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(Methylsulfonyl)acetonitrile → 2-(methylsulfonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile

HRID 716058
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HRID 716058 반응식
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:33][S:34]([CH2:37][C:38]#[N:39])(=[O:36])=[O:35].C(O)(=O)C.N1CCCCC1>C(O)C>[CH3:33][S:34]([C:37](=[CH:21][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:13]2[N:14]=[C:15]3[C:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:8][N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:10]3=[N:11][CH:12]=2)=[CH:24][CH:23]=1)[C:38]#[N:39])(=[O:36])=[O:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 75283(Methylsulfonyl)acetonitrileHCID 9793820Piperidine, acetateHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

생성물 1

HCID 710144052-(methylsulfonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile수율 64%

시약·촉매·용매 1

HCID 702
Ethanol
용매
2회

실험 절차

To a 10 ml seal tube, 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde (0.1 g, 0.00022 mol) and 2-(methylsulfonyl)acetonitrile (0.105 g, 0.00088 mol) were taken in ethanol (5 ml). Piperidine acetate (3.3 M solution in water) (1.0 ml) was added dropwise at RT. After completion of the addition, reaction mixture was refluxed for 24 hr. After completion of the reaction, ethanol was distilled out to obtain crude product. The crude product was purified by column chromatography using 30% ethyl acetate in hexanes to yield 0.078 g of 2-(methylsulfonyl)-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylonitrile which was converted to the title compound as described above.

후처리

  1. customTo a 10 ml seal tube
  2. additionAfter completion of the addition, reaction mixture
  3. temperaturewas refluxed for 24 hr
  4. distillationwas distilled out
  5. customto obtain crude product
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-8c08021df77140a7849b74eb81e1735e
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187487B2

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