Benzaldehyde → HCID 22387800, compound

HRID 1699923Notes

Reaction equation

HRID 1699923 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.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:24]([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)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 240Benzaldehyde2×HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 22388007HCID 22388007, compound

Product 1

HCID 22387800HCID 22387800, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (100 mg) was dissolved in methanol (1 ml), and benzaldehyde (39 mg), zinc chloride (49 mg) and sodium cyanoborohydride (23 mg) were added. The mixture was stirred at room temperature for 2 hr and refluxed under heating for 15 min. Benzaldehyde (16 mg), zinc chloride (21 mg) and sodium cyanoborohydride (10 mg) were added and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added ice water, and then a saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure. Hexane was added to the residue and the precipitated pale-yellow crystals were washed, collected by filtration and dried under reduced pressure to give the objective compound (120 mg).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 15 min
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. additionHexane was added to the residue
  10. washthe precipitated pale-yellow crystals were washed
  11. filtrationcollected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-fdc9d497f1dd48319cc35e19fffc8436
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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