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

HRID 1006669Notes

Reaction equation

HRID 1006669 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-6d5eab0e12094f599a0d133a72b63d0f
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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