Acetic Acid → HCID 22388031, compound

HRID 1072905Notes

Reaction equation

HRID 1072905 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C(O)(=O)C>ClCCCl>[C:24]([NH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 22388007HCID 22388007, compound

Product 1

HCID 22388031HCID 22388031, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (150 mg) was dissolved in 1,2-dichloroethane (1.5 ml), and acetic anhydride (148 mg) and acetic acid (87 mg) were added at room temperature. The mixture was refluxed under heating for 1 hr. The reaction mixture was concentrated under reduced pressure, and ice water, a saturated aqueous sodium hydrogencarbonate solution were successively added to the residue. The precipitated white crystals were collected by filtration, washed with water, and dried under reduced pressure to give the objective compound (139 mg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and ice water
  4. additiona saturated aqueous sodium hydrogencarbonate solution were successively added to the residue
  5. filtrationThe precipitated white crystals were collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-dc4be65e7f094f0a8a75152353939ee3
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…