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3,4,5-Trifluoroaniline → Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[(3,4,5-trifluorophenyl)amino]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71204
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인쇄 미리보기

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HRID 71204 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].Cl[C:12]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][C:30]([CH3:32])=[N:29][CH:28]=4)=[C:23]([O:33][CH3:34])[CH:22]=3)=[N:19][N:20]=[C:13]12>C(=O)([O-])O.[Na+]>[CH3:34][O:33][C:23]1[CH:22]=[C:21]([C:18]2[N:14]3[CH2:15][CH2:16][CH2:17][C:12]([NH:5][C:4]4[CH:3]=[C:2]([F:1])[C:8]([F:9])=[C:7]([F:10])[CH:6]=4)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:13]3=[N:20][N:19]=2)[CH:26]=[CH:25][C:24]=1[C:27]1[O:31][C:30]([CH3:32])=[N:29][CH:28]=1
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참가 물질

4

반응물 2

HCID 27249913,4,5-TrifluoroanilineHCID 66604255Ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

생성물 1

HCID 66608898Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[(3,4,5-trifluorophenyl)amino]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 56.8%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate
용매

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온도
100 °C

실험 절차

To 3,4,5-trifluoroaniline (2.1 g) was added ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1 g) at room temperature, and the mixture was stirred at 100° C. overnight under a nitrogen atmosphere. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (719 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d9a02d6ad4d946b7846ae8d7abb40f30
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822699B2

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