Dimethyl Sulfoxide → 2-Cyanomethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

HRID 1369565Notes

Reaction equation

HRID 1369565 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])=[CH:9][CH:8]=[CH:7][N:6]2[C:21]=1[CH3:22].[C-:23]#[N:24].[K+].CS(C)=O.C(Cl)Cl>O>[C:23]([CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])=[CH:9][CH:8]=[CH:7][N:6]2[C:21]=1[CH3:22])#[N:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 226726282-Chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 226725662-Cyanomethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridineYield 34.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine (2.4 mmol) and potassium cyanide (2.4 mmol) were added to dimethyl sulfoxide (25 ml) and stirred for 2 h. at room temperature. Methylene chloride and water were added to the reaction mixture and the organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent. Crystallization from acetonitrile gave 0.25 g (34%) of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by by column chromatography on silica gel
  5. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-af9c32c019664967b67d89d0c3b9a219
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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