Acetic Anhydride → HCID 18923648, compound

HRID 1900010Notes

Reaction equation

HRID 1900010 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:25])[CH2:23][NH2:24])[CH3:21])[C:14]=3[Cl:26])[C:5]2=[N:4][C:3]=1[CH3:27].[C:28](OC(=O)C)(=[O:30])C>C(O)=O>[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:25])[CH2:23][NH:24][CH:28]=[O:30])[CH3:21])[C:14]=3[Cl:26])[C:5]2=[N:4][C:3]=1[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 10790603HCID 10790603, compound

Product 1

HCID 18923648HCID 18923648, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a suspension of 3-bromo-8-[2,6-dichloro-3-(N-glycyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (150 mg) in formic acid (1 ml) was added acetic anhydride (65 mg), and the mixture was stirred for 1.5 hours. Acetic anhydride (40 mg) was added thereto, and the mixture was stirred for 3 hours. The mixture was concentrated in vacuo, and a saturated aqueous solution of sodium bicarbonate was added thereto, and the mixture was extracted with methylene chloride three times. The organic layers 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=5:1, V/V) to give 3-bromo-8-[2,6-dichloro-3-[N-(formylglycyl)-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (102 mg).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additiona saturated aqueous solution of sodium bicarbonate was added
  4. extractionthe mixture was extracted with methylene chloride three times
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (methylene chloride:methanol=5:1, V/V)

Sources & evidence

ORD record
ord-94d08887570d40b0ad5535577559388f
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

Loading…