Water → {1-[4-(7-Amino-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid (1.20 g, 0.86 mmol) and 10% palladium on carbon (0.2 g) in MeOH (20 mL) in DMF (40 mL) and water (3.4 mL) was added triethylamine (0.38 mL, 2.73 mmol, 1.1 equiv) followed by diphenylphosphoryl azide (751 mg, 2.73 mmol, 1.1 equiv). The resulting mixture was stirred at room temperature 10 minutes, at 100° C. for 6 h, at room temperature for 12 h. To the resulting mixture was added triethylamine (0.38 mL, 2.73 mmol, 1.1 equiv) followed by diphenylphosphoryl azide (751 mg, 2.73 mmol, 1.1 equiv). The resulting mixture was heated at 100° C. for 12 h. The resulting mixture was separated between EtOAc (100 mL) and water (50 mL). The organic phase was dried (Na2SO4 anh) and concentrated under reduced pressure. The remaining material (1.4 g) was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 3.5 min., gradient to 90% CH2Cl2: 10% MeOH over 1 min.; 90% CH2Cl2: 10% MeOH for 5.5 min., gradient to 80% CH2Cl2: 20% MeOH over 6 min., 80% CH2Cl2: 20% MeOH for 10.2 min.) to give {1-[4-(7-amino-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (508 mg, 45%):

Provenance & Evidence