6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline → 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

HRID 1892429노트

반응식

HRID 1892429 반응식
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([CH2:15][C:16]3[C:17]([F:27])=[C:18]4[C:23](=[CH:24][C:25]=3[F:26])[N:22]=[CH:21][CH:20]=[CH:19]4)[N:13]=[N:14][C:9]2=[N:8][CH:7]=1)=[CH2:5])C>C(O)(=O)C.Cl>[F:27][C:17]1[C:16]([CH2:15][N:12]2[C:10]3=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][N:8]=[C:9]3[N:14]=[N:13]2)=[C:25]([F:26])[CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2

참가 물질

4

반응물 1

HCID 698109656-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline

생성물 1

HCID 698122851-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone수율 63%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

To a solution of the 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline (6.0 mg, 0.45 mmol) in acetic acid, 3N HCl (0.1 mL) was added. The solution stirred at it for 2 h. Solvents were removed under reduced pressure. The residue was diluted with water, treated with aqueous NaHCO3 solution, extracted with DCM. The organic layer was washed sequencially with NaHCO3 (aq.) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography with Hexane:ethyl acetate to give yellow solid 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (3.5 mg), yield 63%. LCMS (method B): [MH]+=340.9, tR=2.09 min.

후처리

  1. customSolvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. additiontreated with aqueous NaHCO3 solution
  4. extractionextracted with DCM
  5. washThe organic layer was washed sequencially with NaHCO3 (aq.) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography with Hexane

출처 및 근거

ORD 기록
ord-a30a141f727940fd8108134ddab94eab
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507676B2

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