Methanol → HCID 22388051, compound

HRID 1072929Notes

Reaction equation

HRID 1072929 reaction equation
C([O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[C:14]3=[N:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:18]=[C:13]3[N:12]=[C:11]2[CH3:23])=[C:7]([Cl:26])[CH:6]=1)(=O)C.CO.C(=O)([O-])O.[Na+]>O1CCOCC1.O>[Cl:26][C:7]1[CH:6]=[C:5]([OH:4])[CH:25]=[CH:24][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:18]=[C:13]2[N:12]=[C:11]1[CH3:23]

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium Bicarbonate2×HCID 22388333HCID 22388333, compound

Product 1

HCID 22388051HCID 22388051, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of methyl 3-(4-acetoxy-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (2.87 g), methanol (29 ml), 1,4-dioxane (29 ml) and water (2.9 ml) was added sodium hydrogencarbonate (968 mg), and the mixture was stirred at room temperature for 2.5 hr. 1,4-Dioxane (29 ml) was added to dissolve the insoluble matter, and the mixture was stirred for 2 hr. Sodium hydrogencarbonate (968 mg) was added and the mixture was stirred at room temperature for 2 days and at 60° C. for 3 hr and stood overnight. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous layer was again extracted with ethyl acetate. The organic layers were combined and concentrated to dryness under reduced pressure. The residue was pulverized in ether to give the objective compound (1.94 g) as a pale-yellow powder.

Workup

  1. dissolutionto dissolve the insoluble matter
  2. stirringthe mixture was stirred for 2 hr
  3. stirringthe mixture was stirred at room temperature for 2 days and at 60° C. for 3 hr
  4. waitstood overnight
  5. customThe reaction mixture was partitioned between ethyl acetate and water
  6. extractionthe aqueous layer was again extracted with ethyl acetate
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-28d1fd37cb2449398bee987008b27f4b
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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