Sodium Hydroxide → HCID 86595423, compound

Participants

Reaction Steps

Part A. 6-{4-[1-(tert-Butoxycarbonyl-methyl-amino)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.59 g, 1.79 mmol) was stirred in EtOH (15 mL) and 1N NaOH (3 mL) at rt for 1 h. After evaporation, the mixture was acidified with citric acid. The mixture was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness in vacuo. This acid underwent a series of reactions similar to those used in Part E of Example 1 to afford (1-{4-[3-formyl-1-(4-methoxy-phenyl)-7-oxo-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-phenyl}-cyclopropyl)-methyl-carbamic acid tert-butyl ester (yield: 99%). LC/MS (ESI+) 461.6 (M+H−t-Bu)+, tR=1.2.97 min (10–90% CH3CN/H2O in a 4-min run).

Provenance & Evidence