N,N-Diethylethanamine trihydrofluoride → 1-cyclopropyl-3-((3-(4-fluorobutyl)imidazo[1,2-a]pyrazin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

Participants

Reaction Steps

A suspension of diethylaminodifluorosulfonium tetrafluoroborate (453 mg, 1.982 mmole), 1-cyclopropyl-3-((3-(4-hydroxybutyl)imidazo[1,2-a]pyrazin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one P17 (500 mg, 1.321 mmole), and triethylamine trihydrofluoride (319 mg, 1.5 eq) in DCM (20 mL) was stirred at RT under N2 atmosphere for 60 minutes. 100 mL sat NaHCO3 was then added and the mixture was stirred until gas evolution stopped (10 minutes), then was extracted with 150 mL DCM (2×). Combined organic layers were dried on Na2SO4, filtrated and evaporated to dryness. Purification by Prep HPLC on (RP Vydac Denali C18-10 μm, 250 g, 5 cm) with (0.25% NH4HCO3 solution in water, MeOH) as mobile phase, afforded the target compound P18 in 20% yield. m/z=381 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-0.92 (m, 2H), 1.00-1.10 (m, 2H), 1.46-1.80 (m, 4H), 2.95 (tdd, J=6.96, 6.96, 3.64, 3.51 Hz, 1H), 3.12 (t, J=7.53 Hz, 2H), 4.43 (dt, J=47.43, 6.00 Hz, 2H), 5.23 (s, 2H), 7.24 (dd, J=5.27, 0.75 Hz, 1H), 7.89 (d, J=4.52 Hz, 1H), 8.22 (d, J=5.27 Hz, 1H), 8.41 (s, 1H), 8.47 (dd, J=4.77, 1.51 Hz, 1H), 8.98 (d, J=1.51 Hz, 1H).

Provenance & Evidence