Hydrochloric Acid → HCID 22387764, compound

HRID 2181034Notes

Reaction equation

HRID 2181034 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:24]=[C:23]([NH:25][CH3:26])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20].[CH:27](=O)[CH2:28][CH2:29][CH2:30]C.[C:33]([BH3-])#N.[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[Cl:3][C:4]1[CH:24]=[C:23]([N:25]([CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8063PentanalHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22485098HCID 22485098, compound

Product 1

HCID 22387764HCID 22387764, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-chloro-4-(methylamino)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate dihydrochloride (169 mg) was suspended in methanol (2 ml) and valeraldehyde (70 mg) and sodium cyanoborohydride (51 mg) were added. The mixture was stirred at room temperature for 4 hr. To the reaction mixture was added 1N hydrochloric acid and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to neutralize the solution and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform:methanol=100:1. The objective fraction was concentrated under reduced pressure to give methyl 3-(2-chloro-4-(methyl-(1-pentyl)amino)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (179 mg) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with chloroform
  7. concentrationThe objective fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-386e8294f89f474589ac4175f3a7af34
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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