Formaldehyde → HCID 73291876, compound

Participants

Reaction Steps

To a solution of 2-(5-(4-chlorophenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-1-yl)aniline (Example 62) (25 mg, 0.06 mmol, 1 eq) in THF (2 mL) was added formaldehyde (13.64 of a 37% aqueous solution, 0.18 mmol, 3 eq). After 15 min, acetic acid (0.1 mL) and sodium cyanoborohydride (12 mg, 0.18 mmol, 3 eq) were added and the solution stirred 5 hrs. Aqueous saturated NaHCO3 was added, the solution extracted with DCM, the organics combined, dried over MgSO4 and concentrated. Purification by RP-HPLC, eluting with a linear gradient of 20%-100% CH3CN in 0.1% TFA/H2O followed by freebasing with aqueous MP-carbonate resin in DCM and concentration gave 8.6 mg (32%) the title compound.

Provenance & Evidence