Diisopropylamine → HCID 178516978, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.1099 g, 0.390 mmol), 2-chloroquinazoline (0.128 g, 0.780 mmol, Waterstone), and diisopropylamine (0.204 ml, 1.170 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO. The reaction was heated to 90° C. for 24 h. The reaction was taken up in DCM and loaded onto an Accubond SCX cartridge and washed with DCM (2×), MeOH (2×), and 2.0 ammonia in MeOH (2×). The ammonia fractions were combined and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 1% to 5% MeOH in CH2CL2, to provide the title compound (0.0445 g, 0.119 mmol, 30.6% yield). LCMS showed product peak at 1.511 min (m+1=374.0). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.12-1.23 (m, 4 H) 2.65 (t, J=9.29 Hz, 2 H) 2.97-3.08 (m, 1 H) 3.41-3.53 (m, 2 H) 5.30-5.42 (m, 1 H) 7.36 (t, J=6.85 Hz, 1 H) 7.69 (d, J=8.41 Hz, 1 H) 7.73-7.85 (m, 2 H) 7.92-7.99 (m, 2 H) 9.11 (br. s., 1 H)

Provenance & Evidence