Hydrochloric Acid → HCID 136366033, compound

Participants

Reaction Steps

A mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone oxime (Example 39) (100 mg, 0.42 mmol) and sodium hydride (17 mg of 60% in mineral oil, 0.43 mmol) in N,N-dimethyl formamide (2 mL) was stirred under a nitrogen atmosphere for 0.5 h. A mixture of N-(2-chloroethyl)morpholine hydrochloride (80 mg, 0.43 mmol) and sodium hydride (17 mg of 60% in mineral oil, 0.43 mmol) in N,N-dimethylformamide was added and the reaction mixture was stirred at room temperature for 38 h. The reaction mixture was poured into stirring cold water (25 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated. Purification by Biotage chromatography (1 to 10% methanol in methylene chloride) produced an oil. The oil was dissolved in ethyl acetate (5 mL) and ethereal hydrogen chloride (0.45 mL of a 1 M solution in diethyl ether) was added. The reaction mixture was stirred for 1 h and the precipitate formed. The solvent was decanted and the solid was dried to give phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-[2-(4-morpholinyl)ethyl]oxime hydrochloride, a mixture of isomers, as a pale yellow solid: ESI MS m/z 351 [C20H22N4O2+H]+; HPLC (Method A) >99% (AUC), tR=13.3 and 13.7 min.

Provenance & Evidence