2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → Methyl 5-chloro-2-(4-(dimethylamino)benzamido)-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of methyl 2-amino-5-chloro-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate (27.5 mg, 0.057 mmol), 4-(dimethylamino)benzoyl chloride (52.1 mg, 0.284 mmol), N,N-dimethylpyridin-4-amine (0.693 mg, 5.67 μmol) and 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (78 mg, 0.284 mmol) in DCE (1.5 mL) was stirred at 80° C. for 6 hours. The product was purified by preparative HPLC (0.1% TFA MeOH/H2O) to give 25 mg (49% yield) of methyl 5-chloro-2-(4-(dimethylamino)benzamido)-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate. 1H-NMR (CDCl3, 400 MHz): δ 12.06 (1H, s), 8.53 (1H, s), 8.05-7.99 (3H, m), 7.59 (1H, dd, J1=7.5 Hz, J2=1.5 Hz), 7.53-7.46 (1H, m), 7.15-6.99 (4H, m), 3.95 (3H, s), 3.84 (2H, s), 3.82 (3H, s), 3.28 (2H, s), 3.15 (6H, s), 2.59 (3H, s).

Provenance & Evidence