Acetonitrile → HCID 25269870, compound

Participants

Reaction Steps

A mixture of Example 13D (540 mg, 2.37 mmol) and Example 1A (657 mg, 2.37 mmol) in acetonitrile (6 mL) was heated in a microwave reactor at 150° C. for 20 minutes. The reaction was cooled and the solvent was evaporated. The residue was dissolved in tetrahydrofuran (20 mL) and 10 mL 6N HCl and the mixture was stirred several hours at ambient temperature. The mixture was then diluted with ethyl acetate, and the organic phase was washed with water, brine, dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel using methanol/CH2Cl2 as eluent (2% to 20%) that gave a solid that was further purified by trituration to afford 143 mg (17% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.05 (s, 1H) 7.56 (d, J=7.12 Hz, 1H), 7.48 (s, 4H), 7.10 (t, J=7.80 Hz, 1H), 6.84 (d, J=7.12 Hz, 1H), 4.79 (d, J=3.73 Hz, 1H), 3.92 (bs, 1H), 2.97 (m, 2H), 2.68 (m, 1H), 2.26 (s, 3H), 1.87 (bs, 1H), 1.61 (bs, 1H). MS (ESI+) m/z 354 (M+H)+.

Provenance & Evidence