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 402939Notes

Reaction equation

HRID 402939 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 59754722[4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanoneYield 69.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c6840eee566d4e19b0a32f6307d415b6
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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