Ethyl isothiocyanate → (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide

HRID 444703노트

반응식

HRID 444703 반응식
[Cl:1][C:2]1[C:7]([C:8]([NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:20]([N:22]=[C:23]=[S:24])[CH3:21]>CN(C)C=O>[Cl:1][C:2]1[C:7](/[C:8](/[NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[C:9](\[C:10]#[N:11])/[C:23](=[S:24])[NH:22][CH2:20][CH3:21])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 10966Ethyl isothiocyanateHCID 24758Sodium hydrideHCID 767595953-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile

생성물 1

HCID 58319378(2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide수율 29.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.15 g, 0.606 mmol, 1 eq.) in 2 ml of dimethyl formamide (DMF) was treated with NaH (60% in mineral oil, 0.029 g, 0.727 mmol, 1.2 eq.) and stirring allowed for 1 h. ethylisothiocyanate (0.105 g, 1.21 mmol, 2 eq.) was added and stirring continued overnight. The reaction was quenched with water and extracted with AcOEt. The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide (0.059 g, 27% yield) as a white solid.

후처리

  1. stirringstirring continued overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with AcOEt
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-56cba9f2574e463ea54be08f4a4fb597
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476197B2

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