Triethylamine → HCID 15547425, compound

Participants

Reaction Steps

140 mg (0.728 mmol, 1.1 equiv) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added in one portion to a room temperature solution of 250 mg (0.662 mmol, 1.0 equiv) 4-[(1-cyclopentyl-3-ethyl-1H-indazole-6-carbonyl)-amino]-benzoic acid, 106 mg (0.662 mmol, 1.0 equiv) O-benzylhydroxylamine hydrochloride, 101 mg (0.662 mmol, 1.0 equiv) 1-hydroxybenzotriazole hydrate, and 194 μL (1.39 mmol, 2.1 equiv) triethylamine in 25 mL CH2Cl2. After 18 hours, 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 (2% CH3OH/CH2Cl2, flash) to give 212 mg (66%) of white crystalline solid: mp 194-198° C.; Anal. calcd for C28H30N4O3: C, 72.17; H, 7.10; N, 11.61. Found: C, 71.62; H, 6.47; N, 11.85.

Provenance & Evidence