Potassium Hydroxide → HCID 67487542, compound

Participants

Reaction Steps

Ethyl 3-(5-(3-(2-methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (69.5 mg, 0.130 mmol) was dissolved in iPrOH (5 mL) and potassium hydroxide (72.9 mg, 1.30 mmol) was added. The reaction was heated to reflux for 3 days. More KOH (72.9 mg, 1.30 mmol) was added and the reaction was heated for another 2 days. Water (˜10 drops) was added and the reaction was heated for 1 week. The solution was partitioned between saturated aqueous NH4Cl and CH2Cl2. The aqueous layer was extracted 3 times with CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford crude 3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (45 mg, 0.0973 mmol, 74.8% yield).

Provenance & Evidence