Water → HCID 53710506, compound

HRID 1290221Notes

Reaction equation

HRID 1290221 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:42])[CH2:23][NH:24][C:25](=[O:41])[CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][C:31]([NH:34][C:35]([O:37][CH2:38][CH2:39]Cl)=[O:36])=[CH:30][CH:29]=4)[CH3:21])[C:14]=3[Cl:43])[C:5]2=[N:4][C:3]=1[CH3:44].C[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:42])[CH2:23][NH:24][C:25](=[O:41])[CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH2:39][CH2:38][O:37][C:35]5=[O:36])=[CH:30][CH:29]=4)[CH3:21])[C:14]=3[Cl:43])[C:5]2=[N:4][C:3]=1[CH3:44]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 53702051HCID 53702051, compound

Product 1

HCID 53710506HCID 53710506, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-8-[2,6-dichloro-3-[N-[4-(2-chloroethoxycarbonylamino)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (128 mg) in methanol was added dropwise sodium methanolate (28% in methanol, 37 mg) under nitrogen in ice-water bath and the mixture was stirred for 1 hour at same temperature and then at ambient temperature for 2 hours. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography(ethyl acetate) to give 3-bromo-8-[2,6-dichloro-3-[N-[4-(2-oxo-3-oxazolidinyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (77 mg) as an amorphous powder.

Workup

  1. waitat ambient temperature for 2 hours
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography(ethyl acetate)

Sources & evidence

ORD record
ord-62efcb5cade245ac9e72bc5d074fe652
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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