | null | null | null | null | To a stirred solution of 1.87 g (3.9 mmol) of the product of Step B in 24 mL of DMF at 0° C. was added 7.9 mL of a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred an addition 5 min then it was quenched with 0.45 mL of acetic acid and then partitioned between ethyl acetate and... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Primary amine | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | C1CCOC1.CN(C)C=O | null | null | CC(C)(C)S(=O)(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>C1CCOC1.CN(C)C=O>CC(C)(C)S(=O)(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0072402313da45f9b61c45596ccdd4e7 | CCOC(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>>CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | C(C)OC(COC1=NC(=C(C=C1C#N)C1=CC=C(C=C1)Cl)C1=C(C=CC=C1)Cl)=O.C[Si](C)(C)[NH-].C[Si](C)(C)[NH-].[Li+].[Li+]>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[c:18](-[c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[cH:26][c:27]1[C:28]#[N:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[o:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18]... | CCOC(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N | CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | C1CCOC1.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 59bcb1d0292a9d6aab4c779dc11fad7b9f43062efa223c362ac1ee6a27f4c785 | 9dcfc7fb45090136d7ea5d1e73f2fc7bd6ce09ea58bac801b2d4160abff5cb53 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):[c:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[o;H0;D2;+0:6]:[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:13]):[c;H0;D3;+0:11]:1-[NH2;D1;+0:12] | null | [] | null | null | 20 | MINUTE | To a magnetically stirred solution of 2.69 g (6.30 mmol) of the product of Step A dissolved in 60 mL of DMF was slowly added 12.6 mL of a 1 M solution of lithium bis(trimethylsilylamide) in THF at 0° C. The reaction mixture was stirred at room temperature for 20 min then partitioned between EtOAc and 10% aq. NaHSO4. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Nitrile | Ester.Primary amine | c1ccncc1 | c1cnc2occc2c1 | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | null | C1CCOC1.CN(C)C=O | null | 0.333333 | CCOC(=O)COc1nc(-c2ccccc2Cl)c(-c2ccc(Cl)cc2)cc1C#N>C1CCOC1.CN(C)C=O>CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e819361b5db4ebbb47b90be7f1b7076 | CCN(CC)CC.CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F>>CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F | ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(C(F)(F)F)=O)C(=O)OCC)C2=CC=C(C=C2)Cl.C(C)N(CC)CC.C[Al](C)C>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(C(F)(F)F)=O)C(=O)N(CC)CC)C2=CC=C(C=C2)Cl | CC[N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].CCO[C:6](=[O:7])[c:8]1[o:9][c:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[Cl:19])[c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[cH:28][c:29]2[c:30]1[NH:31][C:32](=[O:33])[C:34]([F:35])([F:36])[F:37]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:... | CCN(CC)CC.CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F | CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F | null | null | C(Cl)Cl.C1(=CC=CC=C1)C | Acylation | OtherReaction | 5b22e18c1bbe6b29953993bf715f188ab0e7b9200aa9e656c76da73ed45c630e | 13232343996a06c885abe6305a0393a1c1a027e6b07bf37e1b7c416b421816a0 | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]:[#7;a:7].C-C-[N;H0;D3;+0:8](-[C:9]-[C;D1;H3:10])-[C:11]-[C;D1;H3:12]>>[#7;a:7]:[c:6]:[#8;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C:9]-[C;D1;H3:10])-[C:11]-[C;D1;H3:12]):[c:4] | null | [] | null | null | 30 | MINUTE | To a magnetically stirred solution of 0.119 mL (1.15 mmol) of triethylamine in 5 mL toluene was added 0.575 mL (1.15 mmol) of a 2.0 M solution of trimethylaluminum in toluene at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 30 min. A solution of 0.300 g (0.57 mmol) of the produc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine | Tertiary amide | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1(=CC=CC=C1)C | null | 0.5 | CCN(CC)CC.CCOC(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F>C(Cl)Cl.C1(=CC=CC=C1)C>CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ac6da8dab584ebf9629637fb9e6f584 | CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F>>CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2NC(C(F)(F)F)=O)C(=O)N(CC)CC)C2=CC=C(C=C2)Cl.C([O-])([O-])=O.[K+].[K+].O>>NC1=C(OC2=NC(=C(C=C21)C2=CC=C(C=C2)Cl)C2=C(C=CC=C2)Cl)C(=O)N(CC)CC | O=C(C(F)(F)F)[NH:31][c:30]1[c:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[o:9][c:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[Cl:19])[c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[cH:28][c:29]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[o:9][c:10]2[n:11][c:12](-[c:13... | CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F | CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccc(-c2cc3ccoc3nc2-c2ccccc2)cc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#7;a:5]):[#8;a:6]:[c:7]:1-[C:8](-[#7:9])=[O;D1;H0:10]>>[#7:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:4](:[#7;a:5]):[c:3]:[c:2]:1-[NH2;D1;+0:1] | null | [] | 60 | CELSIUS | 3 | HOUR | To a magnetically stirred solution of 0.273 g (0.50 mmol) of the product of Example 182 in 5 mL MeOH was added 0.343 g (0.248 mmol) of potassium carbonate and 0.5 mL water. The reaction mixture was stirred at 60° C. for 3 h then cooled to room temperature and partitioned between EtOAc and 10% aq. NaHSO4. The organic ex... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1cnc2occc2c1.c1ccccc1.c1ccccc1 | Other | CO | 60 | 3 | CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1NC(=O)C(F)(F)F>CO>CCN(CC)C(=O)c1oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7fe96d87c28497989d234d770dec179 | CC(C)(C)C(=O)CBr.Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>>Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | ClC1=C(C=CC=C1)C1=C(C=C(C(N1)=O)C(=O)C=1N(C=CN1)C)C1=CC=C(C=C1)Cl.BrCC(C(C)(C)C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>>ClC1=C(C=CC=C1)C1=C(C=C(C(=N1)OCC(C(C)(C)C)=O)C(=O)C=1N(C=CN1)C)C1=CC=C(C=C1)Cl | Br[CH2:30][C:31](=[O:32])[C:33]([CH3:34])([CH3:35])[CH3:36].[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[nH:27][c:28]1=[O:29]>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1[C:7](=[O:8])[c:9]1[c... | CC(C)(C)C(=O)CBr.Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O | Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 017f1986ac01103f0525dbacad19524e64453382475ee28a007aff29ee613a92 | ac82728493611c77c7c1994f790cea214315197e0940bdfcb00528b82f40a945 | O=C(c1cnc(-c2ccccc2)c(-c2ccccc2)c1)c1ncc[nH]1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[#7;a:5]:[c:6](-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](-[c:13]):[nH;D2;+0:14]:[c;H0;D3;+0:15]:1=[O;H0;D1;+0:16]):[#7;a:17]>>[#7;a:5]:[c:6](-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](-[c:13]):[n;H0;D2;+0:14]:[c;H0;D3;+0:15]:1-[O;H0;D2;+0:16]-[CH2;D2;+0:1]-[C:2](-... | null | [] | null | null | 1 | HOUR | To a solution of the product of Step A in 4 mL DMF was added 0.125 g (0.698 mmol) of 1-bromopinacolone and 0.455 g (1.39 mmol) of Cs2CO3. The reaction mixture was stirred at room temperature for 1 h, then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with aq. N... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ether | c1cnccc1 | c1ccncc1 | c1ncc[nH]1.c1ccncc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 1 | CC(C)(C)C(=O)CBr.Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)[nH]c1=O>CN(C)C=O>Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba1760b26e374dbd82c6ff5fe2302808 | Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C>>Cn1ccnc1-c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | ClC1=C(C=CC=C1)C1=C(C=C(C(=N1)OCC(C(C)(C)C)=O)C(=O)C=1N(C=CN1)C)C1=CC=C(C=C1)Cl.N12CCCCCC2=NCCC1>>ClC1=C(C=CC=C1)C1=C(C=C2C(=N1)OC(=C2C=2N(C=CN2)C)C(C(C)(C)C)=O)C2=CC=C(C=C2)Cl | O=[C:7]([c:6]1[n:2]([CH3:1])[cH:3][cH:4][n:5]1)[c:35]1[c:16]([O:15][CH2:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[n:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[Cl:25])[c:26](-[c:27]2[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]2)[cH:34]1>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1-[c:7]1[c:8]([C:9](=[O:10])... | Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C | Cn1ccnc1-c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 6658b0feb74b91a7acd0ca4b28442f33718467434cddc811566102deb8a65181 | 17fbc58a598d113342a42a036a912fac83e383e9122994bfeebfa959aeec122c | c1ccc(-c2cc3c(-c4ncc[nH]4)coc3nc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9]):[#7;a:10]:[c:11])-[c;H0;D3;+0:12]1:[#7;a:13]:[c:14]:[c:15]:[#7;a:16]:1-[C;D1;H3:17]>>[C:8]-[C:7](=[O;D1;H0:9])-[c;H0;D3;+0:6]1:[o;H0;D2;+0:5]:[c:4](:[#7;a:10]:[c:11]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[c;H0;D3;+0:12]1:[#7;a:13]:... | null | [] | 150 | CELSIUS | null | null | A mixture of 0.094 g (0.18 mmol) of the product of Step B and 0.027 g (0.18 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 2 mL DMF was placed in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor. The reaction vessel was sealed, placed in the microwave reactor and heated at 150° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether | Ketone | c1ccncc1 | c1cnc2occc2c1 | c1ncc[nH]1.c1cnc2occc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 150 | null | Cn1ccnc1C(=O)c1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1OCC(=O)C(C)(C)C>CN(C)C=O>Cn1ccnc1-c1c(C(=O)C(C)(C)C)oc2nc(-c3ccccc3Cl)c(-c3ccc(Cl)cc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf1a1dda016e411284aba31e2971cca8 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | ClCC(=O)CCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1 | O=C(CCl)[CH2:14][Cl:15].O=[C:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:13]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]([OH:13])[CH2:14][Cl:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH... | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | null | null | CO.O1CCCC1 | C-C Coupling | OtherReaction | be975736ea4dc284d6befa072d9777b891132a86c932e209ec3849b788893253 | 1c7c048f8a75ee2977c3642525e5bc0c5f72d9781847729e637668c64f734260 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-C-C(=O)-[CH2;D2;+0:1]-[Cl;D1;H0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5](-[C:6])-[#7:7]-[C:8]=[O;D1;H0:9]>>[C:6]-[C:5](-[#7:7]-[C:8]=[O;D1;H0:9])-[C@H;D3;+0:3](-[O;D1;H1:4])-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 48.4 | [{"value": 43.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone (75 g, 0.2 mol) in a mixture of 800 mL of methanol and 800 mL of tetrahydrofuran was added sodium borohydride (13.17 g, 0.348 mol, 1.54 equiv.) over 100 min. The solution was stirred at room temperature for 2 hours and then concentrated in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Ketone | Primary halide.Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | CO.O1CCCC1 | null | 2 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>CO.O1CCCC1>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-628eb046bea2459cafb3dcfec58ecfd5 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | [OH-].[K+].C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1 | Cl[CH2:13][C@H:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:14]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]1[CH2:13][O:14]1)[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | null | null | ClCCl.C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis (intra to epoxy) | ebf120e9288f48b61f87dafb00b4bacd480e273fa54208a20ed1d8b8a8581b3e | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[OH;D1;+0:4]>>[C:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1 | 77.3 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@H]1CO1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of potassium hydroxide (6.52 g. 0.116 mol, 1.2 equiv.) in 970 mL of absolute ethanol was treated with N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (32.3 g, 0.097 mol). This solution was stirred at room temperature for 15 minutes and then concentrated in vacuo to give a white solid. The solid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | C1CO1 | c1ccccc1.C1CO1.c1ccccc1 | HCl | ClCCl.C(C)O | null | 0.25 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1>ClCCl.C(C)O>O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de60f6eb45574755aa855b738efb7294 | CN1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1 | CN1CCNCC1.CCN(CC)CC.ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>CN1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C | [NH:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1.Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)(=[O:5])=[O:6]>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1)[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:... | CN1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 8c5bae95a7afc59a07547e375f0b07a72ef45ce3f019f7996b69ec8802313118 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(CCS(=O)(=O)N1CCNCC1)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | 0 | CELSIUS | null | null | A 100 mL round bottom flask equipped with magnetic stir bar was charged with 0.42 mL (1.05 eq) N-methyl-piperazine, 1 mL NEt3 and 20 mL CH2Cl2. The solution was cooled to 0° C. and 1.0 g of benzyl 3-chlorosulfonyl-2(R)-methylpropionate from Example 3 in 5 mL CH2Cl2 was added. After 1 hour reaction was concentrated in v... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(Cl)Cl | 0 | null | CN1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d7628515bd341bbb48e1be9eb1b5fc1 | C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)O | CN1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>CN1CCN(CC1)S(=O)(=O)C[C@@H](C(=O)O)C | c1ccc(C[O:16][C:14]([C@@H:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]2[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]2)=[O:15])cc1>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1)[C:14](=[O:15])[OH:16] | C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)O | null | [Pd] | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CNCCN1 | [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] | null | [] | null | null | null | null | A 100 mL Fisher/Porter vessel was charged with benzyl 3-[(4-methylpiperizin-1-yl)sulfonyl]-2(R)-methylpropionate in 15 mL MeOH with a catalytic amount of 10% Pd—C. Hydrogenation at 50 psi for 48 hours afforded, after filtration through Celite and concentration in vacuo to yield 3-[(4-methylpiperizin-1-yl)sulfonyl]-2(R)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1C[NH]CC[NH]1 | Other | [Pd].CO | null | null | C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)OCc1ccccc1>[Pd].CO>C[C@@H](CS(=O)(=O)N1CCN(C)CC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d52e816d05f1498dbac26bd0c69dc46e | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.N>>C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1 | ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C.N>>NS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C | Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)(=[O:6])=[O:7].[NH3:5]>>[CH3:1][C@@H:2]([CH2:3][S:4]([NH2:5])(=[O:6])=[O:7])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.N | C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1 | null | null | C(C)(=O)OCC.C(Cl)Cl | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[NH3;D0;+0:9]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](-[NH2;D1;+0:9])(=[O;D1;H0:2])=[O;D1;H0:3] | null | [] | -78 | CELSIUS | null | null | A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1.22 g of benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 15 mL CH2Cl2 and cooled to −78° C. To this solution was added to 10 mL of liquid ammonia at −78° C. After 20 minutes the reaction was warmed to room temperature, concentrated in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(C)(=O)OCC.C(Cl)Cl | -78 | null | C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1.N>C(C)(=O)OCC.C(Cl)Cl>C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-201cd0be739148328f976d03ae2a2f3d | C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1>>C[C@@H](CS(N)(=O)=O)C(=O)O | NS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>NS(=O)(=O)C[C@@H](C(=O)O)C | c1ccc(C[O:10][C:8]([C@@H:2]([CH3:1])[CH2:3][S:4]([NH2:5])(=[O:6])=[O:7])=[O:9])cc1>>[CH3:1][C@@H:2]([CH2:3][S:4]([NH2:5])(=[O:6])=[O:7])[C:8](=[O:9])[OH:10] | C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1 | C[C@@H](CS(N)(=O)=O)C(=O)O | null | [Pd] | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | [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] | 97.9 | [{"value": 97.9, "product": "NS(=O)(=O)C[C@@H](C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A 100 mL Fisher/Porter vessel was charged with 1.1 g of crude benzyl 3-aminosulfonyl-2(R)-methylpropionate in 35 mL MeOH and a catalytic amount of 10% Pd—C. The mixture was hydrogenated at 50 psi for 24 hours, filtered through Celite and concentrated in vacuo to yield 700 mg of 3-aminosulfonyl-2(R)-methylpropionic acid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | null | Other | [Pd].CO | null | 24 | C[C@@H](CS(N)(=O)=O)C(=O)OCc1ccccc1>[Pd].CO>C[C@@H](CS(N)(=O)=O)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32b557efdea34c5b8be247dea7329d6c | CNC.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1 | ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C.CNC>>CN(S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C)C | [NH:7]([CH3:8])[CH3:9].Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)(=[O:5])=[O:6]>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]([CH3:8])[CH3:9])[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CNC.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:10](-[C;D1;H3:9])-[C;D1;H3:11] | null | [] | -78 | CELSIUS | null | null | A 100 mL round bottomed flask equipped with magnetic stir bar was charged with 1.7 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate from Example 3 in 25 mL CH2Cl2. The solution was cooled to −78° C. and 15 mL of anhydrous dimethylamine was slowly added. After 30 minutes the reaction was concentrated in vacuo and the res... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | C(Cl)Cl | -78 | null | CNC.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8439c1cf79f4464094398af5231f416d | C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N(C)C)C(=O)O | CN(S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C)C>>CN(S(=O)(=O)C[C@@H](C(=O)O)C)C | c1ccc(C[O:12][C:10]([C@@H:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]([CH3:8])[CH3:9])=[O:11])cc1>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]([CH3:8])[CH3:9])[C:10](=[O:11])[OH:12] | C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N(C)C)C(=O)O | null | [Pd] | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | [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": "CN(S(=O)(=O)C[C@@H](C(=O)O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A 100 mL Fisher/Porter vessel was charged with 1.4 g of benzyl 3-[(dimethylamino)sulfonyl]-2(R)-methylpropionate in 30 mL acetic acid with a catalytic amount of 10% Pd—C. The reaction was hydrogenated at 50 psi for 24 hours, filtered through Celite and concentrated in vacuo. The residue was azeotroped with toluene then... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | null | Other | [Pd].C(C)(=O)O | null | 24 | C[C@@H](CS(=O)(=O)N(C)C)C(=O)OCc1ccccc1>[Pd].C(C)(=O)O>C[C@@H](CS(=O)(=O)N(C)C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca28cf8a610b4959a5383f714763369d | C1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1 | ClS(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C.N1CCCCC1>>N1(CCCCC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.Cl[S:4]([CH2:3][C@H:2]([CH3:1])[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)(=[O:5])=[O:6]>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21... | C1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(CCS(=O)(=O)N1CCCCC1)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:11](-[C:10]-[C:9])-[C:12]-[C:13] | null | [] | 0 | CELSIUS | 1 | HOUR | A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate from Example 3 in 25 mL CH2Cl2. The solution was cooled to 0° C. and 4 mL of piperdine was slowly added. The reaction was stirred 1 hour then concentrated in vacuo. The residue was partioned be... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | C1CCNCC1.C[C@@H](CS(=O)(=O)Cl)C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a2cbf7437764d01a0233567b8192452 | C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1>>C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)O | N1(CCCCC1)S(=O)(=O)C[C@@H](C(=O)OCC1=CC=CC=C1)C>>N1(CCCCC1)S(=O)(=O)C[C@@H](C(=O)O)C | c1ccc(C[O:15][C:13]([C@@H:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)=[O:14])cc1>>[CH3:1][C@@H:2]([CH2:3][S:4](=[O:5])(=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:13](=[O:14])[OH:15] | C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1 | C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)O | null | [Pd] | null | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CCNCC1 | [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] | null | [] | null | null | 3 | HOUR | A 100 mL Fisher/Porter vessel was charged with 1 g of benzyl 3-(1-piperidinyl)sulfonyl-2(R)-methylpropionate 30 mL MeOH and a catalytic amount of 10% Pd—C. The reaction was hydrogenated at 50 psi for 3 hours. After filtration through Celite and concentration in vacuo of 3-(1-piperidinyl)sulfonyl-2(R)-methylpropionic ac... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CC[NH]CC1 | Other | [Pd] | null | 3 | C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)OCc1ccccc1>[Pd]>C[C@@H](CS(=O)(=O)N1CCCCC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-defc4ba15708436b96ff3719a741c0e0 | COC(=O)[C@@H](C)CS(=O)(=O)Cl.NC(c1ccccc1)c1ccccc1>>COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1 | NC(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.ClS(=O)(=O)C[C@@H](C(=O)OC)C>>C1(=CC=CC=C1)C(NS(=O)(=O)C[C@@H](C(=O)OC)C)C1=CC=CC=C1 | Cl[S:8]([CH2:7][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6])(=[O:9])=[O:10].[NH2:11][CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[CH2:7][S:8](=[O:9])(=[O:10])[NH:11][CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:... | COC(=O)[C@@H](C)CS(=O)(=O)Cl.NC(c1ccccc1)c1ccccc1 | COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(Cc2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[C:10](-[c:11])-[c:12]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:9]-[C:10](-[c:11])-[c:12] | 66.4 | [{"value": 66.4, "product": "C1(=CC=CC=C1)C(NS(=O)(=O)C[C@@H](C(=O)OC)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1 g aminodiphenylmethane, 2 mL triethylamine in 20 mL CH2Cl2. The reaction was cooled to 0° C. and 1 g of methyl 3-chlorosulfonyl-2(R)-methylpropionate was slowly added. The reaction was stirred 1 hour then concentrated in vacuo. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | COC(=O)[C@@H](C)CS(=O)(=O)Cl.NC(c1ccccc1)c1ccccc1>C(Cl)Cl>COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f361e1fb24b4f6abd016d6bd1ac7df4 | BrCc1ccccc1.COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1>>COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(NS(=O)(=O)C[C@@H](C(=O)OC)C)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N(S(=O)(=O)C[C@@H](C(=O)OC)C)C(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[CH2:7][S:8](=[O:9])(=[O:10])[NH:11][CH:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[CH2:7][S:8](=[O:9])(=[O:10])[N:11]([CH2:12][c:13... | BrCc1ccccc1.COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1 | COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | c1ccc(CNC(c2ccccc2)c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10](-[c:11])-[c:12]>>[C:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11])-[c:12] | null | [] | null | null | 8 | HOUR | A 100 mL round bottom flask equipped with magnetic stir bar and N2 inlet was charged with 1.11 g of methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate, 447 mg K2CO3, 347 mL benzyl bromide in 20 mL DMF. The reaction was stirred overnight, concentrated in vacuo and partioned between ethyl acetate and water... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 8 | BrCc1ccccc1.COC(=O)[C@@H](C)CS(=O)(=O)NC(c1ccccc1)c1ccccc1>CN(C)C=O>COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1 |
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