Dimethylformamide → HCID 68683806, compound

Participants

Reaction Steps

N-Ethyldiisopropylamine (0.119 mL, 0.68 mmol) was added to 4-amino-3-methoxybenzoic acid (Aldrich; 114 mg, 0.68 mmol), (1R,5S,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-amine (Bioorganic & Medicinal Chemistry Letters (1992), 2(6), 519-22, 107 mg, 0.68 mmol) and HATU (260 mg, 0.68 mmol) in DMF (5 mL) at 25° C. The resulting solution was stirred at ambient temperature for 6 hours. The DMF was evaporated to give a brown gum as residue, which was purified by ion exchange chromatography, using an SCX-2 (5 g) column pre-wet with methanol. The desired product was eluted from the column using 2M NH3/MeOH and purified fractions were evaporated to dryness to afford a brown gum which was purified by flash silica chromatography, elution gradient 0 to 100% 5% MeOH/DCM in DCM. Pure fractions were combined and evaporated to dryness to afford the title compound as a beige coloured gum (205 mg, 98%).

Provenance & Evidence