Butanoic acid, 4-chloro-4-oxo-, methyl ester → 4-[3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazol-1-yl]-4-oxo-butyric acid methyl ester

HRID 460351

反応式

HRID 460351 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:8]1[NH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:7]=1[CH2:6]2.[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][C:30](Cl)=[O:31].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][C:30]([N:9]1[C:8]2[C:20]3[C:5]([CH2:6][C:7]=2[C:11]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[N:10]1)=[CH:4][C:3]([O:2][CH3:1])=[C:22]([O:23][CH3:24])[CH:21]=3)=[O:31]

参加物

5

反応物 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester2 回HCID 81531DiisopropylethylamineHCID 9797370Jnj-101984092 回

生成物 1

HCID 588248264-[3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazol-1-yl]-4-oxo-butyric acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (0.50 g, 1.5 mmol), 3-Chlorocarbonyl-propionic acid methyl ester (Compound 26a) (0.277 g, 1.8 mmole) and DMF (1.5 mL) was added Diisopropylethylamine (DIEA) (0.52 mL, 3.0 mmole) at room temperature with stirring. The reaction was stirred at room temperature over night. The reaction was quenched with water and extracted with EtOAc. The solvent was removed via rotovap and the crude material was prepped on the reverse phase HPLC. Lyophilization gave the title compound as a white powder. MS m/z439.9 (M+H)+;

後処理

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe solvent was removed via rotovap

出典と根拠

ORDレコード
ord-3032bbf713c84279888a4b6191ba6e7f
出典データセット
uspto-grants-2007_03
特許番号
US07196110B2

関連ノート

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