Hydrochloric Acid → HCID 66593309, compound

Participants

Reaction Steps

To a room temperature solution of 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (630 mg, 1.73 mmol) in dimethylformamide (20 mL) was added DIPEA (661 μL, 3.79 mmol, 2.2 eq.), HBTU (720 mg, 1.90 mmol, 1.1 eq.). After 5 min, 3-(4-morpholinyl)propan-1-amine (277 μL, 1.90 mmol, 1.1 eq.) was added and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with EA (50 mL) and washed three times with 5% aqueous sodium bicarbonate (50 mL each). The EA fraction was decanted, dried over magnesium sulfate, filtered, and concentrated under vacuum to give a yellow solid. About 2 mL of 4.0 M hydrogen chloride in dioxane was added, and the mixture was stirred for 15 min and then concentrated under vacuum to give 2-(5-{[3-(4-morpholinyl)propyl]aminocarbonyl}-1H-benzimidazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetamide hydrochloride (750 mg, 1.52 mmol, 88% yield) as a yellow solid.

Provenance & Evidence