Diisopropylethylamine → HCID 67268025, compound

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Reaction Steps

To a solution of (4-amino-3-methylphenyl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (15.2 mg, 40 mol) in DMF (100 μL) was added a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 27.4 mg, 72 mol) in DMF (100 μL), followed by i-Pr2NEt (25 μL, 144 mol) and piperidin-1-yl-acetic acid (8.6 mg, 60 mol). The resulting mixture was shaken at room temperature for 3 hours after which it was diluted with ethyl acetate (10 mL), washed with saturated aqueous ammonium chloride (2×10 mL), dried over sodium sulfate, and evaporated. The residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield [3-methyl-4-(2-piperidin-1-yl-acetylamino)-phenyl]-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester as a white solid (10.7 mg, 53%). This was dissolved in dichloromethane (200 μL) and trifluoroacetic acid (200 μL), and the solution was kept at room temperature for 30 minutes, after which volatiles were evaporated and the residue was dried in vacuo at 0.1 mmHg and +40° C. for 1 hour. The resulting trifluoroacetic acid addition salt of the title compound was obtained as a yellow semisolid in quantitative yield.

Provenance & Evidence