6-Amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-(methyloxy)-3-pyridinecarboxamide → 6-Amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-oxo-1,2-dihydro-3-pyridinecarboxamide
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8]C)[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:27]>Cl>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:18][CH2:19]2)=[O:11])=[CH:4][C:3]=1[Cl:27]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-(methyloxy)-3-pyridinecarboxamide (109 mg, 0.28 mmol) in 10% methanolic hydrogen chloride (8 ml) was refluxed with stirring for 10 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was suspended in methanol/tetrahydrofuran (1:3, 50 ml) and potassium carbonate (ca. 50 mg) was added to the mixture. The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:3) to give 69 mg (66%) of the title compound as a white solid.
Workup
- customthe solvent was removed in vacuo
- additionpotassium carbonate (ca. 50 mg) was added to the mixture
- filtrationThe mixture was filtered through a pad of Celite
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:3)
Sources & evidence
- ORD record
- ord-0c6179d7e07c4cd28dc6cac3d341172c
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06979690B2
Reaction notes
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