N,N-Dimethylglycine → [8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methyl 2-(dimethylamino)acetate

HRID 1166165Notes

Reaction equation

HRID 1166165 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15]Cl)[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[CH3:23][N:24]([CH3:29])[CH2:25][C:26]([OH:28])=[O:27]>C(#N)C>[CH3:23][N:24]([CH3:29])[CH2:25][C:26]([O:28][CH2:15][C:13]1[N:14]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:2]([CH3:1])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:22])=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:17])=[O:27]

Participants

4

Reactant 2

HCID 673N,N-DimethylglycineHCID 226726282-Chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 9842858[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methyl 2-(dimethylamino)acetateYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-(2,6-dimethylbenzylamino)-2-chloromethyl-3-methylimidazo[1,2-a]pyridine (0.3 g, 1.0 mmol) and N,N-dimethylglycine (0.1 g, 1.0 mmol) were added to acetonitrile (10 ml) and the mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using, dichloromethane:methanol (10:2) as eluent. Recrystallization from acetonitrile gave 0.12 g (32%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel using, dichloromethane:methanol (10:2) as eluent
  4. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-17c27c25c0b84284a21df35d75e9c12e
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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