Triethylamine hydrochloride → HCID 178420382, compound

Participants

Reaction Steps

According to a modification of a literature procedure (Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379-3393) a solution of 35 mg (0.085 mmol) of 6-(4-benzyloxy-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile in 1.5 mL of toluene and 0.5 mL of dimethylformamide was added 71 mg (0.513 mmol) of triethylamine hydrochloride (Et3N—HCl), and 33 mg (0.513 mmol) of sodium azide and the resulting heterogeneous mixture was heated at reflux for 72 h, during which time 71 mg (0.513 mmol) of triethylamine hydrochloride (Et3N—HCl), and 33 mg (0.513 mmol) of sodium azide was added to the reaction mixture after every 24 h. The mixture was then cooled to rt, filtered and concentrated to a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 15 mg (38% yield) of 6-(4-benzyloxy-phenyl)-7-morpholin-4-yl-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidine (370) as a solid as indicated by 1H-NMR. (LC-MS calcd for C24H22N8O2 [M+H]+455.18; found 455.2.

Provenance & Evidence