Beta-Alanine → HCID 86663515, compound

Participants

Reaction Steps

β-Alanine (1.42 g, 16 mmol) and 6-bromopyridine-2-carboxaldehyde (744 mg, 4 mmol) were added successively to a stirred solution of 2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acetamide (276 mg, 1.0 mmol) in ethanol/water (28 mL/17 mL) at room temp. After 72 hours TLC (in 25% EtOAc/Hexane) showed a single product and some starting materials. 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 oil (830 mg) as crude product. The crude material was purified by flash chromatography to afford the title compound as a yellow oil (253 mg) in 57% yield. 1H NMR (500 MHz, CDCl3) δ 7.59 (dd, J=7.9, 7.5 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.6 Hz, 2H), 7.22 (d, J=7.4 Hz, 1H), 6.96 (d, J=8.6 Hz, 2H), 6.82 (s, 1H), 5.19 (s, 2H), 3.85 (t, J=7.6 Hz, 1H), 3.49 (s, 3H), 1.67 (m, 2H), 1.39 (m, 2H), 0.94 (t, J=7.3 Hz, 3H); Mass spec ES+; m/z=444.0 (m+1) and 466.0 (m+Na+).

Provenance & Evidence