Aniline → HCID 59381897, compound

Participants

Reaction Conditions

Reaction Steps

A small microwave reaction vessel was charged with N-(3-(((2-chloro-5-pyrimidinyl)amino)carbonyl)-4-methylphenyl)-2-methyl-3-(trifluoromethyl)benzamide 19 (0.100 g, 0.22 mmol), and pyridin-3-amine (0.10 g, 1.1 mmol) in IPA (1.0 mL). Trifluoroacetic acid (0.034 ml, 0.45 mmol) was added and the vessel was sealed. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 140° C. for 10 min. Monitored the reaction by LCMS and found 50% conversion. Added another 105 mg aniline and 0.05 mL TFA and resumed microwave heating the reaction at 140° C. for 15 min. After about >90% conversion was found by LCMS, the crude reaction mixture was filtered through a Buchner apparatus with micromembrane filter, and the filtrate was washed with copius amounts of MeOH to afford 2-methyl-N-(4-methyl-3-(((2-(3-pyridinylamino)-5-pyrimidinyl)amino)carbonyl)phenyl)-3-(trifluoromethyl)benzamide 20 as an off-white solid after drying. MS m/z found 507.1 [MH+], calc. for C26H21F3N6O2=506.17.

Provenance & Evidence