2-Chloroquinazoline → HCID 178516969, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(trans-3-aminocyclobutyl)-1-cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one hydrochloride (0.458 g, 1.63 mmol), Hunig's base (Aldrich, 1.139 ml, 6.52 mmol), and 2-chloroquinazoline (Waterstone, 0.322 g, 1.956 mmol) in DMSO (3.26 ml) was heated to 120° C. overnight. The reaction mixture was diluted with EtOAc and washed with water and brine. Purification by Biotage (0-100% EtOAc/hexane, 25 g Biotage column) produced 1-cyclopropyl-3-(trans-3-(quinazolin-2-ylamino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.244 g, 0.601 mmol, 37% yield). M+1: 373.0. 1H NMR (300 MHz, MeOH) δ ppm 0.93-1.03 (m, 3 H) 1.06-1.19 (m, 3 H) 2.47-2.64 (m, 2 H) 2.85-3.00 (m, 2 H) 3.42-3.60 (m, 2 H) 5.25-5.45 (m, 1 H) 7.04-7.20 (m, 1 H) 7.20-7.35 (m, 1 H) 7.48-7.64 (m, 3 H) 7.64-7.83 (m, 3 H) 7.99-8.14 (m, 1 H) 8.99-9.12 (m, 1 H).

Provenance & Evidence