Diisopropylethylamine → HCID 178481625, 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-5-fluorobenzo[d]thiazole (0.108 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 3-(trans-3-((5-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.030 g, 0.081 mmol, 14.07% yield). m/z: 370.1 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 8.07 (d, J=4.89 Hz, 1 H), 7.43-7.60 (m, 1 H), 7.23-7.34 (m, 1 H), 7.17 (d, J=7.43 Hz, 1 H), 6.98-7.10 (m, 1 H), 6.84 (t, J=8.71 Hz, 1 H), 6.18 (br. s., 1 H), 5.40 (quin, J=8.36 Hz, 1 H), 4.62 (br. s., 1 H), 3.50-3.67 (m, 2 H), 3.43 (s, 3 H), 2.55 (t, J=10.07 Hz, 2 H).

Provenance & Evidence