Isopropyl chloroformate → HCID 24995278, compound

Participants

Reaction Steps

A mixture of 2-[2-methyl-4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine trifluoroacetate (80 mg, 0.169 mmol), isopropyl chloroformate (1M in toluene, 0.169 mL, 0.169 mmol), and triethylamine (0.070 mL, 0.506 mmol) in CH2Cl2 (3 mL) was stirred at ambient temperature for 1 h, then concentrated. The crude product was purified by reverse-phase preparative HPLC using CH3CN:H2O gradient (5:95 to 90:10) with 0.05% TFA as a modifier, then free-based in CH2Cl2 with MP-Carbonate to give 26 mg (35%) of the title compound as a clear oil. 1H NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=2.5 Hz), 7.86-7.76 (m, 2H), 7.55 (d, 1H, J=7.9 Hz), 7.37-7.31 (m, 1H), 7.29-7.25 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.22 (bs, 2H), 3.90 (d, 2H, J=6.3 Hz), 3.05 (s, 3H), 2.90-2.70 (m, 2H), 2.43 (s, 3H), 2.09-1.95 (m, 1H), 1.95-1.80 (m, 2H), 1.39-1.22 (m, 8H); LRMS (ESI), m/z 447 (M+H).

Provenance & Evidence