Triethylamine → 1-[3-[(N-Benzyl pyrrolidin-3-yl)carbamoyl]phenylcarbamoyl]-5-methylthio-6-trifluoromethyl indoline

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Reaction Steps

The carboxylic acid from Example 12 (0.5 g, 1.25 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.3 ml, 3.4 mmol) and DMF (catalytic). The solution was stirred for 1 hour and evaporated to dryness. The residue in dry THF (3 ml) was added to a stirred solution of triethylamine (0.3ml, 4 mmol) and 3-amino-N-benzyl pyrrolidine (0.79 g, 4.5 mmol) in dry THF (10 ml). Following 3 hours at room temperature the solution was partitioned (H2O/EtOAc). Drying and removal of solvent followed by rexst (EtOAc/60°-80° C. petrol) afforded the title compound (0.62 g, 89%) as a white powder. M.pt. 174°-175° C.

Provenance & Evidence