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m-Chloroperbenzoic acid → 4-(8-Methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 1010884
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HRID 1010884 반응식
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13](SC)[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13][N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 673147444-(8-Methylimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile

생성물 1

HCID 1317290024-(8-Methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

300 mg of the compound [1-6] was dissolved in 6 mL of chloroform, and 368 mg of m-chloroperbenzoic acid was added thereto under an ice-cold condition. After the 30 minutes stirring at the same temperature, to the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, then the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 3 mL of chloroform, poured onto 3 mL of a tetrahydrofuran solution containing 257 mg of S-(−)-1-(4-bromophenyl)ethylamine and 224 μL of triethylamine, and the mixture was stirred overnight at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1), to obtain 252 mg of 2-{[(1S)-1-(4-bromophenyl)ethyl]amino})-4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile [3-1] (hereinafter, referred to as the compound [3-1]) as a pale yellow oily product.

후처리

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 3 mL of chloroform
  6. additionpoured onto 3 mL of a tetrahydrofuran solution
  7. additioncontaining 257 mg of S-(−)-1-(4-bromophenyl)ethylamine and 224 μL of triethylamine
  8. stirringthe mixture was stirred overnight at room temperature
  9. additionTo the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate
  10. extractionthe mixture was extracted with chloroform
  11. washThe obtained organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationThe insolubles were filtered
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-e1822a146df94628b0137935254f39f1
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977336B2

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