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

反応式

HRID 2101339 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 9845Trifluoroacetic anhydride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-754c558a65054f8db6937ccb310854ac
出典データセット
uspto-grants-2009_08
特許番号
US07572808B2

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