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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
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HRID 600347 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c3e673b044d42278900045a8ca9f7ab
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902194B2

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