Aniline → HCID 54373276, compound

Participants

Reaction Steps

46 μL (0.629 mmol, 1.3 equiv) thionyl chloride were added to room temperature solution of 125 mg (0.484 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid and 5 μL DMF in 5 mL anhydrous toluene. The reaction mixture was heated to reflux for 2 h, then cooled to room temperature, concentrated to dryness on a rotary evaporator, and dried at high vacuum, room temperature for several hours. The crude acid chloride was dissolved in 5 mL CH2Cl2 and added to a room temperature solution of 49 μL (0.532 mmol, 1.1 equiv) aniline and 67 μL (0.484 mmol, 1.0 equiv) triethylamine in 5 mL CH2Cl2. After 18 h at room temperature, the reaction mixture was diluted with 75 mL ethyl acetate, washed 1×15 mL each 1N HCl, H2O, brine, and dried over Na2SO4. Filtration, concentration of filtrate and drying gave 180 mg of an amber oil, which was purified on a silica gel column to give 160 mg of an off-white solid. Crystallization from ethyl acetate/hexanes gave 130 mg (81%) of a white crystalline solid: mp 146-147° C.; Anal. calcd for C21H23N3O: C, 75.65; H, 6.95; N, 12.60. Found: C, 75.65; H, 7.03; N, 12.55.

Provenance & Evidence