4-Methoxybenzylamine → N-[(4-Methoxyphenyl)methyl]-3-propyl-3H-imidazo[4,5-b]pyridine-2-methanamine

HRID 916886Notes

Reaction equation

HRID 916886 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH2:11]([N:14]1[C:18]2[N:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:23]Cl)[CH2:12][CH3:13]>C(#N)C>[CH2:11]([N:14]1[C:18]2[N:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:23][NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 224938472-(Chloromethyl)-3-propyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 22493843N-[(4-Methoxyphenyl)methyl]-3-propyl-3H-imidazo[4,5-b]pyridine-2-methanamineYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Methoxybenzylamine (3.8 g, 27 mmol) is dissolved in 20 mL dry acetonitrile. 1-propyl-2-chloromethyl-7-azabenzimidazole (173)(940 mg, 4.5 mmol) dissolved in 4.5 mL acetonitrile is added dropwise. The mixture is stirred 10 hours at room temperature. The solvent is removed in vacuo and the residue dissolved in 20 mL ethyl acetate. This solution is washed once with 20 mL 1 N NaOH, once with 20 mL water, once with 20 mL 5% HOAc in water, then once with 5 N NaOH. The organic phase was dried over MgSO4, filtered, then concentrated in vacuo. The product mixture is purified by flash chromatography eluting with ethyl acetate followed by 95/5/1 ethyl acetate/methanol/triethylamine to afford 850 mg of the 1-propyl-2-(4-methoxybenzylamino)methyl-7-azabenzimidazole (184).

Workup

  1. additionis added dropwise
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in 20 mL ethyl acetate
  4. washThis solution is washed once with 20 mL 1 N NaOH, once with 20 mL water, once with 20 mL 5% HOAc in water
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product mixture is purified by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-77a1918a6cdf44d1b28771289e8f34a0
Source dataset
uspto-grants-2007_09
Patent number
US07271270B2

Reaction notes

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