Trifluoromethanesulfonic anhydride → HCID 69767203, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.216 g of 4-hydroxymethyl-piperidine-1-carboxylic acid, tert-butyl ester (from Step B) in 6 mL of CH2Cl2 at −78° C. was added 0.202 mL of triflic anhydride. After stirring at −78° C. for 5 minutes, 0.151 mL of 2, 6-lutidine was added dropwise. The temperature was maintained below −70° C. throughout the reaction. After stirring for 15 minutes, 0.35 mL of diisopropylethylamine was added dropwise. After 15 minutes, a solution of 0.35 g 2-ethyl-5,7-dimethyl-3-H-imidazo[4,5-b]pyridine (prepared as described by Mantlo et al. U.S. Pat. No. 5, 412,097 and J. Med. Chem. 1991, 34, 2919 ) in 4 mL of CH2Cl2 was added dropwise. After warming to 0° C., the reaction was stirred at rt for 5 hr. The reaction was diluted with Et2O, then washed with H2O. The aqueous phase was extracted with 2×25 mL Et2O. The combined organic phases were dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 50% EtOAc in hexane to give 73 mg of the title compound as an oil.

Provenance & Evidence