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Potassium Carbonate → N-[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]methanesulfonamide

HRID 1063560
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인쇄 미리보기

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HRID 1063560 반응식
[NH:1]([C:8]1[N:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=[C:12](Cl)[N:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[NH:1]([C:8]1[N:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]2[N:11]=[C:12]([NH:34][S:31]([CH3:30])(=[O:33])=[O:32])[CH:13]=[C:14]([C:19]([F:22])([F:21])[F:20])[C:15]=2[C:16](=[O:18])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 219481692-anilino-7-chloro-1-phenyl-5-trifluoromethyl-1,8-naphthyridin-4(1H)-one

생성물 1

HCID 10162479N-[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]methanesulfonamide수율 4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide
용매

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온도
120 °C

실험 절차

To a solution of 2-anilino-7-chloro-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one (100 mg, 0.241 mmol) in DMSO (5 mL) was added methyl sulfonamide and K2CO3 (76.5 mg, 0.554 mmol). The reaction was stirred at 120° C. for 24 h. The reaction was then cooled to room temperature, quenched with water and extracted with Et2O. The organic layers were dried over MgSO4, and concentrated in vacuo. The crude residue was then passed through a plug of silica gel eluting with 1:1 Hex:EtOAc to 9:1 CH2Cl2:MeOH to afford N-[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]methanesulfonamide as a white solid (4.4 mg, 4%): LCMS RT: 2.45, MH+: 475.2.

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. customquenched with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-05b33cd311e14a899670f2944bd1d6ca
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06964971B2

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