1-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(1-isobutyl-4-piperidinyl)-1-propanone → 6-Amino-5-chloro-3-[3-(1-isobutyl-4-piperidinyl)propanoyl]-2(1H)-pyridinone

Participants

Reaction Steps

A mixture of 1-(6-amino-5-chloro-2-methoxy-3-pyridinyl)-3-(1-isobutyl-4-piperidinyl)-1-propanone (step 1 in example 15, 50 mg, 0.141 mmol) in 10% methanolic hydrochloric acid (1 ml) was refluxed for 4 h. To this mixture, concentrated hydrochloric acid (0.2 ml) was added and the mixture was refluxed for 4 h. After cooling to room temperature, the mixture was concentrated in vacuo, treated with SCX column gave brown oil. This oil was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.1:1:10) to give pale yellow solid, which was washed with ethyl acetate to afford 19.5 mg (40%) of the title compound as pale orange solids.

Provenance & Evidence