Diethyl Ether → HCID 59556692, compound

Participants

Reaction Steps

A solution of benzyl 2-(3-(3-chloro-4-isopropoxypheny)-1,2,4-oxadiazol-5-yl)-3-methy-5,6-dihydroimidazo[1,2-a] pyrazine-7(8H)-carboxylate (160 mg, 0.315 mmol) in 33% HBr solution in acetic acid (2.00 mL) containing triisopropylsilane (0.065 mL, 0.315 mmol)) was stirred at room temperature under nitrogen for 10 minutes. Ether (20 ml) was added to precipitate the product. The resulting solid was filtered off, treated with saturated bicarbonate solution (10 ml) and extracted with methylene chloride (2×10 ml). The combined organic layers were dried over sodium sulfate, filtered, concentrated to solids and dried under reduced pressure to yield 2-[3-(3-Chloro -4-isopropoxy-phenyl)-[1,2,4] oxadiazol-5-yl]-3-methyl-5,6,7,8-tetrahydro-imidazo [1,2-a] pyrazine (113 mg, 96%) as an off-white solid. LCMS (Table 1, Method a) Rl=3.14 min, m/z 374.24 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 8.01 (d, 1H), 7.97 (d,d, 1H), 7.36 (d, 1H), 4.81 (m, 1H), 4.66 (s, 2H), 3.90 (s, 2H), 3.87 (t, 2H), 3.12 (t, 2H), 2.60 (s, 3H), 1.34 (d, 6H).

Provenance & Evidence