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Sodium hydride → 5-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one

HRID 600347
Notes
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Reaction equation

HRID 600347 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 9020401-(6-Chloropyridine-3-carbonyl)-4-methylpiperazineHCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 592164415-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-oneYield 26%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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-7c3e673b044d42278900045a8ca9f7ab
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902194B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes