Trifluoroacetic acid → HCID 118093871, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[3,4-diamino-2-(2,4-difluorophenoxyl)phenyl]-6-methyl-2-{[2-(trimethylsilyl)ethoxy]methyl}-2,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one (50.0 mg, 0.0973 mmol) in tetrahydrofuran (0.842 mL) was treated with ethyl orthoformate (48.6 μL, 0.292 mmol) followed by p-toluenesulfonic acid monohydrate (1.85 mg, 0.00973 mmol) and stirred at 50° C. for 1 h. The reaction mixture was diluted with methylene chloride (4.0 mL), treated with trifluoroacetic acid (4.0 mL), and heated at 40° C. for 2 h. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (23 mg, 60%). 1H NMR (500 MHz, DMSO-d6) δ 14.02 (s, 1H), 12.79 (br s, 1H), 8.22 (s, 1H), 7.72 (s, 1H), 7.56 (d, J=8.2 Hz, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.30-7.14 (m, 2H), 6.73 (dd, J=8.0, 8.0 Hz, 1H), 6.66-6.49 (m, 1H), 3.52 (s, 3H); LCMS calculated for C20H14F2N5O2 (M+H)+: m/z=394.1. found: 394.1.

Provenance & Evidence