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Diethyl Carbonate → 2-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-malonic acid diethyl ester

HRID 215993
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HRID 215993 반응식
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[N:11]=[C:10]2[S:12][CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:7]=1)[CH3:2].[C:30](=O)([O:34]CC)[O:31][CH2:32][CH3:33].[H-].[Na+]>C1COCC1.O>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([C:6]1[N:11]=[C:10]2[S:12][CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:7]=1)[C:30]([O:31][CH2:32][CH3:33])=[O:34])[CH3:2]
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반응물 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 68435332{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-acetic acid ethyl ester

생성물 1

HCID 684343652-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-malonic acid diethyl ester

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-acetic acid ethyl ester (180 mg, 0.45 mmol) was dissolved in dry THF (10 ml) under nitrogen. Diethyl Carbonate (0.27 ml, 2.23 mmol) was added and the mixture cooled to 0° C. Sodium Hydride (36 mg, 0.89 mmol) was added and the mixture stirred at 0° C. for a further 10 min, then at room temperature for 20 min, then brought to reflux for 45 min. On cooling, the reaction was diluted with water (100 ml) and extracted with DCM (3×50 ml), the extracts combined, dried over magnesium sulphate and concentrated. The residue was purified on silica, eluting (Ethyl Acetate/DCM), 0-20%) to give 2-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-malonic acid diethyl ester as a yellow solid. Yield=96 mg (45%).

후처리

  1. waitat room temperature for 20 min
  2. temperatureto reflux for 45 min
  3. temperatureOn cooling
  4. extractionextracted with DCM (3×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified on silica
  8. washeluting (Ethyl Acetate/DCM), 0-20%)

출처 및 근거

ORD 기록
ord-be379132baeb41daae63c7c2d3a121b5
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193215B2

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