Acetyl chloride → HCID 178432614, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-cyano-5-(1-methylethyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (compound B in Example 29) (70 mg, 0.35 mmol) in ethanol (4 mL) were added potassium carbonate (23 mg, 1.7 mmol) and hydroxylamine hydrochloride (73 mg, 1 mmol) and the resulting mixture was refluxed. After 15 h, more hydroxylamine hydrochloride (2 equivalent) was added. After a total of 26 h, the mixture was cooled, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by silica gel flash column chromatography eluting with 5% methanol in chloroform to afford a solid which was dissolved in pyridine and treated with acetyl chloride (4 equivalent). The mixture was stirred at 120° C. for 7 h, cooled to RT, dissolved in ethyl acetate and washed with water, 1 N NaOH solution and 1N HCl. The organic layer was dried, concentrated and the residue was purified by silica gel column eluting with 5% methanol in chloroform to afford 5-(1-methylethyl)-6-(5-methyl-[1,2,4]oxadiazol-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4-ol (10 mg, 11% over two steps) as a white solid. LC/MS; (M+H)+=260.2.

Provenance & Evidence