2-Chloroquinazoline → HCID 178481626, compound

Participants

Reaction Conditions

Reaction Steps

3-(Trans-3-aminocyclobutyl)-6-fluoro-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one hydrochloride (0.105 g, 0.385 mmol), 2-chloroquinazoline (0.076 g, 0.462 mmol), and N,N-diisopropylethylamine (0.268 mL, 1.540 mmol) were mixed in DMSO (0.5 mL). The reaction mixture was warmed to 120° C. and stirred for 3 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield 6-fluoro-1-methyl-3-(trans-3-(quinazolin-2-ylamino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3h)-one (0.054 g, 0.148 mmol, 38.5% yield) as a yellow solid. M+1: 365.1. 1H NMR (400 MHz, DMSO-d) δ ppm 2.42-2.50 (m, 2 H) 3.25-3.34 (m, 2 H) 3.35 (s, 3 H) 4.63-4.74 (m, 1 H) 5.25 (quin, J=8.51 Hz, 1 H) 7.22-7.27 (m, 1 H) 7.49 (d, J=8.41 Hz, 1 H) 7.64-7.73 (m, 2 H) 7.81 (dd, J=8.02, 0.78 Hz, 1 H) 7.99 (br. d, J=6.30 Hz, 1 H) 8.05 (t, J=2.25 Hz, 1 H) 9.15 (s, 1 H).

Provenance & Evidence