Diisopropylethylamine → HCID 178496572, compound

Participants

Reaction Steps

N-(Azetidin-3-yl)-6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-amine (100 mg) was dissolved in N,N-dimethylformamide (1 ml), and 4-methoxycyclohexanecarboxylic acid (43 mg), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (142 mg), and N,N-diisopropyl ethylamine (213 μL) were added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was added water (100 ml), followed by extraction with ethyl acetate (100 ml). The extracts were washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and then the solvent was evaporated under reduced pressure. The residue was separated/purified by silica gel column chromatography (from hexane:ethyl acetate=50:50-0:100 to chloroform:methanol=100:0-80:20) to obtain [3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}amino)azetidin-1-yl](cis-4-methoxycyclohexyl)methanone (26 mg) (Example 249-1) and [3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}amino)azetidin-1-yl](trans-4-methoxycyclohexyl)methanone (7.1 mg) (Example 249-2).

Provenance & Evidence