Hydrochloric Acid → HCID 89462656, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-(3,4-dimethyl phenyl)-1-(4-methoxybenzyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-5-yl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetonitrile 267 mg, 0.52 mmol), 20% sodium hydroxide/water (5.0 g, 25 mmol) and EtOH (5 mL) was heated in a sealed tube at 140° C. for 18 h. The mixture was acidified to pH 3 with 1 M hydrochloric acid, diluted with water and extracted with EtOAc. The organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in MeOH (10 mL) and PTS (80 mg, 0.421 mmol) was added. After 1 h at ambient temperature the mixture was treated with TMS-diazomethane (3 mL, 6 mmol, 2M/hexanes) and stirring continued for 1.5 h. Acetic acid was added until bubbling stopped and the mixture was concentrated and purified on silica using EtOAc/hexanes 0-50% to provide the title compound (175 mg, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 7.4-7.5 (m, 3H), 7.1-7.3 (m, 3H), 6.85 (d, 2H), 5.95 (s, 2H), 5.35 (d, 1H), 3.79 (s, 3H), 3.78 (s, 3H), 3.6 (s, 3H), 2.33 (s, 3H), 2.32 (s, 3H); ES-LCMS: 462.22 (M+1).

Provenance & Evidence