Bromine → HCID 58948139, compound

HRID 639598Notes

Reaction equation

HRID 639598 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][C:9](=[O:18])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:5]=[C:4]([CH3:19])[N:3]=1.C([O-])(=O)C.[Na+].[Br:25]Br>C(O)(=O)C.O>[NH2:1][C:2]1[C:7]2[NH:8][C:9](=[O:18])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[C:5]([Br:25])=[C:4]([CH3:19])[N:3]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 49771644HCID 49771644, compound

Product 1

HCID 58948139HCID 58948139, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-Amino-1-benzyl-6-methyl-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (20 mg, 0.08 mmol) was suspended in 5 mL of acetic acid then sodium acetate (5 mg, 0.08 mmol) was added followed by bromine (4□L, 0.08 mmol) dropwise. The mixture was stirred at room temperature for 30 minutes. The mixture was diluted in water (50 mL) and extracted with ethyl acetate (50 mL), the organic layer was separated, dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel using 10% of methanol in ethyl acetate to give 15 mg of the title compound as a brown solid.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel using 10% of methanol in ethyl acetate

Sources & evidence

ORD record
ord-acd4433ea9484e6d9eaaa685d16247ed
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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