Triethylamine → HCID 178426497, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (0.200 g, 0.997 mmol), (INTERMEDIATE 29), in DCE (2 mL) was treated with thionyl chloride (2 ml, 27.4 mmol) at room temperature and the resulting solution heated to 60° C. for 1 h and concentrated. The residue obtained was dissolved in THF (5 mL) and triethylamine (0.416 ml, 2.99 mmol) and cis-N1-(5-methylpyridin-2-yl)cyclobutane-1,3-diamine trihydrochloride (INTERMEDIATE 61) (0.314 g, 1.097 mmol) were added. After stirring at room temperature for 30 minutes, sodium tert-butoxide (0.610 ml, 4.98 mmol) was added. The reaction mixture was stirred at room temperature for another 1 h, then diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO eluting with 0-80% EtOAc/hexanes to afford the title compound 7,7-dimethyl-5-(cis-3-((5-methylpyridin-2-yl)amino)cyclobutyl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.192 g, 0.594 mmol, 59.6% yield). m/z: 324.2 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ; ppm 8.02-8.16 (m, 2 H), 7.93 (d, J=0.78 Hz, 1 H), 7.25-7.31 (m, 2 H), 6.37 (d, J=8.41 Hz, 1 H), 4.99 (d, J=8.41 Hz, 1 H), 4.79 (quin, J=8.71 Hz, 1 H), 4.02-4.26 (m, 1 H), 2.92-3.06 (m, 3 H), 2.74-2.90 (m, 3 H), 2.18 (s, 4 H), 1.44 (s, 8 H).

Provenance & Evidence