Diethyl cyanophosphonate → HCID 67067457, 화합물

HRID 1009360노트

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HRID 1009360 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](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][C:33](=[O:42])[CH2:32][NH:31][C:27](=[O:29])/[CH:26]=[CH:25]/[C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)=[CH:40][CH:39]=1

참가 물질

8

반응물 4

HCID 76257Diethyl cyanophosphonateHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 86585896Sodium bicarbonate water

생성물 1

HCID 67067457HCID 67067457, 화합물수율 13.6%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

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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 (0.54 mL) in DMF (2 mL), and the reaction solution was stirred at 0° C. for 30 minutes. A solution of 1-amino-3-(4-fluorophenyl)propan-2-one hydrochloride (CAS#93102-98-8, 158 mg) in DMF (1 mL) was added dropwise to the reaction solution over 20 minutes, and the reaction solution was stirred at 0° C. for 1.5 hours. 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 43 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 1.5 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-0b07587a414b4009a2e894cbbe13a35f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

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