Diisopropylethylamine → 3-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

Participants

Reaction Steps

A solution of [4-(1H-tetrazol-1-yl)phenyl]acetic acid (101 mg, 0.49 mmol) in DCM (1271 μl) was treated with HATU (189 mg, 0.49 mmol) at room temp. After 5 minutes a solution of of 3-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one (110 mg, 0.38 mmol) and DIEA (167 μl, 0.954 mmol) in DCM (1271 μl) was added and the reaction allowed to stir overnight at room temp. The reaction was quenched with water and SPE purification gives crude product which was purified via reverse phase HPLC (5-85% gradient elution ACN/H2O with 0.5% TFA) to obtain 3-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 475 [M+1]+.

Provenance & Evidence