Diisopropylethylamine → HCID 89692898, compound

Participants

Reaction Steps

In a 40 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the 2-chloro-4-[4-(5-fluoro-2-methyl-phenyl)-piperazin-1-yl]-5-nitro-benzoic acid 16e (110.60 mg, 0.28 mmol) was taken up in clean, dry dichloromethane (3.00 ml, 46.52 mmol) and was allowed to stir at room temperature under nitrogen until all solids were in solution. To this was then added the HATU (128.10 mg, 0.34 mmol) followed by the N,N-diisopropylethylamine (0.15 ml, 0.86 mmol) and again the mixture was stirred until all solids were dissolved. The 1-(3-amino-propyl)-pyrrolidin-2-one 1e (59.90 mg, 0.42 mmol) was added to the reaction and the mixture stirred at room temperature overnight. The reaction was diluted with 10 ml of water and 10 ml of dichloromethane. The layers were separated and the product was extracted from the aqueous using dichloromethane (3×15 ml). The organic phases were washed with brine (1×25 ml) and dried over MgSO4. The solution was then filtered under vacuum and the collected solution was concentrated under reduced pressure. The resultant orange oil was purified using silica gel column chromatography, eluting a gradient of 100% dichloromethane to 10% MeOH in dichloromethane. The product, 2-chloro-4-[4-(5-fluoro-2-methyl-phenyl)-piperazin-1-yl]-5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide 16f (140.10 mg, 0.27 mmol), was isolated as a yellow solid and was carried forward without further purification. LCMS (m/e)=518 (M+H).

Provenance & Evidence