4-Piperidinemethanol → HCID 59013774, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amide (50 mg, 0.11 mmol, prepared in Example 10b) was dissolved in 330 μL of t-butanol along with 4-piperadine methanol (38 mg, 0.33 mmol). Then, 330 μL of 1.0 M potassium t-butoxide in t-butanol was added. The reaction mixture was heated to 50° C. overnight. The reaction was quenched with the addition of a few drops of trifluoroacetic acid and the solution was diluted to 2 mL in volume with methanol. The reaction mixture was purified by reverse phase HPLC to give 9 mg of the product as a white solid. 1H NMR DMSO-d6) δ 9.37 (s, 1H), 8.25 (s, 2H), 7.62 (s, 1H), 4.28 (d, 2H), 3.63 (m, 4H), 3.54 (m, 4H), 3.08 (d, 2H), 2.59 (t, 2H), 1.93 (m, 1H), 1.71 (d, 2H), 1.29 (qd, 2H) ppm.

Provenance & Evidence