Ethyl Acetate → Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate

HRID 1181318

반응식

HRID 1181318 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:20]1(/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1.C1C=CC2C(=NO[N+]=2[O-])C=1.C(OCC)(=O)C>CO.C(#N)C>[CH:14]1([N:13]2[C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=3[N:1]=[C:26]2[C:23]2[CH:24]=[CH:25][C:20](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 68075BenzofuroxanHCID 4068248Ferrostatin-1HCID 53758764-Formyl-trans-stilbene

생성물 1

HCID 10114855Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate수율 63%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

Ethyl 3-amino-4-cyclohexylaminobenzoate (500 mg) obtained in Example 1, Step 3, was dissolved in methyl alcohol (6 ml) and trans-4-stilbenecarbaldehyde (397 mg) was added under ice-cooling. The mixture was stirred overnight at room temperature. The reaction mixture was ice-cooled and benzofuroxan (259 mg) dissolved in acetonitrile (2 ml) was added. The mixture was stirred for 7 hr at 50° C., The reaction mixture was ice-cooled. After 1N sodium-hydroxide was added, ethyl acetate was added and the mixture was extracted. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to give the title compound (540 mg, yield 63%).

후처리

  1. temperaturecooling
  2. temperaturecooled
  3. additionwas added
  4. stirringThe mixture was stirred for 7 hr at 50° C.
  5. temperaturecooled
  6. additionAfter 1N sodium-hydroxide was added
  7. extractionthe mixture was extracted
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-4fab5b69516e43e587c8bb1a1e14fa77
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285551B2

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