Trifluoroacetic acid → HCID 58328161, compound

Participants

Reaction Steps

To a solution of 3-amino-N-cyclopropyl-4-methylbenzamide (0.025 g, 0.11 mmol) in anhydrous DMF (0.5 mL), are sequentially added 1-(ethoxycarbonyl)-1H-indole-6-carboxylic acid (0.026 g, 0.11 mmol, prepared according to a similar procedure outlined for step A, Example 128 in WO 2002/014308) triethylamine (61 μL, 0.44 mmol) and BOP (0.098 g, 0.22 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h, diluted with MeOH (0.5 mL) and subjected to reverse phase preparative HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The desired fractions were collected, and concentrated using speedVac® Plus (SC250DDA) to yield the title compound (Example 218, 0.010 g). HPLC Ret. time (YMC S5 Combiscreen ODS; 4.6×50 mm (4 min. gradient); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; solvent B=90% MeOH, 10% H2O, 0.2% H3PO4): 3.18 min. LCMS [M+H]+ 406.3.

Provenance & Evidence