Acetic Acid → HCID 22388070, compound

HRID 1072904Notes

Reaction equation

HRID 1072904 reaction equation
N[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=O.[C:26]([BH3-])#[N:27].[Na+].[C:30](O)(=O)C>C(#N)C>[Cl:23][C:4]1[CH:3]=[C:2]([N:27]([CH3:26])[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

6

Reactant 4

HCID 176Acetic AcidHCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 22388007HCID 22388007, compound

Product 1

HCID 22388070HCID 22388070, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (100 mg) was dissolved in acetonitrile (1 ml), and a 37% aqueous formaldehyde solution (0.123 ml) and sodium cyanoborohydride (29 mg) were added, and the mixture was stirred at room temperature for 1 hr. Then, a 37% aqueous formaldehyde solution (0.123 ml) and sodium cyanoborohydride (29 mg) were added, and acetic acid was added to neutralize the reaction mixture, which was followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and ice water was added to the residue. A saturated aqueous sodium hydrogencarbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed successively with an aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, dried and filtrated. The filtrate was concentrated under reduced pressure. Hexane was added to the residue and the precipitated pale-yellow crystals were washed, filtered, and dried under reduced pressure to give the objective compound (97 mg).

Workup

  1. stirringby stirring at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and ice water
  3. additionwas added to the residue
  4. additionA saturated aqueous sodium hydrogencarbonate solution was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed successively with an aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customdried
  9. filtrationfiltrated
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. additionHexane was added to the residue
  12. washthe precipitated pale-yellow crystals were washed
  13. filtrationfiltered
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-0cb4db2369c24947a2079fd7a35548b4
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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