Sodium Acetate → HCID 67624987, compound

HRID 1290220Notes

Reaction equation

HRID 1290220 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 s 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 s the solvent
  7. customwas removed in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-19e34b3d662548a78be858779aae0dc8
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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