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Ethyl isocyanate → (E)-3-[6-(3-Ethylureido)pyridin-3-yl]-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide

HRID 2112713
ノート
印刷プレビュー

反応式

HRID 2112713 の反応式
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:29])[CH2:18][C:19]2[N:20]([CH3:28])[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:29])[CH2:18][C:19]2[N:20]([CH3:28])[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=[CH:9][CH:8]=1)[CH3:2]
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 8022Ethyl isocyanateHCID 8471TriethylamineHCID 52877203-(6-Aminopyridin-3-Yl)-N-Methyl-N-((1-Methyl-1h-Indol-2-Yl)Methyl)Acrylamide

生成物 1

HCID 9930369(E)-3-[6-(3-Ethylureido)pyridin-3-yl]-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide収率 24.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ethyl isocyanate (0.13 mL, 1.68 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (0.27 g, 0.84 mmole) and triethylamine (0.29 mL, 2.1 mmole) in DMF (30 mL) at RT. The reaction was stirred for 6 days, then was concentrated in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. Flash chromatography on silica gel (ethyl acetate) gave the title compound (80 mg, 24%) as a light yellow solid: MS (ES) m/e 392 (M+H)+.

後処理

  1. concentrationwas concentrated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5c864b83aea645799adefb71ac9d5018
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07524843B2

反応ノート

読み込み中…

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