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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
ノート
印刷プレビュー

反応式

HRID 716058 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c08021df77140a7849b74eb81e1735e
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187487B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート