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
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8]C)[C:5]([C:10](=[O:23])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:24]>Cl>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:10](=[O:23])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:24]Participants
3
Procedure
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.
Workup
- temperaturewas refluxed for 4 h
- temperaturethe mixture was refluxed for 4 h
- concentrationthe mixture was concentrated in vacuo
- additiontreated with SCX column
- customgave brown oil
- customThis oil was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.1:1:10)
- customto give pale yellow solid, which
- washwas washed with ethyl acetate
Sources & evidence
- ORD record
- ord-a9d152923ed6494db68851d14c89efce
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06979690B2
Reaction notes
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