Diisopropylethylamine → HCID 178459258, compound

Participants

Reaction Conditions

Reaction Steps

Hunig's base (0.01 mL, 0.06 mmol) was added to a solution of 5-methyl-4-(methylsulfonyl)-2-({1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}amino)phenol (D89, 14 mg, 0.03 mmol) in DCM (3 mL) at rt under Ar. The reaction was cooled to 0° C. and the triphosgene (5 mg, 0.02 mmol) was added. The mixture was stirred for 2 h at 0° C. The reaction was quenched with sat. NaHCO3 (5 mL) and partitioned between DCM and H2O. The aqueous layer was extracted with DCM (2×) and the combined organics were dried (Na2SO4) and concentrated by rotary evaporation to give a yellow oil, which was purified via flash column chromatography (silica, DCM to 0.5% NH3/9.5% MeOH/90% DCM) to give the free base of the title compound as a pale yellow oil. HCl (0.1 mL, 0.1 mmol, 1 M in Et2O) was added to a solution of the free base in DCM (0.5 mL) and the solvent was removed by rotary evaporation. The resulting solid was triturated with Et2O to give 6-methyl-5-(methylsulfonyl)-3-{1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-benzoxazol-2(3H)-one hydrochloride (E31; 11 mg, 62%) as a cream solid.

Provenance & Evidence