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Sodium hydride → HCID 57677077, 화합물

HRID 491263
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HRID 491263 반응식
[Cl:1][C:2]1[C:10]2[C:9]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[C:21]([C:25]1[O:29]C(=O)[N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33](F)[N:32]=2)[N:26]=1)([CH3:24])([CH3:23])[CH3:22].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:9]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:33]4[N:32]=[C:31]([NH:27][NH:26][C:25](=[O:29])[C:21]([CH3:23])([CH3:22])[CH3:24])[CH:36]=[CH:35][CH:34]=4)=[CH:16][CH:15]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 67309598HCID 67309598, 화합물HCID 68856325HCID 68856325, 화합물

생성물 1

HCID 57677077HCID 57677077, 화합물수율 6.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}phenol (0.152 g, 0.5 mmol) and 5-(tert-butyl)-3-(6-fluoropyridin-2-yl)-3H-[1,3,4]oxadiazol-2-one (0.119 g, 0.5 mmol) in anhydrous DMF (4 mL) was added 60 percent sodium hydride in mineral oil (30 mg, 0.75 mmol) portionwise. The mixture was then stirred at 100° C. overnight. After cooling the reaction was quenched with methanol. The solvent was removed in vacuo and the residue was triturated in CH2Cl2 and water. The organic phase was separated, dried over anhydrous Na2SO4, filtered, concentrated, and purified on preparative HPLC to give the decarboxylated product as a brownish foam, 16 mg, 0.03 mmol, 6.5 percent yield.

후처리

  1. temperatureAfter cooling the reaction
  2. customwas quenched with methanol
  3. customThe solvent was removed in vacuo
  4. customthe residue was triturated in CH2Cl2
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on preparative HPLC

출처 및 근거

ORD 기록
ord-360676f7054c4803b2b5b0b227ab094f
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531482B2

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