Sodium Bicarbonate → HCID 178508477, compound

Participants

Reaction Steps

A solution of trans-4-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (150.0 mg, 0.3390 mmol) in THF (10 mL, 0.1 mol) was cooled to −78° C., and 1.0 M of LiAlH4 in THF (1.50 mL) was added dropwise. The solution was allowed to warm to rt. Sat. NaHCO3 (10 mL) was added to quench, and the THF was removed in vacuo. DCM was added, and the mixture was transferred to a separatory funnel. The organic layer was extracted with sat. NaHCO3, washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ=1.15-1.27 (m, 2H), 1.65-1.70 (m, 1H), 1.84-1.96 (m, 2H), 1.98-2.05 (m, 2H), 2.10-2.16 (m, 2H), 2.87-2.97 (m, 1H), 3.56 (d, J=6.3 Hz, 2H), 5.06 (br. s., 2H), 7.07 (dd, J=6.9, 1.9 Hz, 3H), 7.10-7.18 (m, 3H), 7.23 (d, J=5.1 Hz, 1H), 7.35-7.40 (m, 2H), 7.60-7.63 (m, 2H). MS (ES+): m/z 416.34 (100) [MH+]. HPLC: tR=2.34 min (polar—5 min).

Provenance & Evidence