Hydrochloric Acid → HCID 11772917, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-{[3-(2,2-dimethylpropyl)-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}nicotinate (266 mg, 0.68 mmol) (step 1) in a mixture of ethanol (1 mL) and THF (1 mL) was added lithium hydroxide monohydrate (284 mg, 6.8 mmol) in water (2 mL), and the mixture was then heated to 40° C. for 1 h. The reaction mixture was cooled to rt, the pH of the solution was adjusted to 5 by addition of 0.5 N hydrochloric acid solution, and was concentrated to dryness. The crude product was redissolved in methanol and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 240 mg (97%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 10.39 (s, 1H), 8.43 (dd, 1H), 8.14 (dd, 1H), 7.25-7.42 (m, 4H), 6.81-6.86 (m, 2H), 2.57 (s, 2H), 2.05 (s, 3H), 1.00 (s, 9H); ES-MS m/z 365.3 (MH+); HPLC RT (min) 3.67.

Provenance & Evidence