Ammonium trifluoroacetate → 3-Cyclopropyl-5-pyridin-3-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester

HRID 545341노트

반응식

HRID 545341 반응식
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([N:14]([CH:28]1[CH2:30][CH2:29]1)[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)[C:6](=O)[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].FC(F)(F)C([O-])=O.[NH4+:39]>CCO>[CH2:1]([O:3][C:4]([C:5]1[N:14]([CH:28]2[CH2:30][CH2:29]2)[C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)=[N:39][C:6]=1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:31])[CH3:2]

참가 물질

4

반응물 2

HCID 2724268Ammonium trifluoroacetateHCID 671330912-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-3-pyridin-3-yl-propionic acid ethyl ester

생성물 1

HCID 671331703-Cyclopropyl-5-pyridin-3-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester수율 80%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
110 °C

실험 절차

To 1.2 g (3 mmol) of 2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-3-pyridin-3-yl-propionic acid ethyl ester in 10 ml of EtOH was added 1.4 g (11 mmol) of ammonium trifluoroacetate. The EtOH was evaporated and the residue heated to 110° C. for 4 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1] afforded 0.9 g (80%) of the title compound as a colorless solid. MS: 418.2 (MH+).

후처리

  1. customThe EtOH was evaporated
  2. customThe cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1]

출처 및 근거

ORD 기록
ord-b0a82083842f42729063092905c2c2fd
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

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