Ethoxyacetic acid → HCID 10010071, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 12 μL (13.2 mg, 0.127 mmol) of ethoxyacetic acid, 20.6 mg (0.127 mmol) of 1,1'-carbonyldiimidazole (CDI), and 1 mL of dry THF was stirred at 60° C. for 4 hours. To this solution was then added 40 mg (0.0635 mmol) of 2-(5-amino2-chlorophenyl)-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C) dissolved in THF, followed by 19 μL (19.3 mg, 0.127 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After being stirred overnight at 60° C., the reaction mixture was diluted with 5% citric acid (aqueous) and extracted 2× with ethyl acetate. The combined organic fractions were washed twice with water, then with brine, and dried over Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed on silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2), yielding 9 mg (20%) of the title compound as a white, glassy solid, mp 100°-102° C.; satisfactory purity by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 622 (M+Li)+.

Provenance & Evidence