Diisopropylethylamine → HCID 22709446, compound

Participants

Reaction Steps

In N,N-dimethylformamide (15 ml) were dissolved 1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-[3-(thien-2-yl)propyl]piperazine (257 mg), lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (129 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (131 mg) and 1-hydroxybenzotriazole hydrate (76.4 mg). Under ice cooling, diisoproylethylamine (180 μl) was added dropwise to the resulting solution, followed by stirring at room temperature for 15.5 hours. The reaction mixture was extracted with methylene chloride and water. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to column chromatography (2% methanol—methylene chloride) using as a carrier silica gel. After conversion into the corresponding hydrochloride by the addition of 1N aqueous hydrochloric acid in ethanol, methylene chloride-methanol-ether was added to solidify the hydrochloride. The resulting solid was purified again by subjecting it to thin-layer chromatography (10% methanol—methylene chloride), followed by the addition of 1N aqueous hydrochloric acid in ethanol to form the corresponding hydrochloride. Methylene chloride-methanol-ether was added to solidify the hydrochloride. The resulting solid was collected by filtration, washed with ether and then dried, whereby the title compound (62.6 mg) was obtained as colorless powder.

Provenance & Evidence