Diisopropylethylamine → (R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-ethoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

Participants

Reaction Steps

To a solution of methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinate (200 mg, 0.663 mmol) in DMF (5 mL) was added DIPEA (0.232 mL, 1.326 mmol) and (R)-tert-butyl 1-amino-3-ethoxypropan-2-ylcarbamate (174 mg, 0.795 mmol). The reaction mixture was stirred at RT overnight. Additional (R)-tert-butyl 1-amino-3-ethoxypropan-2-ylcarbamate (231.25 mg, 1.061 mmol) was added and the mixture was heated at 65° C. for 1 h. After cooling to RT, the reaction mixture was diluted with EtOAc (30 mL) and washed with water (2×20 mL) and brine (20 mL). The combined organic layers were dried over Na2SO4 and concentrated to thick yellow oil. The crude product was used in the next step without further purification (415 mg). [M+H] calc'd for C25H33N5O5, 484; found, 484.

Provenance & Evidence