Tetrabutylammonium Fluoride → HCID 86623806, compound

Participants

Reaction Steps

Treat (±)-(cis)-6-(4-{2-[3-(tert-butyldimethyl-silyloxy)cyclohexylamino]ethyl}phenoxy)nicotinamide (56.8 mg, 0.12 mmol) in THF (1.0 mL) with 1.0 M tetrabutylammonium fluoride (TBAF) in THF (0.5 eq) for 1 hour. Add another 0.5 eq of 1.0 M TBAF and stir for 4 hours. Add 1.0 eq of 1.0 M TBAF and stir for 2.5 days. Concentrate and purify by flash chromatography, eluting with 10% (2.0 M NH3 in MeOH) in CH2Cl2. Repeat the chromatography to afford the title compound (29.9 mg, 70%): MS ES+ 356.0 (M+H)+, HRMS calcd for C21H28N3O2 356.1974 (M+H)+, found 356.1965, time 0.41 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-99% over 19 min], tR=7.11 min, 100% purity; Anal. Calcd for C20H25N3O3.0.4CH2Cl2.0.4MeOH: C, 62.11; H, 6.87; N, 10.45. Found: C, 61.95; H, 6.88; N, 10.36.

Provenance & Evidence