Diethyl cyanophosphonate → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-(2-oxo-2-phenylethyl)acrylic acid amide

HRID 1009329노트

반응식

HRID 1009329 반응식
C(P(=O)(OCC)OCC)#N.[CH3:11][O:12][C:13]1[CH:14]=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=O)[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1.Cl.[NH2:31][CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34].O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15](/[CH:25]=[CH:26]/[C:27]([NH:31][CH2:32][C:33](=[O:34])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:29])[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1

참가 물질

8

반응물 4

HCID 76257Diethyl cyanophosphonateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 86585896Sodium bicarbonate water

생성물 1

HCID 67067346(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-(2-oxo-2-phenylethyl)acrylic acid amide수율 68.8%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Diethyl cyanophosphonate (0.12 mL) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (200 mg) and triethylamine (0.22 mL) in DMF (1 mL) at 0° C. The reaction solution was stirred at 0° C. for 30 minutes, and then α-aminoacetophenone hydrochloride (133 mg) was added in small portions to the reaction solution over 30 minutes. The reaction solution was stirred at 0° C. for 2.5 hours. Then, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 200 mg of the title compound. The property values of the compound are as follows.

후처리

  1. stirringThe reaction solution was stirred at 0° C. for 2.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

출처 및 근거

ORD 기록
ord-35c50774050e49f4ac8e4f5668db69ca
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

반응 노트

불러오는 중…