Sodium hydride → HCID 59216441, compound

HRID 1644191Notes

Reaction equation

HRID 1644191 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[NH2:17][C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[CH:23]=1.[H-].[Na+]>CN(C)C=O>[Br:24][C:22]1[CH:23]=[C:18]([NH:17][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)=[O:9])=[CH:6][N:7]=2)[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 902040HCID 902040, compoundHCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 59216441HCID 59216441, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (6-Chloro-pyridin-3-yl)-(4-methyl-piperazin-1-yl)-methanone (2.00 g, 7.46 mmol) in 10 mL dimethylformamide was added 3-Amino-5-bromo-1-methyl-1H-pyridin-2-one (1.80 g, 8.95 mmol) and sodium hydride (537 mg, 22.4 mmol). After stirring for 18 hours, this was quenched with water. This was extracted with ethylacetate. The ethylacetate layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 0 to 5% methanol/dichloromethane) to yield 5-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one (900 mg, 1.94 mmol). MS (ESI) 406.0 (M+H)+.

Workup

  1. customthis was quenched with water
  2. extractionThis was extracted with ethylacetate
  3. dry with materialThe ethylacetate layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (gradient elution 0 to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a12265c1f6944105821abdb27f8557be
Source dataset
uspto-grants-2012_02
Patent number
US08124604B2

Reaction notes

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