Pentylamine → HCID 178446446, compound

Participants

Reaction Conditions

Reaction Steps

A solution of thiosemicarbazide (2.73 g, 30 mmol) in ethanol is treated with methyl iodate (1.96 mL, 31.5 mmol), heated at 60° C. for 1 h, cooled to room temperature, stored at −20° C. for 18 h and filtered. The filtercake is washed with cold ethanol and dried in vacuo. The thus-obtained S-methylisothiosemicarbazide hydrogen iodide (46.6 mg, 0.2 mmol) is dissolved in methanol, treated with pentylamine (24 μL, 0.22 mmol), heated at 60° C. for 2 h, cooled to room temperature and concentrated in vacuo. The resultant residue, 4-pentylaminoguanidine hydrogen iodide (0.2 mmol), is suspended in isopropanol, added to a suspension of 3-acetyl-N-(phenylsulfonyl) indole (59 mg, 0.2 mmol) in isopropanol and concentrated HCl (50 μL), heated at 80° C. for 4 h, cooled to room temperature and concentrated in vacuo to give a residue. This residue is purified by HPLC to give the title product, 17.9 mg (21% yield), identified by HPLC and mass spectral analyses, (M+H) 426; retention time 4.75 min.

Provenance & Evidence