Isothiocyanatotrimethylsilane → HCID 86684679, 화합물

HRID 75541

반응식

HRID 75541 반응식
[CH3:1][O:2][C:3]1[C:8](/[C:9](/[NH:16][CH2:17][CH2:18][OH:19])=[CH:10]/[C:11]([O:13]CC)=O)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1.C[Si]([N:26]=[C:27]=[S:28])(C)C>CC1OCCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]([C:9]2[N:16]([CH2:17][CH2:18][OH:19])[C:27](=[S:28])[NH:26][C:11](=[O:13])[CH:10]=2)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1

참가 물질

5

반응물 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 86684678HCID 86684678, 화합물

생성물 1

HCID 86684679HCID 86684679, 화합물수율 16%

시약·촉매·용매 2

HCID 73012-Methyltetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of (Z)-ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate (100 mg, 0.34 mmol) in 2-MeTHF (1.0 mL) was added (trimethylsilyl)isothiocyanate (0.30 mL, 2.0 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The cooled reaction mixture was diluted with EtOAc and washed with a saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was concentrated in vacuo. The residue was triturated with MeOH and the resulting solids were collected by vacuum filtration to give the title compound (16 mg, 16%) as a white solid.

후처리

  1. customThe cooled reaction mixture
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe residue was triturated with MeOH
  6. filtrationthe resulting solids were collected by vacuum filtration

출처 및 근거

ORD 기록
ord-57d982c63b564ccf8f14e28d8af23c19
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835449B2

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