(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 386666ノート

反応式

HRID 386666 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-048c777770ca4d15b134dd81ecb0c5f4
出典データセット
uspto-grants-2013_02
特許番号
US08372865B2

反応ノート

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