Dichloromethane → HCID 86613775, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round-bottomed flask was added anhydrous DCM (25 mL, 383 mmol) and N-((S)-2-amino-3-(3-methoxy-4-(trifluoromethyl)phenyl)-propyl)-5-(isoquinolin-7-yl)thiazol-2-amine (0.040 g, 0.086 mmol). The suspension was stirred at −78° C. and treated drop wise via syringe with boron tribromide (0.082 mL, 0.86 mmol). The solution was stirred at −78° C. for 1 hour and warmed to −12° C. and stirred for 1 hour and then stirred for 3 hours at room temperature. The reaction was quenched with NaHCO3 and ether, and the separated aqueous layer was extracted with ether (3×50 mL). The combined organic layers were washed with saturated sodium chloride, dried over Na2SO4, and concentrated to give the crude residue which was purified with flash column chromatography ((5%→20% MeOH in DCM) to obtain the desired product as an off white solid of 5-((S)-2-amino-3-(5-(isoquinolin-7-yl)thiazol-2-ylamino)propyl)-2-(trifluoromethyl)phenol (0.018 g, 46% yield). m/z (%): 445.4 (100%, M++H).

Provenance & Evidence