Diisopropylamine → HCID 11398881, compound

Participants

Reaction Steps

3-(4-Fluorophenylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)-ethylamino]propionic acid (146 mg) and 4-aminotetrahydrothiopyran-4-carbonitrile (104 mg) were weighed into a 4 mL vial fitted with a stir bar and cap and DMF (2 mL) was added to give a dark amber solution. Diisopropylamine (0.23 mL) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (271 mg) were added and the vial was flushed the vial with nitrogen and sealed with the cap. After 1 h, the reaction mixture was diluted with a 9:1 mixture of CH2Cl2:EtOAc (40 mL)) and washed with 1.0M aqueous KHSO4, water, a 1:1 H2O: saturated aqueous NaHCO3, and brine and dried over anhydrous MgSO4. After concentration, the residue was purified by flash chromatography on 20 cm3 silica gel using 9:1 CHCl3: EtOAc eluent to give the N-(4-cyanotetrahydrothiopyran-4-yl)-3-(4-fluorophenylmethanesulfonyl)-2(R)-(2,2,2-trifluoro-1(S)-4-fluorophenylethylamino)-propionamide (30 mg) as a beige solid.

Provenance & Evidence