2-Morpholinoethylamine → HCID 118093785, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-(2,4-difluorophenoxy)-6-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbaldehyde (25.0 mg, 0.0423 mmol) and N-(2-aminoethyl)morpholine (0.0111 mL, 0.0847 mmol) in methanol (0.40 mL) and methylene chloride (0.40 mL) was heated to 60° C. and stirred at 60° C. for 1 h. The reaction mixture was cooled to 0° C., treated with sodium cyanoborohydride (0.0106 g, 0.169 mmol), warmed to RT and stirred for at RT 15 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in methanol (0.50 mL), treated with sodium cyanoborohydride (0.00532 g, 0.0847 mmol), and stirred at 60° C. for 3 h. The reaction mixture was diluted with acetonitrile, methanol and a few drops of water and purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (11.9 mg, 40%). LCMS calculated for C35H35F2N6O6S (M+H)+: m/z=705.2. found: 705.2.

Provenance & Evidence