Water → 6-Amino-N-[(1-butyl-4-piperidinyl)methyl]-5-chloro-1-methyl-2-oxo-1,2-dihydro-3-pyridinecarboxamide

HRID 489788Notes

Reaction equation

HRID 489788 reaction equation
Cl.Cl.[NH2:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:16]2)=[O:12])=[CH:6][C:5]=1[Cl:25].[H-].[Na+].I[CH3:29].O>CN(C)C=O>[NH2:3][C:4]1[N:9]([CH3:29])[C:8](=[O:10])[C:7]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:16]2)=[O:12])=[CH:6][C:5]=1[Cl:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22262588HCID 22262588, compound

Product 1

HCID 222626216-Amino-N-[(1-butyl-4-piperidinyl)methyl]-5-chloro-1-methyl-2-oxo-1,2-dihydro-3-pyridinecarboxamideYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-amino-N-[(1-butyl-4-piperidinyl)methyl]-5-chloro-2-oxo-1,2-dihydro-3-pyridinecarboxamide dihydrochloride (step 2 in example 3, 80 mg, 0.19 mmol) in N,N-dimethylformamide (3 ml), sodium hydride (60% dispersion in mineral oil, 39 mg, 0.97 mmol) was added at 0° C. and the mixture was stirred for 15 min at room temperature. The mixture was cooled to 0° C. and iodomethane (1.0 M in N,N-dimethylformamide, 0.19 ml, 0.19 mmol) was added. After stirring for 18 h at room temperature, the mixture was poured into water, extracted with ethyl acetate (50 ml×2), washed with water (50 ml) and brine (50 ml) and dried over magnesium sulfate. Removal of solvent gave pale yellow oil, which was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:12) to give 4 mg (6%) of the title compound as a white solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringAfter stirring for 18 h at room temperature
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washwashed with water (50 ml) and brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent
  7. customgave pale yellow oil, which
  8. customwas chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:12)

Sources & evidence

ORD record
ord-a9da5968560f4d3d9c757b0582f123a0
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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