Sodium Acetate → HCID 67624987, compound

HRID 1900035Notes

Reaction equation

HRID 1900035 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:43])[CH2:23][NH:24][C:25](=[O:42])[CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=O)=[CH:30][CH:29]=4)[CH3:21])[C:14]=3[Cl:44])[C:5]2=[N:4][C:3]=1[CH3:45].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[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:43])[CH2:23][NH:24][C:25](=[O:42])[CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:38](=[O:40])[CH2:37][CH2:36][C:35]5=[O:41])=[CH:30][CH:29]=4)[CH3:21])[C:14]=3[Cl:44])[C:5]2=[N:4][C:3]=1[CH3:45]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 54095300HCID 54095300, compound

Product 1

HCID 67624987HCID 67624987, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 3-bromo-8-[3-[N-[4-(3-carboxypropionamido)cinnamoylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (110 mg) and anhydrous sodium acetate (16 mg) in acetic anhydride (1.1 ml) was refluxed for 5 hours. After cooling, the solvent was removed in vacuo. The residue was dissolved in dichloromethane (5 ml) and washed with water, saturated sodium bicarbonate twice and brine. After dried over magnesium sulfate, the solvent was removed in vacuo. The residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol) to give 3-bromo-8-[2,6-dichloro-3-[N-[4-(succinimido)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (12 mg) as amorphous.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (5 ml)
  5. washwashed with water, saturated sodium bicarbonate twice
  6. dry with materialAfter dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-e4bf91338e85449a8186a6e536d496bf
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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