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

A mixture of 1-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-(1-butyl-4-piperidinyl)-1-propanone (step 1 in example 10, 50 mg, 0.129 mmol) in 10% methanolic hydrochloric acid (2 ml) was refluxed for 1 h. The mixture was added concentrated hydrochloric acid (0.6 ml) and the resulting mixture was refluxed for 6 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate (150 ml) and tetrahydrofuran (150 ml), washed with 2 N aqueous sodium hydroxide (10 ml), water (20 ml) and brine (20 ml), and dried over potassium carbonate. Removal of solvent gave a pale red solid, which was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:10 ) to afford a pale yellow solid. The solid was washed with ethyl acetate to yield 5.5 mg (13%) of the title compound as a pale yellow solid.

1. temperaturewas refluxed for 1 h
2. temperaturethe resulting mixture was refluxed for 6 h
3. concentrationthe mixture was concentrated in vacuo
4. dissolutionThe residue was dissolved in a mixture of ethyl acetate (150 ml) and tetrahydrofuran (150 ml)
5. washwashed with 2 N aqueous sodium hydroxide (10 ml), water (20 ml) and brine (20 ml)
6. dry with materialdried over potassium carbonate
7. customRemoval of solvent
8. customgave a pale red solid, which
9. customwas chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:10 )
10. customto afford a pale yellow solid
11. washThe solid was washed with ethyl acetate

ORD record

ord-509ab9927f404ced9fbdfed71940e8ea

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06979690B2