Formaldehyde → HCID 178448146, compound

Participants

Reaction Steps

To a solution of (4S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-1-(2-(piperidin-3-yl)ethyl)imidazolidin-2-one bis(2,2,2-trifluoroacetate) (Example 39; 40 mg, 0.055 mmol) in acetonitrile (2 mL) was added formaldehyde (45 mg, 37% solution in water) followed by sodium borohydride and the reaction stirred at ambient temperature for 2 hours. Water (2 mL), was added, and the reaction mixture was concentrated in vacuo. The residue purified by reverse preparative HPLC to give (4S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-1-(2-(piperidin-3-yl)ethyl)imidazolidin-2-one (6.7 mg, 19%) as the mono TFA salt. LCMS (APCI+) m/z 514 [M+H]+.

Provenance & Evidence