Dimethylamine → HCID 69106354, compound

Participants

Reaction Steps

2.0 g (5.7 mmol) 8-(trans-2,3-dihydro-2-hydroxy-1-indenyloxy)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid and 2.4 g (7.4 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) are suspended in 100 ml dichloromethane and 2.1 ml (11.4 mmol) dimethylamine (5.6 M in ethanol) are added to the reaction mixture. After stirring for 3 h at room temperature, the reaction mixture is hydrolyzed with saturated aqueous sodium hydrogen carbonate. The organic phase is separated and the aqueous layer is extracted with dichloromethane The combined organic phases are dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) and crystallization from methanol/light petroleum ether yields 1.18 g (57%) of the title compound as a colourless solid (m.p. 182-184° C.).

Provenance & Evidence