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-41bb6c0ccf86424caf87f07adfde958c | CCOC(C)=O.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC=O)C.CCCCCC.C(C)(=O)OCC>>C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C | CCO[C:4](C)=[O:5].[CH3:1][c:2]1[cH:3][c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][CH:12]=[O:13])[CH:14]([c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[cH:22][cH:23]1)[CH2:24][O:25]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][CH:12]=[O:13])[CH:14]([c:15]1[cH:16][cH:17][c:18]([CH:19]([C... | CCOC(C)=O.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | C-C Coupling | OtherReaction | 2ca0c0d3b49721488f46a629c9ef66812e09f5949b927e1102590183256d1725 | 77724e9f3c3ba29a4aa00a2bd379f1beb2d911c11d7760b291574be7e0156860 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C:3]-[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8](-[C;D1;H3:9]):[c:10] | 92 | [{"value": 92.0, "product": "C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 58, the title compound was synthesized in the same manner as in Example 20. Yield: 92%. Melting point: 123-124° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8bb230f936d14bc9acacdd6519ad8b1d | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)[C@@H]1COC2=C1C(=C(C(=C2)C)N)C.CCCCCC.C(C)(=O)OCC.C(Cl)(Cl)Cl>>C(C)(C)C1=CC=C(C=C1)[C@@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C | CC[CH2:15][CH2:16][CH2:13][CH3:14].CCO[C:10](=[O:11])[CH3:12].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[C@H:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]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])([CH3:1... | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)CO2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc([C@@H]2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].C-C-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[C;H0;D4;+0:6](-[CH3;D1;+0:4])(-[CH3;D1;+0:5])-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 84 | [{"value": 84.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (S)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 326, the title compound was synthesized in the same manner as in Example 1. Yield: 84%. Melting point: 147-148° C. (hexane-ethyl acetate). [α]D20=−93° (c=0.497, chloroform).
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f48851790fb44b19e91491c3ddacb67 | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2 | CC1=C(C(=C(C2=C1C(CO2)C2=CC=CC=C2)C)C)N.C(C)(=O)OCC>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=CC=C2)C1C)C)C)(C)C | O([C:11](=[O:12])[CH3:13])[CH2:14][CH3:15].[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][cH:22][cH:23][cH:24]1)[CH2:25][O:26]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][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([c:19]1[... | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](-[CH3;D1;+0:4])=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH2;D2;+0:4]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 50 | [{"value": 50.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=CC=C2)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4,6,7-trimethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 306, the title compound was synthesized in the same manner as in Example 1. Yield: 50%. Melting point: 146-147° C. (ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 306 | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | null | null | null | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dbc21e3c322e472a927bb306def0822a | CCOC(C)=O.Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1>>Cc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | CC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C)C)C)N.C(C)(=O)OCC>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C)C1C)C)C)(C)C | O([C:16](=[O:17])[CH3:18])[CH2:19][CH3:20].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH2:15])[c:23]([CH3:24])[c:25]32)[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]... | CCOC(C)=O.Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 | Cc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](-[CH3;D1;+0:4])=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH2;D2;+0:4]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 80 | [{"value": 80.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4,6,7-trimethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 307, the title compound was synthesized in the same manner as in Example 1. Yield: 80%. Melting point: 176-177° C. (ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Exam... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | null | null | null | CCOC(C)=O.Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1>>Cc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdbdeef76f924032aaa5c33184aa18bb | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(-c3ccccc3)cc1)CO2 | C1(=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C)C2=CC=CC=C2.C(C)(=O)OCC>>C1(=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2 | O([C:11](=[O:12])[CH3:13])[CH2:14][CH3:15].[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]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]1)[CH2:31][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:11](=[O:12])[CH2:13][C:14]... | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(-c3ccccc3)cc1)CO2 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(-c2ccc(C3COc4ccccc43)cc2)cc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](-[CH3;D1;+0:4])=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH2;D2;+0:4]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 71 | [{"value": 71.0, "product": "C1(=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(biphenyl-4-yl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 309, the title compound was synthesized in the same manner as in Example 1. Yield: 71%. Melting point: 218-219° C. (ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Examp... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | null | null | null | null | CCOC(C)=O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(-c3ccccc3)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d62f685675d4844acf435735c109172 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>>C=Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=C)C)NC(CC(C)(C)C)=O)C | O[CH:2]([CH3:1])[c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[O:19][CH2:20][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH2:1]=[CH:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | C=Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | c06343e37ff0939df950b5fe01f861debeaf008021ce125a302eecb04407d3bc | ec6eec0da237b876ad744e7d30baaa345f156f05f882d5d77f49bb1798d3b15e | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]-[#8:6]>>[#8:6]-[c:5]:[c:3](-[CH;D2;+0:1]=[CH2;D1;+0:2]):[c:4] | 89 | [{"value": 89.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of N-(7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.23 g, 3.02 mmol) obtained in Example 22 and p-toluenesulfonic acid monohydrate (20 mg) in toluene (20 mL) was refluxed with heating at 80° C. for 1 hour under an argon atmosphere. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Vinyl | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 80 | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>C1(=CC=CC=C1)C>C=Cc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-078076ce0f6143238ef8f85f7be2ca1e | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)CO)OCC2c1ccc(C(C)C)cc1>>Cc1c(CCO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | OC(CO)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>OCCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | O[CH:4]([c:3]1[c:2]([CH3:1])[c:11]([NH:12][C:13](=[O:14])[CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:9]([CH3:10])[c:8]2[c:7]1[O:31][CH2:30][CH:20]2[c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1)[CH2:5][OH:6]>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][OH:6])[c:7]2[c:8]([c:9]([CH3:10])[c:11]1[NH:12][C:13... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)CO)OCC2c1ccc(C(C)C)cc1 | Cc1c(CCO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | [OH-].[OH-].[Pd+2] | C(C)O | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[C:2]-[O;D1;H1:3])-[c:4](:[c:5]):[c:6]-[#8:7]>>[#8:7]-[c:6]:[c:4](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3]):[c:5] | 21 | [{"value": 21.0, "product": "OCCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.8, "product": "OCCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(7-(1,2-dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (200 mg, 0.455 mmol) obtained in Example 84 and palladium hydroxide on carbon (20 mg) in ethanol (20 mL) was stirred at 60° C. for 3 hours under a hydrogen atmosphere. The catalyst was remove... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | [OH-].[OH-].[Pd+2].C(C)O | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)CO)OCC2c1ccc(C(C)C)cc1>[OH-].[OH-].[Pd+2].C(C)O>Cc1c(CCO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-000b3c39fb8043d2a150d9df44ebb1db | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>CCC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(CC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C(CC)=O)C)NC(CC(C)(C)C)=O)C | [CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]2[c:20]1[O:21][CH2:22][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[CH2:... | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | CCC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[C;D1;H3:7]):[c:8]>>[#8:1]-[c:2]:[c:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C;D1;H3:7]):[c:8] | 18 | [{"value": 18.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C(CC)=O)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a diastereo mixture of N-(7-(1-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in the synthesis in Examples 30 and 31, the title compound was synthesized in the same manner as in Example 32. Yield: 18%. Melting point: 163-164° C. (hexane-ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | null | CCCCCC.C(C)(=O)OCC | null | null | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>CCC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-948dc36d5f504e2688fc34a3d7b5e4ca | CCOC(C)=O.Cc1c(C)c2c(c(Br)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1c(NC(=O)CC(C)(C)C)c(C)c(C)c2c1C(c1ccc(C(C)C)cc1)CO2 | BrC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C(C)C)C)C)NC(CC(C)(C)C)=O.CCCCCC.C(C)(=O)OCC>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)OC | CCO[C:1](C)=[O:2].Br[c:3]1[c:4]([NH:5][C:6](=[O:7])[CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]([CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][O:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12])[c:... | CCOC(C)=O.Cc1c(C)c2c(c(Br)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | COc1c(NC(=O)CC(C)(C)C)c(C)c(C)c2c1C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d6498ace3fd4b04fcd053b8f11cca1308ae891716caacafdfea7563f75659df2 | 5c46ebc63b29f5e7138723258aaaa965349a056969ed2898b01eaa65c7960fb8 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3]-[#8:4])-[C:5]):[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10].C-C-O-[C;H0;D3;+0:11](-C)=[O;H0;D1;+0:12]>>[#8:4]-[c:3]:[c:2](:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[CH3;D1;+0:11]):[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10])-[C:5] | 21 | [{"value": 21.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(4-bromo-3-(4-isopropylphenyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 63, the title compound was synthesized in the same manner as in Example 36. Yield: 21%. Melting point: 161-162° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | null | null | null | CCOC(C)=O.Cc1c(C)c2c(c(Br)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1c(NC(=O)CC(C)(C)C)c(C)c(C)c2c1C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef007c88dda746b9a10e9423698c2094 | CCOC(C)=O.Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>COc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | BrC1=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C(=C1NC(CC(C)(C)C)=O)C)C.CCCCCC.C(C)(=O)OCC>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)OC)NC(CC(C)(C)C)=O)C | CCO[C:1](C)=[O:2].Br[c:3]1[c:4]([CH3:5])[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])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])... | CCOC(C)=O.Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | COc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d6498ace3fd4b04fcd053b8f11cca1308ae891716caacafdfea7563f75659df2 | 5c46ebc63b29f5e7138723258aaaa965349a056969ed2898b01eaa65c7960fb8 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[#7:3]-[C:4]=[O;D1;H0:5]):[c:6]):[c:7](-[C;D1;H3:8]):[c:9]-[#8:10].C-C-O-[C;H0;D3;+0:11](-C)=[O;H0;D1;+0:12]>>[#8:10]-[c:9]:[c:7](-[C;D1;H3:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[CH3;D1;+0:11]):[c:2](-[#7:3]-[C:4]=[O;D1;H0:5]):[c:6] | 37 | [{"value": 37.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)OC)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(6-bromo-3-(4-isopropylphenyl)-4,7-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 87, the title compound was synthesized in the same manner as in Example 36. Yield: 37%. Melting point: 162-163° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | null | null | null | CCOC(C)=O.Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>COc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a861f7d89c4c4ef5bffbc8a110b887da | CC[CH2][Mg][Cl].Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(CC)[Mg]Cl.C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>OC(CCC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [Cl][Mg][CH2:3][CH2:2][CH3:1].[CH:4](=[O:5])[c:6]1[c:7]([CH3:8])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[c:20]2[c:21]1[O:22][CH2:23][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[c:6]1[c:7]([CH3:8])[c:9]([... | CC[CH2][Mg][Cl].Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | O | C-C Coupling | Grignard from aldehyde to alcohol | fec51c6fbcca146daa523566f7e8d93ddaee19549cd7ca45d0ef939f0a2ea2fd | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6].[C;D1;H3:7]-[C:8]-[CH2;D2;+0:9]-[Mg]-[Cl]>>[#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:9]-[C:8]-[C;D1;H3:7]):[c:6] | 26 | [{"value": 26.0, "product": "OC(CCC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.7, "product": "OC(CCC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To propylmagnesium chloride (2.0 M, THF solution 10.0 mL, 20.0 mmol) was added N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (2.2 g, 5.40 mmol) obtained in Example 20 at 0° C. and the reaction solution was stirred at the same temperature for 1 hour. The reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Mg | O | null | 1 | CC[CH2][Mg][Cl].Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>O>CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3394c5065634a8cad46aba0fbd368a3 | CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>CCCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(CCC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(CCC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | O[CH:4]([CH2:3][CH2:2][CH3:1])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]2[c:20]1[O:21][CH2:22][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[C... | CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | CCCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]-[#8:7]>>[#8:7]-[c:6]:[c:4](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:5] | 33 | [{"value": 33.0, "product": "C(CCC)C1=C(C(=C(C=2C(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 a diastereo mixture of N-(7-(1-hydroxybutyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Examples 90 and 91, the title compound was synthesized in the same manner as in Example 23. Yield: 33%. Melting point: 149-151° C. (hexane-ethyl acetate).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | CCCCCC.C(C)(=O)OCC | null | null | CCCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>CCCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3663bbe295f746509477c55cc56f4f34 | Brc1ccccc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1 | II.C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.BrC1=CC=CC=C1.[Mg]>>OC(C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2 | Br[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:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH:17]=[O:18])[O:25][CH2:26][CH:27]2[c:28]1[cH:29][cH:30][c:31]([CH:32]([CH3:33])[CH3:34])[cH:35][cH:36]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8](... | Brc1ccccc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c: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](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11] | 107.6 | [{"value": 99.0, "product": "OC(C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.6, "product": "OC(C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of bromobenzene (770 mg, 4.91 mmol) in THF (10 mL) was added under an argon atmosphere to a mixture of magnesium (119 mg, 4.91 mmol) and a catalytic amount of iodine, and the resulting mixture was stirred at room temperature for 20 minutes. To the reaction solution was added dropwise a solution of N-(7-formy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | Br- | C1CCOC1 | null | 1 | Brc1ccccc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3fb60e7579594bb483f1a87fad5524b0 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1>>Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | OC(C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=CC=C2>>C(C1=CC=CC=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(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:35][CH2:34][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1)[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][c... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1 | Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | [Pd] | C(C)(=O)O | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(Cc2cccc3c2OCC3c2ccccc2)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] | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "C(C1=CC=CC=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(7-(hydroxy(phenyl)methyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (512 mg, 1.05 mmol) obtained in Example 94 and 10% palladium on carbon (water content: 50%, 50 mg) in acetic acid (20 mL) was stirred at 80° C. for 1.5 hours under hydrogen atmosphere. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | Other | [Pd].C(C)(=O)O | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccccc1)OCC2c1ccc(C(C)C)cc1>[Pd].C(C)(=O)O>Cc1c(Cc2ccccc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7c2cc32d4814478a5d0e71d53dbc04c | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccc(C(C)C)cc1>>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | OC(C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C>>C(C)(C)C1=CC=C(CC2=C(C(=C(C=3C(COC32)C3=CC=C(C=C3)C(C)C)C)NC(CC(C)(C)C)=O)C)C=C1 | O[CH:4]([c:3]1[c:2]([CH3:1])[c:18]([NH:19][C:20](=[O:21])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:16]([CH3:17])[c:15]2[c:14]1[O:38][CH2:37][CH:27]2[c:28]1[cH:29][cH:30][c:31]([CH:32]([CH3:33])[CH3:34])[cH:35][cH:36]1)[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccc(C(C)C)cc1 | Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(Cc2cccc3c2OCC3c2ccccc2)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] | 64 | [{"value": 64.0, "product": "C(C)(C)C1=CC=C(CC2=C(C(=C(C=3C(COC32)C3=CC=C(C=C3)C(C)C)C)NC(CC(C)(C)C)=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-(hydroxy(4-isopropylphenyl)methyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 95, the title compound was synthesized in the same manner as in Example 96. Yield: 64%. Melting point: 157-158° C. (hexane-ethyl acetate).
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>Cc1c(Cc2ccc(C(C)C)cc2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89f26d39ae0845e9b3cb6f22b15073c8 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OO>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)O)OCC2c1ccc(C(C)C)cc1 | C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.P(=O)(O)(O)[O-].[Na+].OO.Cl(=O)[O-].[Na+].Cl.S(=O)(O)[O-].[Na+]>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(=O)O)C)(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])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH:17]=[O:18])[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1.O[OH:19]>>[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]([CH... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OO | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)O)OCC2c1ccc(C(C)C)cc1 | null | null | C(C)#N.O | Acylation | OtherReaction | 11d630bd7a8d05707fc5eb890f030e7a5b49b94409f282ce03ce1d79527e12ed | 6fc85d54cb1f6b8147c0611acc28512113e77428616f7c82161971cc3447bea3 | c1ccc(C2COc3ccccc32)cc1 | O-[OH;D1;+0:1].[#8:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;D1;H0:6]):[c:7]>>[#8:2]-[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:1]):[c:7] | 269.1 | [{"value": 73.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(=O)O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 269.1, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(=O)O)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixed solution of N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.23 mmol) obtained in Example 20, sodium dihydrogenphosphate (40 mg), and hydrogen peroxide (0.125 mL) in acetonitrile (5 mL)-water (2 mL) was added at room temperature a solution of sod... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Peroxide | Carboxylic acid | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)#N.O | null | 2 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OO>C(C)#N.O>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(=O)O)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5ad57cd9f9a490b9d705f36aaf9fef8 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C#N)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.[Cu](C#N)C#N.N>>C(#N)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:3]1[c:2]([CH3:1])[c:10]([NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:8]([CH3:9])[c:7]2[c:6]1[O:30][CH2:29][CH:19]2[c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1>>[CH3:1][c:2]1[c:3]([C:4]#[N:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:1... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C#N)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CS(=O)C | Miscellaneous | OtherReaction | f2b914b0a250ca07de86c8d60c4e985e91adcbdd5b628aa702a5c7f73383d705 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8]>>[C:8]-[#8:7]-[c:5](:[c:6]):[c;H0;D3;+0:1](-[C:9]#[N;D1;H0:10]):[c:2](-[C;D1;H3:3]):[c:4] | 82 | [{"value": 82.0, "product": "C(#N)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "C(#N)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (0.5 g, 1.09 mmol) obtained in Example 35 and copper cyanide (300 mg 3.27 mmol) in dimethylsulfoxide (30 mL) was heated at 180° C. for 14 hours. To the reaction solution was added aqueous ammonia and the pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Br- | CS(=O)C | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CS(=O)C>Cc1c(C#N)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8622227d8ca64372aa4c2f1ce39b1f04 | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[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.CCCCCC.C(C)(=O)OCC>>C(C)(=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 | CCO[C:2]([CH3:1])=[O:3].[cH:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][C@H:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([... | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@H]2c1ccc(C(C)C)cc1 | null | null | C(Cl)(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 28f2f6cc408f923b8c3457aa0fbfe9d1e77f90e3dc0517dc3bc7197dff7a6080 | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc([C@@H]2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[C;D1;H3:10]):[c:11]>>[C:4]-[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9](-[C;D1;H3:10]):[c:11] | 46 | [{"value": 46.0, "product": "C(C)(=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-((3S)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 71, the title compound was synthesized in the same manner as in Example 38. Yield: 46%. Melting point: 177-178° C. (hexane-ethyl acetate). [α]D20=−6.0° (c=0.510, chloroform).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-859c1da22d334c14a6c745b6d633db32 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].COCCOC>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)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:23][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])(... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 57.1 | [{"value": 57.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.1, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (300 mg, 0.654 mmol) obtained in Example 35, phenylboronic acid (88 mg, 0.720 mmol), and palladium (0) tetrakis(triphenylphosphine) (27 mg, 0.023 mmol) in an aqueous 2 M sodium carbonate solution (10 mL)-1,2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(C)(=O)OCC | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(C)(=O)OCC>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bfa268d1bff48a582954c9379b59add | COc1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cn1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.COC1=CC=C(C=N1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC(=CC2)OC)C)NC(CC(C)(C)C)=O)C | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:36][cH:35]1.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][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:... | COc1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cn1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccnc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:[c:14]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:[c:14]:1):[c:6](-[C;D1;H3:7]):[c:8] | 48 | [{"value": 48.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC(=CC2)OC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (6-methoxypyridin-3-yl)boronic acid, the title compound was synthesized in the same manner as in Example 101. Yield: 48%. Melting point: 120-123° C. (hexane-ethyl acetate).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | COc1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e371230b6fad407db71d6fc6d3647c9d | COc1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.COC1=CC=C(C=C1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=C(C=C2)OC)C)NC(CC(C)(C)C)=O)C | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]1.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][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c... | COc1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 40 | [{"value": 40.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=C(C=C2)OC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (4-methoxyphenyl)boronic acid, the title compound was synthesized in the same manner as in Example 101. Yield: 40%. Melting point: 129-131° C. (hexane-ethyl acetate).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | COc1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>COc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2774ab138ea042bdb7eb0b20042f00f1 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccc(F)nc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(F)nc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.FC1=CC=C(C=N1)B(O)O>>FC1=CC=C(C=N1)C1=C(C(=C(C=2C(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:24][CH2:25][CH:26]2[c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1.OB(O)[c:17]1[cH:18][cH:19][c:20]([F:21])[n:22][cH:23]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccc(F)nc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(F)nc1)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccnc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:6](-[C;D1;H3:7]):[c:8] | 58 | [{"value": 58.0, "product": "FC1=CC=C(C=N1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (6-fluoropyridin-3-yl)boronic acid, the title compound was synthesized in the same manner as in Example 101. Yield: 58%. Melting point: 135-137° C. (hexane-ethyl acetate).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccc(F)nc1>CCCCCC.C(C)(=O)OCC>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(F)nc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-284f62b8e1204a308bb97e2f150587af | COc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.COC=1C=C(C=CC1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)OC)C)NC(CC(C)(C)C)=O)C | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36]1.Br[c:8]1[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]2[c:23]1[O:24][CH2:25][CH:26]2[c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c... | COc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | COc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 64 | [{"value": 64.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)OC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (3-methoxyphenyl)boronic acid, the title compound was synthesized in the same manner as in Example 101. Yield: 64%. Melting point: 209-210° C. (hexane-ethyl acetate).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | COc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>COc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79a1f093871245b1b73b7d203f981f4f | Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.OB(O)c1ccccc1>>Cc1c2c(c(C)c(NC(=O)CC(C)(C)C)c1-c1ccccc1)C(c1ccc(C(C)C)cc1)CO2 | BrC1=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C(=C1NC(CC(C)(C)C)=O)C)C.C1(=CC=CC=C1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C2=CC=CC=C2)NC(CC(C)(C)C)=O)C | Br[c:16]1[c:2]([CH3:1])[c:3]2[c:4]([c:5]([CH3:6])[c:7]1[NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:23]([c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1)[CH2:33][O:34]2.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH3:6])[c:7]([NH:8][C:9](=... | Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.OB(O)c1ccccc1 | Cc1c2c(c(C)c(NC(=O)CC(C)(C)C)c1-c1ccccc1)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]-[#8:5]):[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8:5]-[c:4]:[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10] | 42 | [{"value": 42.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C2=CC=CC=C2)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(6-bromo-3-(4-isopropylphenyl)-4,7-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 87 and phenylboronic acid, the title compound was synthesized in the same manner as in Example 101. Yield: 42%. Melting point: 212-213° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(Br)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.OB(O)c1ccccc1>CCCCCC.C(C)(=O)OCC>Cc1c2c(c(C)c(NC(=O)CC(C)(C)C)c1-c1ccccc1)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7eda4f957b4a4067806aa8d928b1227c | CC(=O)Nc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)NC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(C)O>>C(C)(=O)NC=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | OB(O)[c:9]1[cH:8][cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:38]1.Br[c:10]1[c:11]([CH3:12])[c:13]([NH:14][C:15](=[O:16])[CH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]([CH3:23])[c:24]2[c:25]1[O:26][CH2:27][CH:28]2[c:29]1[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]1>>[CH3:1][C:2](=[O:3])[NH:4][c:... | CC(=O)Nc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:8]-[#8:7]-[c:5](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2](-[C;D1;H3:3]):[c:4] | 86 | [{"value": 86.0, "product": "C(C)(=O)NC=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "C(C)(=O)NC=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 150 | CELSIUS | null | null | A solution of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (321 mg, 0.7 mmol) obtained in Example 35, (3-(acetylamino)phenyl)boronic acid (188 mg, 0.7 mmol), palladium(0) tetrakis(triphenylphosphine) (40.5 mg, 0.035 mmol), and an aqueous 2 N sodium carbonate soluti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C(OC)COC | 150 | null | CC(=O)Nc1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].O.C(OC)COC>CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-588436dde3784f1bbcb2f548bffca8de | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(F)c1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(F)c1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.FC=1C=C(C=CC1)B(O)O>>FC=1C=C(C=CC1)C1=C(C(=C(C=2C(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:24][CH2:25][CH:26]2[c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([F:22])[cH:23]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([C... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(F)c1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(F)c1)OCC2c1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 67 | [{"value": 67.0, "product": "FC=1C=C(C=CC1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (3-fluorophenyl)boronic acid, the title compound was synthesized in the same manner as in Example 107. Yield: 67%. Melting point: 182-183° C. (ethyl acetate-hexane).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(F)c1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(F)c1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a19b12829f8841dbb6b24494b490f7d8 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=[N+]([O-])c1cccc(B(O)O)c1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc([N+](=O)[O-])c1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>[N+](=O)([O-])C=1C=C(C=CC1)C1=C(C(=C(C=2C(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:26][CH2:27][CH:28]2[c:29]1[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=[N+]([O-])c1cccc(B(O)O)c1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc([N+](=O)[O-])c1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 59 | [{"value": 59.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (3-nitrophenyl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 59%. Melting point: 209-210° C. (ethyl acetate-hexane).
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=[N+]([O-])c1cccc(B(O)O)c1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc([N+](=O)[O-])c1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-803c149c869a4534a81a00c8a584da0e | CC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)C=1C=C(C=CC1)B(O)O>>C(C)(=O)C=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:37]1.Br[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][CH2:26][CH:27]2[c:28]1[cH:29][cH:30][c:31]([CH:32]([CH3:33])[CH3:34])[cH:35][cH:36]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:... | CC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]):[c:15]:[c:16]>>[C:8]-[#8:7]-[c:5](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]):[c:15]:[c:16]):[c:2](-[C;D1;H3:3]):[c:4] | 79 | [{"value": 79.0, "product": "C(C)(=O)C=1C=C(C=CC1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (3-acetylphenyl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 79%. Melting point: 209-210° C. (ethyl acetate-hexane).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ecad4b0e208491db2bd483b7e9da673 | CCOC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CCOC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)OC(=O)C=1C=C(C=CC1)B(O)O>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C=1C=C(C(=O)OCC)C=CC1)C)(C)C | OB(O)[c:10]1[cH:9][cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:39]1.Br[c:11]1[c:12]([CH3:13])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([CH3:24])[c:25]2[c:26]1[O:27][CH2:28][CH:29]2[c:30]1[cH:31][cH:32][c:33]([CH:34]([CH3:35])[CH3:36])[cH:37][cH:38]1>>[CH3:1][CH2:2][O:3][C:... | CCOC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CCOC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12](-[#8:13])=[O;D1;H0:14]):[c:15]:[c:16]>>[#8:13]-[C:12](=[O;D1;H0:14])-[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6])-[#8:7]-[C:8]):[c:15]:[c:16] | 63 | [{"value": 63.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C=1C=C(C(=O)OCC)C=CC1)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and 3-(ethoxycarbonyl)phenylboronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 63%. Melting point: 175-177° C. (ethyl acetate-hexane).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CCOC(=O)c1cccc(B(O)O)c1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CCOC(=O)c1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4618fc5e417b44998ad960f904922569 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.Cc1ccc(B(O)O)cc1>>Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.CC1=CC=C(C=C1)B(O)O>>CC1=CC=C(C=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:6]1[c:7]([CH3:8])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[c:20]2[c:21]1[O:22][CH2:23][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([CH3:8]... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.Cc1ccc(B(O)O)cc1 | Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 68 | [{"value": 68.0, "product": "CC1=CC=C(C=C1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (4-methylphenyl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 68%. Melting point: 194-195° C. (ethyl acetate-hexane).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.Cc1ccc(B(O)O)cc1>>Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f05f99235832432d92760c37dfa6c5ab | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccnc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccnc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.N1=CC(=CC=C1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC=CC2)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:23][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccnc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccnc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccnc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:6](-[C;D1;H3:7]):[c:8] | 32 | [{"value": 32.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC=CC2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and pyridin-3-ylboronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 32%. Melting point: 142-144° C. (ethyl acetate-hexane).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccnc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccnc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0999c1a1bdb448d3a1edeca7d8f65339 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccncc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccncc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.N1=CC=C(C=C1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=NC=C2)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:23][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1.OB(O)[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccncc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccncc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccncc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1):[c:6](-[C;D1;H3:7]):[c:8] | 72 | [{"value": 72.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=NC=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and pyridin-4-ylboronic acid, the title compound was obtained in the same as in Example 107.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccncc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccncc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36b659c1d9d046cb82e144050b9193ea | Brc1ccccn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccn1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC1=NC=CC=C1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=NC=CC=C2)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1.OB(O)[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:23][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([... | Brc1ccccn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccn1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccccn4)cccc32)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11](-[C;D1;H3:12]):[c:13] | 53 | [{"value": 53.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=NC=CC=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-bromopyridine, the title compound was obtained in the same manner as in Example 107.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Brc1ccccn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccccn1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86c7d9975bab40adbf3753dbe7691429 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1ccc(Br)nc1>>Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)nc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC1=NC=C(C=C1)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=NC=C(C=C2)C)C)NC(CC(C)(C)C)=O)C | OB(O)[c:6]1[c:7]([CH3:8])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[c:20]2[c:21]1[O:22][CH2:23][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][n:34]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([CH3:8])... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1ccc(Br)nc1 | Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)nc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccccn4)cccc32)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11](-[C;D1;H3:12]):[c:13] | 67 | [{"value": 67.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=NC=C(C=C2)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-bromo-5-methylpyridine, the title compound was obtained in the same manner as in Example 107. Yield: 67%. Melting point: 228-229° C. (ethyl acetate-hexane).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1ccc(Br)nc1>>Cc1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b908b3bfc5843479e251c0fe16394f1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Nc1cccc(Br)n1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.NC1=NC(=CC=C1)Br>>NC1=CC=CC(=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | OB(O)[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:24][CH2:25][CH:26]2[c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1.Br[c:17]1[cH:18][cH:19][cH:20][c:21]([NH2:22])[n:23]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Nc1cccc(Br)n1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccccn4)cccc32)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11](-[C;D1;H3:12]):[c:13] | 68 | [{"value": 68.0, "product": "NC1=CC=CC(=N1)C1=C(C(=C(C=2C(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 (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-amino-6-bromopyridine, the title compound was obtained in the same manner as in Example 107. Yield: 68%. Melting point: 237-239° C. (ethyl acetate-hexane).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Nc1cccc(Br)n1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41653d6f439c4b4db61be7a7a1af9298 | CN(C)c1cccc(Br)c1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N(C)C)c1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1C=C(N(C)C)C=CC1>>CN(C=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C | Br[c:17]1[cH:18][cH:19][cH:20][c:21]([N:22]([CH3:23])[CH3:24])[cH:25]1.OB(O)[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:26][CH2:27][CH:28]2[c:29]1[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:... | CN(C)c1cccc(Br)c1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N(C)C)c1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | 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])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11](-[C;D1;H3:12]):[c:13] | 77 | [{"value": 77.0, "product": "CN(C=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 3-bromo-N,N-dimethylaniline, the title compound was obtained in the same manner as in Example 107. Yield: 77%. Melting point: 197-199° C. (ethyl acetate-hexane).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CN(C)c1cccc(Br)c1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N(C)C)c1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c8807a394154cb890ba1d043f876d55 | CC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1>>CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 | NC1=CC=CC(=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)NC1=CC=CC(=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[c:11]([CH3:12])[c:13]([NH:14][C:15](=[O:16])[CH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]([CH3:23])[c:24]3[c:25]2[O:26][CH2:27][CH:28]3[c:29]2[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]2)[n:38]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[... | CC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1 | CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 | null | null | C([O-])(O)=O.[Na+].C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(C2COc3c(-c4ccccn4)cccc32)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 50 | [{"value": 50.0, "product": "C(C)(=O)NC1=CC=CC(=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "C(C)(=O)NC1=CC=CC(=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 1 | HOUR | To a solution of N-(7-(6-aminopyridin-2-yl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (94.3 mg, 0.2 mmol) and triethylamine (0.042 mL, 0.3 mmol) in THF (1 mL) was added acetyl chloride (0.015 mL, 0.22 mmol) at 0° C. and the resulting mixture was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | C([O-])(O)=O.[Na+].C1CCOC1 | null | 1 | CC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)n1)OCC2c1ccc(C(C)C)cc1>C([O-])(O)=O.[Na+].C1CCOC1>CC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94295ee65fbe4f3582458be16428fd22 | CCC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)c1)OCC2c1ccc(C(C)C)cc1>>CCC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | NC=1C=C(C=CC1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(CC)(=O)Cl>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)NC(CC)=O)C)NC(CC(C)(C)C)=O)C | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[c:12]([CH3:13])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([CH3:24])[c:25]3[c:26]2[O:27][CH2:28][CH:29]3[c:30]2[cH:31][cH:32][c:33]([CH:34]([CH3:35])[CH3:36])[cH:37][cH:38]2)[cH:39]1>>[CH3:1][CH2:2][C:3](=[O:... | CCC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)c1)OCC2c1ccc(C(C)C)cc1 | CCC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 84 | [{"value": 84.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)NC(CC)=O)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-(3-aminophenyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 122 and propionyl chloride, the title compound was obtained in the same manner as in Example 121. Yield: 84%. Melting point: 237-239° C. (ethyl acetate-hexane).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | null | null | null | CCC(=O)Cl.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N)c1)OCC2c1ccc(C(C)C)cc1>>CCC(=O)Nc1cccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-678ea277330241baae58f7002dac2c69 | Brc1cncnc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cncnc1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1C=NC=NC1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC=NC2)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[cH:18][n:19][cH:20][n:21][cH:22]1.OB(O)[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:23][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([C... | Brc1cncnc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cncnc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki | 651f57f47af816cdb773c531ed2942d02c6e268aa0360db28cee44bddd1a0cfe | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cncnc4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8](:[c:9])-[#8:10]-[C:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[C:11]-[#8:10]-[c:8](:[c:9]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:12](-[C;D1;H3:13]):[c:14] | 77 | [{"value": 77.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2C=NC=NC2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 5-bromopyrimidine, the title compound was obtained in the same manner as in Example 107. Yield: 77%. Melting point: 167-169° C. (ethyl acetate-hexane).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccc2c(c1)CCO2 | c1cncnc1.c1ccc2c(c1)CCO2 | c1cncnc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Brc1cncnc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cncnc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b9416e512ac4cdda5cf3df93426ac60 | Brc1nccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1nccs1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1SC=CN1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=CN2)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[n:18][cH:19][cH:20][s:21]1.OB(O)[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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])... | Brc1nccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1nccs1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5888eafdf381978ea5d6e597571a0e11c4dfc381df4e284ddb56e0815c961e4e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4nccs4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:11](-[C;D1;H3:12]):[c:13] | 64 | [{"value": 64.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=CN2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-bromo-1,3-thiazole, the title compound was obtained in the same manner as in Example 107. Yield: 64%. Melting point: 164-166° C. (ethyl acetate-hexane).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cscn1.c1ccc2c(c1)CCO2 | c1cscn1.c1ccc2c(c1)CCO2 | c1cscn1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Brc1nccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1nccs1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4ac77d63b1c466db7777a10d0eb1dbf | Brc1ccsc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccsc1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC1=CSC=C1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CSC=C2)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[cH:18][cH:19][s:20][cH:21]1.OB(O)[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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10]... | Brc1ccsc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccsc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ec44a395046935ec0c6139ddc9c1c5c75f8b771625b07532d2754b85f724f85e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccsc4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1):[c:11](-[C;D1;H3:12]):[c:13] | 49 | [{"value": 49.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CSC=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 3-bromothiophene, the title compound was obtained in the same manner as in Example 107. Yield: 49%. Melting point: 172-174° C. (ethyl acetate-hexane).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Brc1ccsc1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccsc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-914b075bd1f54ed784cb654dc2fce93a | Brc1c[nH]cn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1c[nH]cn1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1N=CNC1>>N1C=NC(=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[cH:18][nH:19][cH:20][n:21]1.OB(O)[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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10]... | Brc1c[nH]cn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1c[nH]cn1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 88ae710bc9cfc9b1f1f14bc5f2f1411e507a2d8ba58e5da1bad9de2f46d7053a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4c[nH]cn4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:1):[c:11](-[C;D1;H3:12]):[c:13] | 48 | [{"value": 48.0, "product": "N1C=NC(=C1)C1=C(C(=C(C=2C(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 (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 4-bromoimidazole, the title compound was obtained in the same manner as in Example 107. Yield: 48%. Melting point: 277-279° C. (ethyl acetate).
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1c[nH]cn1.c1ccc2c(c1)CCO2 | c1c[nH]cn1.c1ccc2c(c1)CCO2 | c1c[nH]cn1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Brc1c[nH]cn1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1c[nH]cn1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bdcd0c2176f4ea58b0a85860ba155f0 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccoc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccoc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.O1C=C(C=C1)B(O)O>>O1C=C(C=C1)C1=C(C(=C(C=2C(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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.OB(O)[c:17]1[cH:18][cH:19][o:20][cH:21]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10]... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccoc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccoc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5e2e72c4f0a5f9a54b80b57a71732e2ef5931d22f478d73c65daf10aadd3f341 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccoc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#8;a:12]:[c:13]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#8;a:12]:[c:13]:1):[c:6](-[C;D1;H3:7]):[c:8] | 51 | [{"value": 51.0, "product": "O1C=C(C=C1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and 3-furylboronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 51%. Melting point: 183-185° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccoc1 | c1ccoc1.c1ccc2c(c1)CCO2 | c1ccoc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccoc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccoc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af89933829cb40b7b579fef0154709da | CC(C)(C)OC(=O)n1cccc1B(O)O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc[nH]1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(C)(C)OC(=O)N1C(=CC=C1)B(O)O>>N1C(=CC=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | CC(C)(C)OC(=O)[n:21]1[c:17](B(O)O)[cH:18][cH:19][cH:20]1.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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([... | CC(C)(C)OC(=O)n1cccc1B(O)O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc[nH]1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | OtherReaction | 31efabbdaceed61b66f0ab7fe835ce34837a6837c4d42b883ecb5789b568ab4d | 9170b599aa65cddc078fed37cb24db8248064288b25a25958e4580283ddab1df | c1ccc(C2COc3c(-c4ccc[nH]4)cccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:1-B(-O)-O>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[nH;D2;+0:9]:1):[c:6](-[C;D1;H3:7]):[c:8] | 19 | [{"value": 19.0, "product": "N1C(=CC=C1)C1=C(C(=C(C=2C(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-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl) boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 19%. Melting point: 188-190° C. (ethyl acetate).
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Boronic acid.Boc | null | c1ccc[nH]1.c1ccc2c(c1)CCO2 | c1cc[nH]c1.c1ccc2c(c1)CCO2 | c1cc[nH]c1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)OC(=O)n1cccc1B(O)O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc[nH]1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f20f306be8446459a0dbc56b84d6bdf | Brc1cccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccs1)OCC2c1ccc(C(C)C)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1SC=CC1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=CC2)C)NC(CC(C)(C)C)=O)C | Br[c:17]1[cH:18][cH:19][cH:20][s:21]1.OB(O)[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][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10]... | Brc1cccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccs1)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | ec44a395046935ec0c6139ddc9c1c5c75f8b771625b07532d2754b85f724f85e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccs4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[c:11](-[C;D1;H3:12]):[c:13] | 58 | [{"value": 58.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=CC2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl) boronic acid obtained in Example 116 and 2-bromothiophene, the title compound was synthesized in the same manner as in Example 107. Yield: 58%. Melting point: 155-156° C. (hexane-ethyl acetate).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | Brc1cccs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccs1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9deced6416f248cbb60c1db670d69c67 | CC(=O)c1ccc(Br)s1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>CC(=O)c1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)s1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.C(C)(=O)C=1SC(=CC1)Br>>C(C)(=O)C1=CC=C(S1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[s:36]1.OB(O)[c:8]1[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]2[c:23]1[O:24][CH2:25][CH:26]2[c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](... | CC(=O)c1ccc(Br)s1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | CC(=O)c1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)s1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | ec44a395046935ec0c6139ddc9c1c5c75f8b771625b07532d2754b85f724f85e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccs4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[C;D1;H3:5])=[O;D1;H0:6]):[c:7]:[c:8]:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10](:[c:11])-[#8:12]-[C:13]):[c:14](-[C;D1;H3:15]):[c:16]>>[C:13]-[#8:12]-[c:10](:[c:11]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[C;D1;H3:5])=[O;D1;H0:6]):[c:7]:[c:8]:1):[c:14](-[C;D1;H3:15]):[... | 65 | [{"value": 65.0, "product": "C(C)(=O)C1=CC=C(S1)C1=C(C(=C(C=2C(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 (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-acetyl-5-bromothiophene, the title compound was synthesized in the same manner as in Example 107. Yield: 65%. Melting point: 157-158° C. (hexane-ethyl acetate).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | CC(=O)c1ccc(Br)s1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>CC(=O)c1ccc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06ea90f3387c468383e809f2ee3313da | CC(=O)c1cc(Br)cs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>>CC(=O)c1cc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cs1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.C(C)(=O)C=1SC=C(C1)Br>>C(C)(=O)C1=CC(=CS1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[s:36][cH:35]1.OB(O)[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][CH2:24][CH:25]2[c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]... | CC(=O)c1cc(Br)cs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1 | CC(=O)c1cc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cs1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | ec44a395046935ec0c6139ddc9c1c5c75f8b771625b07532d2754b85f724f85e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4ccsc4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8]:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10](:[c:11])-[#8:12]-[C:13]):[c:14](-[C;D1;H3:15]):[c:16]>>[C:13]-[#8:12]-[c:10](:[c:11]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8]:1):[c:14](-[C;D1;H3:15]):[... | 62 | [{"value": 62.0, "product": "C(C)(=O)C1=CC(=CS1)C1=C(C(=C(C=2C(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 (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-acetyl-4-bromothiophene, the title compound was synthesized in the same manner as in Example 107. Yield: 62%. Melting point: 133-134° C. (hexane-ethyl acetate).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2 | c1ccsc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | CC(=O)c1cc(Br)cs1.Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>CC(=O)c1cc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b819b98b773e4fd19c7ae4da55b7e5b6 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1csc(Br)n1>>Cc1csc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)B(O)O)C)(C)C.BrC=1SC=C(N1)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=C(N2)C)C)NC(CC(C)(C)C)=O)C | OB(O)[c:6]1[c:7]([CH3:8])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[c:20]2[c:21]1[O:22][CH2:23][CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.Br[c:5]1[s:4][cH:3][c:2]([CH3:1])[n:34]1>>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[c:7]([CH3:8])[c:9]([NH... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1csc(Br)n1 | Cc1csc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 | null | null | CCCCCC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 5888eafdf381978ea5d6e597571a0e11c4dfc381df4e284ddb56e0815c961e4e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4nccs4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7](:[c:8])-[#8:9]-[C:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C:10]-[#8:9]-[c:7](:[c:8]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:11](-[C;D1;H3:12]):[c:13] | 62 | [{"value": 62.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C=2SC=C(N2)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (5-((3,3-dimethylbutanoyl)amino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)boronic acid obtained in Example 116 and 2-bromo-4-methyl-1,3-thiazole, the title compound was synthesized in the same manner as in Example 107. Yield: 62%. Melting point: 240-241° C. (hexane-ethyl acetate).
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1cscn1 | c1cscn1.c1ccc2c(c1)CCO2 | c1cscn1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1B(O)O)OCC2c1ccc(C(C)C)cc1.Cc1csc(Br)n1>CCCCCC.C(C)(=O)OCC>Cc1csc(-c2c(C)c(NC(=O)CC(C)(C)C)c(C)c3c2OCC3c2ccc(C(C)C)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fd392326ccd4329b8d837b844243b10 | COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C>>OC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | C[O:4][c:3]1[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]([CH3:8])[c:6]2[c:5]1[O:29][CH2:28][CH:18]2[c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1>>[CH3:1][c:2]1[c:3]([OH: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])... | COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(C2COc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5]>>[#8:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 78 | [{"value": 78.0, "product": "OC1=C(C(=C(C=2C(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-(3-(4-isopropylphenyl)-7-methoxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 36, the title compound was synthesized in the same manner as in Example 134. Yield: 78%. Melting point: 181-182° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cdf3121ad06049d491cff1c51c93d687 | CCOS(=O)(=O)OCC.Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CCOc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | O.OC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C([O-])([O-])=O.[K+].[K+].S(=O)(=O)(OCC)OCC>>C(C)OC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | CCOS(=O)(=O)O[CH2:2][CH3:1].[OH:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][... | CCOS(=O)(=O)OCC.Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CCOc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-S(=O)(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[#8:3]-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[#8:3]-[c:4]:[c:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:7] | 117.4 | [{"value": 78.0, "product": "C(C)OC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 117.4, "product": "C(C)OC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of N-(7-hydroxy-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 135 (300 mg, 0.76 mmol), potassium carbonate (105 mg, 0.76 mmol) and diethyl sulfate (117 mg, 0.76 mmol) in acetone (15 mL) was refluxed with heating for 14 hours. Water was adde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CC(=O)C | null | null | CCOS(=O)(=O)OCC.Cc1c(O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CC(=O)C>CCOc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d93ac12e90a4fd7af28ad30a43e13f3 | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)N1CCCC1)C(c1ccc(C(C)C)cc1)CO2 | O.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.N1CCCC1.C(C)(C)N(CC)C(C)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)N2CCCC2)C | [NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2)=[O:12]>>[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])[N:13]1... | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)N1CCCC1)C(c1ccc(C(C)C)cc1)CO2 | null | null | CS(=O)C | Acylation | OtherReaction | f3ad5bd793fe0cfe04e971323618eb11dcfabc9852083b5acc4f6f5ed901d689 | 49ed575548abd680f94161a6250635a5c380709cba6ad7d6b8434a91fd188103 | O=C(Nc1ccc2c(c1)C(c1ccccc1)CO2)N1CCCC1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:3]-[c:4])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 44.2 | [{"value": 44.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)N2CCCC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.2, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)N2CCCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate (353 mg, 0.75 mmol) obtained in Example 138 and pyrrolidine (0.076 mL, 0.9 mmol) in dimethylsulfoxide (5 mL) was added diisopropylethylamine (0.13 mL, 0.75 mmol) at room temperature, and the resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Secondary amine | Urea | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CS(=O)C | 50 | null | C1CCNC1.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>CS(=O)C>Cc1c(C)c2c(c(C)c1NC(=O)N1CCCC1)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be13b12673fe44cbbc1c851e1a3b8c05 | CCNCC.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>CCN(CC)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.C(C)NCC>>C(C)N(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].ClC(Cl)(Cl)CO[C:6](=[O:7])[NH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13... | CCNCC.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | CCN(CC)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 3c891efac2a7a54d8bdf39e8e4003e0742390554851803dd18489cce1007c413 | 49ed575548abd680f94161a6250635a5c380709cba6ad7d6b8434a91fd188103 | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C;D1;H3:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C;D1;H3:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 68 | [{"value": 68.0, "product": "C(C)N(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and diethylamine, the title compound was obtained in the same manner as in Example 143.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Secondary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | null | null | null | CCNCC.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>CCN(CC)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-205a6d0b740449438047020adbd8edc2 | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO>>Cc1c(C)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.OCCN>>OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2)=[O:12].[NH2:13][CH2:14][CH2:15][OH:16]>>[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])[NH:13][CH2:14][C... | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO | Cc1c(C)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 89 | [{"value": 89.0, "product": "OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 2-hydroxyethylamine, the title compound was obtained in the same manner as in Example 143.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | null | null | null | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO>>Cc1c(C)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a173dcbda4a4f2e8115579deb92abfe | COCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>COCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.COCCN>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)NCCOC)C | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].ClC(Cl)(Cl)CO[C:6](=[O:7])[NH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[NH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[c... | COCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | COCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 58 | [{"value": 58.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)NCCOC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 2-methoxyethylamine, the title compound was synthesized in the same manner as in Example 143. Yield: 58%. Melting point: 172-173° C. (hexane-ethyl acetate).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | COCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>COCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57265737341f45738149791b0c2c1a83 | CN(C)CCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)NCCN(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.CN(CCN)C>>CN(CCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)C | [NH2:13][CH2:14][CH2:15][N:16]([CH3:17])[CH3:18].ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2)=[O:12]>>[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])... | CN(C)CCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)NCCN(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 54 | [{"value": 54.0, "product": "CN(CCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 2-(dimethylamino)ethylamine, the title compound was synthesized in the same manner as in Example 143. Yield: 54%. Melting point: 133-134° C. (hexane-ethyl acetate).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | CN(C)CCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>Cc1c(C)c2c(c(C)c1NC(=O)NCCN(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce9cdda876094bd68092140ba0e7d18a | CCc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>>CCc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCO>>C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCO)C | ClC(Cl)(Cl)CO[C:8]([NH:7][c:6]1[c:4]([CH3:5])[c:3]([CH2:2][CH3:1])[c:17]2[c:16]([c:14]1[CH3:15])[CH:20]([c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1)[CH2:19][O:18]2)=[O:9].[NH2:10][CH2:11][CH2:12][OH:13]>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][OH:13])... | CCc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO | CCc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 57 | [{"value": 57.0, "product": "C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (7-ethyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 139 and 2-aminoethanol, the title compound was synthesized in the same manner as in Example 143. Yield: 57%. Melting point: 147-148° C. (hexane-ethyl acetate).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | CCCCCC.C(C)(=O)OCC | null | null | CCc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>CCCCCC.C(C)(=O)OCC>CCc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26660c8722254d219455ab9d1b34457a | COc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>>COc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2OC)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCO>>OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)OC)C | ClC(Cl)(Cl)CO[C:8]([NH:7][c:6]1[c:4]([CH3:5])[c:3]([O:2][CH3:1])[c:17]2[c:16]([c:14]1[CH3:15])[CH:20]([c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1)[CH2:19][O:18]2)=[O:9].[NH2:10][CH2:11][CH2:12][OH:13]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][OH:13])[c:1... | COc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO | COc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 59 | [{"value": 59.0, "product": "OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-7-methoxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 140 and 2-aminoethanol, the title compound was synthesized in the same manner as in Example 143. Yield: 59%. Melting point: 127-129° C. (hexane-ethyl acetate).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | CCCCCC.C(C)(=O)OCC | null | null | COc1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>CCCCCC.C(C)(=O)OCC>COc1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4e480ac12b5412eb17401c98ae3a631 | Cc1c(CCCO)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO>>Cc1c(CCCO)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 | OCCCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCO>>OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)CCCO)C | ClC(Cl)(Cl)CO[C:14]([NH:13][c:12]1[c:2]([CH3:1])[c:3]([CH2:4][CH2:5][CH2:6][OH:7])[c:8]2[c:9]([c:10]1[CH3:11])[CH:20]([c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1)[CH2:30][O:31]2)=[O:15].[NH2:16][CH2:17][CH2:18][OH:19]>>[CH3:1][c:2]1[c:3]([CH2:4][CH2:5][CH2:6][OH:7])[c:8]2[c:9]([c:10]([CH3:11])... | Cc1c(CCCO)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO | Cc1c(CCCO)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 53 | [{"value": 53.0, "product": "OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)CCCO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (7-(3-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 141 and 2-aminoethanol, the title compound was synthesized in the same manner as in Example 143. Yield: 53%. Melting point: 153-154° C. (hexane-ethyl acetate).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(CCCO)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCO>CCCCCC.C(C)(=O)OCC>Cc1c(CCCO)c2c(c(C)c1NC(=O)NCCO)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc50d20058d24117b1fc031ff5e57a1b | CCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>CCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.C(CC)N>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)NCCC)C | [CH3:1][CH2:2][CH2:3][NH2:4].ClC(Cl)(Cl)CO[C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:16])[CH:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14](... | CCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | CCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 53 | [{"value": 53.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(=O)NCCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 1-propylamine, the title compound was synthesized in the same manner as in Example 143. Yield: 53%. Melting point: 177-178° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | CCCN.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>CCCNC(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71d1240377494e1dbd86926861516839 | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCO>>Cc1c(NC(=O)NCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCO>>OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C | ClC(Cl)(Cl)CO[C:5]([NH:4][c:3]1[c:2]([CH3:1])[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:14]2[c:13]([c:11]1[CH3:12])[CH:24]([c:25]1[cH:26][cH:27][c:28]([CH:29]([CH3:30])[CH3:31])[cH:32][cH:33]1)[CH2:23][O:22]2)=[O:6].[NH2:7][CH2:8][CH2:9][OH:10]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][OH:... | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCO | Cc1c(NC(=O)NCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 59 | [{"value": 59.0, "product": "OCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6-dimethyl-7-phenyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 142 and 2-aminoethanol, the title compound was synthesized in the same manner as in Example 143. Yield: 59%. Melting point: 152-155° C. (hexane-ethyl acetate).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCO>CCCCCC.C(C)(=O)OCC>Cc1c(NC(=O)NCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fc88dfe36404b12b66b013d683fbb5c | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCCO>>Cc1c(NC(=O)NCCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCCO>>OCCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C | ClC(Cl)(Cl)CO[C:5]([NH:4][c:3]1[c:2]([CH3:1])[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:15]2[c:14]([c:12]1[CH3:13])[CH:25]([c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1)[CH2:24][O:23]2)=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7][CH2:8][CH... | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCCO | Cc1c(NC(=O)NCCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 65 | [{"value": 65.0, "product": "OCCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6-dimethyl-7-phenyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 142 and 3-amino-1-propanol, the title compound was synthesized in the same manner as in Example 143. Yield: 65%. Melting point: 145-146° C. (hexane-ethyl acetate).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1.NCCCO>CCCCCC.C(C)(=O)OCC>Cc1c(NC(=O)NCCCO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a0bcfe2fa414f2ba82efd0fefc34fde | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCCO>>Cc1c(C)c2c(c(C)c1NC(=O)NCCCO)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCCCO>>OCCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2)=[O:12].[NH2:13][CH2:14][CH2:15][CH2:16][OH:17]>>[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])[NH:13][C... | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCCO | Cc1c(C)c2c(c(C)c1NC(=O)NCCCO)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 33 | [{"value": 33.0, "product": "OCCCNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 3-amino-1-propanol, the title compound was synthesized in the same manner as in Example 143. Yield: 33%. Melting point: 185-186° C. (hexane-ethyl acetate).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NCCCO>CCCCCC.C(C)(=O)OCC>Cc1c(C)c2c(c(C)c1NC(=O)NCCCO)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba28542c02924cd7bec75db4ce5cfb98 | CC(C)(N)CO.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)CO)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.NC(CO)(C)C>>OCC(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | [NH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][OH:18].ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2)=[O:12]>>[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]... | CC(C)(N)CO.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)CO)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 39 | [{"value": 39.0, "product": "OCC(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and 2-amino-2-methyl-1-propanol, the title compound was synthesized in the same manner as in Example 143. Yield: 39%. Melting point: 157-158° C. (hexane-ethyl acetate).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | CCCCCC.C(C)(=O)OCC | null | null | CC(C)(N)CO.Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)CO)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10e1dd923bd74498b6989f5d1672924b | CC(C)(N)CO.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)NC(C)(C)CO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(OCC(Cl)(Cl)Cl)=O)C.NC(CO)(C)C>>OCC(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C | [NH2:7][C:8]([CH3:9])([CH3:10])[CH2:11][OH:12].ClC(Cl)(Cl)CO[C:5]([NH:4][c:3]1[c:2]([CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:16]2[c:15]([c:13]1[CH3:14])[CH:26]([c:27]1[cH:28][cH:29][c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35]1)[CH2:25][O:24]2)=[O:6]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7]... | CC(C)(N)CO.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)NC(C)(C)CO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 49 | [{"value": 49.0, "product": "OCC(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6-dimethyl-7-phenyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 142 and 2-amino-2-methyl-1-propanol, the title compound was synthesized in the same manner as in Example 143. Yield: 49%. Melting point: 181-182° C. (hexane-ethyl acetate).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | CCCCCC.C(C)(=O)OCC | null | null | CC(C)(N)CO.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>Cc1c(NC(=O)NC(C)(C)CO)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da28de75f169461ca66e769b0d787b4a | CC(O)CN.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)NCC(C)O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC(OCC(Cl)(Cl)Cl)=O)C.NCC(C)O>>OC(CNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C)C | [NH2:7][CH2:8][CH:9]([CH3:10])[OH:11].ClC(Cl)(Cl)CO[C:5]([NH:4][c:3]1[c:2]([CH3:1])[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:15]2[c:14]([c:12]1[CH3:13])[CH:25]([c:26]1[cH:27][cH:28][c:29]([CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1)[CH2:24][O:23]2)=[O:6]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7][CH2:8][C... | CC(O)CN.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)NCC(C)O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | null | C(C)O.CCCCCC | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 58 | [{"value": 58.0, "product": "OC(CNC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C1=CC=CC=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (3-(4-isopropylphenyl)-4,6-dimethyl-7-phenyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 142 and 1-amino-2-propanol, the title compound was synthesized in the same manner as in Example 143. Yield: 58%. Melting point: 171-182° C. (ethanol-hexane).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HCl | C(C)O.CCCCCC | null | null | CC(O)CN.Cc1c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1>C(C)O.CCCCCC>Cc1c(NC(=O)NCC(C)O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0eb903074e084a77b13656f11b66ca5b | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.CCCCCC.C(C)(=O)OCC>>C(=O)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | CCO[C:4](C)=[O:5].[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])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][S:30]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])[CH... | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | null | null | null | C-C Coupling | OtherReaction | be0e8277f994e3d631ef7541cd7a6fa9bbd967f8cefe698c436309fb9634ce5a | 77724e9f3c3ba29a4aa00a2bd379f1beb2d911c11d7760b291574be7e0156860 | c1ccc(C2CSc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[#16:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C:3]-[#16:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8](-[C;D1;H3:9]):[c:10] | 65 | [{"value": 65.0, "product": "C(=O)C1=C(C(=C(C=2C(CSC21)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-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide obtained in Example 161, the title compound was synthesized in the same manner as in Example 20. Yield: 65%. Melting point: 134-140° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2 | c1ccccc1.c1ccc2c(c1)CCS2 | HO- | null | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15810e0ecd594a7a8a8ddff38dd1bea0 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | C[Mg]Br.C(=O)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | O=[CH:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[S:19][CH2:20][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14]... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | null | null | O | Miscellaneous | OtherReaction | a770df96f6a4be1205d13d8d885b5204da0714b3274f022584db751708ae7dde | 236fb416ed9d7dc0a069e43e118ef194ae8f5bcc33c36e67bb2c8f8e39c21895 | c1ccc(C2CSc3ccccc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#16:5]>>[#16:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[C;D1;H3:6]):[c:3] | 57.3 | [{"value": 57.0, "product": "C(C)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "C(C)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To methylmagnesium bromide (1.0 M, THF solution, 10 mL, 10 mmol) was added at 0° C. N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (600 mg, 1.42 mmol) obtained in Example 163 and the reaction solution was stirred at room temperature for 1 hour. The reaction solution... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccc2c(c1)CCS2.c1ccccc1 | null | O | null | 0.5 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>O>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58d1bf4d2c224d13bc8d41580bfbde7a | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | C(=O)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)[Mg]Br>>C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C | O=[CH:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[S:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14]... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Miscellaneous | OtherReaction | a770df96f6a4be1205d13d8d885b5204da0714b3274f022584db751708ae7dde | 236fb416ed9d7dc0a069e43e118ef194ae8f5bcc33c36e67bb2c8f8e39c21895 | c1ccc(C2CSc3ccccc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#16:5]>>[#16:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[C:6]-[C;D1;H3:7]):[c:3] | 22 | [{"value": 22.0, "product": "C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide obtained in Example 163 and ethylmagnesium bromide, the title compound was synthesized in the same manner as in Example 164. Yield: 22%. Melting point: 159-160° C. (hexane-ethyl acetate).
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccc2c(c1)CCS2.c1ccccc1 | null | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>CCCCCC.C(C)(=O)OCC>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f3031edae534452a0fc812b81b276ac | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.CCCCCC.C(C)(=O)OCC>>C(C)(=O)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | CCO[C:2]([CH3:1])=[O:3].[cH:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[S:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([C... | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 6ab7eee088bb82a232b30012a7b110b79381b8b7f9a423c061dd7370c04602b3 | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc(C2CSc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#16:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[C;D1;H3:10]):[c:11]>>[C:4]-[#16:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9](-[C;D1;H3:10]):[c:11] | 69 | [{"value": 69.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(CSC21)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-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide obtained in Example 161, the title compound was synthesized in the same manner as in Example 38. Yield: 69%. Melting point: 218-219° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2.c1ccccc1 | HO- | null | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffcf186109dd4e5e994ade3dc1ccbe92 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)CC2c1ccc(C(C)C)cc1 | S(=O)(O)[O-].[Na+].C(C)(=O)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(O)([O-])=O.[Na+].ClC1=CC(=CC=C1)C(=O)OO>>C(C)(=O)C1=C(C(=C(C=2C(CS(C21)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[S:20][CH2:22][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1.O=C(O[OH:21])c1cccc(Cl)c1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:... | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)CC2c1ccc(C(C)C)cc1 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl_peroxide | 855f96dcfeb90214bfc8161ece716cb622fd808d3ac5d3de2139172259cf8697 | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S1CC(c2ccccc2)c2ccccc21 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[S;H0;D2;+0:10]-1>>[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[S;H0;D3;+0:10]-1=[O;H0;D1;+0:1] | 12.4 | [{"value": 12.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(CS(C21)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.4, "product": "C(C)(=O)C1=C(C(=C(C=2C(CS(C21)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of N-(7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (960 mg, 2.19 mmol) obtained in Example 166 and sodium hydrogen carbonate (276 mg, 3.29 mmol) in dichloromethane (20 mL) was added m-chloroperbenzoic acid (530 mg, 3.07 mmol) at 0° C. and the resulting m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccc2c(c1)CCS2.c1ccccc1 | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2.c1ccccc1 | HCl | ClCCl | null | 2 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1>ClCCl>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)CC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95b05c10564b4bb4a9e664b4b0b2f376 | BrBr.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2.O=C(OO)c1cccc(Cl)c1>>Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2(=O)=O | C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.ClC1=CC(=CC=C1)C(=O)OO.BrBr.C(O)([O-])=O.[Na+].S(=O)(O)[O-].[Na+]>>BrC1=C(C(=C(C=2C(CS(C21)(=O)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Br[Br:4].[CH3:1][c:2]1[cH:3][c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][S:29]2.Clc1cccc(C(O[OH:31])=[O:30])c1>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:1... | BrBr.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2.O=C(OO)c1cccc(Cl)c1 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2(=O)=O | null | [Fe] | ClCCl.O | Oxidation | OtherReaction | 6d959e0676cf297c5eb76e6620465a0336a46646576e36ebcd89a39159ed5e06 | 7d22cf4c4b9eb53b72248f8298160fc2d339c943d70025ff6dab054e318b63e0 | O=S1(=O)CC(c2ccccc2)c2ccccc21 | Br-[Br;H0;D1;+0:1].Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:2])-O-[OH;D1;+0:3]):c:1.[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[S;H0;D2;+0:12]-1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:5](-[C;D1;H3:4]):[c:6]):[c:8]1:[c:9]-[C:10]-[C:11]-[S;H0;D4;+0:12]-1(=[O;H0;D1;+0:2])=[O;H0;D1;+0:3] | 55 | [{"value": 55.0, "product": "BrC1=C(C(=C(C=2C(CS(C21)(=O)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (560 mg, 1.41 mmol) obtained in Example 161 and iron powder (5.2 mg, 0.094 mmol) in dichloromethane (10 mL) was added bromine (225 mg, 1.41 mmol) at 0° C. and the resulting mixture was stirred at the same tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Aromatic halide.Sulfone | c1ccc2c(c1)CCS2.c1ccccc1 | c1ccc2c(c1)CCS2 | c1ccccc1.c1ccc2c(c1)CCS2 | HCl.Br- | [Fe].ClCCl.O | null | 1 | BrBr.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2.O=C(OO)c1cccc(Cl)c1>[Fe].ClCCl.O>Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CS2(=O)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc7565b44c4f4dff87191ed334e04cf6 | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1>>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)(=O)CC2c1ccc(C(C)C)cc1 | S(=O)(O)[O-].[Na+].C(C)C1=C(C(=C(C=2C(CSC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(O)([O-])=O.[Na+].ClC1=CC(=CC=C1)C(=O)OO>>C(C)C1=C(C(=C(C=2C(CS(C21)(=O)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[S:19][CH2:22][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1.OOC(c1cccc(Cl)c1)=[O:20]>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:... | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1 | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)(=O)CC2c1ccc(C(C)C)cc1 | null | null | ClCCl | Oxidation | OtherReaction | 9ee788c8a638432248ddb2ab73cda37a63ded85198f53acf2b6fae6c06a21906 | dc6f43112eef310adb122ebf81e1733b34eff292ed27058fb45445842d61d3da | O=S1(=O)CC(c2ccccc2)c2ccccc21 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-O):c:1.[c:2]:[c:3]1:[c:4]-[C:5]-[C:6]-[S;H0;D2;+0:7]-1>>[O;D1;H0:8]=[S;H0;D4;+0:7]1(=[O;H0;D1;+0:1])-[C:6]-[C:5]-[c:4]:[c:3]-1:[c:2] | 28 | [{"value": 28.0, "product": "C(C)C1=C(C(=C(C=2C(CS(C21)(=O)=O)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of N-(7-ethyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (225 mg, 0.512 mmol) obtained in Example 164 and sodium hydrogen carbonate (250 mg, 0.590 mmol) in dichloromethane (20 mL) was added m-chloroperbenzoic acid (283 mg, 1.65 mmol) at 0° C. and the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfone | c1ccc2c(c1)CCS2.c1ccccc1 | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2.c1ccccc1 | HCl | ClCCl | null | 2 | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1SCC2c1ccc(C(C)C)cc1.O=C(OO)c1cccc(Cl)c1>ClCCl>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1S(=O)(=O)CC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0130ad8cbdc647e38c790ac2ea76dc80 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C3OCCO3)c1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2 | O1C(OCC1)C=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.[NH+]1=CC=CC=C1.O>>C(=O)C=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | C1C[O:25][CH:24]([c:23]2[cH:22][cH:21][cH:20][c:19]([CH:18]3[c:6]4[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]4[CH3:8])[O:28][CH2:27]3)[cH:26]2)O1>>[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(c1cccc(C3OCCO3)c1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2 | null | null | CC(=O)C.C(C)(=O)OCC | 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] | 96.1 | [{"value": 96.0, "product": "C(=O)C=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "C(=O)C=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of N-(3-(3-(1,3-dioxolan-2-yl)phenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (910 mg, 2.15 mmol) obtained in Example 73 and pyridinium p-toluenesulfonic acid (25 mg) in acetone (20 mL)-water (1.5 mL) was refluxed with heating for 30 minutes. The reaction solution was dilu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CC(=O)C.C(C)(=O)OCC | null | null | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C3OCCO3)c1)CO2>CC(=O)C.C(C)(=O)OCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-007ca34b9b1446fba269011010dedfe9 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C3OCCO3)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2 | O1C(OCC1)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C>>C(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | C1C[O:24][CH:23]([c:22]2[cH:21][cH:20][c:19]([CH:18]3[c:6]4[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]4[CH3:8])[O:28][CH2:27]3)[cH:26][cH:25]2)O1>>[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(c1ccc(C3OCCO3)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | 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] | 95 | [{"value": 95.0, "product": "C(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-(1,3-dioxolan-2-yl)phenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 82, the title compound was synthesized in the same manner as in Example 173. Yield: 95%. Melting point: 195-196° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C3OCCO3)cc1)CO2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfdbbe330fc644a7a4539b79d81db0d7 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2 | C(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.C[Mg]Br>>OC(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | [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])([CH3:16])[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]=[O:25])[cH:26][cH:27]1)[CH2:28][O:29]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][C:14]([CH3:15])([CH3:1... | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2 | null | null | null | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(C2COc3ccccc32)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 93 | [{"value": 93.0, "product": "OC(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-formylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 174 and methylmagnesium bromide, the title compound was synthesized in the same manner as Example 22.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | null | null | null | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-659f87b9e3db40fcbf6b41640f3288c2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2>>CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | OC(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.C1CCOC1.C(C)(C)OC(C)C>>C(C)(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | [CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][c:11]3[c:12]([CH3:13])[c:14]([CH3:15])[c:16]([NH:17][C:18](=[O:19])[CH2:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]([CH3:26])[c:27]32)[cH:28][cH:29]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][c:11]3[c:12]([CH3:13])[c:14]([CH3:15]... | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2 | CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | null | null | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6] | 65 | [{"value": 65.0, "product": "C(C)(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-(1-hydroxyethyl)phenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 175, the title compound was synthesized in the same manner as in Example 32. Yield: 65%. Melting point: 181-182° C. (THF-diisopropyl ether).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | null | null | null | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)O)cc1)CO2>>CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-145810a8102a40548c80632ed0a2a3b5 | CCOC(=O)CP(=O)(OCC)OCC.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2>>CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | C(=O)C=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.O.[H-].[Na+].C(C)OP(=O)(OCC)CC(=O)OCC>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)/C=C/C(=O)OCC)C1C)C)C)(C)C | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH:13]2[CH2:14][O:15][c:16]3[c:17]([CH3:18])[c:19]([CH3:20])[c:21]([NH:22][C:23](=[O:24])[CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]([CH3:31])[c:32]32)[cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9... | CCOC(=O)CP(=O)(OCC)OCC.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2 | CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | null | null | CN(C)C=O | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])/[CH;D2;+0:1]=[CH;D2;+0:6]/[c:7](:[c:8]):[c:9] | 93 | [{"value": 93.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)/C=C/C(=O)OCC)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)/C=C/C(=O)OCC)C1C)C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of sodium hydride (a 60% dispersion in liquid paraffin, 79 mg, 1.98 mmol) in DMF (10 mL) was added dropwise at 0° C. under an argon atmosphere ethyl diethylphosphonoacetate (444 mg, 1.98 mmol) and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise at 0° C. a solution of N-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CN(C)C=O | null | 0.5 | CCOC(=O)CP(=O)(OCC)OCC.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1cccc(C=O)c1)CO2>CN(C)C=O>CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-931b9c0c91cb459daaff478b356b3ad6 | CCOC(C)=O.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2>>CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | C(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)/C=C/C(=O)OCC)C1C)C)C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH:12]2[CH2:13][O:14][c:15]3[c:16]([CH3:17])[c:18]([CH3:19])[c:20]([NH:21][C:22](=[O:23])[CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]([CH3:30])[c:31]32)[cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11... | CCOC(C)=O.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2 | CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(C2COc3ccccc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:9])/[CH;D2;+0:8]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 81 | [{"value": 81.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)/C=C/C(=O)OCC)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-formylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 174, the title compound was synthesized in the same manner as in Example 177. Yield: 81%. Melting point: 176-177° C. (ethyl acetate).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CCOC(C)=O.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C=O)cc1)CO2>>CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd339f4723704fef8073fbaad9f7ff6a | CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1>>CCOC(=O)CCc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)/C=C/C(=O)OCC)C1C)C)C)(C)C.C(C)(=O)OCC>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)CCC(=O)OCC)C1C)C)C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][cH:11][c:12]([CH:13]2[CH2:14][O:15][c:16]3[c:17]([CH3:18])[c:19]([CH3:20])[c:21]([NH:22][C:23](=[O:24])[CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]([CH3:31])[c:32]32)[cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11]... | CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | CCOC(=O)CCc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(C2COc3ccccc32)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7](:[c:8]):[c:9]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | 81.1 | [{"value": 81.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)CCC(=O)OCC)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=C(C=CC2)CCC(=O)OCC)C1C)C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of ethyl (2E)-3-(3-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)acrylate (400 mg, 0.89 mmol) obtained in Example 177 and 10% palladium on carbon (water content: 50%, 40 mg) in ethanol (3 mL)-ethyl acetate (5 mL) was stirred at room temperature for 2 hours under ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | [Pd].C(C)O | null | null | CCOC(=O)/C=C/c1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1>[Pd].C(C)O>CCOC(=O)CCc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a94ff38ef0ee49da9ef807b459bea5d4 | CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)/C=C/C(=O)OCC)C1C)C)C)(C)C>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)CCC(=O)OCC)C1C)C)C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([CH:12]2[CH2:13][O:14][c:15]3[c:16]([CH3:17])[c:18]([CH3:19])[c:20]([NH:21][C:22](=[O:23])[CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]([CH3:30])[c:31]32)[cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11](... | CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(C2COc3ccccc32)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7](:[c:8]):[c:9]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | 84 | [{"value": 84.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)CCC(=O)OCC)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl (2E)-3-(4-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)acrylate obtained in Example 178, the title compound was synthesized in the same manner as in Example 180. Yield: 84%. Melting point: 103-105° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)/C=C/c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>C(C)(=O)OCC.CCCCCC>CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdf4cc428e844cc29307a1609504802f | CCOC(=O)/C=C(\C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)/C(=C/C(=O)OCC)/C)C1C)C)C)(C)C>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)OCC)C)C1C)C)C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[C:7](\[CH3:8])[c:9]1[cH:10][cH:11][c:12]([CH:13]2[CH2:14][O:15][c:16]3[c:17]([CH3:18])[c:19]([CH3:20])[c:21]([NH:22][C:23](=[O:24])[CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]([CH3:31])[c:32]32)[cH:33][cH:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH3:8])[c:9]1[cH... | CCOC(=O)/C=C(\C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(C2COc3ccccc32)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[C;H0;D3;+0:6](\[C;D1;H3:7])-[c:8](:[c:9]):[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[c:8](:[c:9]):[c:10] | 76 | [{"value": 76.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)OCC)C)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl (2E)-3-(4-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)but-2-enoate obtained in Example 179, the title compound was synthesized in the same manner as in Example 180. Yield: 76%. Melting point: 100-101° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)/C=C(\C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>C(C)(=O)OCC.CCCCCC>CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34246ebfd074467796614738a5990535 | CC(=O)Cl.COc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1>>COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O | O.C(C)(=O)Cl.COC=1C=C(C=CC1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(=O)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC | Cl[C:29]([CH3:30])=[O:31].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([CH3:24])[c:25]32)[cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13]... | CC(=O)Cl.COc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1 | COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc(C2COc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | 89 | [{"value": 89.0, "product": "C(C)(=O)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of N-(3-(3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.0 g, 2.62 mmol) obtained in Example 72 in dichloromethane (20 mL) was added at −50° C. under an argon atmosphere aluminum chloride (769 mg, 5.77 mmol) and the resulting mixture was stirred for 10 minutes. To... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | ClCCl | null | 0.166667 | CC(=O)Cl.COc1cccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)c1>ClCCl>COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50157387383742d4843444ee37a06c46 | COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O.C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC | O.C(C)(=O)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC.CC(C)([O-])C.[K+].[I-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(=C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC | O=[C:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][c:11]3[c:12]([CH3:13])[c:14]([CH3:15])[c:16]([NH:17][C:18](=[O:19])[CH2:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]([CH3:26])[c:27]32)[cH:28][c:29]1[O:30][CH3:31].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH3:1])cc1>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]... | COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O.C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 5091263b16bea7283e1deb2e72ccad76e9a2b569f39b77a679a8e53cdbc2e783 | 93d1d0c14c74e7b67ee3b36f962bbc71783135eee73a676c6ddf9dcb58a45254 | c1ccc(C2COc3ccccc32)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[CH2;D1;+0:6])-[c:3](:[c:4]):[c:5] | 84 | [{"value": 84.0, "product": "C(=C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "C(=C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1 | HOUR | To a solution of potassium tert-butoxide (818 mg, 7.29 mmol) in toluene (45 mL) was added methyl triphenylphosphonium iodide (2.94 g, 7.29 mmol) and the resulting mixture was stirred at 120° C. for 1 hour under an argon atmosphere. To the reaction solution was added N-(3-(4-acetyl-3-methoxyphenyl)-4,6,7-trimethyl-2,3-d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C1(=CC=CC=C1)C | 120 | 1 | COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)=O.C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f1a0951785b4998b2807713894724fe | C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC>>COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C | C(=C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC>>C(C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([CH3:24])[c:25]32)[cH:26][cH:27][c:28]1[C:29]([CH3:30])=[CH2:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[... | C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC | COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6] | 93 | [{"value": 93.0, "product": "C(C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "C(C)(C)C1=C(C=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of N-(3-(4-isopropenyl-3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.93 g, 4.58 mmol) obtained in Example 184 and 10% palladium on carbon (water content: 50%, 193 mg) in ethanol (10 mL) was stirred at room temperature for 2 hours under a hydrogen atmosphere. ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | [Pd].C(C)O | null | null | C=C(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1OC>[Pd].C(C)O>COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfaa8c2e44be4996be35a4e3f9a95f33 | CCOC(=O)COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)c(OCCO)c1)CO2 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C=2C=CC(=C(OCC(=O)OCC)C2)C(C)C)C1C)C)C)(C)C.[Li].O>>OCCOC=1C=C(C=CC1C(C)C)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | CCO[C:29]([CH2:28][O:27][c:26]1[c:22]([CH:23]([CH3:24])[CH3:25])[cH:21][cH:20][c:19]([CH:18]2[c:6]3[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]3[CH3:8])[O:33][CH2:32]2)[cH:31]1)=[O:30]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C... | CCOC(=O)COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)c(OCCO)c1)CO2 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 71 | [{"value": 71.0, "product": "OCCOC=1C=C(C=CC1C(C)C)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "OCCOC=1C=C(C=CC1C(C)C)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | To a solution of ethyl (5-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)-2-isopropylphenoxy)acetate (200 mg, 0.49 mmol) obtained in Example 188 in THF (5 mL) was added with ice-cooling lithium borotetrahydride (43 mg, 2.00 mmol). The reaction solution was warmed to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C1CCOC1 | null | 60 | CCOC(=O)COc1cc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)ccc1C(C)C>C1CCOC1>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)c(OCCO)c1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bf96d7ec6e54d97b1442bd1b9bafaba | CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(CCCO)cc1)CO2 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)CCC(=O)OCC)C1C)C)C)(C)C>>OCCCC1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | CCO[C:25]([CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([CH:18]2[c:6]3[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]3[CH3:8])[O:30][CH2:29]2)[cH:28][cH:27]1)=[O: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:... | CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(CCCO)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2COc3ccccc32)cc1 | 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] | 77 | [{"value": 77.0, "product": "OCCCC1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl 3-(4-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)propanoate obtained in Example 181, the title compound was synthesized in the same manner as in Example 193. Yield: 77%. Melting point: 119-120° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)CCc1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(CCCO)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-063d3b821dec49829ae6cbbc47d50570 | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CCO)cc1)CO2 | CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)OCC)C)C1C)C)C)(C)C>>OCCC(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | CCO[C:26]([CH2:25][CH:23]([c:22]1[cH:21][cH:20][c:19]([CH:18]2[c:6]3[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]3[CH3:8])[O:31][CH2:30]2)[cH:29][cH:28]1)[CH3:24])=[O: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])[C... | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CCO)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2COc3ccccc32)cc1 | 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] | 85 | [{"value": 85.0, "product": "OCCC(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl 3-(4-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)butanoate obtained in Example 182, the title compound was synthesized in the same manner as in Example 193. Yield: 85%. Melting point: 145-147° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CCO)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f44babae51794874b6280f40c93e6995 | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CC(=O)O)cc1)CO2 | Cl.CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)OCC)C)C1C)C)C)(C)C.[OH-].[Na+].C1CCOC1>>CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)O)C)C1C)C)C)(C)C | CC[O:28][C:26]([CH2:25][CH:23]([c:22]1[cH:21][cH:20][c:19]([CH:18]2[c:6]3[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]3[CH3:8])[O:32][CH2:31]2)[cH:30][cH:29]1)[CH3:24])=[O: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:1... | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CC(=O)O)cc1)CO2 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C2COc3ccccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 76.4 | [{"value": 74.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)O)C)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(CC(=O)O)C)C1C)C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 3-(4-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)butanoate (150 mg, 0.32 mmol) obtained in Example 182, 1 N aqueous sodium hydroxide solution (2 mL) and THF (3 mL)-methanol (3 mL) were stirred at room temperature for 16 hours. To the reaction solution was added hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CO | null | null | CCOC(=O)CC(C)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>CO>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)CC(=O)O)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f8110193ad448edba16e062e00e06ea | CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)O)cc1)CO2 | C(C)(=O)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.C[Mg]Br>>OC(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | [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])([CH3:16])[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([C:23]([CH3:25])=[O:26])[cH:27][cH:28]1)[CH2:29][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][C:14]([CH3:15... | CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)O)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Miscellaneous | OtherReaction | 7e61014f084ef66fe8691c8f1abaf493e11079effe9d87ae329e041d937b8b3a | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:7]-[C;H0;D4;+0:2](-[C;D1;H3:1])(-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 42 | [{"value": 42.0, "product": "OC(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-acetylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 176 and methylmagnesium bromide, the title compound was synthesized in the same manner as in Example 22. Yield: 42%. Melting point: 132-134° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | CC(=O)c1ccc(C2COc3c(C)c(C)c(NC(=O)CC(C)(C)C)c(C)c32)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)(C)O)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21c66ba13d5445a6965b6966a9b82316 | CC(=O)Cl.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2>>CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC=O)C.C(C)(=O)Cl>>C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[c:5]([CH3:6])[c:7]([NH:8][CH:9]=[O:10])[c:11]([CH3:12])[c:13]2[c:14]1[O:15][CH2:16][CH:17]2[c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][CH:9]=[O:10])[c:11]([CH3:12])[c:13]2[c:14]1[O:15][CH2:16][CH:17]2[c:18]1[c... | CC(=O)Cl.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | f8d339b78f15a4d82452b51f6749e04de87b23cf8586247567d903b7cafd77bf | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc(C2COc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[C;D1;H3:10]):[c:11]>>[C:4]-[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9](-[C;D1;H3:10]):[c:11] | 48 | [{"value": 48.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 58 and acetyl chloride, the title compound was obtained in the same manner as in Example 38. Yield: 48%. Melting point: 177-179° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | null | null | null | CC(=O)Cl.Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2>>CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af1990caf7b34e9b9fec885fd104bfbd | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NC1CCCCC1>>Cc1c(C)c2c(c(C)c1NC(=O)NC1CCCCC1)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(OCC(Cl)(Cl)Cl)=O)C.C1(CCCCC1)N>>C1(CCCCC1)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | ClC(Cl)(Cl)CO[C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:20]([c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1)[CH2:30][O:31]2)=[O:12].[NH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[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]... | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NC1CCCCC1 | Cc1c(C)c2c(c(C)c1NC(=O)NC1CCCCC1)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | O=C(Nc1ccc2c(c1)C(c1ccccc1)CO2)NC1CCCCC1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4])-[C:8] | 92 | [{"value": 92.0, "product": "C1(CCCCC1)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2,-trichloroethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 138 and cyclohexylamine, the title compound was obtained in the same manner as in Example 143.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | C1CCCCC1.c1ccccc1.c1ccc2c(c1)CCO2 | HCl | null | null | null | Cc1c(C)c2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2.NC1CCCCC1>>Cc1c(C)c2c(c(C)c1NC(=O)NC1CCCCC1)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d9877c49aeb46139b99bfe0849b1864 | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCCO>>CC(=O)c1c(C)c(NC(=O)NCCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(OCC(Cl)(Cl)Cl)=O)C.OCCCN>>C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCCO)C | ClC(Cl)(Cl)CO[C:9]([NH:8][c:7]1[c:5]([CH3:6])[c:4]([C:2]([CH3:1])=[O:3])[c:19]2[c:18]([c:16]1[CH3:17])[CH:22]([c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1)[CH2:21][O:20]2)=[O:10].[NH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[NH:11][C... | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCCO | CC(=O)c1c(C)c(NC(=O)NCCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 59 | [{"value": 59.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCCO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 206 and 3-hydroxypropylamine, the title compound was obtained in the same as manner as in Example 143. Yield: 59%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | null | null | null | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCCO>>CC(=O)c1c(C)c(NC(=O)NCCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d07e7d4a88b14e7ebe3265d9df62d5b4 | CC(=O)c1c(C)c(NC(=O)NC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>Cc1c(NC(=O)NC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NC(C)(C)C)C.[BH4-].[Na+]>>C(C)(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(C)O)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[C:17]([CH3:18])=[O:19])[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[NH:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:... | CC(=O)c1c(C)c(NC(=O)NC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | Cc1c(NC(=O)NC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | null | null | O.CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;H0;D1;+0:6]):[c:7]>>[#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[C;D1;H3:5])-[OH;D1;+0:6]):[c:7] | 16 | [{"value": 16.0, "product": "C(C)(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(C)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "C(C)(C)(C)NC(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C(C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of N-(7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-N′-(tert-butyl)urea (718 mg, 1.7 mmol) obtained in Example 204 in methanol (10 mL) was added sodium borohydride (64.3 mg, 1.7 mmol) at 0° C., and the resulting mixture was stirred for 3 hours. The reaction solution was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | null | O.CO | null | 3 | CC(=O)c1c(C)c(NC(=O)NC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>O.CO>Cc1c(NC(=O)NC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e3dd1b7b81e4126b2fdba7528467f35 | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>>CC(=O)c1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(OCC(Cl)(Cl)Cl)=O)C.OCCN>>C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCO)C | ClC(Cl)(Cl)CO[C:9]([NH:8][c:7]1[c:5]([CH3:6])[c:4]([C:2]([CH3:1])=[O:3])[c:18]2[c:17]([c:15]1[CH3:16])[CH:21]([c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1)[CH2:20][O:19]2)=[O:10].[NH2:11][CH2:12][CH2:13][OH:14]>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[NH:11][CH2:12][C... | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO | CC(=O)c1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc(C2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 66 | [{"value": 66.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(=O)NCCO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,2-trichloroethyl (7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 206 and 2-hydroxyethylamine, the title compound was obtained in the same manner as in Example 143. Yield: 66%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | null | null | null | CC(=O)c1c(C)c(NC(=O)OCC(Cl)(Cl)Cl)c(C)c2c1OCC2c1ccc(C(C)C)cc1.NCCO>>CC(=O)c1c(C)c(NC(=O)NCCO)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bdb400d422048ef9a9c9bceb2a23787 | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(N2CCCC2)c1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N3CCCC3)c1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.N1(CCCC1)C=1C=C(C=CC1)B(O)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)N2CCCC2)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:28][CH2:29][CH:30]2[c:31]1[cH:32][cH:33][c:34]([CH:35]([CH3:36])[CH3:37])[cH:38][cH:39]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1>>[CH3:1][c:2]1[c:3](... | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(N2CCCC2)c1 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N3CCCC3)c1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccc(N5CCCC5)c4)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-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 17 | [{"value": 17.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC(=CC=C2)N2CCCC2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (3-(1-pyrrolidinyl)phenyl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 17%. Melting point: 206-207° C. (ethyl acetate-hexane).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.C1CC[NH]C1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1cccc(N2CCCC2)c1>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1cccc(N3CCCC3)c1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9f277646e1e4dbf934ce22a16ac77dd | CN(C)c1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)cc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.CN(C1=CC=C(C=C1)B(O)O)C>>CN(C1=CC=C(C=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C | OB(O)[c:17]1[cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[cH:24][cH:25]1.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:26][CH2:27][CH:28]2[c:29]1[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:... | CN(C)c1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)cc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | 17 | [{"value": 17.0, "product": "CN(C1=CC=C(C=C1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (4-(dimethylamino)phenyl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 17%. Melting point: 180-181° C. (ethyl acetate-hexane).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CN(C)c1ccc(B(O)O)cc1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)cc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f36062e570b41ccbfd4eb4f548bda0a | CN(C)c1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)nc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.CN(C1=CC=C(C=N1)B(O)O)C>>CN(C1=CC=C(C=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C | OB(O)[c:17]1[cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[n:24][cH:25]1.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:26][CH2:27][CH:28]2[c:29]1[cH:30][cH:31][c:32]([CH:33]([CH3:34])[CH3:35])[cH:36][cH:37]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6... | CN(C)c1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)nc1)OCC2c1ccc(C(C)C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0311ed2d555bc274a96a1ae88766d2b78d4ef6f45f337a2549772e8fe7c98b9a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2COc3c(-c4cccnc4)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-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:6](-[C;D1;H3:7]):[c:8] | 26 | [{"value": 26.0, "product": "CN(C1=CC=C(C=N1)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 35 and (6-(dimethylamino)pyridin-3-yl)boronic acid, the title compound was obtained in the same manner as in Example 107. Yield: 26%. Melting point: 217-220° C. (ethyl acetate-hexane).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | null | null | null | CN(C)c1ccc(B(O)O)cn1.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1-c1ccc(N(C)C)nc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97b186c5631f443c9e04d3e1c7207130 | CC(C)(C)CC(=O)Cl.Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2>>Cc1c2c(c(C(C)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OCC2 | OC(C)(C1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=2CCOC21)C)NC(OC(C)(C)C)=O)C.C(C)(C)(C)CC(=O)Cl>>C(C)(C)C1=CC=C(C=C1)C(C)C1=C(C(=C(C=2CCOC21)C)NC(CC(C)(C)C)=O)C | Cl[C:21](=[O:22])[CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27].CC(C)(C)OC(=O)[NH:20][c:19]1[c:2]([CH3:1])[c:3]2[c:4]([c:5]([C:6](O)([CH3:7])[c:8]3[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]3)[c:17]1[CH3:18])[O:28][CH2:29][CH2:30]2>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]([CH:6]([CH3:7])[c:8]3[cH:9][cH:10][c:11]([C... | CC(C)(C)CC(=O)Cl.Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2 | Cc1c2c(c(C(C)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OCC2 | null | null | C(C)(=O)OCC.CCCCCC | Acylation | OtherReaction | 7bb4234609c581727aa6f3e5957832115e102939a133dd6b69a72cab2d976127 | f5f5eb42e082f86e30d9cf62aec67db7b159aa8c1ad02271f9c6ab8b8b45211d | c1ccc(Cc2cccc3c2OCC3)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D4;+0:6](-O)(-[C;D1;H3:7])-[c:8](:[c:9]):[c:10]):[c:11]-[#8:12].Cl-[C;H0;D3;+0:13](=[O;D1;H0:14])-[C:15]-[C:16]>>[#8:12]-[c:11]:[c:5](-[CH;D3;+0:6](-[C;D1;H3:7])-[c:8](:[c:9]):[c:10]):[c:4]:[c:2](-[NH;D2;+0:1]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[C:15]-[C:16]... | 61 | [{"value": 61.0, "product": "C(C)(C)C1=CC=C(C=C1)C(C)C1=C(C(=C(C=2CCOC21)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using tert-butyl (7-(1-hydroxy-1-(4-isopropylphenyl)ethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 223 and tert-butylacetyl chloride, the title compound was synthesized in the same manner as in Example 224. Yield: 61%. Melting point: 189-190° C. (ethyl acetate-hexane).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester.Ether.Tertiary alcohol.Boc | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | C(C)(=O)OCC.CCCCCC | null | null | CC(C)(C)CC(=O)Cl.Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2>C(C)(=O)OCC.CCCCCC>Cc1c2c(c(C(C)c3ccc(C(C)C)cc3)c(C)c1NC(=O)CC(C)(C)C)OCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a576b47b6bd54d92a70871b2c27b4558 | CC(C)c1ccc(Br)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccccc1 | II.C(C)(C)C1=CC=C(C=C1)Br.[Mg].C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=CC=C2)C)NC(CC(C)(C)C)=O)C>>OC(C1=C(C(=C(C=2C(COC21)C2=CC=CC=C2)C)NC(CC(C)(C)C)=O)C)C2=CC=C(C=C2)C(C)C | Br[c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1.[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]([c:16]1[CH:17]=[O:18])[O:28][CH2:29][CH:30]2[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8](... | CC(C)c1ccc(Br)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c: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](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11] | null | [] | null | null | 20 | MINUTE | To a mixture of magnesium (119 mg, 4.91 mmol) and a catalytic amount of iodine was added dropwise under an argon atmosphere a solution of 4-isopropyl-1-bromobenzene (978 mg, 4.91 mmol) in THF (10 mL) and the mixture was stirred at room temperature for 20 minutes. To the reaction solution was added dropwise a solution o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | Br- | C1CCOC1 | null | 0.333333 | CC(C)c1ccc(Br)cc1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccccc1)CO2>C1CCOC1>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(O)c1ccc(C(C)C)cc1)OCC2c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f12e193c980f4fa39b0ec2133a6c6002 | 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)C2O | CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C)(C)C>>OC1C(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])[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:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[CH:21]2[O... | 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)C2O | 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] | 92 | [{"value": 92.0, "product": "OC1C(OC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,3-dimethyl-N-(2,2,6,7-tetramethyl-3-oxo-2,3-dihydro-1-benzofuran-5-yl)butanamide obtained in Reference Example 65, the title compound was synthesized in the same manner as in Example 234. Yield: 92%. Melting point: 184-185° C. (THF-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in R... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | C1CCOC1.CCCCCC | null | null | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>C1CCOC1.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2O |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.