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 (SM1-B, 10 g, 32 mmol) in DMF (100 ml) was added HATU (15.5 g, 42 mmol), followed by DIEA (12.4 g, 96 mmol) while the temperature was maintained below 0° C. After stirring for 2 h at this temperature, methylamine (2M in THF, 32 mL, 63 mmol) was added. The reaction mixture was warmed to rt and stirred for 16 h. The solution was diluted with ethyl acetate (500 mL); washed with water (200 mL), 0.1 M hydrochloride (100 mL), saturated NaHCO3 (100 mL), and brine (100 mL); dried over Na2SO4; and concentrated and purified by column chromatography (DCM:MeOH=200:1) to give product (2-B) (10 g, 96%) as a white solid. LC-MS (M+H)+=330.

Provenance & Evidence