Benzaldehyde → HCID 178522223, compound

Participants

Reaction Steps

Step (b) A flask was charged with (S)-1-(2-(1H-imidazol-4-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (107 mg, 0.252 mmol), benzaldehyde (0.154 mL, 1.51 mmol), methanol (10 mL) and sodium triacetoxyborohydride (534 mg, 2.52 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with deionized water (15 mL). The mixture was washed with ethylene chloride (20 mL) and the aqueous layer was basified with 2N sodium hydroxide (40 mL) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give Compound 175 (S)-1-(2-(1H-imidazol-4-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (41 mg, 32% yield), as an off-white solid. 1H-NMR (400 MHz, CDCl3): 10.23 (s, 1H), 7.63-7.18 (m, 8H), 7.02-6.82 (m, 7H), 5.42 (s, 1H), 4.02-3.90 (m, 1H), 3.88-3.80 (m, 1H), 3.78-3.61 (m, 2H), 3.58-3.34 (m, 2H), 3.08-2.97 (m, 1H), 2.78-2.64 (m 1H), 2.28-2.18 (m, 1H), 2.11-2.00 (m, 1H). MS (EI) for C29H28FN5O3. found 514.3 (MH+).

Provenance & Evidence