Dimethyl Sulfoxide → HCID 178498839, compound

Participants

Reaction Steps

A solution of 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 1.00 g, 3.55 mmol), methyl 2-chloro-4-thiazolecarboxylate (0.820 g, 4.61 mmol), and diisopropylethylamine (3.09 mL, 17.75 mmol) in DMSO (10 mL) was stirred at 120° C. for 18 h. The reaction was allowed to cool to room temperature, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silica gel column eluting with 0-70% EtOAc/hexane to give the title compound methyl 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylate (0.380 g, 0.983 mmol, 27.7% yield). m/z: 387.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 8.38 (d, J=6.46 Hz, 1 H), 7.99 (q, J=3.26 Hz, 2 H), 7.60 (s, 1 H), 5.15 (t, J=8.31 Hz, 1 H), 4.28-4.47 (m, 1 H), 3.77 (s, 3 H), 3.18-3.30 (m, 2 H), 2.88-3.07 (m, 1 H), 2.34-2.47 (m, 2 H), 0.91-1.13 (m, 4 H).

Provenance & Evidence