Diisopropylethylamine → HCID 59632892, compound

Participants

Reaction Steps

To a solution of 1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-1H-pyrazole-3-carbonyl chloride (0.23 mmol crude from previous step) in CDCl3 (12 ml) was added N,N-diisopropylethylamine (150 μL, 0.86 mmol) and a small amount of DMAP. The resulting mixture was treated with methyl isonipecotate (62 μL, 0.46 mmol). After stirring for 3 hours at ambient temperature the reaction was quenched by dilution with H2O, and dilution with CH2Cl2. The layers were separated and the basic aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude product. This material was purified by flash column chromatography eluting with a gradient from 0% to 16% MeCN in CH2Cl2 to afford methyl 1-{[1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]carbonyl}piperidine-4-carboxylate (11 mg, 8% yield) as a white powder. MS(ES): 584 [M+H]+.

Provenance & Evidence