Methylamine → HCID 89691388, compound

Participants

Reaction Steps

To a solution of (R)-2-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (SM2-A, 10 g, 32 mmol) in dimethylformamide (DMF, 100 ml) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 15.5 g, 42 mmol), followed by diisopropylethylamine (DIEA, 12.4 g, 96 mmol) while the temperature was maintained below 0° C. After stirring at this temperature for 2 hours (h), methylamine (32 mL, 63 mmol, 2 M in THF) was added. The reaction mixture was warmed to rt and stirred at rt for 16 h. The solution was diluted with ethyl acetate (500 mL); washed with water (200 mL), 0.1 M of hydrochloride (100 mL), saturated NaHCO3 (100 mL), and then brine (100 mL); dried over Na2SO4; and concentrated and purified by column chromatograph (CC, dichloromethane (DCM): MeOH=200:1) to give product (4-A) (10 g, 96%) as a white solid. LC-MS (M+H)+=330.

Provenance & Evidence