Triethylamine → 5-chloro-N'-hydroxy-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridine-4-carboximidamide

Participants

Reaction Conditions

Reaction Steps

A solution of 5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (Example 138A (160 mg, 0.388 mmol)) in ethanol (4 mL) and water (0.33 mL) was treated with hydroxylamine hydrochloride (54.0 mg, 0.777 mmol) and triethylamine (0.271 mL, 1.942 mmol). The reaction vessel was sealed, and the reaction mixture was heated for 30 minutes at 80° C. Additional hydroxylamine hydrochloride (10.0 mg, 0.143 mmol) added, and the reaction heated for 1 hour at 80° C. The reaction was cooled, diluted with water, and extracted with dichloromethane. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 50 to 70% ethyl acetate in hexanes, to provide the title compound. MS ESI(+) m/z 445.4 [M+H]+.

Provenance & Evidence