Hydrochloride methanol → HCID 86663516, compound

Participants

Reaction Steps

3-(6-bromopyridin-2-yl)-2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acrylamide (14 mg, 0.031 mmol) was dissolved into HCl/MeOH (1.25 M, 2 mL). This solution was stirred at room temperature for 18 hours. TLC (in 50% EtOAc/Hexane) showed a single product. The mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The separated organic layer was washed with sat. brine and dried with sodium sulfate and concentrated to give a light amber solid (20 mg) as crude product. The crude material was purified by preparative TLC to afford the title compound as a light yellow solid (12 mg) in 95% yield. 1H NMR (500 MHz, CDCl3/CD3OD) δ 7.55 (dd, J=7.8, 7.5 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.18 (d, J=7.4 Hz, 1H), 1H), 7.07 (d, J=7.4 Hz, 2H), 6.78 (s, 1H), 6.68 (d, J=8.3 Hz, 1H), 3.78 (t, J=7.6 Hz, 1H), 1.62 (m, 2H), 1.34 (m, 2H), 0.88 (t, J=7.3 Hz, 3H). 1H NMR (500 MHz, CDCl3/CD3OD) δ 161.9, 157.2, 151.4, 142.0, 140.8, 139.0, 131.9, 129.4, 128.9, 124.5, 116.5, 115.8, 115.2, 49.5, 29.2, 20.09, 13.7; Mass spec ES+; m/z=422 (m+Ma+); mp (195° C. decomposition starts). Elemental analysis: C=56.73%, H=4.51%, N=10.33%. (calc: C=57.01%, H=4.53%, N=10.50%).

Provenance & Evidence