Water → HCID 44211736, compound

HRID 1900004Notes

Reaction equation

HRID 1900004 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([C:22](=[O:33])[CH2:23][NH:24][C:25](=[O:32])[CH2:26][O:27]S(C)(=O)=O)[CH3:21])[C:14]=3[Cl:34])[C:5]2=[N:4][C:3]=1[CH3:35].[CH3:36][O-].[Na+].O>CO>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([C:22](=[O:33])[CH2:23][NH:24][C:25](=[O:32])[CH2:26][O:27][CH3:36])[CH3:21])[C:14]=3[Cl:34])[C:5]2=[N:4][C:3]=1[CH3:35]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium Methoxide2×HCID 18923573HCID 18923573, compound

Product 1

HCID 44211736HCID 44211736, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-8-[2,6-dichloro-3-[N-(N-mesyloxyacetylglycyl)-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (100 mg) in methanol (2 ml) was added sodium methoxide (317 mg), and the mixture was stirred for 1 hour. Sodium methoxide (200 mg) was added thereto, and the mixture was stirred for 3 hours. To the reaction mixture was added water, and the mixture was extracted with methylene chloride 3 times. The extracts were combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (methylene chloride:methanol =10:1, V/V) to give 3-bromo-8-[2,6-dichloro-3-[N-(methoxyacetylglycyl)-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (60 mg).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. extractionthe mixture was extracted with methylene chloride 3 times
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (methylene chloride:methanol =10:1, V/V)

Sources & evidence

ORD record
ord-8c13932d148c406c8e7be6d6a7ec5f84
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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