HCID 67365110, compound → HCID 67364087, compound

HRID 245687Notes

Reaction equation

HRID 245687 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12>Cl>[NH:14]1[CH2:15][CH:12]([C:4]2[N:5]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]3=[C:2]([Br:1])[N:3]=2)[CH2:13]1

Participants

3

Reactant 1

HCID 67365110HCID 67365110, compound

Product 1

HCID 67364087HCID 67364087, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Benzyl 3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)azetidine-1-carboxylate (1.58 g) was dissolved in 37% hydrochloric acid (14.84 ml) and stirred at room temperature. After one hour the reaction mixture was concentrated in vacuo and coevaporated with toluene. Then the residue was dissolved in dichloromethane/methanol, 15 gram of Silica-carbonate (0.77 mmol/gram) was added and the suspension was stirred for 15 minutes. The suspension was filtered, the solids rinsed with methanol and the filtrate was concentrated in vacuo to give crude 3-(azetidin-3-yl)-1-bromo-8-methylimidazo[1,5-a]pyrazine (1.1 g).

Workup

  1. concentrationAfter one hour the reaction mixture was concentrated in vacuo
  2. dissolutionThen the residue was dissolved in dichloromethane/methanol
  3. addition15 gram of Silica-carbonate (0.77 mmol/gram) was added
  4. stirringthe suspension was stirred for 15 minutes
  5. filtrationThe suspension was filtered
  6. washthe solids rinsed with methanol
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1616f826527d480290a5478276339e2f
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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