Triethylamine → 6-Benzylamino-2-methylimidazo[1,2-a]pyridine-3-acetonitrile

HRID 544468Notes

Reaction equation

HRID 544468 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[CH:24]([C:28](=O)[CH3:29])[CH2:25][C:26]#[N:27]>C(#N)C>[CH2:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:24]([CH2:25][C:26]#[N:27])=[C:28]([CH3:29])[N:1]=2)[CH:4]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139002363-Chloro-4-oxopentanenitrileHCID 204590262-Amino-5-benzylamino pyridine

Product 1

HCID 204590346-Benzylamino-2-methylimidazo[1,2-a]pyridine-3-acetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-amino-5-benzylamino pyridine (4.0 g), triethylamine (2.1 g),3-chloro-4-oxopentanenitrile (2.7 g) and acetonitrile (50 ml) is stirred and heated under reflux for 18 hr. The solvent is removed in vacuo, and the residue is dissolved in chloroform (200 ml). The solution is washed with water (4×100 ml), dried over anhydrous potassium carbonate and the chloroform is removed in vacuo. The residue is chromatographed on silica gel (200 g) using chloroform as the eluant. The product is obtainedand crystallized from acetonitrile.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hr
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue is dissolved in chloroform (200 ml)
  5. washThe solution is washed with water (4×100 ml)
  6. dry with materialdried over anhydrous potassium carbonate
  7. customthe chloroform is removed in vacuo
  8. customThe residue is chromatographed on silica gel (200 g)
  9. customThe product is obtainedand crystallized from acetonitrile

Sources & evidence

ORD record
ord-1acab7348d6b4a308be0540ea08a4a21
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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