Hydrochloric Acid → HCID 59464253, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(1-{3-methyl-5-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridine-2-yl}piperidin-4-yl)propanoate (Example 692) (70 mg; 0.13 mmol) was dissolved in dry THF (2.0 mL), treated with potassium trimethylsilanolate (167 mg; 1.30 mmol) and placed in a Biotage ‘Initiator’ microwave. The reaction was heated at 90° C. for 35 mins., monitoring by LCMS, as a yellow precipitate formed. The reaction was incomplete (˜9% ester remained). A further portion of potassium trimethylsilanolate (17 mg) was added and the reaction was returned to the microwave for 15 mins. Very little more reaction was seen (ie ˜5% of starting ester remained). The resulting yellow suspension was treated with water (3 mL) and acidified, to about pH 2, with dropwise addition of aq. 1M HCl. With vigorous stirring for ˜15 mins, a white precipitate formed which was filtered, washed with water and dried under vacuum at 60° C. to give the title compound (45 mg; 79% yield).

Provenance & Evidence