Potassium Carbonate → 7-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101339

반응식

HRID 2101339 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:30])[N:15]([CH2:17][C:18]4[C:19]([CH3:29])=[N+:20]([O-])[C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:38].[K+].[K+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:30])[N:15]([CH2:17][C:18]4[C:19]([CH2:29][OH:38])=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 577993553-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

생성물 1

HCID 160048747-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 9845Trifluoroacetic anhydride용매

실험 절차

The title compound was also prepared as follows: A solution of 3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide (770 mg, 1.50 mmol) in trifluoroacetic anhydride (7 mL) and CH2Cl2 (7 mL) in a sealed tube was stirred at 50° C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was dissolved in methanol (14 mL), and 1.0 M aqueous K2CO3 solution (7 mL, 7 mmol) was added. The resulting mixture was stirred at room temperature for 30 min, then concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc (50 mL×2). The combined EtOAc extracts were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was purified using a silica gel cartridge (80 g) eluted with a gradient of ethyl acetate (50-100%) in hexanes to afford 660 mg (86%, 2 steps) of the title compound as a yellow foam. HPLC/MS: retention time=2.68 min, [M+H]+=512.1.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe crude product was dissolved in methanol (14 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc (50 mL×2)
  6. washThe combined EtOAc extracts were washed with saturated aqueous NaCl
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe product was purified
  11. washeluted with a gradient of ethyl acetate (50-100%) in hexanes

출처 및 근거

ORD 기록
ord-754c558a65054f8db6937ccb310854ac
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572808B2

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