Triethylamine → HCID 54529817, compound

Participants

Reaction Steps

134 mg (0.697 mmol, 1.0 equiv) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added in one portion to a room temperature solution of 180 mg (0.697 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid, 87.5 mg (0.697 mmol, 1.0 equiv) glycine methyl ester hydrochloride, 107 mg (0.697 mmol, 1.0 equiv) 1-hydroxybenzotriazole hydrate, and 194 μL (1.39 mmol, 2.0 equiv) triethylamine in 5 mL CH2Cl2. After 18 h, the reaction mixture was diluted with 150 mL ethyl acetate, washed 1×25 mL each 1N HCl, H2O, brine, and dried over Na2SO4. The crude product was purified on a silica gel column (40% ethyl acetate/hexanes, flash) to give 187 mg (66%) of a white waxy solid: mp 89-93° C.; Anal. calcd for C18H23N3O3; C, 65.63; H, 7.04; N, 12.76. Found: C, 65.74; H, 7.02; N, 12.74.

Provenance & Evidence