Acrylic Acid → 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1375689노트

반응식

HRID 1375689 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=O)=O.C(O)(=O)C=C.[CH:19]1[CH:20]=[CH:21][C:22]2[N:27](O)N=[N:25][C:23]=2[CH:24]=1.CCN=C=NCCCN(C)C.[O:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]1[O:46][NH2:47].CCN(C(C)C)C(C)C>CCO.CN(C=O)C.O>[NH:27]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:24][C:23]=2[N:25]=[C:1]1[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]([NH:47][O:46][CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][O:40]2)=[O:10])[CH:11]=[CH:12][CH:13]=1

참가 물질

10

반응물 6

HCID 6581Acrylic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 542035293-Formylcinnamic acid

생성물 1

HCID 724240283-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of the appropriate 3-formyl-cinnamic acid (3, 0.57 mmol) and the appropriate substituted-phenyl-1,2-diamine (0.57 mmol) in EtOH (5.0 mL) was refluxed for 24 hrs. The reaction was cooled, evaporated to dryness, and the resulting acrylic acid was used without further purification. To a solution of the acrylic acid (0.25 mmol) and HOBt (0.38 mmol) in DMF (5.0 mL) was added EDCI (0.38 mmol), O-(tetrahydro-pyran-2-yl)-hydroxylamine (0.38 mmol), and DIEA (0.75 mmol). The reaction was stirred at ambient temperature for 18 hrs. The resulting mixture was poured into H2O, extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated to dryness. The resulting material was purified via flash chromatography to yield the desired 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (11).

후처리

  1. temperatureThe reaction was cooled
  2. customevaporated to dryness
  3. customthe resulting acrylic acid was used without further purification
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe resulting material was purified via flash chromatography

출처 및 근거

ORD 기록
ord-8cde58567e614073b8279e1218da31a8
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169801B2

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