1,2-Dichloroethane → Dihydropyridone indazole amide 10

HRID 734671ノート

反応式

HRID 734671 の反応式
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH2:31])=[CH:28][CH:29]=2)[CH:24]=[N:23]1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH:31][C:17]([C:10]3[CH:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:8][CH:7]=4)[CH2:14][C:13](=[O:15])[NH:12][C:11]=3[CH3:16])=[O:18])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 880121H-Indazol-5-amineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid

生成物 1

HCID 11189172Dihydropyridone indazole amide 10収率 33%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The product of step 2 (146 mg, 0.512 mmol, 1.00 equiv), 1H-indazol-5-amine (68 mg, 0.512 mmol, 1.00 equiv) and EDC (118 mg, 0.615 mmol, 1.20 equiv) were suspended in 8.0 mL DMF. Et3N (0.086 mL, 0.615 mmol, 1.20 equiv) was added and the solution was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (100% EtOAc) to provide 0.070 g (33%) of the title compound as a white solid. MS (ES+) m/e 415 [M+H]+

後処理

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by flash chromatography (100% EtOAc)

出典と根拠

ORDレコード
ord-b01322396f4d493bab760eb89b7f6196
出典データセット
uspto-grants-2009_09
特許番号
US07592357B2

反応ノート

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