Acetonitrile → HCID 25269871, compound

Participants

Reaction Steps

A mixture of Example 14D (0.840 g, 3.76 mmol) and Example 1A (1.04 g, 3.76 mmol) in acetonitrile (19 mL) was heated in a microwave reactor at 150° C. for 20 minutes. Two drops of aqueous concentrated HCl were added and the reaction was reheated in the microwave to 150° C. for 20 min. The volatiles were evaporated and the crude material was dissolved in tetrahydrofuran (20 mL), followed by addition of 10 mL 6N HCl. The mixture was stirred overnight at ambient temperature, then diluted with ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel using methanol/CH2Cl2 as eluent (2% to 20%), followed by triturating with diethyl ether to afford 122 mg (9% yield) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1H), 7.60 (d, J=7.93 Hz, 1H), 7.42 (d, J=9.12 Hz, 2H), 7.04 (m, 3H), 6.81 (d, J=7.54 Hz, 1H), 4.80 (d, J=3.97 Hz, 1H), 3.92 (bs, 1H), 3.78 (s, 3H), 2.90 (m, 2H), 2.75 (m, 1H), 2.22 (s, 3H), 1.87 (bs, 1H), 1.62 (bs, 1H). MS (ESI) m/z 350 (M+H)+.

Provenance & Evidence