Cesium carbonate → 5-Bromo-1-methyl-3-(5-methyl-1-(oxetan-3-yl)-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

HRID 1022191노트

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HRID 1022191 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.I[CH:18]1[CH2:21][O:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[N:13]([CH:18]3[CH2:21][O:20][CH2:19]3)[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 133566863-IodooxetaneHCID 580441425-Bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

생성물 1

HCID 866845625-Bromo-1-methyl-3-(5-methyl-1-(oxetan-3-yl)-1H-pyrazol-3-ylamino)pyridin-2(1H)-one수율 50%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of 5-bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one 115a (200 mg, 0.71 mmol), 3-iodooxetane (647 mg, 3.53 mmol), Cs2CO3 (1150 mg, 3.53 mmol), and acetonitrile (5 mL) was heated at 80° C. in a sealed tube overnight. The mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford the 312a as a yellow solid (120 mg, 50%). MS-ESI: [M+H]+ 339.1

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel column chromatography
  5. washeluting with 20:1 dichloromethane/methanol

출처 및 근거

ORD 기록
ord-3ba97a3b070c4749b65943544b9b816e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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