Cresopirine → HCID 59314302, compound

Participants

Reaction Steps

A 40 mL vial containing a stirring bar is charged with 2-acetoxyl-3-methyl-benzoic acid (1 g, 4.87 mmol) and dry DCM (14 mL), and stirring is initiated. After dissolution is complete, HBTU (1.85 g, 4.87 mmoles) is added. After 5 min, 2-amino-indane-2-carboxylic acid ethyl ester (1 g, 4.87 mmol) is added followed by DIPEA (2.1 mL, 12.18 mmol). The reaction is allowed to stir for 110 h. Analysis by tlc of the reaction mixture (silica, 5% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a reparatory funnel and diluted with EtOAc (100 mL). This is washed consecutively with dilute aqueous HCl (3%, 40 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 3 g of a light orange solid. This material is dissolved in 15 mL of DCM. This material is purified utilizing an ISCO Companion with an 80 g cartridge of silica. The gradient is 10% EtOAc in heptanes over 3 column volumes followed by a linear gradient to 50% EtOAc over 12 column volumes. Fractions 19 through 27 are combined and evaporated in vacuo to give 1.38 g of white solid.

Provenance & Evidence