Diisopropylethylamine → HCID 178481287, compound

Participants

Reaction Steps

The title compound was synthesized following the procedure described for INTERMEDIATE 10, using 3-(trans-3-aminocyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one hydrochloride (0.147 g, 0.577 mmol), 2-chloro-1-methyl-1 h-benzoimidazole (0.096 g, 0.577 mmol), diisopropylethylamine (1 ml, 5.75 mmol) and 4-dimethylaminopyridine (7.05 mg, 0.058 mmol) in DMSO (0.5 mL) and purified by ISCO on silica gel column using 0-80% EtOAc/hexanes to afford 1-methyl-3-(trans-3-((1-methyl-1H-benzo[d]imidazol-2-yl)amino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.103 g, 0.296 mmol, 51.2% yield). m/z: 366.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 8.04 (dd, J=5.28, 1.17 Hz, 1 H), 7.50 (dd, J=7.82, 1.17 Hz, 1 H), 7.19-7.24 (m, 1 H), 7.13-7.18 (m, 1 H), 7.10 (dd, J=7.73, 5.18 Hz, 1 H), 7.02 (d, J=6.46 Hz, 1 H), 6.88-6.98 (m, 2 H), 5.32 (t, J=8.41 Hz, 1 H), 4.51-4.69 (m, 1 H), 3.56 (s, 3 H), 3.26-3.40 (m, 5 H), 2.41-2.57 (m, 2 H).

Provenance & Evidence