Hydrochloric Acid → HCID 178520484, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-{4-[4-(3-{[4-chloro-3-(trifluoromethyl)phenyl]amino}-3-oxopropyl)phenoxy]pyridin-2-yl}-4,5-dihydro-1H-imidazole-4-carboxylate (107 mg, 0.20 mmol) in MeOH (2 mL), at 0° C., was added sodium borohydride (8.0 mg, 0.22 mmol) portionwise. The reaction mixture was stirred at 0° C. for 45 min, and then warmed to rt and stirred for 18 h. After this time additional sodium borohydride (8.0 mg, 0.22 mmol) was added and the mixture was heated at 60° C. for 18 h. The reaction was then cooled to rt, and 1N HCl was added. The solvents were evaporated and the residue was purified by HPLC (250 mm C18 column) eluting with ACN containing 30% to 100% of 0.1% FA in water (20 min gradient) to give A-243 (6.0 mg, 5.8%). 1H NMR (300 MHz, CD3OD) δ: 8.55 (d, 1H), 8.08 (d, 1H), 7.76-7.72 (m, 1H), 7.61 (d, 1H), 7.53 (d, 1H), 7.41-7.38 (m, 2H), 7.11-7.08 (m, 3H), 4.45-4.35 (m, 1H), 4.06 (t, 1H), 3.90-3.83 (m, 1H), 3.74-3.61 (m, 2H), 3.06 (t, 2H), and 2.73 (t, 2H). LCMS: (FA) ES+ 519.1 (M+1).

Provenance & Evidence