(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 386666Notes

Reaction equation

HRID 386666 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(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).

Workup

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

Sources & evidence

ORD record
ord-048c777770ca4d15b134dd81ecb0c5f4
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

Loading…