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

HRID 402942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402942
[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.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CC(O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([CH:16]3[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]3)=[CH:20][CH:21]=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 150258436,8-Dibromoimidazo[1,2-a]pyrazineHCID 219595294-(1-Methylpiperidin-4-yl)aniline

Produkt 1

HCID 86686841(6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-methyl-piperidin-4-yl)-phenyl]-amineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (500 mg, 1.8 mmol), 4-(1-methylpiperidin-4-yl)benzenamine (376 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), NaHCO3 solution (10 mL) was added to adjust pH=8. The organic layer was dried over Na2SO4 and evaporated. The residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1) to afford the desired product as a yellow solid (400 mg, 58% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in DCM (30 mL)
  3. additionNaHCO3 solution (10 mL) was added
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-01965b3274434ea4b74cf8545607539d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742098B2

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