Diisopropylethylamine → HCID 59463243, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxyaniline hydrochloride (34.5 mg, 0.146 mmol) in DCE (1 mL) was added a solution of DIPEA (0.0525 mL, 0.302 mmol) in DCE (0.5 mL) at rt. Upon cooling to −78° C., triphosgene (14.4 mg, 0.0487 mmol) in DCE (1.0 mL) was added and the reaction mixture was allowed to warm to rt and stir for 1 h. The reaction mixture was then heated at 60° C. for and 2 h. The solution was allowed to cool to rt and then cooled to −78° C. whereupon a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (35.0 mg, 0.146 mmol) in DMF (0.5 mL) was added. The reaction mixture was shaken at rt for 15 hours. The reaction was quenched with the addition of water (2 mL) and extracted with DCM. The organic solutions were combined, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give N-[2-(benzyloxy)phenyl]-5-(2-hydroxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (19.20 mg, 28.2%). LCMS: (FA) ES+ 465.6, ES-463.2.

Provenance & Evidence