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

반응식

HRID 460351 반응식
[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]

참가 물질

5

반응물 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester2회HCID 81531DiisopropylethylamineHCID 9797370Jnj-101984092회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+;

후처리

  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

출처 및 근거

ORD 기록
ord-3032bbf713c84279888a4b6191ba6e7f
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196110B2

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