1,2-Dichloroethane → HCID 178474402, compound

Participants

Reaction Steps

Acetyl isothiocyanate (1.755 mL, 19.97 mmol) was added to a heated (100° C. oil bath) solution of cis-4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)-N-isopropylcyclohexanecarbox-amide (8.06 g, 19.97 mmol) in dioxane (100 mL). After 5 minutes, complete conversion to the thiourea intermediate was observed. The reaction was cooled to RT, and EDC (11.49 g, 59.9 mmol) and DIPEA (12.56 mL, 71.9 mmol) were added. Heating was resumed at 60° C. for 2.5 hours. The reaction mixture was pre-absorbed onto silica gel, and purified via silica gel chromatography, eluting with 90:10:1 DCM:MeOH:NH4OH to yield cis-4-(2-acetamido-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-1-yl)-N-isopropylcyclohexanecarboxamide (8.56 g, 18.19 mmol, 91% yield) as an orange solid. MS m/z=471.2 [M+H], calc 470.61 for C25H38N6O3.

Provenance & Evidence