dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51ac1af8916c422c846a2f1145220efe | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(=O)C(C)(C)O2>>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2 | BrC1=C(C(=C(C=2C(C(OC21)(C)C)=O)C)NC(OC(C)(C)C)=O)C>>BrC1=C(C(=C(C=2C(C(OC21)(C)C)O)C)NC(OC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18](=[O:19])[C:20]([CH3:21])([CH3:22])[O:23]2>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([OH:19])[C:20]([CH3:... | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(=O)C(C)(C)O2 | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Reduction of ketone to secondary alcohol | 755c7bdda3ccaa9e2a097b82c386f43f2881f1d49e6c3707dce72c3ac00b51db | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCO2 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 98 | [{"value": 98.0, "product": "BrC1=C(C(=C(C=2C(C(OC21)(C)C)O)C)NC(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using tert-butyl (7-bromo-2,2,4,6-tetramethyl-3-oxo-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Reference Example 66, the title compound was synthesized in the same manner as in Example 234. Yield: 98%. Melting point: 187-188° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(=O)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe3a53b97cdb4a26909256e73167e286 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O.ClCCc1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1 | CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C)(C)C.II.ClCCC1=CC=CC=C1.[Mg]>>OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)CCC2=CC=CC=C2 | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[C:21]2=[O:22].Cl[CH2:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O.ClCCc1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | 563b0ff0be58ea81a6e7fdabfbcf3e4ac52f14f4a892daa5b8631b0389fb70cd | afe96a58b8c6ca4e103c0c96e2a417cdee8e581054f8e646150ad555cb751905 | c1ccc(CCC2COc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[c:3].[C;D1;H3:4]-[C:5]1(-[C;D1;H3:6])-[#8:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:12]>>[C;D1;H3:4]-[C:5]1(-[C;D1;H3:6])-[#8:7]-[c:8]:[c:9](:[c:10])-[C;H0;D4;+0:11]-1(-[OH;D1;+0:12])-[CH2;D2;+0:1]-[C:2]-[c:3] | 51 | [{"value": 51.0, "product": "OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)CCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)CCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2-chloroethylbenzene (648 mg, 4.6 mmol) in THF (5 mL) was added dropwise under an argon atmosphere to a mixture of magnesium (112 mg, 4.6 mmol) and a catalytic amount of iodine, and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of 3,3-dimethyl-N-(2,2,6,7-te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C1CCOC1 | null | 1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O.ClCCc1ccccc1>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00fb6e557afa41648e170278eb1ee31d | Brc1cccc(C2OCCO2)c1.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1 | O.CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C)(C)C.BrC=1C=C(C=CC1)C1OCCO1.C(CCC)[Li]>>O1C(OCC1)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O | Br[c:23]1[cH:24][cH:25][cH:26][c:27]([CH:28]2[O:29][CH2:30][CH2:31][O:32]2)[cH:33]1.[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[C:21]2=[O:22]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3... | Brc1cccc(C2OCCO2)c1.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | dc15c67ee64d6e57d57db2cb0f918b6b1d8338f80afda9b1c0093977e8b590e6 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(C2OCCO2)cc(C2COc3ccccc32)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D4;+0:13]-1(-[OH;D1;+0:14])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 92.2 | [{"value": 92.0, "product": "O1C(OCC1)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "O1C(OCC1)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-(3-bromophenyl)-1,3-dioxolane (1.65 mL, 10.9 mmol) in THF (20 mL) was added dropwise at −78° C. under an argon atmosphere n-butyllithium (1.59 M hexane solution, 6.4 mL, 10.2 mmol), and the resulting mixture was stirred for 30 minutes. To the reaction solution was added dropwise at −78° C. a solution... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccc2c(c1)CCO2.c1ccccc1.C1COCO1 | Br- | C1CCOC1 | null | 0.5 | Brc1cccc(C2OCCO2)c1.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9257c40e2a744189bec7fe5243ba4197 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C=O)c1 | O.O1C(OCC1)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O.O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>C(=O)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O | C1C[O:29][CH:28]([c:27]2[cH:26][cH:25][cH:24][c:23]([C:21]3([OH:22])[c:13]4[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]4[O:17][C:18]3([CH3:19])[CH3:20])[cH:30]2)O1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C=O)c1 | null | null | CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1):[c:5]>>[O;H0;D1;+0:4]=[CH;D2;+0:3]-[c:2](:[c:1]):[c:5] | 72 | [{"value": 72.0, "product": "C(=O)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "C(=O)C=1C=C(C=CC1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-(3-bromophenyl)-1,3-dioxolane (1.65 mL, 10.9 mmol) in THF (20 mL) was added dropwise at −78° C. under an argon atmosphere n-butyllithium (1.59 M hexane solution, 6.4 mL, 10.2 mmol), and the resulting mixture was stirred for 30 minutes. To the reaction solution was added dropwise at −78° C. a solution... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CC(=O)C | null | 0.5 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C2OCCO2)c1>CC(=O)C>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8f35692df354ba7abd2b77e287f8506 | Cc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>>Cc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | O.OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=C(C=CC=C2)C.C(C)[SiH](CC)CC>>CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=C(C=CC=C2)C)C1)C)C)(C)C | O[C:8]1([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)[c:9]2[cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([CH3:21])[c:22]([CH3:23])[c:24]2[O:25][C:26]1([CH3:27])[CH3:28]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]1[c:9]2[cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][C:16]([C... | Cc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | Cc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 81.7 | [{"value": 79.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=C(C=CC=C2)C)C1)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=C(C=CC=C2)C)C1)C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of N-(3-hydroxy-2,2,6,7-tetramethyl-3-(2-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (120 mg, 0.3 mmol) obtained in Example 242 in trifluoroacetic acid (2 mL) was added triethylsilane (71 mg, 0.6 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. T... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | FC(C(=O)O)(F)F | null | 1 | Cc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>FC(C(=O)O)(F)F>Cc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-894fe2805def44b4b5cb8c936f409e15 | Cc1cccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1>>Cc1cccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC(=CC=C2)C>>CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=CC(=CC=C2)C)C1)C)C)(C)C | O[C:7]1([c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:28]2)[c:8]2[cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([CH3:20])[c:21]([CH3:22])[c:23]2[O:24][C:25]1([CH3:26])[CH3:27]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[c:8]3[cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])... | Cc1cccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | Cc1cccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=CC(=CC=C2)C)C1)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-3-(3-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 239, the title compound was synthesized in the same manner as in Example 271. Yield: 87%. Melting point: 156-157° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1cccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1>C(C)(=O)OCC.CCCCCC>Cc1cccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-355b7715808448da9dcda9f0253a7e91 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccc(C(C)C)c1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC(=CC=C2)C(C)C>>C(C)(C)C=1C=C(C=CC1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:21]1([c:22]2[cH:23][cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccc(C(C)C)c1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 65 | [{"value": 65.0, "product": "C(C)(C)C=1C=C(C=CC1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(3-isopropylphenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 245, the title compound was synthesized in the same manner as in Example 271. Yield: 65%. Melting point: 162-163° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccc(C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0d8beb0051c429984643fb71aafaa8a | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccccc1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC=CC=C2>>CC1(OC2=C(C1C1=CC=CC=C1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | O[C:21]1([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccccc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "CC1(OC2=C(C1C1=CC=CC=C1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 243, the title compound was synthesized in the same manner as in Example 271. Yield: 82%. Melting point: 182-183° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccccc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fb14a02cd934b179861e70d1e17e7b5 | COc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>>COc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=C(C=CC=C2)OC>>COC1=C(C=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:9]1([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:10]2[cH:11][c:12]([NH:13][C:14](=[O:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[c:21]([CH3:22])[c:23]([CH3:24])[c:25]2[O:26][C:27]1([CH3:28])[CH3:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[c:10]2[cH:11][c:12]([NH:13][C:14](=[O:15])[CH2:... | COc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | COc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "COC1=C(C=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(2-methoxyphenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 246, the title compound was synthesized in the same manner as in Example 271. Yield: 82%. Melting point: 169-170° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1ccccc1C1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>C(C)(=O)OCC.CCCCCC>COc1ccccc1C1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87d599f031cc4641919e2431d8a51076 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccccc1 | C(C1=CC=CC=C1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O>>C(C1=CC=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:21]1([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccccc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(CC2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]-[c:3])-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[C:8]1(-[C;D1;H3:10])-[#8:7]-[c:6]:[c:4](:[c:5])-[CH;D3;+0:1]-1-[C:2]-[c:3] | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-benzyl-3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 249, the title compound was synthesized in the same manner as in Example 271. Yield: 56%. Melting point: 186-187° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccccc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-291590a8275e448d84f60d5bf9b8b3bb | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccc(C(C)C)cc1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)CC2=CC=C(C=C2)C(C)C>>C(C)(C)C1=CC=C(CC2C(OC3=C2C=C(C(=C3C)C)NC(CC(C)(C)C)=O)(C)C)C=C1 | O[C:21]1([CH2:22][c:23]2[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(CC2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]-[c:3])-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[C:8]1(-[C;D1;H3:10])-[#8:7]-[c:6]:[c:4](:[c:5])-[CH;D3;+0:1]-1-[C:2]-[c:3] | 63 | [{"value": 63.0, "product": "C(C)(C)C1=CC=C(CC2C(OC3=C2C=C(C(=C3C)C)NC(CC(C)(C)C)=O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(4-isopropylbenzyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 250, the title compound was synthesized in the same manner as in Example 271. Yield: 63%. Melting point: 130-132° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)Cc1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Cc1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb0f18cd48104d3dbc2f08888f549d62 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccs1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccs1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C=2SC=CC2>>CC1(OC2=C(C1C=1SC=CC1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | O[C:21]1([c:22]2[cH:23][cH:24][cH:25][s:26]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccs1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccs1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1csc(C2COc3ccccc32)c1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[#16;a:4]:[c:5])-[c:6](:[c:7]):[c:8]-[#8:9]-[C:10]-1(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:11]-[C:10]1(-[C;D1;H3:12])-[#8:9]-[c:8]:[c:6](:[c:7])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[#16;a:4]:[c:5] | 65 | [{"value": 65.0, "product": "CC1(OC2=C(C1C=1SC=CC1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-3-(2-thienyl)-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 248, the title compound was synthesized in the same manner as in Example 271. Yield: 65%. Melting point: 137-138° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccsc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccs1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c7dec7e32f5459982e82dbc8734203d | CCCCC1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>>CCCCC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | C(CCC)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O>>C(CCC)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]([CH3:20])[c:21]2[O:22][C:23]1([CH3:24])[CH3:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:... | CCCCC1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | CCCCC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc2c(c1)CCO2 | O-[C;H0;D4;+0:1]1(-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C:3]-[C:2]-[CH;D3;+0:1]1-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10] | 77 | [{"value": 77.0, "product": "C(CCC)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-butyl-3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 251, the title compound was synthesized in the same manner as in Example 271. Yield: 77%. Melting point: 129-130° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | CCCCC1(O)c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C>C(C)(=O)OCC.CCCCCC>CCCCC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-231df57612eb464f9b642537ecdceb90 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccco1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccco1 | O1C(=CC=C1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O>>O1C(=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:21]1([c:22]2[cH:23][cH:24][cH:25][o:26]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccco1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccco1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1coc(C2COc3ccccc32)c1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[#8;a:4]:[c:5])-[c:6](:[c:7]):[c:8]-[#8:9]-[C:10]-1(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:11]-[C:10]1(-[C;D1;H3:12])-[#8:9]-[c:8]:[c:6](:[c:7])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[#8;a:4]:[c:5] | 67 | [{"value": 67.0, "product": "O1C(=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(2-furyl)-3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 252, the title compound was synthesized in the same manner as in Example 271. Yield: 67%. Melting point: 126-127° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccoc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccco1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccco1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f87d936db2784380a7afd7222688173a | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2CCc1ccccc1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)CCC2=CC=CC=C2>>CC1(OC2=C(C1CCC1=CC=CC=C1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | O[C:21]1([CH2:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2CCc1ccccc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(CCC2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C:3]-[C:2]-[CH;D3;+0:1]1-[c:4](:[c:5]):[c:6]-[#8:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10] | 92 | [{"value": 92.0, "product": "CC1(OC2=C(C1CCC1=CC=CC=C1)C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 240, the title compound was synthesized in the same manner as in Example 271. Yield: 92%. Melting point: 158-159° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2CCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e1cfc9769544739abc8f4574e85c4e3 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(Br)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)O>>BrC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:21]1([c:22]2[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]2)[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(Br)cc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 88 | [{"value": 88.0, "product": "BrC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-bromophenyl)-3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 254, the title compound was synthesized in the same manner as in Example 271. Yield: 88%. Melting point: 171-172° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(Br)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41a10df72bc54ba193ac157ac3602436 | COc1ccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC=C(C=C2)OC>>COC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[C:7]1([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][cH:28]2)[c:8]2[cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([CH3:20])[c:21]([CH3:22])[c:23]2[O:24][C:25]1([CH3:26])[CH3:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[c:8]3[cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3... | COc1ccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | COc1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "COC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(4-methoxyphenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 255, the title compound was synthesized in the same manner as in Example 271. Yield: 82%. Melting point: 169-170° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1ccc(C2(O)c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1>C(C)(=O)OCC.CCCCCC>COc1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c4a1a73ed684871a11a947c8c1bbe66 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)(C1CCCCC1)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C1CCCCC1)C(C)(C)O2 | C1(CCCCC1)C1(C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C)O>>C1(CCCCC1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C | O[C:18]1([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[c:6]2[c:5]([c:3]([CH3:4])[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]2[CH3:8])[O:28][C:25]1([CH3:26])[CH3:27]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15... | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)(C1CCCCC1)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C1CCCCC1)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc2c(c1)OCC2C1CCCCC1 | O-[C;H0;D4;+0:1]1(-[C:2](-[C:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C:3]-[C:2](-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11])-[C:4] | 48 | [{"value": 48.0, "product": "C1(CCCCC1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-cyclohexyl-3-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 256, the title compound was synthesized in the same manner as in Example 271. Yield: 48%. Melting point: 198-199° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | C1CCCCC1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)(C1CCCCC1)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C1CCCCC1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a15852cd96445fdbeb2fb743bbb3d8b | COc1ccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | OC1(C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C)C2=CC=C(C=C2)OC>>COC1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C | O[C:7]1([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[c:8]2[c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([CH3:21])[c:22]([CH3:23])[c:24]2[O:25][C:26]1([CH3:27])[CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[c:8]3[c:9]([CH3:10])[c:11]([NH:12][C:13](=[O:14])[... | COc1ccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | COc1ccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 40 | [{"value": 40.0, "product": "COC1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(4-methoxyphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 258, the title compound was synthesized in the same manner as in Example 271. Yield: 40%. Melting point: 175-176° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1ccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1>C(C)(=O)OCC.CCCCCC>COc1ccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70a3c1695a874e4d8f72cf791ff9086a | COc1cccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1>>COc1cccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | OC1(C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C)C2=CC(=CC=C2)OC>>COC=1C=C(C=CC1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C | O[C:8]1([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30]2)[c:9]2[c:10]([CH3:11])[c:12]([NH:13][C:14](=[O:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[c:21]([CH3:22])[c:23]([CH3:24])[c:25]2[O:26][C:27]1([CH3:28])[CH3:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[c:9]3[c:10]([CH3:11])[c:12]([NH:13][C:14](=[... | COc1cccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | COc1cccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 77 | [{"value": 77.0, "product": "COC=1C=C(C=CC1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(3-methoxyphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 259, the title compound was synthesized in the same manner as in Example 271. Yield: 77%. Melting point: 166-167° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1cccc(C2(O)c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1>C(C)(=O)OCC.CCCCCC>COc1cccc(C2c3c(C)c(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01720a442f7f4388be26681812de12ca | Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(O)(c1ccc(C(C)C)cc1)C(C)(C)O2>>Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(c1ccc(C(C)C)cc1)C(C)(C)O2 | OC1(C(OC2=C1C(=C(C(=C2NC(CC(C)(C)C)=O)C)C)C)(C)C)C2=CC=C(C=C2)C(C)C>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2NC(CC(C)(C)C)=O)C)C)C)(C)C | O[C:18]1([c:19]2[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]2)[c:15]2[c:14]([c:5]([NH:6][C:7](=[O:8])[CH2:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:3]([CH3:4])[c:2]([CH3:1])[c:16]2[CH3:17])[O:31][C:28]1([CH3:29])[CH3:30]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]([NH:6][C:7](=[O:8])[CH2:9][C:10]([CH3:11])([CH3:12... | Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(O)(c1ccc(C(C)C)cc1)C(C)(C)O2 | Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(c1ccc(C(C)C)cc1)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 1ebd4d04be1df91ab8b75d180b7bca5ec72f9272208744cc19838116c6c36ac8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[C:9]1(-[C;D1;H3:11])-[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 53 | [{"value": 53.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2NC(CC(C)(C)C)=O)C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-3-(4-isopropylphenyl)-2,2,4,5,6-pentamethyl-2,3-dihydro-1-benzofuran-7-yl)-3,3-dimethylbutanamide obtained in Example 260, the title compound was synthesized in the same manner as in Example 271. Yield: 53%. Melting point: 152-153° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(O)(c1ccc(C(C)C)cc1)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c(NC(=O)CC(C)(C)C)c2c(c1C)C(c1ccc(C(C)C)cc1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aef7a54c7be84ad7b1189f12acb893c8 | CN(C)C=O.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1 | O.CN(C)C=O.BrC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.C(CCC)[Li]>>C(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | CN(C)[CH:26]=[O:27].Br[c:25]1[cH:24][cH:23][c:22]([CH:21]2[c:13]3[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]3[O:17][C:18]2([CH3:19])[CH3:20])[cH:29][cH:28]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14... | CN(C)C=O.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1 | null | null | C1CCOC1 | C-C Coupling | Bouveault aldehyde synthesis | 4664d189e1ff40b394aee0a7d0943c7bfc06c1f81f238cff6865649dda594153 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[CH;D2;+0:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 46 | [{"value": 46.0, "product": "C(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.9, "product": "C(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(3-(4-bromophenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.13 mmol) obtained in Example 284 in THF (10 mL) was added dropwise at −78° C. under an argon atmosphere n-butyllithium (1.59 M hexane solution, 1.56 mL, 2.48 mmol), and the mixture was stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)CCO2.c1ccccc1 | HBr | C1CCOC1 | null | 0.5 | CN(C)C=O.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d16cb88d3b864edd8725c4df963c7682 | CC(=O)N(C)C.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1>>CC(=O)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | BrC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.CN(C(C)=O)C>>C(C)(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | CN(C)[C:2]([CH3:1])=[O:3].Br[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([CH3:21])[c:22]([CH3:23])[c:24]3[O:25][C:26]2([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][c:11]([NH:12][C:13](=[O... | CC(=O)N(C)C.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1 | CC(=O)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | C-C Coupling | Asymmetric ketones from N,N-dimethylamides | 99face78a8bbaa38ff4dd2141c4a0df3e690005988b6fb5a9a2afc6a90da7e24 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8]>>[C;D1;H3:7]-[C;H0;D3;+0:6](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 20 | [{"value": 20.0, "product": "C(C)(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-bromophenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 284 and N,N-dimethylacetamide, the title compound was synthesized in the same manner as in Example 292. Yield: 20%. Melting point: 195-196° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | C(C)(=O)OCC.CCCCCC | null | null | CC(=O)N(C)C.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(Br)cc1>C(C)(=O)OCC.CCCCCC>CC(=O)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-187d7351c9af48449b1a4c2b8b8231d6 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(CO)cc1 | C(=O)C1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.C1CCOC1.C(C)(C)OC(C)C>>OCC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]=[O:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(CO)cc1 | null | null | null | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(C2COc3ccccc32)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 80 | [{"value": 80.0, "product": "OCC1=CC=C(C=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-formylphenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 292, the title compound was synthesized in the same manner as in Example 21. Yield: 80%. Melting point: 162-163° C. (THF-diisopropyl ether).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | null | null | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(C=O)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2c1ccc(CO)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eee1b0a17473431e843179437fc797c6 | CC(C)c1ccccc1Br.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1 | CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C)(C)C.II.BrC1=C(C=CC=C1)C(C)C.[Mg]>>OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC(=CC=C2)C(C)C | Br[c:31]1[cH:23][cH:24][cH:25][cH:26][c:27]1[CH:28]([CH3:29])[CH3:30].[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[C:21]2=[O:22]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c... | CC(C)c1ccccc1Br.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | dc15c67ee64d6e57d57db2cb0f918b6b1d8338f80afda9b1c0093977e8b590e6 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[c:4]:[c:5]:[c:6]:1-[C:7].[C;D1;H3:8]-[C:9]1(-[C;D1;H3:10])-[#8:11]-[c:12]:[c:13](:[c:14])-[C;H0;D3;+0:15]-1=[O;H0;D1;+0:16]>>[C:7]-[c:6]1:[c:5]:[c:4]:[c:3]:[c;H0;D3;+0:2](-[C;H0;D4;+0:15]2(-[OH;D1;+0:16])-[c:13](:[c:14]):[c:12]-[#8:11]-[C:9]-2(-[C;D1;H3:8])-[C;D1;H3:10]):[cH;D2;+0... | 16.2 | [{"value": 16.0, "product": "OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC(=CC=C2)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.2, "product": "OC1(C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)C2=CC(=CC=C2)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-bromo-2-isopropylbenzene (1.20 g, 6.03 mmol) in THF (5 mL) was added dropwise under an argon atmosphere to a mixture of magnesium (147 mg, 6.03 mmol) and a catalytic amount of iodine, and the mixture was stirred at 70° C. for 30 minutes. To the reaction solution was added dropwise a solution of 3,3-dime... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccc2c(c1)CCO2.c1ccccc1 | Br- | C1CCOC1 | null | null | CC(C)c1ccccc1Br.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1cccc(C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6465a122a88446adb7b6ae6e5a95ae60 | C1CCNCC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCCC1)C(C)(C)O2 | N1CCCCC1.CS(=O)(=O)Cl.OC1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C.C(C)N(CC)CC>>CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)N2CCCCC2)C1C)C)C)(C)C | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.O[CH:18]1[c:6]2[c:5]([c:3]([CH3:4])[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]2[CH3:8])[O:28][C:25]1([CH3:26])[CH3:27]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15... | C1CCNCC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCCC1)C(C)(C)O2 | null | null | ClCCl.O | Heteroatom Alkylation and Arylation | OtherReaction | ff764035e14a0e265d5118c5ee8287c96fc78766bbde588c108e1e9046e67926 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCC2N1CCCCC1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8])-[C:12]-[C:13] | 50 | [{"value": 50.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)N2CCCCC2)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.5, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)N2CCCCC2)C1C)C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(3-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (450 mg, 1.41 mmol) obtained in Example 234 in dichloromethane (3 mL) was added triethylamine (0.79 mL, 5.64 mmol), and then added dropwise with ice-cooling methanesulfonyl chloride (0.22 mL, 2.82 mmol). The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2c(c1)CCO2 | C1CC[NH]CC1.c1ccc2c(c1)CCO2 | C1CC[NH]CC1.c1ccc2c(c1)CCO2 | HO- | ClCCl.O | null | 0.5 | C1CCNCC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>ClCCl.O>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCCC1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a98078a9a7541c8a82f984070e184ac | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCC1)C(C)(C)O2 | OC1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C.N1CCCC1>>CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)N2CCCC2)C1C)C)C)(C)C | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.O[CH:18]1[c:6]2[c:5]([c:3]([CH3:4])[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]2[CH3:8])[O:27][C:24]1([CH3:25])[CH3:26]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:... | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCC1)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | d62fd34598227e71b85f4f82f3c82197e8e9e1572341582353e8206a4de7ad6a | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCC2N1CCCC1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:9]-[C:10]-[C:11]-[C:12]-1 | 36 | [{"value": 36.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)N2CCCC2)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 234 and pyrrolidine, the title compound was synthesized in the same manner as in Example 297. Yield: 36%. Melting point: 197-198° C. (ethyl acetate-hexane). 1H-NMR (CDCl3) δ: 1.16 (9H, s), 1.23 (3H, s), 1.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2c(c1)CCO2 | C1CC[NH]C1.c1ccc2c(c1)CCO2 | C1CC[NH]C1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(N1CCCC1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b3e124980e744e0b25a7999fa3846d5 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1 | OC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.NC1=CC=CC=C1>>N(C1=CC=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | O[CH:21]1[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20].[NH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | b0d566c6cee33406f459c0a34d8385bfeec7008a02c9ebef94a1acddc66053ca | c4940c2a97a655ce3fe0da51f34327276f5fad64d656fcfdbcd714b6aae5a34d | c1ccc(NC2COc3ccccc32)cc1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH;D3;+0:1]-1-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 79 | [{"value": 79.0, "product": "N(C1=CC=CC=C1)C1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 235 and aniline, the title compound was synthesized in the same manner as in Example 297. Yield: 79%. Melting point: 151-152° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Primary amine | Secondary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a123d68b17d1404c8ec9edcc21858444 | COc1ccccc1N.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O>>COc1ccccc1NC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | OC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.COC1=C(C=CC=C1)N>>COC1=C(C=CC=C1)NC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].O[CH:10]1[c:11]2[cH:12][c:13]([NH:14][C:15](=[O:16])[CH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]([CH3:23])[c:24]([CH3:25])[c:26]2[O:27][C:28]1([CH3:29])[CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH:10]1[c:11]2[cH:12][c:13]([NH:14][C:15](... | COc1ccccc1N.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O | COc1ccccc1NC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | b0d566c6cee33406f459c0a34d8385bfeec7008a02c9ebef94a1acddc66053ca | c4940c2a97a655ce3fe0da51f34327276f5fad64d656fcfdbcd714b6aae5a34d | c1ccc(NC2COc3ccccc32)cc1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH;D3;+0:1]-1-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 75 | [{"value": 75.0, "product": "COC1=C(C=CC=C1)NC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 235 and (2-methoxyphenyl)amine, the title compound was synthesized in the same manner as in Example 297. Yield: 75%. Melting point: 184-185° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Primary amine | Secondary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | COc1ccccc1N.Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O>C(C)(=O)OCC.CCCCCC>COc1ccccc1NC1c2cc(NC(=O)CC(C)(C)C)c(C)c(C)c2OC1(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e31ca748c08c48e197a16a25edf78df5 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1OC(F)(F)F>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1OC(F)(F)F | OC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C.FC(OC1=C(C=CC=C1)N)(F)F>>FC(OC1=C(C=CC=C1)NC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)(F)F | O[CH:21]1[c:13]2[cH:12][c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:2]([CH3:1])[c:15]([CH3:16])[c:14]2[O:17][C:18]1([CH3:19])[CH3:20].[NH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[O:29][C:30]([F:31])([F:32])[F:33]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11]... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1OC(F)(F)F | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1OC(F)(F)F | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | b0d566c6cee33406f459c0a34d8385bfeec7008a02c9ebef94a1acddc66053ca | c4940c2a97a655ce3fe0da51f34327276f5fad64d656fcfdbcd714b6aae5a34d | c1ccc(NC2COc3ccccc32)cc1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH;D3;+0:1]-1-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 73 | [{"value": 73.0, "product": "FC(OC1=C(C=CC=C1)NC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-hydroxy-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 235 and (2-(trifluoromethoxy)phenyl)amine, the title compound was synthesized in the same manner as in Example 297. Yield: 73%. Melting point: 196-197° C. (ethyl acetate-hexane).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Primary amine | Secondary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O.Nc1ccccc1OC(F)(F)F>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2Nc1ccccc1OC(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62c790db8db3440d9e9cacf986bbb711 | C1CCNC1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2>>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N1CCCC1)C(C)(C)O2 | BrC1=C(C(=C(C=2C(C(OC21)(C)C)O)C)NC(OC(C)(C)C)=O)C.N1CCCC1>>BrC1=C(C(=C(C=2C(C(OC21)(C)C)N2CCCC2)C)NC(OC(C)(C)C)=O)C | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.O[CH:18]1[c:6]2[c:5]([c:3]([Br:4])[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]2[CH3:8])[O:27][C:24]1([CH3:25])[CH3:26]>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[C... | C1CCNC1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2 | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N1CCCC1)C(C)(C)O2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d62fd34598227e71b85f4f82f3c82197e8e9e1572341582353e8206a4de7ad6a | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)OCC2N1CCCC1 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH;D3;+0:1]-1-[N;H0;D3;+0:13]1-[C:9]-[C:10]-[C:11]-[C:12]-1 | 43 | [{"value": 43.0, "product": "BrC1=C(C(=C(C=2C(C(OC21)(C)C)N2CCCC2)C)NC(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using tert-butyl (7-bromo-3-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 236 and pyrrolidine, the title compound was synthesized in the same manner as in Example 297.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2c(c1)CCO2 | C1CC[NH]C1.c1ccc2c(c1)CCO2 | C1CC[NH]C1.c1ccc2c(c1)CCO2 | HO- | null | null | null | C1CCNC1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2>>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N1CCCC1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7315b98894c34b2c873d39d3fc2fd56b | CNC.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2>>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N(C)C)C(C)(C)O2 | BrC1=C(C(=C(C=2C(C(OC21)(C)C)O)C)NC(OC(C)(C)C)=O)C.CNC>>BrC1=C(C(=C(C=2C(C(OC21)(C)C)N(C)C)C)NC(OC(C)(C)C)=O)C | [NH:19]([CH3:20])[CH3:21].O[CH:18]1[c:6]2[c:5]([c:3]([Br:4])[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]2[CH3:8])[O:25][C:22]1([CH3:23])[CH3:24]>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([... | CNC.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2 | Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N(C)C)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 35dde167c67039e14c2875582c1fe3e52dbd4073bf09935dc720edc7d3d40622 | 540f526ef204b9f0fcb7b9bc2402af132d75c889d3e4a156b292e80c37384c80 | c1ccc2c(c1)CCO2 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8] | 89 | [{"value": 89.0, "product": "BrC1=C(C(=C(C=2C(C(OC21)(C)C)N(C)C)C)NC(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using tert-butyl (7-bromo-3-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 236 and dimethylamine, the title compound was synthesized in the same manner as in Example 297. Yield: 89%. Melting point: 111-112° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | CNC.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(O)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)C(N(C)C)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f798a01a9497439baa1ca3c2091e0bfb | CC(C)c1ccc(C=O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)CC(C)(C)O2>>Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OC(C)(C)C2 | O.C(C)(C)C1=CC=C(C=O)C=C1.BrC1=C(C(=C(C=2CC(OC21)(C)C)C)NC(OC(C)(C)C)=O)C.C(CCC)[Li]>>OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(OC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C | [CH:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1.Br[c:5]1[c:4]2[c:3]([c:2]([CH3:1])[c:19]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:17]1[CH3:18])[CH2:32][C:29]([CH3:30])([CH3:31])[O:28]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([OH:7])[c:8]3[cH:9][cH:10][c:11]([CH:... | CC(C)c1ccc(C=O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)CC(C)(C)O2 | Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OC(C)(C)C2 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | a56606a78163c88dc4bf48a7c5ab26b38cb3fda591dd4b56afdf051b12beb5dd | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2cccc3c2OCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8].[O;H0;D1;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#8:7]-[c:5](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:10](-[OH;D1;+0:9])-[c:11](:[c:12]):[c:13]):[c:2](-[C;D1;H3:3]):[c:4] | 59 | [{"value": 59.0, "product": "OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(OC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.1, "product": "OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(OC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of tert-butyl (7-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl) carbamate (1.77 g, 4.78 mmol) obtained in Example 238 in THF (20 mL) was added dropwise at −78° C. under argon atmosphere n-butyllithium (1.60 M hexane solution, 6.25 mL, 10.0 mmol), and the mixture was stirred for 30 minutes. To th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Br- | C1CCOC1 | null | 0.5 | CC(C)c1ccc(C=O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)OC(C)(C)C)CC(C)(C)O2>C1CCOC1>Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e260cacfcc8646cc9b5ae0ac5ee2fa82 | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2 | C(C)N(CC)CC.Cl.C(C)(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)N)C)(C)C.O.C(C)(C)(C)CC(=O)Cl>>C(C)(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C | Cl[C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:18]([c:19]1[cH:20][cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][cH:28]1)[C:29]([CH3:30])([CH3:31])[O:32]2>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:1... | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(C2COc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 41 | [{"value": 41.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-(4-tert-butylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine hydrochloride obtained in Reference Example 76 (400 mg, 1.16 mmol) and tert-butylacetyl chloride (0.17 mL, 1.22 mmol) in dichloromethane (10 mL) was added triethylamine (0.35 mL, 2.50 mmol) at room temperature, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | ClCCl | null | 1 | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2>ClCCl>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)C)cc1)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e32cd18d0c434933a8134449efee42fc | CC(C)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)ccc3OC2(C)C)cc1.CI>>CC(C)c1ccc(C2c3cc(N(C)C(=O)CC(C)(C)C)ccc3OC2(C)C)cc1 | CI.C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)NC(CC(C)(C)C)=O)(C)C.[H-].[Na+].O>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)N(C(CC(C)(C)C)=O)C)(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][c:11]([NH:12][C:14](=[O:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]3[O:24][C:25]2([CH3:26])[CH3:27])[cH:28][cH:29]1.I[CH3:13]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][c:11]([N:12]([CH3:13])[C:14](=[O:15... | CC(C)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)ccc3OC2(C)C)cc1.CI | CC(C)c1ccc(C2c3cc(N(C)C(=O)CC(C)(C)C)ccc3OC2(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 780d850c4b8333c4b07101ff526eea0725c627f5cbcabe141bddc514762f1fac | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | c1ccc(C2COc3ccccc32)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6](:[c:7]):[c:8] | 41 | [{"value": 41.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)N(C(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)N(C(CC(C)(C)C)=O)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(3-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (110 mg, 290 mmol) obtained in Example 320 in DMF (3 mL) was added sodium hydride (a 60% dispersion in liquid paraffin, 12.8 mg, 319 mmol) at 0° C. and the mixture was stirred at room temperature for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HI | CN(C)C=O | null | 0.5 | CC(C)c1ccc(C2c3cc(NC(=O)CC(C)(C)C)ccc3OC2(C)C)cc1.CI>CN(C)C=O>CC(C)c1ccc(C2c3cc(N(C)C(=O)CC(C)(C)C)ccc3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1ab015e52c94396bf1ab34fb627b562 | C1CCNC1.Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CI)O2>>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CN1CCCC1)O2 | ICC1(OC2=C(C1)C(=C(C(=C2CC2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C.N1CCCC1>>C(C)(C)C1=CC=C(CC2=C(C(=C(C=3CC(OC32)(CN3CCCC3)C)C)NC(CC(C)(C)C)=O)C)C=C1 | [NH:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.I[CH2:30][C:28]1([CH3:29])[CH2:27][c:15]2[c:14]([c:3]([CH2:4][c:5]3[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13]3)[c:2]([CH3:1])[c:18]([NH:19][C:20](=[O:21])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:16]2[CH3:17])[O:36]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH... | C1CCNC1.Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CI)O2 | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CN1CCCC1)O2 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(Cc2cccc3c2OC(CN2CCCC2)C3)cc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C:4])-[#8:5]-[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:4]-[C:2](-[C;D1;H3:3])(-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1)-[#8:5]-[c:6] | 95 | [{"value": 95.0, "product": "C(C)(C)C1=CC=C(CC2=C(C(=C(C=3CC(OC32)(CN3CCCC3)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(2-(iodomethyl)-7-(4-isopropylbenzyl)-2,4,6-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (102 mg, 0.19 mmol) obtained in Example 336 and pyrrolidine (1.5 mL) was reacted using a microwave reactor (110° C., hold time 20 min, 250 W). Water was added to the reaction solution and the produ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccc2c(c1)CCO2.C1CC[NH]C1 | HI | O | null | null | C1CCNC1.Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CI)O2>O>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(CN1CCCC1)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb149d5c9e914050af85929948d5d321 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | CC(CC(=O)NC=1C(=CC2=C(C(C(O2)(C)C)=O)C1C)C)(C)C>>CC(CC(=O)NC=1C(=CC2=C(C(C(O2)(C)C)O)C1C)C)(C)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[O:22]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH:17]([OH:18])[C:19]([CH3:20])([CH3:21... | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | null | null | C1CCOC1.CCCCCC | Reduction | Reduction of ketone to secondary alcohol | 755c7bdda3ccaa9e2a097b82c386f43f2881f1d49e6c3707dce72c3ac00b51db | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCO2 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 82 | [{"value": 82.0, "product": "CC(CC(=O)NC=1C(=CC2=C(C(C(O2)(C)C)O)C1C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,3-dimethyl-N-(2,2,4,6-tetramethyl-3-oxo-2,3-dihydro-1-benzofuran-5-yl)butanamide obtained in Reference Example 342, the title compound was synthesized in the same manner as in Example 234. Yield: 82%. Melting point: 217-218° C. (THF-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | C1CCOC1.CCCCCC | null | null | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2>C1CCOC1.CCCCCC>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ede3feeabda640c189b8f1a2ab96f142 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | CC(CC(=O)NC=1C(=CC2=C(C(C(O2)(C)C)O)C1C)C)(C)C.C(C)[SiH](CC)CC.O>>CC(CC(=O)NC=1C(=CC2=C(CC(O2)(C)C)C1C)C)(C)C | O[CH:17]1[c:5]2[c:4]([cH:3][c:2]([CH3:1])[c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:6]2[CH3:7])[O:21][C:18]1([CH3:19])[CH3:20]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][C:18]([CH3:19])([CH3:20])[O:21]2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 245ff09e99bd927b769decf1658bc3ac2fdc02bd9658b4c8501cb5895aec2e56 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc2c(c1)CCO2 | O-[CH;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[#8:5]-[C:6]-1(-[C;D1;H3:7])-[C;D1;H3:8]>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[#8:5]-[c:4]:[c:2](:[c:3])-[CH2;D2;+0:1]-1 | 92.3 | [{"value": 92.0, "product": "CC(CC(=O)NC=1C(=CC2=C(CC(O2)(C)C)C1C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "CC(CC(=O)NC=1C(=CC2=C(CC(O2)(C)C)C1C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixed solution of 3,3-dimethyl-N-(3-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)butanamide (2.0 g, 6.55 mmol) obtained in Example 338 in trifluoroacetic acid (3 mL) was added dropwise with ice-cooling triethylsilane (2.09 g, 13.10 mmol). The reaction solution was warmed to room temperature and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | Other | FC(C(=O)O)(F)F | null | 0.5 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2>FC(C(=O)O)(F)F>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-847bb5d87bcf44399a482f511bdc4c23 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | CC(CC(=O)NC=1C(=CC2=C(CC(O2)(C)C)C1C)C)(C)C.C1CCOC1.CCCCCC>>C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[cH:3][c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][C:20]([CH3:21])([CH3:22])[O:23]2>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][C:20]([CH3:21])([CH3:... | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | null | null | null | Miscellaneous | OtherReaction | c575f431b3127090be8382568230b261240de97350cb8e70e8cf496a0db5ebef | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc2c(c1)CCO2 | [C:1]-[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[C:1]-[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[C:9]=[O;D1;H0:10]):[c:6](-[C;D1;H3:7]):[c:8] | 85 | [{"value": 85.0, "product": "C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,3-dimethyl-N-(2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)butanamide obtained in Example 339, the title compound was synthesized in the same manner as in Example 20. Yield: 85%. Melting point: 180-181° C. (THF-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | Other | null | null | null | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-084a2665c8a94bc79cbdee373c01ca3a | Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2>>Cc1c2c(c(C(=O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C>>C(C)(C)C1=CC=C(C(=O)C2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1 | [CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([OH:7])[c:8]3[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]3)[c:17]([CH3:18])[c:19]1[NH:20][C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[O:28][C:29]([CH3:30])([CH3:31])[CH2:32]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][c:11]([CH:12... | Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | Cc1c2c(c(C(=O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | null | [O-2].[O-2].[Mn+4] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1cccc2c1OCC2 | [#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[c:6](:[c:7]):[c:8]):[c:9]>>[#8:1]-[c:2]:[c:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6](:[c:7]):[c:8]):[c:9] | 75 | [{"value": 75.0, "product": "C(C)(C)C1=CC=C(C(=O)C2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "C(C)(C)C1=CC=C(C(=O)C2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of N-(7-(hydroxy(4-isopropylphenyl)methyl)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (209 mg, 0.48 mmol) obtained in Example 341 in dichloromethane (7 mL) was added manganese dioxide (415 mg, 4.8 mmol) and the mixture was stirred at room temperature for 8 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | [O-2].[O-2].[Mn+4].ClCCl | null | 8 | Cc1c2c(c(C(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2>[O-2].[O-2].[Mn+4].ClCCl>Cc1c2c(c(C(=O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1d8416ab2ff4079bb13186497debdc0 | CC(C)c1ccc(O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c2c(c(Oc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | O.BrC1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(C)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)C1=CC=C(OC2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1 | [OH:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]1.Br[c:5]1[c:4]2[c:3]([c:2]([CH3:1])[c:18]([NH:19][C:20](=[O:21])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:16]1[CH3:17])[CH2:31][C:28]([CH3:29])([CH3:30])[O:27]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([O:6][c:7]3[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3... | CC(C)c1ccc(O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | Cc1c2c(c(Oc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | null | [Cu](I)I | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 578bd76ed7d2745c52e52e1f4b95973294b57f760b3539fd8789e06e384e3d04 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2cccc3c2OCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:8]-[#8:7]-[c:5](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2](-[C;D1;H3:3]):[c:4] | 40 | [{"value": 40.0, "product": "C(C)(C)C1=CC=C(OC2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.9, "product": "C(C)(C)C1=CC=C(OC2=C(C(=C(C=3CC(OC32)(C)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 60 | HOUR | A mixed solution of N-(7-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.36 mmol) obtained in Example 343, 4-isopropylphenol (556 mg, 4.08 mmol) and potassium carbonate (188 mg, 1.36 mmol) in pyridine (16 mL) was stirred at 140° C. under argon atmosphere for 1 hour. Copper iod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | [Cu](I)I.N1=CC=CC=C1 | 140 | 60 | CC(C)c1ccc(O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>[Cu](I)I.N1=CC=CC=C1>Cc1c2c(c(Oc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d36096385fdc4bcfa8681acda7277228 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.Cc1ccc(O)cc1>>Cc1ccc(Oc2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OC(C)(C)C3)cc1 | BrC1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.CC1=CC=C(C=C1)O>>CC(CC(=O)NC=1C(=C(C2=C(CC(O2)(C)C)C1C)OC1=CC=C(C=C1)C)C)(C)C | Br[c:7]1[c:8]([CH3:9])[c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([CH3:20])[c:21]2[c:22]1[O:23][C:24]([CH3:25])([CH3:26])[CH2:27]2.[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[c:8]([CH3:9])[c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.Cc1ccc(O)cc1 | Cc1ccc(Oc2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OC(C)(C)C3)cc1 | null | null | CCCCCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 578bd76ed7d2745c52e52e1f4b95973294b57f760b3539fd8789e06e384e3d04 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2cccc3c2OCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:6](-[C;D1;H3:7]):[c:8] | 19 | [{"value": 19.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(CC(O2)(C)C)C1C)OC1=CC=C(C=C1)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 343 and 4-methylphenol, the title compound was synthesized in the same manner as in Example 344. Yield: 19%. Melting point: 182-184° C. (hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | CCCCCC | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.Cc1ccc(O)cc1>CCCCCC>Cc1ccc(Oc2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OC(C)(C)C3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dec4719147be4ef5a8b7050314002040 | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2>>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | C(C)(C)C1=CC=C(CC2=C(C(=C(C=3C(C(OC32)(C)C)=O)C)NC(CC(C)(C)C)=O)C)C=C1>>OC1C(OC2=C1C(=C(C(=C2CC2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)(C)C | [CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13]2)[c:14]2[c:15]([c:16]([CH3:17])[c:18]1[NH:19][C:20](=[O:21])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[O:32]2>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c... | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2 | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 | null | null | C1CCOC1.CCCCCC | Reduction | Reduction of ketone to secondary alcohol | 755c7bdda3ccaa9e2a097b82c386f43f2881f1d49e6c3707dce72c3ac00b51db | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2cccc3c2OCC3)cc1 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 81 | [{"value": 81.0, "product": "OC1C(OC2=C1C(=C(C(=C2CC2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-(4-isopropylbenzyl)-2,2,4,6-tetramethyl-3-oxo-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Reference Example 330, the title compound was synthesized in the same manner as in Example 234. Yield: 81%. Melting point: 244-245° C. (THF-hexane).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | null | C1CCOC1.CCCCCC | null | null | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2>C1CCOC1.CCCCCC>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d350f32048f4cc39455ea1396d729e5 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2>>Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C([C@@H]([C@@H](O2)C)C2=CC=C(C=C2)C(C)C)C1C)C)C>>C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=C(C(=C2C)C)N)C)C | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[C@H:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[C@H:21]([CH3:22])[O:23]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[C@H:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:1... | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc([C@@H]2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 83 | [{"value": 83.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=C(C(=C2C)C)N)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (cis)-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 352, (cis)-5-bromo-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was synthesized in the same manner as in Reference Example 23. Using the compound, (cis)-N-benzyl-3-(4-isopropylphenyl)-2,4,6... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2>CCCCCC>Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6dc3ca0a13854c11804e68d97016a881 | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)C(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | C(C)(C)C1=CC=C(C=C1)C1=C(OC2=C1C(=CC(=C2C)C)C)C.C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)N)C)C.BrC=1C(=C(C2=C(C(C(O2)C)C2=CC=C(C=C2)C(C)C)C1C)C)C.C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(C(O2)C)C2=CC=C(C=C2)C(C)C)C1C)C)C.C(C)(C)(C)CC(=O)Cl.C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C.C(C)(C)C1=CC=C(C=C1)C1C(... | Cl[C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH:28]([CH3:29])[O:30]2>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13... | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)C(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | null | null | CCCCCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc([C@H]2COc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 18 | [{"value": 18.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1[C@@H](OC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-1-benzofuran obtained in Reference Example 347, a mixture of cis isomer and trans isomer (3:2) of 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was synthesized in the same manner as in Reference Example 199. Using the mixture as it is as the compound,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC | null | null | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)C(C)O2>CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)[C@H](C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e04c28df7834e6d803b1b3a9415436c | Brc1ccccn1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c2c(c(C(O)c3ccccn3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | O.C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.BrC1=NC=CC=C1.C(CCC)[Li]>>OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=NC=CC=C2 | Br[c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]=[O:7])[c:14]([CH3:15])[c:16]1[NH:17][C:18](=[O:19])[CH2:20][C:21]([CH3:22])([CH3:23])[CH3:24])[O:25][C:26]([CH3:27])([CH3:28])[CH2:29]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([OH:7])[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14]([CH3:15])... | Brc1ccccn1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | Cc1c2c(c(C(O)c3ccccn3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | null | null | CCCCCC.C(C)OCC.C(C)(=O)OCC.C1CCOC1 | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2cccc3c2OCC3)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[c:7]:[c:8](-[CH;D2;+0:9]=[O;H0;D1;+0:10]):[c:11]>>[#8:6]-[c:7]:[c:8](-[CH;D3;+0:9](-[OH;D1;+0:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11] | 68.1 | [{"value": 68.0, "product": "OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=NC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-bromopyridine (553 mg, 3.5 mmol) in diethyl ether (3.0 mL) was added dropwise at −70° C. under argon atmosphere n-butyllithium (1.6 M, hexane solution, 2.13 mL, 3.4 mmol) and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise at −70° C. a solution of N-(7-formyl-2,2,4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | Br- | CCCCCC.C(C)OCC.C(C)(=O)OCC.C1CCOC1 | null | 0.5 | Brc1ccccn1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>CCCCCC.C(C)OCC.C(C)(=O)OCC.C1CCOC1>Cc1c2c(c(C(O)c3ccccn3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3f7727984eb4879a3d98382b548bdbb | CC(C)c1ccc(CCl)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c2c(c(C(O)Cc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(C)C1=CC=C(CCl)C=C1>>OC(CC1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C | Cl[CH2:8][c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]=[O:7])[c:18]([CH3:19])[c:20]1[NH:21][C:22](=[O:23])[CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])[O:29][C:30]([CH3:31])([CH3:32])[CH2:33]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([OH:7])[CH2:8][c:9]3[cH:10][c... | CC(C)c1ccc(CCl)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | Cc1c2c(c(C(O)Cc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | null | null | null | C-C Coupling | Grignard_alcohol | 983d8b8e9b89ba290d93feeffe843caf411eba49bd1aefb21a784058d86f3a30 | 3e80fe0b4a87df3724831714de4ab23fef101254d00d9b3074e300e6e8f4b9ea | c1ccc(CCc2cccc3c2OCC3)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[c:6]:[c:7](-[CH;D2;+0:8]=[O;H0;D1;+0:9]):[c:10]>>[#8:5]-[c:6]:[c:7](-[CH;D3;+0:8](-[OH;D1;+0:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10] | 92 | [{"value": 92.0, "product": "OC(CC1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-formyl-2,2,4,6-tetramethyl-2,3-dihydro-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 340 and 4-isopropylbenzyl chloride, the title compound was synthesized in the same manner as in Example 341. Yield: 92%. Amorphous substance.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Secondary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | null | null | null | CC(C)c1ccc(CCl)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2>>Cc1c2c(c(C(O)Cc3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eac1af74b66642eeaa051c87ce0afb7b | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.[Br][Mg][c]1ccccc1>>Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.C1(=CC=CC=C1)[Mg]Br>>OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2 | [CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]=[O:7])[c:14]([CH3:15])[c:16]1[NH:17][C:18](=[O:19])[CH2:20][C:21]([CH3:22])([CH3:23])[CH3:24])[O:25][C:26]([CH3:27])([CH3:28])[CH2:29]2.[Br][Mg][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([OH:7])[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:14]([... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.[Br][Mg][c]1ccccc1 | Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2cccc3c2OCC3)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6].[Br]-[Mg]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:6] | null | [] | null | null | null | null | Using N-(7-formyl-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethyl-butanamide obtained in Example 340 and phenylmagnesium bromide, the title compound was synthesized in the same manner as in Example 239. The yield was quantitative. Amorphous substance.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | Br-.Mg | null | null | null | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2.[Br][Mg][c]1ccccc1>>Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a98f2d1812c46c6b79416641375d74c | Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2>>Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2>>C(C1=CC=CC=C1)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C | O[CH:4]([c:3]1[c:2]([CH3:1])[c:15]([NH:16][C:17](=[O:18])[CH2:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:13]([CH3:14])[c:12]2[c:11]1[O:28][C:25]([CH3:26])([CH3:27])[CH2:24]2)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[c:12]([c:13]([CH3:14])[c:15]1[NH:16... | Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2 | Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(Cc2cccc3c2OCC3)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4]-[#8:5])-[c:6](:[c:7]):[c:8]>>[#8:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[c:6](:[c:7]):[c:8]):[c:3] | 74 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-(1-hydroxy(phenyl)methyl)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 355, the title compound was synthesized in the same manner as in Example 271. Yield: 74%. Melting point: 129-130° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c2c(c(C(O)c3ccccc3)c(C)c1NC(=O)CC(C)(C)C)OC(C)(C)C2>C(C)(=O)OCC.CCCCCC>Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)CC(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd92e462bd684b0c99efd27a6afd2d5d | Cc1ccccc1C(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2>>Cc1ccccc1Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2 | C(=O)C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C.CC1=C(C=CC=C1)[Mg]Br.OC(C1=C(C(=C(C=2CC(OC21)(C)C)C)NC(CC(C)(C)C)=O)C)C2=C(C=CC=C2)C>>CC(CC(=O)NC=1C(=C(C2=C(CC(O2)(C)C)C1C)CC1=C(C=CC=C1)C)C)(C)C | O[CH:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)[c:9]1[c:10]([CH3:11])[c:12]([NH:13][C:14](=[O:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[c:21]([CH3:22])[c:23]2[c:24]1[O:25][C:26]([CH3:27])([CH3:28])[CH2:29]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][c:9]1[c:10]([CH3:11])[c:12]([NH:13][C:14](=[O:15... | Cc1ccccc1C(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2 | Cc1ccccc1Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(Cc2cccc3c2OCC3)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8]>>[#8:8]-[c:7]:[c:5](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:6] | 24 | [{"value": 24.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(CC(O2)(C)C)C1C)CC1=C(C=CC=C1)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-formyl-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethyl-butanamide obtained in Example 340 and 2-methylphenylmagnesium bromide, N-(7-(hydroxy(2-methylphenyl)methyl)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide was synthesized in the same manner as in Example 239. U... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1ccccc1C(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2>C(C)(=O)OCC.CCCCCC>Cc1ccccc1Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC(C)(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5883eec30c541afa315dc4ca3ef04ed | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.OC(c1ccccc1)(c1ccccc1)c1ccco1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccco1)OC[C@@H]2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.O1C(=CC=C1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1>>O1C(=CC=C1)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:16]1[c:2]([CH3:1])[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]2[c:15]1[O:22][CH2:23][C@@H:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.OC(c1ccccc1)(c1ccccc1)[c:17]1[cH:18][cH:19][cH:20][o:21]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.OC(c1ccccc1)(c1ccccc1)c1ccco1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccco1)OC[C@@H]2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | OtherReaction | 57c5bce7e1a5a9f9b79d58f07e4edf3da216e36ad50665faf134816123195c64 | 114d675bc7fdea12dfa57325db5a3226d8dc86de2fe70e8df765ce123a092f0e | c1ccc([C@H]2COc3c(-c4ccco4)cccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-C(-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1):[c:6](-[C;D1;H3:7]):[c:8] | 6 | [{"value": 6.0, "product": "O1C(=CC=C1)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (−)-N-((3R)-7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 51 and 2-furyl(diphenyl)methanol, the title compound was obtained in the same manner as in Example 107. Yield: 6%. Melting point: 214-217° C. (ethyl acetate-hexane).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary alcohol | null | c1ccc2c(c1)CCO2.c1ccccc1.c1ccccc1.c1ccoc1 | c1ccoc1.c1ccc2c(c1)CCO2 | c1ccoc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.OC(c1ccccc1)(c1ccccc1)c1ccco1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccco1)OC[C@@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc8e4278023241ac8e2e77c808542cb0 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.O=C(Cl)c1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)c1ccccc1)OC[C@@H]2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([cH:16]1)[O:25][CH2:26][C@@H:27]2[c:28]1[cH:29][cH:30][c:31]([CH:32]([CH3:33])[CH3:34])[cH:35][cH:36]1.Cl[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C... | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.O=C(Cl)c1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)c1ccccc1)OC[C@@H]2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | f8d339b78f15a4d82452b51f6749e04de87b23cf8586247567d903b7cafd77bf | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1cccc2c1OC[C@@H]2c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11](-[C;D1;H3:12]):[c:13]>>[C:6]-[#8:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:11](-[C;D1;H3:12]):[c:13] | 74 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-N-((3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 37 and benzoyl chloride, the title compound was obtained in the same manner as in Example 38.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | null | null | null | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2.O=C(Cl)c1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)c1ccccc1)OC[C@@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a0364f1f29e4deba1874f3ffb7124bc | CCOc1ccc(Br)c(F)c1F.O=C1CCC(C2CCC3(CC2)OCCO3)CC1>>CCOc1ccc(C2(O)CCC(C3CCC4(CC3)OCCO4)CC2)c(F)c1F | [Cl-].[NH4+].O1CCOC12CCC(CC2)C2CCC(CC2)=O.BrC1=C(C(=C(C=C1)OCC)F)F.[Mg]>>O1CCOC12CCC(CC2)C2CCC(CC2)(O)C2=C(C(=C(C=C2)OCC)F)F | Br[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([F:28])[c:25]1[F:26].[C:8]1(=[O:9])[CH2:10][CH2:11][CH:12]([CH:13]2[CH2:14][CH2:15][C:16]3([CH2:17][CH2:18]2)[O:19][CH2:20][CH2:21][O:22]3)[CH2:23][CH2:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]2([OH:9])[CH2:10][CH2:11][CH:12]([CH:13]3[CH2:14][CH2:15][C:1... | CCOc1ccc(Br)c(F)c1F.O=C1CCC(C2CCC3(CC2)OCCO3)CC1 | CCOc1ccc(C2(O)CCC(C3CCC4(CC3)OCCO4)CC2)c(F)c1F | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Grignard_alcohol | a931995fda9e1945c54e5e8576d835233f84350823d88bf0c76b4c2a9041417b | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2CCC(C3CCC4(CC3)OCCO4)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]-[C:12]>>[C:7]-[C:8]-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6])-[C:11]-[C:12] | 120.3 | [{"value": 120.3, "product": "O1CCOC12CCC(CC2)C2CCC(CC2)(O)C2=C(C(=C(C=C2)OCC)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 60 | MINUTE | First Step: 6.1 g of well dried magnesium and 20 mL of THF were placed in a reactor under nitrogen atmosphere, and heated to 40° C. 59.7 g of 1-bromo-4-ethoxy-2,3-difluorobenzene (1) dissolved in 300 mL of THF was slowly added dropwise thereto at a temperature range of from 40 to 60° C., followed by stirring for 60 min... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.C1CCCCC1 | c1ccccc1.C1CCCCC1 | c1ccccc1.C1CCCCC1.C1CCC2(CC1)OCCO2 | Br- | C1(=CC=CC=C1)C.C1CCOC1 | 40 | 1 | CCOc1ccc(Br)c(F)c1F.O=C1CCC(C2CCC3(CC2)OCCO3)CC1>C1(=CC=CC=C1)C.C1CCOC1>CCOc1ccc(C2(O)CCC(C3CCC4(CC3)OCCO4)CC2)c(F)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6083e81a01643d0841d43c181bf2951 | CCOC(=O)CP(=O)(OCC)OCC.O=C1CCC2(CC1)OCCO2>>CCOC(=O)C=C1CCC2(CC1)OCCO2 | C(C)O.[O-]CC.[Na+].O1CCOC12CCC(CC2)=O.C(C)OP(=O)(OCC)CC(=O)OCC.C1(=CC=CC=C1)C>>C(C)OC(C=C1CCC2(OCCO2)CC1)=O | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[C:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2 | CCOC(=O)CP(=O)(OCC)OCC.O=C1CCC2(CC1)OCCO2 | CCOC(=O)C=C1CCC2(CC1)OCCO2 | null | null | O | C-C Coupling | Wittig with Phosphonium | 862f028e4f08b3ca1ddc1f5da0783dd840c14e5eddbcce43498a5769f99cd130 | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | [CH]=C1CCC2(CC1)OCCO2 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[C;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10]>>[C:8]-[C:7]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:9]-[C:10] | 92.3 | [{"value": 92.3, "product": "C(C)OC(C=C1CCC2(OCCO2)CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 2 | HOUR | First Step: 200.0 g of 1,4-dioxaspiro[4,5]decan-8-one (10), 301.4 g of ethyl diethylphosphonoacetate and 1,000 mL of toluene were added to a reactor under nitrogen atmosphere, and stirred at 5° C. 457.5 g of a 20% sodium ethoxide ethanol solution was added dropwise thereto at a temperature range of from 5 to 11° C. ove... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | HO- | O | 5 | 2 | CCOC(=O)CP(=O)(OCC)OCC.O=C1CCC2(CC1)OCCO2>O>CCOC(=O)C=C1CCC2(CC1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf277ac2859a4c17bd2edeb5e6c4525f | CCOC(=O)C=C1CCC2(CC1)OCCO2>>CCOC(=O)CC1CCC2(CC1)OCCO2 | C(C)OC(C=C1CCC2(OCCO2)CC1)=O.C(C)(C)O>>C(C)OC(CC1CCC2(OCCO2)CC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2 | CCOC(=O)C=C1CCC2(CC1)OCCO2 | CCOC(=O)CC1CCC2(CC1)OCCO2 | null | [Pd] | C1(=CC=CC=C1)C | Reduction | Hydrogenation (double to single) | 70b19490e3afff6a088807b4052319b48651269c86ee25b6c8718d2f01378486 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | C1CCC2(CC1)OCCO2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[C:9]-[C:10]>>[C:1]-[C:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[C:9]-[C:10] | 94.6 | [{"value": 94.6, "product": "C(C)OC(CC1CCC2(OCCO2)CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Second Step: 267.3 g of the compound (11), 5.0 g of Pd/C, 500 mL of isopropyl alcohol (IPA) and 500 mL of toluene were added to a reactor, and stirred under hydrogen atmosphere for 24 hours. After confirming that the reaction had been completed by GC analysis, the Pd/C was filtered off, and the solvent was removed by d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | null | [Pd].C1(=CC=CC=C1)C | null | 24 | CCOC(=O)C=C1CCC2(CC1)OCCO2>[Pd].C1(=CC=CC=C1)C>CCOC(=O)CC1CCC2(CC1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fadece5a1ce4652ac2d89ceccc5b5c3 | CCOC(=O)CC1CCC2(CC1)OCCO2>>OCCC1CCC2(CC1)OCCO2 | [OH-].[Na+].CC(=O)C.C(C)OC(CC1CCC2(OCCO2)CC1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O1CCOC12CCC(CC2)CCO | CCO[C:2](=[O:1])[CH2:3][CH:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2 | CCOC(=O)CC1CCC2(CC1)OCCO2 | OCCC1CCC2(CC1)OCCO2 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCC2(CC1)OCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 98.5 | [{"value": 98.5, "product": "O1CCOC12CCC(CC2)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 3 | CELSIUS | 2 | HOUR | Third Step: 20.0 g of lithium aluminum hydride (LAH) and 800 mL of THF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. 190.0 g of the compound (12) dissolved in 200 mL of THF was added dropwise thereto at a temperature range of from 0 to 7° C. over 2 hours, followed by further stirring at 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCC2(CC1)OCCO2 | HO- | C1CCOC1 | 3 | 2 | CCOC(=O)CC1CCC2(CC1)OCCO2>C1CCOC1>OCCC1CCC2(CC1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec9a38dac2904d76b2f0d5edc213a51a | II.OCCC1CCC2(CC1)OCCO2>>ICCC1CCC2(CC1)OCCO2 | II.O1CCOC12CCC(CC2)CCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1>>ICCC1CCC2(OCCO2)CC1 | I[I:1].O[CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2>>[I:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2 | II.OCCC1CCC2(CC1)OCCO2 | ICCC1CCC2(CC1)OCCO2 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | C1CCC2(CC1)OCCO2 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[I;H0;D1;+0:1] | 93.9 | [{"value": 93.9, "product": "ICCC1CCC2(OCCO2)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 3 | CELSIUS | null | null | Fourth Step: 150.0 g of the compound (13), 274.3 g of triphenylphosphine (Ph3P), 71.3 g of imidazole and 900 mL of toluene were added to a reactor under nitrogen atmosphere, and stirred at 3° C. 255.5 g of iodine was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C., followed by furt... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | C1CCC2(CC1)OCCO2 | HI | C1(=CC=CC=C1)C | 3 | null | II.OCCC1CCC2(CC1)OCCO2>C1(=CC=CC=C1)C>ICCC1CCC2(CC1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f75e17883ca9440191277de326bd4422 | ICCC1CCC2(CC1)OCCO2>>C=CC1CCC2(CC1)OCCO2 | CCCCCCC.ICCC1CCC2(OCCO2)CC1.CN(C)C=O.CC(C)([O-])C.[K+]>>C(=C)C1CCC2(OCCO2)CC1 | I[CH2:1][CH2:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>>[CH2:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2 | ICCC1CCC2(CC1)OCCO2 | C=CC1CCC2(CC1)OCCO2 | null | null | O | Functional Group Interconversion | OtherReaction | 7ab0e2f027b53e55482844c76b9fa28a39b9b7fc9a3ebfe2bc7a12b2880fc3e9 | 390fd58f5ee2898074a21589b1498013a0dd9c1d8d67db11ba35b62c01461363 | C1CCC2(CC1)OCCO2 | I-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH;D2;+0:2]=[CH2;D1;+0:1])-[C:5] | 81.5 | [{"value": 81.5, "product": "C(=C)C1CCC2(OCCO2)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 3 | CELSIUS | null | null | Fifth Step: 223.0 g of the compound (14) and 800 mL of DMF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. under cooling with ice. 92.9 g of potassium t-butoxide (t-BuOK) was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C., followed by further stirring at 0°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Vinyl | null | null | C1CCC2(CC1)OCCO2 | HI | O | 3 | null | ICCC1CCC2(CC1)OCCO2>O>C=CC1CCC2(CC1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bfe50ff125145438fbeea6ec4d98764 | C=CC1CCC2(CC1)OCCO2>>C=CC1CCC(=O)CC1 | C(=C)C1CCC2(OCCO2)CC1.C(=O)O.C1(=CC=CC=C1)C>>C(=C)C1CCC(CC1)=O | C1C[O:7][C:6]2(O1)[CH2:5][CH2:4][CH:3]([CH:2]=[CH2:1])[CH2:9][CH2:8]2>>[CH2:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6](=[O:7])[CH2:8][CH2:9]1 | C=CC1CCC2(CC1)OCCO2 | C=CC1CCC(=O)CC1 | null | null | [Cl-].[Na+].O | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCCCC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 87.5 | [{"value": 87.5, "product": "C(=C)C1CCC(CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sixth Step: 103.3 g of the compound (15), 86.5 g of 98% formic acid and 200 mL of toluene were added to a reactor in a nitrogen atmosphere, and stirred under refluxing and heating for 2 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with 500 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | C1CCCCC1 | HO- | [Cl-].[Na+].O | null | null | C=CC1CCC2(CC1)OCCO2>[Cl-].[Na+].O>C=CC1CCC(=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c247215d61e04eb0be154eeb7de1132d | C=CC1CCC(=O)CC1.CCOc1ccc(Br)c(F)c1F>>C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1 | Cl.C(=C)C1CCC(CC1)=O.BrC1=C(C(=C(C=C1)OCC)F)F.[Mg]>>C(C)OC1=C(C(=C(C=C1)C1(CCC(CC1)C=C)O)F)F | [CH2:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6](=[O:7])[CH2:19][CH2:20]1.Br[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH3:14])[c:15]([F:16])[c:17]1[F:18]>>[CH2:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6]([OH:7])([c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][CH3:14])[c:15]([F:16])[c:17]2[F:18])[CH2:19][CH2:20]1 | C=CC1CCC(=O)CC1.CCOc1ccc(Br)c(F)c1F | C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Grignard_alcohol | a931995fda9e1945c54e5e8576d835233f84350823d88bf0c76b4c2a9041417b | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]-[C:12]>>[C:7]-[C:8]-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6])-[C:11]-[C:12] | 135.6 | [{"value": 135.6, "product": "C(C)OC1=C(C(=C(C=C1)C1(CCC(CC1)C=C)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 53 | CELSIUS | 30 | MINUTE | Seventh Step: 1.76 g of well dried magnesium and 10 mL of THF were placed in a reactor under nitrogen atmosphere, and heated to 53° C. 17.2 g of the compound (1) dissolved in 30 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 56° C., followed by stirring for 30 minutes. Thereafter, 6.0 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1 | Br- | C1(=CC=CC=C1)C.C1CCOC1 | 53 | 0.5 | C=CC1CCC(=O)CC1.CCOc1ccc(Br)c(F)c1F>C1(=CC=CC=C1)C.C1CCOC1>C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bcefbca7a829467ca19117d743d02534 | C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1>>C=CC1CC=C(c2ccc(OCC)c(F)c2F)CC1 | C(C)OC1=C(C(=C(C=C1)C1(CCC(CC1)C=C)O)F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C.O.O>>C(C)OC1=C(C(=C(C=C1)C1=CCC(CC1)C=C)F)F | O[C:6]1([c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH3:13])[c:14]([F:15])[c:16]2[F:17])[CH2:5][CH2:4][CH:3]([CH:2]=[CH2:1])[CH2:19][CH2:18]1>>[CH2:1]=[CH:2][CH:3]1[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH3:13])[c:14]([F:15])[c:16]2[F:17])[CH2:18][CH2:19]1 | C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1 | C=CC1CC=C(c2ccc(OCC)c(F)c2F)CC1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | bb751e8d8bac081516d1433e6fec088b316018c4b9e2465f1f9c878bad0b1e7c | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2ccccc2)CCCC1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5]-[C:6]-[C:7](-[C:8]=[C;D1;H2:9])-[C:10]-[CH2;D2;+0:11]-1>>[C;D1;H2:9]=[C:8]-[C:7]1-[C:6]-[C:5]-[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])=[CH;D2;+0:11]-[C:10]-1 | 14.9 | [{"value": 14.9, "product": "C(C)OC1=C(C(=C(C=C1)C1=CCC(CC1)C=C)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Eighth Step: 18.5 g of the compound (17), 0.4 g of p-toluenesulfonic acid and 60 mL of toluene were mixed, and the mixture was refluxed under heating for 1 hour while water distilled out was removed. After cooling the resulting reaction mixture to 25° C., 100 mL of water and 100 mL of toluene were added to and mixed wi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | C=CC1CCC(O)(c2ccc(OCC)c(F)c2F)CC1>C1(=CC=CC=C1)C>C=CC1CC=C(c2ccc(OCC)c(F)c2F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50835a222ae84471986cf124d7fc7be9 | CC(C)(C)CC(=O)Cl.Cc1ccccc1>>Cc1ccc(C(=O)CC(C)(C)C)cc1 | [Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)C.C(C)(C)(C)CC(=O)Cl>>C(C)(C)(C)CC(=O)C1=CC=C(C=C1)C | Cl[C:6](=[O:7])[CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:13][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1 | CC(C)(C)CC(=O)Cl.Cc1ccccc1 | Cc1ccc(C(=O)CC(C)(C)C)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | 27 g of aluminum chloride and 100 ml of toluene were mixed and 25 g of t-butylacetyl chloride was added dropwise to this under ice cooling, After reaction at room temperature for 2 hours, the reaction solution was poured on ice. This was extracted with hexane, and the organic phase was rinsed with water and an aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | CC(C)(C)CC(=O)Cl.Cc1ccccc1>>Cc1ccc(C(=O)CC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-742de45adb86474ab21a2f02f9bda3fd | C=CCBr.O=C1CCCCO1>>C=CCC1CCCOC1=O | BrCCCCCCCCC=C.C1(CCCCO1)=O.C(C=C)Br.C1(CCO1)=O>>C(C=C)C1C(OCCC1)=O | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]1[CH2:5][CH2:6][CH2:7][O:8][C:9]1=[O:10]>>[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][O:8][C:9]1=[O:10] | C=CCBr.O=C1CCCCO1 | C=CCC1CCCOC1=O | null | null | null | C-C Coupling | OtherReaction | 5e149175aefbee30c162b3a3075c29479cdb101586c7d71ed9ec450a792d4d49 | 004d9bbde855ea6a20935a7929fb4c869d25b8db6104e99b9ee1ab33b13dc784 | O=C1CCCCO1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[O;D1;H0:4]=[C:5]1-[#8:6]-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[#8:6]-[C:5]-1=[O;D1;H0:4] | 70 | [{"value": 70.0, "product": "C(C=C)C1C(OCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 9.81 g of tetrahydro-3-(2-propenyl)-2H-pyrane-2-one of interest were prepared in the same manner as in Preparation Example 2Z-3 except that 10.01 g (100.0 mmol) of δ-valerolactone and 14.52 g (110.0 mmol) of allyl bromide were used instead of β-propiolactone and 10-bromo-1-decene described in Preparation Example 2Z-3, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Allyl | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HBr | null | null | null | C=CCBr.O=C1CCCCO1>>C=CCC1CCCOC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-519710125ed744478ae901138672da1b | C=CCBr.O=C1CCCCCO1>>C=CCC1CCCCOC1=O | BrCCCCCCCCC=C.C1(CCCCCO1)=O.C(C=C)Br.C1(CCO1)=O>>C(C=C)C1C(OCCCC1)=O | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1=[O:11]>>[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1=[O:11] | C=CCBr.O=C1CCCCCO1 | C=CCC1CCCCOC1=O | null | null | null | C-C Coupling | OtherReaction | 363b8e42e934fdb30262add36d1a73eb773241a701c30579d7daa2520cddc53c | 004d9bbde855ea6a20935a7929fb4c869d25b8db6104e99b9ee1ab33b13dc784 | O=C1CCCCCO1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[C:4]-[C:5]-[CH;D3;+0:6](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 65 | [{"value": 65.0, "product": "C(C=C)C1C(OCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10.02 g of 3-(2-propenyl)-2-oxepanone of interest were prepared in the same manner as in Preparation Example 2Z-3 except that 11.41 g (100.0 mmol) of ε-caprolactone and 14.52 g (110.0 mmol) of allyl bromide were used instead of β-propiolactone and 10-bromo-1-decene described in Preparation Example 2Z-0.3, respectively.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Allyl | C1CCCOCC1 | C1CCCOCC1 | C1CCCOCC1 | HBr | null | null | null | C=CCBr.O=C1CCCCCO1>>C=CCC1CCCCOC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c94ef083630f4ea7b850549dc77877de | O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>O=C(O)C(=O)C[C@H](O)[C@H](O)CO | Cl.O=C([C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[O-].[Na+].[Cl-].[Mg+2].[Cl-].O=C([C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[O-].[Na+].[Cl-].[Mg+2].[Cl-].O=C([C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[O-]>>C([C@@H]([C@@H](CO)O)O)C(=O)C(=O)O | [O-][C:4](=[O:5])[C@H:6](O)[C@@H:7]([OH:8])[C@H:9]([OH:10])[C@@H:11](CO)[OH:12].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C:2](=[O:1])[O-:3]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][C@H:7]([OH:8])[C@H:9]([OH:10])[CH2:11][OH:12] | O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | O=C(O)C(=O)C[C@H](O)[C@H](O)CO | null | null | C(C(CO)(CO)N)O | C-C Coupling | OtherReaction | 91086317a4f9c4524ffb39162c8af5db371b2d665057eabec19e0749b09f4b82 | 3aae38b179617a95974acc106905a62497db93050dfd106690016d6f45669511 | null | O-C-[C@@H;D3;+0:1](-[O;D1;H1:2])-[C:3](-[O;D1;H1:4])-[C:5](-[O;D1;H1:6])-[C@@H;D3;+0:7](-O)-[C;H0;D3;+0:8](-[O-])=[O;D1;H0:9].O-C-[C@@H](-O)-[C@@H](-O)-[C@H](-O)-[C@@H](-O)-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[C;H0;D3;+0:10](-[OH;D1;+0:11])-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C:5](-[O;D1;... | null | [] | null | null | 2 | HOUR | Samples of the purified gluconate dehydratase solution prepared in Example 3, which was dissolved in the 30 mM Tris buffer (pH 8.5) containing 1 mM sodium D-gluconate and 1 mM magnesium chloride, were allowed to stand for 30 minutes, 2 hours, or 12 hours at 4, 20, 30, 40, 50, 55, 60, 65, or 70° C. Another sample was al... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Carboxylic acid.Ketone.Primary alcohol | null | null | null | HO- | C(C(CO)(CO)N)O | null | 2 | O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>C(C(CO)(CO)N)O>O=C(O)C(=O)C[C@H](O)[C@H](O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fa032c3423f4293a87febfd758fb8d0 | O=C(O)C(O)(O)C[C@H](O)[C@H](O)CO>>O=CC[C@H](O)[C@H](O)CO | Cl[O-].[Na+].OC(C(=O)O)(O)C[C@H](O)[C@H](O)CO.Cl.Cl[O-].[Na+]>>O=CC[C@H](O)[C@H](O)CO | O=C(O)[C:2](O)([OH:1])[CH2:3][C@H:4]([OH:5])[C@H:6]([OH:7])[CH2:8][OH:9]>>[O:1]=[CH:2][CH2:3][C@H:4]([OH:5])[C@H:6]([OH:7])[CH2:8][OH:9] | O=C(O)C(O)(O)C[C@H](O)[C@H](O)CO | O=CC[C@H](O)[C@H](O)CO | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | c83db7e4056c797d5d7c6f77e6359e4872db4f88c6a6501d6ea339d94b7ab091 | 282094f219aa74de9d3503dee64970c0f093d54639444ad5781e9cc8554a9619 | null | O-C(=O)-[C;H0;D4;+0:1](-O)(-[OH;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:1]=[O;H0;D1;+0:2] | null | [] | null | null | 1 | HOUR | The pH of the resulting reaction mixture containing the 2-hydroxy-3-deoxy-D-gluconic acid was adjusted to 5.0 with 35% hydrochloric acid solution. Into the reaction mixture was dripped 377 g of 13% sodium hypochlorite solution to perform decarboxylation over a period of 1 hour with the reaction temperature adjusted to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary alcohol.Tertiary alcohol | Aldehyde | null | null | null | HO- | C(C)(=O)O | null | 1 | O=C(O)C(O)(O)C[C@H](O)[C@H](O)CO>C(C)(=O)O>O=CC[C@H](O)[C@H](O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91e3c3347aaa46518e183d5c7f5d63ac | C1CSCCN1>>C1CSCCN1 | C(C)(=O)[O-].CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C.N1CCSCC1.C([O-])([O-])=O.[K+].[K+]>>CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([... | [CH2:86]1[CH2:87][S:88][CH2:89][CH2:90][NH:91]1>>[CH2:86]1[CH2:87][S:88][CH2:89][CH2:90][NH:91]1 | C1CSCCN1 | C1CSCCN1 | null | null | CO.C(Cl)Cl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CSCCN1 | null | 46.9 | [{"value": 33.0, "product": "CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C.N1CCSCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value":... | null | null | 8 | HOUR | A solution of the acetate of cyclosporin allylic chloride from Example 35 (60 mg, 0.047 mmol) and thiomorpholine (48 mg, 0.47 mmol) in methylene chloride (3 mL) was stirred overnight at room temperature under N2 atmosphere. The mixture was concentrated in vacuo. The residue and potassium carbonate (102 mg, 0.740 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CSCCN1 | null | CO.C(Cl)Cl.C(C)(=O)OCC | null | 8 | C1CSCCN1>CO.C(Cl)Cl.C(C)(=O)OCC>C1CSCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edbb2d1407944e10a6863d654c15a5cf | COc1ccc(-c2ccccc2)cc1N=NC(=O)OC(C)C.O=C(OO)c1cccc(Cl)c1>>COc1ccc(-c2ccccc2)cc1[N+]([O-])=NC(=O)OC(C)C | COC1=C(C=C(C=C1)C1=CC=CC=C1)N=NC(=O)OC(C)C.ClC1=CC(=CC=C1)C(=O)OO>>COC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=NC(=O)OC(C)C)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[N:15]=[N:17][C:18](=[O:19])[O:20][CH:21]([CH3:22])[CH3:23].O=C(O[OH:16])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[N+:15]([O-:16])=[N:17][C:18](=[O:19])[O:20][CH:2... | COc1ccc(-c2ccccc2)cc1N=NC(=O)OC(C)C.O=C(OO)c1cccc(Cl)c1 | COc1ccc(-c2ccccc2)cc1[N+]([O-])=NC(=O)OC(C)C | null | null | ClCCl | Miscellaneous | OtherReaction | d5217bdd79a0360fd41d080b4d230abee2664b51ebf8a2fb02e4749c29968002 | 381ef8b9335b580e8926b6fdccc2843c211e4480b7abfde442a1e2f94f46eb4c | c1ccc(-c2ccccc2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[N+;H0;D3:6](-[O-;H0;D1:1])-[c:7](:[c:8]):[c:9] | 90.6 | [{"value": 90.6, "product": "COC1=C(C=C(C=C1)C1=CC=CC=C1)[N+](=NC(=O)OC(C)C)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-methylethyl (4-methoxy-[1,1′-biphenyl]-3-yl)diazenecarboxylate (10.25 g) in dichloromethane (160 mL) was cooled in an ice bath and meta-chloroperbenzoic acid (14.8 g) was added in portions with stirring. Additional dichloromethane (90 mL) was added and the solution left to stir at room temperature for 3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Diazene.Peroxide | null | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COc1ccc(-c2ccccc2)cc1N=NC(=O)OC(C)C.O=C(OO)c1cccc(Cl)c1>ClCCl>COc1ccc(-c2ccccc2)cc1[N+]([O-])=NC(=O)OC(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-332f061087324574bde7861097887232 | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1>>Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1 | C(C1=CC=CC=C1)OC1=C(C(=CC(=C1)C)OCC1=CC=CC=C1)C(C)=O.C1=C(C=CC2=CC=CC=C12)C=O>>OC1=C(C(=CC(=C1)C)O)C(CCC1=CC=2CCCCC2C=C1)=O | c1ccc(C[O:5][c:4]2[cH:3][c:2]([CH3:1])[cH:23][c:21]([O:22]Cc3ccccc3)[c:6]2[C:7](=[O:8])[CH3:9])cc1.O=[CH:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[cH:17][cH:18][cH:19][cH:20]2>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[CH2:17][CH2:18][CH2:19][CH... | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1 | Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1 | null | null | null | C-C Coupling | OtherReaction | a439652a13dde3282ba205540b7ed6f7cc5b9181cf04466803597623e6a23ce8 | 12f62631063bf464607920629837e3c85e8060bc45180357ec9dd6bf577ced50 | O=C(CCc1ccc2c(c1)CCCC2)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10]:2:[c:11]:1.[CH3;D1;+0:12]-[C:13](=[O;D1;H0:14])-[c:15](:[c:16](-[O;H0;D2;+0:17]-C-c1:c:c:c:c:c:1):[c:18]):[c:19](-[O;H0;D2;+0:20]-C-c1:c:c:c:c:c:1):[c:21]>>[O;D1;H0:14]=[C:13](-[CH2;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[... | null | [] | null | null | null | null | The intermediate, 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 2-naphthaldehyde as described in Example 1, Part B. Subsequent catalytic hydrogenation as described in Example 1, Part C, provided 1-(2,6-Dihydroxy-4-methyl-phenyl)-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1 -one as a by-product. Fu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ether.Ether | Ketone.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1>>Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3134bb06bc124c018e58493231cca07b | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1>>COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1 | C(C1=CC=CC=C1)OC1=C(C(=CC(=C1)C)OCC1=CC=CC=C1)C(C)=O.COC=1C=C2C=CC(=CC2=CC1)C=O>>OC1=C(C(=CC(=C1)C)O)C(CCC1=CC=2CCC(CC2C=C1)OC)=O | c1ccc(C[O:15][c:14]2[c:13]([C:11]([CH3:10])=[O:12])[c:20]([O:21]Cc3ccccc3)[cH:19][c:17]([CH3:18])[cH:16]2)cc1.O=[CH:9][c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][c:24]2[cH:23][cH:22]1>>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][c:6]2[cH:7][c:8]([CH2:9][CH2:10][C:11](=[O:12])[c:13]3[c:14]([OH:15])[cH:16][c:17]([CH3:... | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1 | COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1 | null | null | null | C-C Coupling | OtherReaction | 1d74c26f0b54826bde53498c1b1ccad0c5ce09a5d28cb36902f3f9cebb72ee4d | 50e927d848c47a415c1ffe91ec6f26ec0e8cee684590dd7a854ff7d46022aa7b | O=C(CCc1ccc2c(c1)CCCC2)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[#8:8]-[C;D1;H3:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:2:[c:13]:1.[CH3;D1;+0:14]-[C:15](=[O;D1;H0:16])-[c:17](:[c:18](-[O;H0;D2;+0:19]-C-c1:c:c:c:c:c:1):[c:20]):[c:21](-[O;H0;D2;+0:22]-C-c1:c:c:c:c:c:1):[c:23]>>[C;D1;H3:9]-[#8:8]-[CH;D3;+0:7]1-[CH2;D... | null | [] | null | null | null | null | Intermediate 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 6-methoxynaphthalene-2-carbaldehyde as described in Example 1, Part B. Subsequent catalytic hydrogenation as described in Example 1, Part C, provided 1-(2,6-dihydroxy-4-methyl-phenyl)-3-(6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ether.Ether.Ether | Ketone.Ether.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | null | null | null | CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1>>COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdaeae1224e84dbf81af983a18131230 | CC(=O)O[C@H]1O[C@@H](COC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1>>O=C(OC[C@@H]1O[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H]1OC(=O)c1ccccc1)c1ccccc1 | C(C)(=O)O[C@@H]1[C@@H](OC(C2=CC=CC=C2)=O)[C@@H](OC(C2=CC=CC=C2)=O)[C@@H](O1)COC(C1=CC=CC=C1)=O.C(Cl)Cl.Br>>C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O)[C@@H](OC(C2=CC=CC=C2)=O)[C@@H](O1)COC(C1=CC=CC=C1)=O | CC(=O)[O:8][C@H:7]1[O:6][C@@H:5]([CH2:4][O:3][C:2](=[O:1])[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C@H:19]([O:20][C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[C@@H:17]1[O:18][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([O:3][CH2:4][C@@H:5]1[O:6][C@@H:7]([O:8][C:9](=[O:10])[c:... | CC(=O)O[C@H]1O[C@@H](COC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | O=C(OC[C@@H]1O[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H]1OC(=O)c1ccccc1)c1ccccc1 | null | null | O | Miscellaneous | OtherReaction | 8622fd0de0af0dc20b1e4ade2df0ceb0c375fdb902c9bb49011faaf73efc4a95 | e284aa7e883c7cb56b45d7d945b08264874004ea1a9689cf16d1bd7955c4e2a8 | O=C(OC[C@@H]1O[C@@H](OC(=O)c2ccccc2)C[C@H]1OC(=O)c1ccccc1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[C:5]-[C:6]-1-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12]>>[O;D1;H0:9]=[C;H0;D3;+0:8](-[O;H0;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[C:5]-[C:6]-1-[OH;D1;+0:7])-[c:10](:[c:11]):[c:12] | 150.3 | [{"value": 75.5, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O)[C@@H](OC(C2=CC=CC=C2)=O)[C@@H](O1)COC(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 150.3, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O)[C@@H](OC(C2=CC=CC=C2)=O)[C@@H](O1)COC(C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIEL... | 0 | CELSIUS | 3.5 | HOUR | Compound 10 (9 g, 17.84 mmol) was stirred in 100 mL of CH2C12 at 0° C. while 70 mL of CH2Cl2 containing HBr (3.2 g, 30.5 mmol) was added in one portion. The mixture was stirred at 0° C. for 3.5 hrs, water (55 ml) was added and the mixture stirred at room temperature for 18 hours. The organic layer was separated, washed... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Secondary alcohol | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O | 0 | 3.5 | CC(=O)O[C@H]1O[C@@H](COC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1>O>O=C(OC[C@@H]1O[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H]1OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-287249cd39474ef7aeb17f0bcef2f647 | O=C(Cl)OCc1ccccc1.O=C(O)[C@@H]1C[C@@H](O)CN1>>O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCc1ccccc1 | ClC(=O)OCC1=CC=CC=C1.O[C@@H]1C[C@H](NC1)C(=O)O.C(=O)(O)[O-].[Na+].O>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O | Cl[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][C@@H:6]([OH:7])[CH2:8][NH:9]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][C@@H:6]([OH:7])[CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=C(Cl)OCc1ccccc1.O=C(O)[C@@H]1C[C@@H](O)CN1 | O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | CCOCC | Protection | N-alkylation of secondary amines with alkyl halides | 9dfceb007b1ffbcf1807491089b61fcc6b42027629f9ce16a6b45690ed8aec78 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[C:9]-[C:8]-1-[C:6](=[O;D1;H0:5])-[O;D1;H1:7] | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of benzyl chloroformate (50 mL, 0.35 mol) in Et2O (160 mL) was added dropwise, during 10 min, to a rapidly stirred mixture of trans-4-hydroxy-L-proline (39.8 g, 0.308 mol), NaHCO3 (63.7 g, 0.758 mol) and H2O (660 mL). The reaction mixture was stirred at room temperature for 20 h. The layers were separated, a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HCl | CCOCC | null | 20 | O=C(Cl)OCc1ccccc1.O=C(O)[C@@H]1C[C@@H](O)CN1>CCOCC>O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb73cd21ff05482d962b58edb9c03ea4 | CC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Br)c1>>CC(C)(C)OC(=O)CC(=O)c1cccc(Br)c1 | C(C)(=O)OC(C)(C)C.C[Si](C)(C)N[Si](C)(C)C.[Li]CCCC.BrC=1C=C(C(=O)OCC)C=CC1>>C(C)(C)(C)OC(CC(=O)C1=CC(=CC=C1)Br)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].CCO[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]1 | CC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Br)c1 | CC(C)(C)OC(=O)CC(=O)c1cccc(Br)c1 | null | null | CC(C)(C)OC | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[CH2;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Prepared from hexamethyldisilizane (16.5 mL, 79 mmol) and n-BuLi (48.4 mL, 77 mmol) in TBME (40 mL), then commercially available ethyl 3-bromobenzoate (7.55 g, 33 mmol) and tert-butyl acetate (4.86 mL, 36 mmol) in TBME (80 mL) according to the general procedure III. Obtained as a light yellow oil (9.934 g, 101%; 95% pu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccccc1 | HO- | CC(C)(C)OC | null | null | CC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Br)c1>CC(C)(C)OC>CC(C)(C)OC(=O)CC(=O)c1cccc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee0b72bd5af844a990b77c922a2d5d3a | Cc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | C(C)(C)(C)OC(NC1=C(C=C(C(=C1)C)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O.C(=O)(C(F)(F)F)O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)C)C(F)(F)F | CC(C)(C)OC(=O)[NH:24][c:4]1[cH:3][c:2]([CH3:1])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5]1[NH:12][C:13](=[O:14])[CH2:15][C:16](=O)[c:17]1[cH:18][cH:19][cH:20][c:21]([Br:22])[cH:23]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([F:9])([F:10])[F:11])[NH:12][C:13](=[O:14])[CH2:15][C:16]([c:17]1[cH:18][cH:19][cH:20]... | Cc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 64 | [{"value": 64.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-5-methyl-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (3.50 g, 6.79 mmol) and TFA (20 mL) in DCM (60 mL) according to general procedure I step 2. Obtained as a light yellow solid (1.79 g, 64%). MS (ISP) 3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | Cc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>C(Cl)Cl>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-daae4e2bc2b94444b3f4b9cd9502bddc | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1NC(=O)CC(=O)c1cccc(Br)c1>>O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1 | C(C)(C)(C)OC(NC1=C(C=C(C=C1)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C=C2)C(F)(F)F | CC(C)(C)OC(=O)[NH:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][c:22]1[NH:23][C:2](=[O:1])[CH2:3][C:4](=O)[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]2)=[N:12][c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][... | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1NC(=O)CC(=O)c1cccc(Br)c1 | O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1 | null | null | C(=O)(C(F)(F)F)O | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 82 | [{"value": 82.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (1.152 g, 2.30 mmol) and TFA (10 mL) according to general procedure I step 2. Obtained as a light yellow solid (0.730 g, 82%). MS (ISP) 383.0 [(M+H)+] and 385.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | c1ccccc1.C1=Nc2ccccc2NCC1 | HO- | C(=O)(C(F)(F)F)O | null | null | CC(C)(C)OC(=O)Nc1ccc(C(F)(F)F)cc1NC(=O)CC(=O)c1cccc(Br)c1>C(=O)(C(F)(F)F)O>O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5440bf8de9da4754ab76a2702ef7c71b | CCOc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | C(C)(C)(C)OC(NC1=C(C=C(C(=C1)OCC)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)OCC)C(F)(F)F | CC(C)(C)OC(=O)[NH:26][c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]1[NH:14][C:15](=[O:16])[CH2:17][C:18](=O)[c:19]1[cH:20][cH:21][cH:22][c:23]([Br:24])[cH:25]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[C:10]([F:11])([F:12])[F:13])[NH:14][C:15](=[O:16])[CH2:17][C:18](... | CCOc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | null | null | C(=O)(C(F)(F)F)O | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 82 | [{"value": 82.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-5-ethoxy-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (1.459 g, 2.675 mmol) and TFA (10 mL) according to general procedure I step 2. Obtained as a light yellow solid (0.940 g, 82%). MS (ISP) 427.1 [(M+H)+... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | C(=O)(C(F)(F)F)O | null | null | CCOc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>C(=O)(C(F)(F)F)O>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0c4299669e74c4990e962fecdbce022 | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2F)cc1NC(=O)CC(=O)c1cccc(Br)c1>>O=C1CC(c2cccc(Br)c2)=Nc2ccc(-c3ccccc3F)cc2N1 | C(C)(C)(C)OC(NC1=C(C=C(C=C1)C1=C(C=CC=C1)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O.C(=O)(C(F)(F)F)O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C=C2)C2=C(C=CC=C2)F | CC(C)(C)OC(=O)[NH:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[F:23])[cH:24][c:25]1[NH:26][C:2](=[O:1])[CH2:3][C:4](=O)[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1>>[O:1]=[C:2]1[CH2:3][C:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]2)=[N:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][... | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2F)cc1NC(=O)CC(=O)c1cccc(Br)c1 | O=C1CC(c2cccc(Br)c2)=Nc2ccc(-c3ccccc3F)cc2N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccc(-c3ccccc3)cc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {3-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-2′-fluoro-biphenyl-4-yl}-carbamic acid tert-butyl ester (2.15 g, 4.076 mmol, 90% purity) and TFA (15 mL) according to general procedure I step 2. Obtained as a light yellow solid (1.25 g, 75%). MS (ISP) 409.0 [(M+H)+... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | c1ccccc1.C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2F)cc1NC(=O)CC(=O)c1cccc(Br)c1>>O=C1CC(c2cccc(Br)c2)=Nc2ccc(-c3ccccc3F)cc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bafa2403e8f54a4599e4d11dcb8b0ccb | CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | C(C)(C)(C)OC(NC1=C(C=C(C(=C1)N(C)C)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O.C(=O)(C(F)(F)F)O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)N(C)C)C(F)(F)F | CC(C)(C)OC(=O)[NH:26][c:6]1[cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]1[NH:14][C:15](=[O:16])[CH2:17][C:18](=O)[c:19]1[cH:20][cH:21][cH:22][c:23]([Br:24])[cH:25]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[C:10]([F:11])([F:12])[F:13])[NH:14][C:15](=[O:16])[CH2:17][C:... | CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 93 | [{"value": 93.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-5-dimethylamino-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (2.2 g, 4.04 mmol) and TFA (15 mL) in DCM (45 mL) according to general procedure I step 2. Obtained as an off-white solid (1.61 g, 93%). MS (IS... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>C(Cl)Cl>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb627504b6aa47ae94aef6195273078e | CC(C)CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | C(C)(C)(C)OC(NC1=C(C=C(C(=C1)N(C)CC(C)C)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O.C(=O)(C(F)(F)F)O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)N(C)CC(C)C)C(F)(F)F | CC(C)(C)OC(=O)[NH:29][c:9]1[cH:8][c:7]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:6])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][c:10]1[NH:17][C:18](=[O:19])[CH2:20][C:21](=O)[c:22]1[cH:23][cH:24][cH:25][c:26]([Br:27])[cH:28]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH3:6])[c:7]1[cH:8][c:9]2[c:10]([cH:11][c:12]1[C:13]([F:14... | CC(C)CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 81 | [{"value": 81.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-5-(isobutyl-methyl-amino)-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (1.01 g, 1.72 mmol) and TFA (6.5 mL) in DCM (20 mL) according to general procedure I step 2. Obtained as a white solid (0.65 g, 81%).... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(C)CN(C)c1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>C(Cl)Cl>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3836a7a608774b60ad153350925398f8 | CC(C)CNc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | C(C)(C)(C)OC(NC1=C(C=C(C(=C1)NCC(C)C)C(F)(F)F)NC(CC(=O)C1=CC(=CC=C1)Br)=O)=O.C(=O)(C(F)(F)F)O>>BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)NCC(C)C)C(F)(F)F | CC(C)(C)OC(=O)[NH:28][c:8]1[cH:7][c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10][c:9]1[NH:16][C:17](=[O:18])[CH2:19][C:20](=O)[c:21]1[cH:22][cH:23][cH:24][c:25]([Br:26])[cH:27]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[cH:7][c:8]2[c:9]([cH:10][c:11]1[C:12]([F:13])([F:14])[F:15])[... | CC(C)CNc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a3daa3bce705c3d288afff47038f048ebda3288e2e19557bda1f779cd5e31067 | e05aa79ef606717adc4e7888ef27556c844e93bba271333333a92976508744aa | O=C1CC(c2ccccc2)=Nc2ccccc2N1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=O)-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:2](:[c:3])-[N;H0;D2;+0:1]=[C;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C:8]-1 | 92 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described {2-[3-(3-bromo-phenyl)-3-oxo-propionylamino]-5-isobutylamino-4-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester (1.03 g, 1.8 mmol) and TFA (7 mL) in DCM (20 mL) according to general procedure I step 2. Obtained as a light yellow solid (0.75 g, 92%). MS (I... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | Substituted imine | null | C1=Nc2ccccc2NCC1 | C1=Nc2ccccc2NCC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(C)CNc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(Br)c2)cc1C(F)(F)F>C(Cl)Cl>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7e54c41871d45068095c800ea1d96b8 | CC1(C)OB(c2ccc(S(N)(=O)=O)cc2)OC1(C)C.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)C)C(F)(F)F.CC1(OB(OC1(C)C)C1=CC=C(C=C1)S(=O)(=O)N)C>>CC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C1)C(F)(F)F | CC1(C)OB([c:22]2[cH:23][cH:24][c:25]([S:26]([NH2:27])(=[O:28])=[O:29])[cH:30][cH:31]2)OC1(C)C.Br[c:21]1[cH:20][cH:19][cH:18][c:17]([C:16]2=[N:33][c:4]3[cH:3][c:2]([CH3:1])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5]3[NH:12][C:13](=[O:14])[CH2:15]2)[cH:32]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([F:9])([F:10]... | CC1(C)OB(c2ccc(S(N)(=O)=O)cc2)OC1(C)C.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-O-C-1(-C)-C>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 69 | [{"value": 69.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.1) (200 mg, 0.50 mmol) and commercially available 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenesulfonamide [CAS-no. 214360-51-7] (170 mg, 0.60 mmol) according to the general pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CC1(C)OB(c2ccc(S(N)(=O)=O)cc2)OC1(C)C.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebd43b2f02dc4ad38b4b194b418d7df2 | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)C)C(F)(F)F.C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)B(O)O>>C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)C)=O | OB(O)[c:22]1[cH:23][cH:24][cH:25][c:26]([S:27](=[O:28])(=[O:29])[NH:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1.Br[c:21]1[cH:20][cH:19][cH:18][c:17]([C:16]2=[N:37][c:4]3[cH:3][c:2]([CH3:1])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5]3[NH:12][C:13](=[O:14])[CH2:15]2)[cH:36]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7... | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.1) (200 mg, 0.50 mmol) and commercially available 3-tert-butylsulfamoyl-benzeneboronic acid [CAS-no. 221290-14-8] (155 mg, 0.60 mmol) according to the general procedure II. Obtained as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4ab1af87c204696937469e4353715b3 | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)C)=O.C(=O)(C(F)(F)F)O>>CC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C1)C(F)(F)F | CC(C)(C)[NH:28][S:27]([c:26]1[cH:25][cH:24][cH:23][c:22](-[c:21]2[cH:20][cH:19][cH:18][c:17]([C:16]3=[N:33][c:4]4[cH:3][c:2]([CH3:1])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5]4[NH:12][C:13](=[O:14])[CH2:15]3)[cH:32]2)[cH:31]1)(=[O:29])=[O:30]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([F:9])([F:10])[F:11])[NH:... | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | null | null | C(Cl)Cl | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 73 | [{"value": 73.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3′-(8-methyl-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-3-sulfonic acid tert-butylamide (Example 2) (220 mg, 0.39 mmol) and TFA (5 mL) in DCM (1 mL) according to the general procedure I step 2. Obtained as a light yellow solid (136 mg, 73%). MS (ISP)... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | null | Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>C(Cl)Cl>Cc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53639d835f1340f78a250a63080956d8 | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1>>CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C=C2)C(F)(F)F.C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)B(O)O>>C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C(F)(F)F)=O | OB(O)[c:13]1[cH:12][cH:11][cH:10][c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[cH:36]1.Br[c:14]1[cH:15][cH:16][cH:17][c:18]([C:19]2=[N:20][c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][c:30]3[NH:31][C:32](=[O:33])[CH2:34]2)[cH:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(... | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1 | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 12 | [{"value": 12.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.2) (200 mg, 0.50 mmol) and commercially available 3-tert-butylsulfamoyl-benzeneboronic acid [CAS-no. 221290-14-8] (161 mg, 0.60 mmol) according to the general procedure II. Obtained as an off-whi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1 | HBr.B | null | null | null | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1>>CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fed843b7d96437da0a9eb35bf4dd31f | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1>>CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C=C2)C(F)(F)F.C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)B(O)O>>C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C(F)(F)F)=O | OB(O)[c:12]1[cH:11][cH:10][c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[cH:36][cH:35]1.Br[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]2=[N:19][c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][c:29]3[NH:30][C:31](=[O:32])[CH2:33]2)[cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(... | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1 | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 46 | [{"value": 46.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.2) (200 mg, 0.50 mmol) and commercially available 4-tert-butylsulfamoyl-benzeneboronic acid [CAS-no. 208516-15-8] (161 mg, 0.60 mmol) according to the general procedure II. Obtained as a white so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1 | HBr.B | null | null | null | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.O=C1CC(c2cccc(Br)c2)=Nc2ccc(C(F)(F)F)cc2N1>>CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8280b64e2c0c46b788ede3effa681c4c | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)OCC)C(F)(F)F.C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)B(O)O>>C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)OCC)=O | OB(O)[c:24]1[cH:25][cH:26][cH:27][c:28]([S:29](=[O:30])(=[O:31])[NH:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37]1.Br[c:23]1[cH:22][cH:21][cH:20][c:19]([C:18]2=[N:39][c:6]3[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]3[NH:14][C:15](=[O:16])[CH2:17]2)[cH:38]1>>[CH3:1][CH2:2][O:3][c:4]1[c... | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-7-ethoxy-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.3) (200 mg, 0.50 mmol) and commercially available 3-tert-butylsulfamoyl-benzeneboronic acid [CAS-no. 221290-14-8] (144 mg, 0.55 mmol) according to the general procedure II. Obtained as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b0bbf88ba7545c3a514412ad15517ec | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | BrC=1C=C(C=CC1)C1=NC2=C(NC(C1)=O)C=C(C(=C2)OCC)C(F)(F)F.C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)B(O)O>>C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)OCC)=O | OB(O)[c:24]1[cH:25][cH:26][c:27]([S:28](=[O:29])(=[O:30])[NH:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:36][cH:37]1.Br[c:23]1[cH:22][cH:21][cH:20][c:19]([C:18]2=[N:39][c:6]3[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]3[NH:14][C:15](=[O:16])[CH2:17]2)[cH:38]1>>[CH3:1][CH2:2][O:3][c:4]1[c... | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 63 | [{"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(3-bromo-phenyl)-7-ethoxy-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.3) (200 mg, 0.50 mmol) and commercially available 4-tert-butylsulfamoyl-benzeneboronic acid [CAS-no. 208516-15-8] (144 mg, 0.55 mmol) according to the general procedure II. Obtained as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)NS(=O)(=O)c1ccc(B(O)O)cc1.CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(Br)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2181e5f559bc44a69f7f82f40bac6fb8 | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1>>NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C(F)(F)F)=O.C(=O)(C(F)(F)F)O>>O=C1NC2=C(N=C(C1)C=1C=C(C=CC1)C1=CC(=CC=C1)S(=O)(=O)N)C=CC(=C2)C(F)(F)F | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]3=[N:16][c:17]4[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]4[NH:27][C:28](=[O:29])[CH2:30]3)[cH:31]2)[cH:32]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH... | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 | NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 77 | [{"value": 77.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3′-(4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-3-sulfonic acid tert-butylamide (Example 4) (177 mg, 0.3 mmol) and TFA (5 mL) according to the general procedure I step 2. Obtained as an off-white solid (122 mg, 77%). MS (ISP) 460.0 [(M+H)+]; mp 170° C... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1 | Other | null | null | null | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1>>NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3620a895c3b46169045aa097af17697 | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1>>NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C(F)(F)F)=O.C(=O)(C(F)(F)F)O>>O=C1NC2=C(N=C(C1)C=1C=C(C=CC1)C1=CC=C(C=C1)S(=O)(=O)N)C=CC(=C2)C(F)(F)F | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]3=[N:15][c:16]4[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]4[NH:26][C:27](=[O:28])[CH2:29]3)[cH:30]2)[cH:31][cH:32]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:... | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 | NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 58 | [{"value": 58.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3′-(4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid tert-butylamide (Example 5) (235 mg, 0.5 mmol) and TFA (5 mL) according to the general procedure I step 2. Obtained as a yellow solid (122 mg, 58%). MS (ISP) 460.1 [(M+H)+]; mp 195-210° C... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1 | Other | null | null | null | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1>>NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(C(F)(F)F)cc4NC(=O)C3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b92e5268b2604f4da35c6a11228aca47 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)OCC)=O.C(=O)(C(F)(F)F)O>>C(C)OC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C1)C(F)(F)F | CC(C)(C)[NH:30][S:29]([c:28]1[cH:27][cH:26][cH:25][c:24](-[c:23]2[cH:22][cH:21][cH:20][c:19]([C:18]3=[N:35][c:6]4[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]4[NH:14][C:15](=[O:16])[CH2:17]3)[cH:34]2)[cH:33]1)(=[O:31])=[O:32]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[C:10... | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 69 | [{"value": 69.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3′-(8-ethoxy-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-3-sulfonic acid tert-butylamide (Example 6) (238 mg, 0.4 mmol) and TFA (5 mL) according to the general procedure I step 2. Obtained as an off-white solid (147 mg, 69%). MS (ISP) 503.8 [(M+H)+]; ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-602ad76da3a54db6ad3823f5f4cd2ec0 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)OCC)=O.C(=O)(C(F)(F)F)O>>C(C)OC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C1)C(F)(F)F | CC(C)(C)[NH:29][S:28]([c:27]1[cH:26][cH:25][c:24](-[c:23]2[cH:22][cH:21][cH:20][c:19]([C:18]3=[N:35][c:6]4[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]4[NH:14][C:15](=[O:16])[CH2:17]3)[cH:34]2)[cH:33][cH:32]1)(=[O:30])=[O:31]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[C:10... | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 51 | [{"value": 51.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3′-(8-ethoxy-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid tert-butylamide (Example 7) (205 mg, 0.4 mmol) and TFA (5 mL) according to the general procedure I step 2. Obtained as an off-white solid (94 mg, 51%). MS (ISP) 503.8 [(M+H)+]; m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CCOc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2f26cb1ec79475fac2712e7283ce88f | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)N(C)C)=O.C(=O)(C(F)(F)F)O>>CN(C=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C1)C(F)(F)F)C | CC(C)(C)[NH:29][S:28]([c:27]1[cH:26][cH:25][c:24](-[c:23]2[cH:22][cH:21][cH:20][c:19]([C:18]3=[N:35][c:6]4[cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]4[NH:14][C:15](=[O:16])[CH2:17]3)[cH:34]2)[cH:33][cH:32]1)(=[O:30])=[O:31]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[... | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 22 | [{"value": 22.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-(8-dimethylamino-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid tert-butylamide (132 mg) and TFA (3 mL) according to the general procedure I step 2. Obtained as a white solid (55 mg, 22%). MS (ISP) 501.4 [(M−H)−];... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad04d136af4a4590bc2c869e4bd85f7e | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)N(C)C)=O.C(=O)(C(F)(F)F)O>>CN(C=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C1)C(F)(F)F)C | CC(C)(C)[NH:30][S:29]([c:28]1[cH:27][cH:26][cH:25][c:24](-[c:23]2[cH:22][cH:21][cH:20][c:19]([C:18]3=[N:35][c:6]4[cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7]4[NH:14][C:15](=[O:16])[CH2:17]3)[cH:34]2)[cH:33]1)(=[O:31])=[O:32]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[... | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 16 | [{"value": 16.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-(8-dimethylamino-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-3-sulfonic acid tert-butylamide (130 mg) and TFA (3 mL) according to the general procedure I step 2. Obtained as a light yellow solid (40 mg, 16%). MS (ISN) 501.4 [(... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa2176ad90f842f192b095316d88e53e | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)N(C)CC(C)C)=O.C(=O)(C(F)(F)F)O>>C(C(C)C)N(C=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C1)C(F)(F)F)C | CC(C)(C)[NH:32][S:31]([c:30]1[cH:29][cH:28][c:27](-[c:26]2[cH:25][cH:24][cH:23][c:22]([C:21]3=[N:38][c:9]4[cH:8][c:7]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:6])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][c:10]4[NH:17][C:18](=[O:19])[CH2:20]3)[cH:37]2)[cH:36][cH:35]1)(=[O:33])=[O:34]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5... | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 39 | [{"value": 39.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-[8-(isobutyl-methyl-amino)-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-biphenyl-4-sulfonic acid tert-butylamide (250 mg) and TFA (5 mL) according to the general procedure I step 2. Obtained as a white solid (107 mg, 39%). MS (ISN) 543.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b7763b0d4e14d54b1c4da87d0286f1b | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)N(C)CC(C)C)=O.C(=O)(C(F)(F)F)O>>C(C(C)C)N(C=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C1)C(F)(F)F)C | CC(C)(C)[NH:33][S:32]([c:31]1[cH:30][cH:29][cH:28][c:27](-[c:26]2[cH:25][cH:24][cH:23][c:22]([C:21]3=[N:38][c:9]4[cH:8][c:7]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:6])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][c:10]4[NH:17][C:18](=[O:19])[CH2:20]3)[cH:37]2)[cH:36]1)(=[O:34])=[O:35]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5... | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 25 | [{"value": 25.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-[8-(isobutyl-methyl-amino)-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (250 mg) and TFA (5 mL) according to the general procedure I step 2. Obtained as a light yellow solid (69 mg, 25%). MS (ISN... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CC(C)CN(C)c1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70d944b056f64f358edc2f3181205a0a | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1>>NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C2=C(C=CC=C2)F)=O.C(=O)(C(F)(F)F)O>>FC1=C(C=CC=C1)C1=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C=C1 | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]3=[N:15][c:16]4[cH:17][cH:18][c:19](-[c:20]5[cH:21][cH:22][cH:23][cH:24][c:25]5[F:26])[cH:27][c:28]4[NH:29][C:30](=[O:31])[CH2:32]3)[cH:33]2)[cH:34][cH:35]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH... | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1 | NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccc(-c3ccccc3)cc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | ) The title compound was prepared from the above described 3′-[7-(2-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-biphenyl-4-sulfonic acid tert-butylamide (310 mg, 0.573 mmol, 45% purity) and TFA (5 mL) according to the general procedure I step 2. Obtained as an off-white solid (20 mg, 13%, 80% purity... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1.c1ccccc1 | Other | null | null | null | CC(C)(C)NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1>>NS(=O)(=O)c1ccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3aa9669757f74ea39d07bd98c7b1dab4 | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1>>NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=CC(=C2)C2=C(C=CC=C2)F)=O.C(=O)(C(F)(F)F)O>>FC1=C(C=CC=C1)C1=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C=C1 | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]3=[N:16][c:17]4[cH:18][cH:19][c:20](-[c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]5[F:27])[cH:28][c:29]4[NH:30][C:31](=[O:32])[CH2:33]3)[cH:34]2)[cH:35]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:... | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1 | NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccc(-c3ccccc3)cc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 99 | [{"value": 99.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-[7-(2-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (430 mg, 0.795 mmol) and TFA (5 mL) according to the general procedure I step 2. Obtained as a white solid (380 mg, 99%). MS (ISP) 486.0 [(M+H)+]; ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1=Nc2ccccc2NCC1.c1ccccc1 | Other | null | null | null | CC(C)(C)NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1>>NS(=O)(=O)c1cccc(-c2cccc(C3=Nc4ccc(-c5ccccc5F)cc4NC(=O)C3)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30cd979e920349b6ae76ec83c97f3609 | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)NCC(C)C)=O.C(=O)(C(F)(F)F)O>>C(C(C)C)NC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC=C(C=C2)S(=O)(=O)N)C1)C(F)(F)F | CC(C)(C)[NH:31][S:30]([c:29]1[cH:28][cH:27][c:26](-[c:25]2[cH:24][cH:23][cH:22][c:21]([C:20]3=[N:37][c:8]4[cH:7][c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10][c:9]4[NH:16][C:17](=[O:18])[CH2:19]3)[cH:36]2)[cH:35][cH:34]1)(=[O:32])=[O:33]>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[... | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2 | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 47 | [{"value": 47.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-(8-isobutylamino-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid tert-butylamide (275 mg) and TFA (6 mL) according to the general procedure I step 2. Obtained as a yellow solid (126 mg, 47%). MS (ISN) 529.4 [(M−H)−... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(=O)(=O)NC(C)(C)C)cc3)c1)=N2>>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3ccc(S(N)(=O)=O)cc3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1385443903594c5488f9bd8f3b60430d | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | C(C)(C)(C)NS(=O)(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C=1CC(NC2=C(N1)C=C(C(=C2)C(F)(F)F)NCC(C)C)=O.C(=O)(C(F)(F)F)O>>C(C(C)C)NC=1C(=CC2=C(N=C(CC(N2)=O)C=2C=C(C=CC2)C2=CC(=CC=C2)S(=O)(=O)N)C1)C(F)(F)F | CC(C)(C)[NH:32][S:31]([c:30]1[cH:29][cH:28][cH:27][c:26](-[c:25]2[cH:24][cH:23][cH:22][c:21]([C:20]3=[N:37][c:8]4[cH:7][c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10][c:9]4[NH:16][C:17](=[O:18])[CH2:19]3)[cH:36]2)[cH:35]1)(=[O:33])=[O:34]>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[... | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2 | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 | null | null | null | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1CC(c2cccc(-c3ccccc3)c2)=Nc2ccccc2N1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ) The title compound was prepared from the above described 3′-(8-isobutylamino-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-3-sulfonic acid tert-butylamide (275 mg) and TFA (6 mL) according to the general procedure I step 2. Obtained as a yellow solid (172 mg, 65%). MS (ISN) 529.4 [(M−H)−... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | C1=Nc2ccccc2NCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(=O)(=O)NC(C)(C)C)c3)c1)=N2>>CC(C)CNc1cc2c(cc1C(F)(F)F)NC(=O)CC(c1cccc(-c3cccc(S(N)(=O)=O)c3)c1)=N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af36c5e5e898450ebf6f9c4a5cc84507 | Cc1ccc(C)c(N)c1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>Cc1ccc(C)c(NS(=O)(=O)c2ccccc2[N+](=O)[O-])c1 | CC1=C(N)C=C(C=C1)C.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl.N1=CC=CC=C1>>[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)NC1=C(C=CC(=C1)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([NH2:8])[cH:21]1.Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[N+:18](=[O:19])[O-:20])[cH:21]1 | Cc1ccc(C)c(N)c1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | Cc1ccc(C)c(NS(=O)(=O)c2ccccc2[N+](=O)[O-])c1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 2,5-dimethyl-aniline (2.4 g, 20 mmol) and 2-nitrobenzenesulfonyl chloride (4.4 g, 20 mmol) are dissolved in CH2Cl2 and treated with pyridine (1.8 mL, 22 mmol). The reaction mixture is stirred at room temperature until TLC shows no starting material. The reaction mixture is quenched with dilute HCl, and the organic laye... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | Cc1ccc(C)c(N)c1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>C(Cl)Cl>Cc1ccc(C)c(NS(=O)(=O)c2ccccc2[N+](=O)[O-])c1 |
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