(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide → (4S)-4-(4-fluorophenyl)-N-[1-(2-hydroxyethyl)-5-methylindazol-6-yl]-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide

HRID 386666노트

반응식

HRID 386666 반응식
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH3:35])=[C:15]([NH:18][C:19]([C:21]3[C@H:26]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:25][C:24](=[O:34])[NH:23][CH:22]=3)=[O:20])[CH:16]=2)[CH:11]=[N:10]1)(C)(C)C>C(O)(=O)C.O.C1COCC1>[OH:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH3:35])=[C:15]([NH:18][C:19]([C:21]3[C@H:26]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH2:25][C:24](=[O:34])[NH:23][CH:22]=3)=[O:20])[CH:16]=2)[CH:11]=[N:10]1

참가 물질

5

반응물 1

HCID 59377449(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide

생성물 1

HCID 59377426(4S)-4-(4-fluorophenyl)-N-[1-(2-hydroxyethyl)-5-methylindazol-6-yl]-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide수율 70.6%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

(S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide (46 mg, 0.09 mmol) was dissolved in 3 ml of a 3:1:1 mixture of acetic acid, water and THF. The mixture was allowed to stir overnight at room temperature. The solution was concentrated in vacuo, and the residue was purified by flash chromatography (95:5 dichloromethane/methanol) to give 24 mg (70.6%) of (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid [1-(2-hydroxy-ethyl)-5-methyl-1H-indazol-6-yl]-amide white crystalline solid; MS (ES+) m/z 409 (M+H).

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (95:5 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-048c777770ca4d15b134dd81ecb0c5f4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372865B2

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