HCID 22672590, compound → HCID 22672573, compound

HRID 1369570Notes

Reaction equation

HRID 1369570 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)#[N:2].[H][H]>N.[Ni]>[NH2:2][CH2:1][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 22672590HCID 22672590, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22672573HCID 22672573, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To a solution of 8-(2-cyano-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.42 g, 1.44 mmol) in ammonia saturated ethanol/methanol (10/2.5)(30 ml) was added Raney nickel (50% in water)(0.45 g) The mixture was hydrogenated at room temperature and atmospheric pressure until the uptake of hydrogen ceased. Following filtration through celite, the solvents were evaporated under reduced pressure and the residue was purified by by column chromatography on silica gel using methylene chloride:methanol (10:2) as eluent. Recrystallization from methylene chloride/ diethyl ether gave 0.052 g (12%) of the desired product.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationfiltration through celite
  3. customthe solvents were evaporated under reduced pressure
  4. customthe residue was purified by by column chromatography on silica gel
  5. customRecrystallization from methylene chloride/ diethyl ether

Sources & evidence

ORD record
ord-eaa705aac6ad4f319e0fb78d425d6490
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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