Diisopropylethylamine → HCID 86710230, compound

Participants

Reaction Steps

To a solution of ((2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (30 mg, 0.091 mmol, 1 eq) in dichloromethane (5 mL) under nitrogen, was added DIPEA (24.9 mg, 0.193 mmol, 0.0340 mL, 2.12 eq) followed by 1-hydroxybenzotriazole monohydrate (27.0 mg, 0.176 mmol, 1.93 eq). The solution was allowed to stir for 30 minutes before being treated with O-tetrahydro-2H-pyran-2-yl-hydroxylamine (14.3 mg, 0.122 mmol, 1.34 eq) and then dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (24.9 mg, 0.130 mmol, 1.43 eq). The mixture was then allowed to stir for 3 hours at RT. The reaction mixture was then adsorbed onto silica gel and purified by flash chromatography eluting with 5-100% EtOAc/Hpt to give (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (8.8 mg, 23% yield). LC-MS M+H+428.1.

Provenance & Evidence