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

HRID 130586ノート

反応式

HRID 130586 の反応式
[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

参加物

10

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-70a8c43909ae4209b4fa101ca0b68437
出典データセット
uspto-grants-2008_06
特許番号
US07381825B2

反応ノート

読み込み中…