Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → [4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone

HRID 402939

Reaktionsgleichung

Reaktionsgleichung von HRID 402939
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CC(O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[O:20])=[CH:17][CH:18]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5778154-(Morpholine-4-carbonyl)anilineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Produkt 1

HCID 59754722[4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanoneAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (500 mg, 1.8 mmol), (4-aminophenyl)(morpholino)-methanone (408 mg, 1.98 mmol) and CSA (356 mg, 1.53 mmol) in iPrOH (30 mL) was stirred at 90° C. overnight. The solvent was evaporated. The residue was dissolved in DCM (30 mL). A NaHCO3 solution (10 mL) was added to adjust to pH=8. The organic layer was separated and dried over Na2SO4. The drying agent was removed by filtration and the resultant solution was concentrated in vacuo. The residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1) to give the desired product as a yellow solid (500 mg, 69% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in DCM (30 mL)
  3. additionA NaHCO3 solution (10 mL) was added
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customThe drying agent was removed by filtration
  7. concentrationthe resultant solution was concentrated in vacuo
  8. customThe residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c6840eee566d4e19b0a32f6307d415b6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742098B2

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