Diisopropylethylamine → 3-(4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazine (0.800 g, 2.54 mmol) [prepared as described for 2-chloro-4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine in Example AAA] in isopropanol (8 mL) was added DIPEA (0.7 mL, 3.81 mmol) and 3-amino-N-methylbenzamide (382 mg, 2.54 mmol). The reaction mixture was stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-(4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide (0.537 g, 53%) as a solid. Observed mass (M+1): 428.9.

Provenance & Evidence