Trifluoroacetic acid → N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-5-benzyl-1,3,4-oxadiazole-2-carboxamide

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Reaction Steps

A mixture of (5-{[(5-Benzyl-[1,3,4]oxadiazole-2-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (412 mg, 0.94 mmol), 4 mL TFA and 8 mL DCM was stirred of room temperature for 2 h. The mixture was evaporated in vacuo and the residue was purified by preparative HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40ml/min). The product containing fractions were lyophilised, then dissolved in 1 mL MeOH and the resulting mixture was filtered over a MeOH flushed PL-HCO3 MP-resin column. The column was washed with MeOH, the solvent was removed and the crude product was dissolved in water/ACN and lyophilised to yield the title compound. 1H-NMR (DMSO-d6, 400 MHz) 9.33 (t, 1H), 7.29-7.39 (m, 5H), 6.11 (s, 1H), 5.71 (bs, 2H), 4.34-4.36 (m, 4H), 2.30 (s, 3 H), 2.17 (s, 3H); LCMS (method A) RtA=0.814 min; [M+H]+=338.0.

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