Diisopropylethylamine → HCID 11296493, compound

Participants

Reaction Steps

A reaction mixture containing (2-bromo-5-methoxy-4-sulfamoylphenyl)acetic acid 12f from Example 12 (18 mg, 0.06 mmol), 1-(4-methoxyphenyl)-1-(2-methyl-6-piperidin-1-ylphenyl)methylamine 8c from Example 8 (25.9 mg, 0.08 mmol), HATU (45.6 mg, 0.12 mmol) and DIPEA (0.06 ml, 0.3 mmol) in a solvent mixture of THF (1 mL) and DMF (0.3 mL) was stirred under argon at RT for 1 hour. The mixture was then diluted with EtOAc (7 mL) and the organic layer was washed with 1.0 M aqueous HCl (2 mL), saturated NaHCO3 (2 mL), dried over Na2SO4, concentrated to a minimum volume (˜1 mL) and purified by preparative TLC (eluent EtOAc:hexane:AcOH 60:40:1) to obtain 31 mg of the semi-pure final inhibitor (˜85% purity by 1H-NMR). The pure inhibitor 2-(2-bromo-5-methoxy-4-sulfamoylphenyl)-N-[1-(4-methoxyphenyl)-1-(2-methyl-6-piperidin-1-ylphenyl)methyl]acetamide 301 (Table 3) was isolated after further purification by C18 reversed phase HPLC.

Provenance & Evidence