Piperidine → HCID 67319043, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-(chloromethyl)-N-[6-(6-fluoro-1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.088 mmol) in acetonitrile (2 ml) was added piperidine (0.02 ml, 0.18 mmol) and the mixture was heated to 80° C. for 2 hours. Further piperidine (0.02 ml, 0.18 mmol) was added and heating was continued at 80° C. for 30 mins. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in MeOH and 2M aqueous NaOH (5 ml, 1:1, v.v) and stirred at room temperature for 1 hour, then neutralised with 2M aqueous HCl to ˜pH=5 and extracted with DCM (3×5 ml). The extracts were combined and the solvent removed under a stream of nitrogen. The residue was taken up again in MeOH and 2M aqueous NaOH (5 ml, 1:1, v/v) and stirred at room temperature for 3 hours. The mixture was neutralised with 2M aqueous HCl to ˜pH=7 and the MeOH was blown off under a stream of nitrogen. A precipitate was observed which was collected by filtration, then dissolved in 1 ml DMSO/MeOH (1:1) and purified by MDAP (Method B). The product-containing fractions were blown down under a stream of nitrogen to give a clear oil which was dissolved in dioxane/water (2 ml, 1:1, v/v) and freeze dried to give the title compound as a white solid (10 mg).

Provenance & Evidence