Acrylamide → (2E)-3-[3-(4,4-dibutyl-7-fluoro-1-hydroxy-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]acrylamide

HRID 494492노트

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HRID 494492 반응식
[CH2:1]([C:5]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([OH:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][C:25](I)=[CH:26][C:20]=3[S:19](=[O:29])(=[O:28])[N:18]=2)[C:6]1=[O:30])[CH2:2][CH2:3][CH3:4].[C:35]([NH2:39])(=[O:38])[CH:36]=[CH2:37].C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([C:5]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([OH:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][C:25](/[CH:37]=[CH:36]/[C:35]([NH2:39])=[O:38])=[CH:26][C:20]=3[S:19](=[O:29])(=[O:28])[N:18]=2)[C:6]1=[O:30])[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 6579AcrylamideHCID 8471TriethylamineHCID 1364037811,1-Dibutyl-6-fluoro-4-hydroxy-3-(7-iodo-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)naphthalen-2(1h)-one

생성물 1

HCID 136375604(2E)-3-[3-(4,4-dibutyl-7-fluoro-1-hydroxy-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]acrylamide수율 56%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A solution of the compound of Example 20B (65 mg, 0.11 mmol), acrylamide (9 mg, 0.12 mmol), triethylamine (45 μL, 0.33 mmol), and palladium (II) acetate (1.2 mg, 0.005 mmol) in N,N-dimethylformamide (1.5 mL) in a resealable pressure tube was degassed by evacuation and purging with nitrogen. The pressure tube was sealed and warmed at 100° C. for 1 h. The solution was cooled and diluted with ethyl acetate and water. The mixture was acidified by addition of citric acid solution (1 M, 2 mL). The organic layer was extracted with water (2×) and with saturated NaCl solution. Drying (Na2SO4) and concentration in vacuo afforded a solid, which was purified by flash chromatography eluting with methanol in dichloromethane. These procedures afforded the title compound (33 mg, 56%) as a light amber solid.

후처리

  1. custompurging with nitrogen
  2. customThe pressure tube was sealed
  3. temperatureThe solution was cooled
  4. additiondiluted with ethyl acetate and water
  5. additionThe mixture was acidified by addition of citric acid solution (1 M, 2 mL)
  6. extractionThe organic layer was extracted with water (2×) and with saturated NaCl solution
  7. customDrying
  8. concentration(Na2SO4) and concentration in vacuo
  9. customafforded a solid, which
  10. customwas purified by flash chromatography
  11. washeluting with methanol in dichloromethane

출처 및 근거

ORD 기록
ord-8d1cff42620b4d1caadebb9956146272
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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