Dimethylformamide → 3-(4-(4-(3,4-Dimethyl-phenyl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-1,3,5-triazine (50.0 mg, 0.333 mmol) in DMF (1334 μL, 0.333 mmol) was added N-ethyl-N-isopropylpropan-2-amine (174 μL, 1.000 mmol). The reaction mixture was cooled in an ice-water bath prior to the addition of 3-amino-2-methylbenzamide (50.1 mg, 0.333 mmol). The reaction mixture was stirred for 1 h at 0° C. at which time LC-MS revealed complete conversion to 3-(4-chloro-1,3,5-triazin-2-ylamino)-2-methylbenzamide. To this yellow solution was added 1-(3,4-dimethylphenyl)piperazine (63.4 mg, 0.333 mmol). The reaction mixture was allowed to stir and warm slowly to RT over 3 h. Water was added yielding a precipitate, which was filtered off, washed with water, and then purified further by reverse phase liquid chromatography using TFA as a modifier. Fractions containing the product were combined and washed with sat. NaHCO3. The product was extracted with CH2Cl2. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to afford 3-(4-(4-(3,4-dimethyl-phenyl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide (78 mg, 0.187 mmol, 56.0% yield) was obtained as a white solid.

Provenance & Evidence