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Sodium Bicarbonate → 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

HRID 716031
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HRID 716031 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[C:12]3[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][CH:7]=3)[N:11]=2)[N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:17]=1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 710153161-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde수율 73.6%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
5 °C

실험 절차

To a 100 ml three necked round bottom flask 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (2.3 g, 0.0051 mole) was taken in CH2Cl2 (25 ml). The reaction mixture was cooled to 5° C. and PCC (4.84 g, 0.0225 mole) was added at the same temperature under nitrogen atmosphere. The reaction mixture was warmed up to RT and then stirred for 2 hr. After completion of the reaction, the reaction mixture was poured into saturated NaHCO3 solution (50 ml) under stifling at 10° C. and the aq. layer was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting the compound with 15-20% ethyl acetate in hexanes to yield 1.7 g of 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde.

후처리

  1. temperatureThe reaction mixture was warmed up to RT
  2. customAfter completion of the reaction
  3. customunder stifling at 10° C.
  4. extractionthe aq. layer was extracted with CH2Cl2
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product which
  9. customwas purified
  10. customcolumn purification
  11. washby eluting the compound with 15-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-71dd95b6ac124c208aec7eb40bc311c2
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187487B2

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