HCID 16772160, compound → HCID 11719943, compound

Participants

Reaction Steps

A mixture of cyclopropyl(1-pyridin-2-yl)ethylamine (73.5 mg, 0.453 mmol), 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride (144 mg, 0.453 mmol), PS-piperidinomethyl (155 mg, 0.542 mmol, beads) and dichloromethane (5 mL) is stirred at room temperature overnight. The reaction mixture is filtered and the filtrate is evaporated. The residue is purified by chromatography on an ISCO Redisep 10 g cartridge eluting with ethyl acetate-5% methanol to afford 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonic acid cyclopropyl(1-pyridin-2-yl)ethylamide (85 mg, 43% yield) as a white solid. A hydrochloride salt is prepared by dissolving the amine (85 mg, 0.192 mmol) in methanol (2 mL), adding 1 M ethereal hydrochloric acid (0.3 mL), some methanol is removed, more ether added and the hydrochloride salt is collected by filtration (50 mg, 54% yield as an off white solid). RT=2.93 min; m/e=444; 1H NMR (δ, ppm): 11.84 (1H, br s), 8.6 (1H, d), 8.02 (1H, m), 7.69 (1H, d), 7.61 (1H, d), 7.50 (1H, m), 7.37 (1H, s), 5.24 (1H, d), 5.27 (2H, m), 2.40 (2H, m), 2.33 (3H, s), 1.53 (3H, d), 1.13 (3H, t), 0.6-0.96 (4H, m).

Provenance & Evidence