1,2-Dichloroethane → N-(3-Ethyl-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734688ノート

反応式

HRID 734688 の反応式
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][C:16](=[O:18])[NH:15][C:14]([CH3:19])=[C:13]1[C:20](O)=[O:21].[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][N:28]=[C:27]2[CH2:33][CH3:34].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[CH2:33]([C:27]1[C:26]2[C:30](=[CH:31][CH:32]=[C:24]([NH:23][C:20]([C:13]3[CH:12]([C:3]4[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:7][C:2]=4[F:1])[CH2:17][C:16](=[O:18])[NH:15][C:14]=3[CH3:19])=[O:21])[CH:25]=2)[NH:29][N:28]=1)[CH3:34]

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688271204-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178438005HCID 178438005、化合物

生成物 1

HCID 178438008N-(3-Ethyl-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide収率 34.4%

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 Example 21, Step 2 (50 mg, 0.158 mmol, 1.00 equiv), 5-amino-3-ethylindazole (25 mg, 0.158 mmol, 1.0 equiv), and EDC (36 mg, 0.189 mmol, 1.20 equiv) were suspended in 0.5 mL DMF. Et3N (0.026 mL, 0.189 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. 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 (20-100% EtOAc in Hexanes) to provide 25 mg (34%) of the title compound as an off white solid. MS (ES+) m/e 461 [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 (20-100% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-4ff799b05c8f467eacfc78499db6f867
出典データセット
uspto-grants-2009_09
特許番号
US07592357B2

反応ノート

読み込み中…