Propylamine → 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-N-propyl-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427481Notes

Reaction equation

HRID 427481 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21](OCC)=[O:22])=[CH:6][N:5]2[C:26]=1[CH3:27].[CH2:28]([NH2:31])[CH2:29][CH3:30].[C-]#N.[Na+]>CO>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([NH:31][CH2:28][CH2:29][CH3:30])=[O:22])=[CH:6][N:5]2[C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 7852Propylamine2×HCID 8929Sodium CyanideHCID 11003040Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 98211372,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-N-propyl-imidazo[1,2-a]pyridine-6-carboxamideYield 42.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate (0.12 g, 0.33 mmol), propylamine (1.0 g, 17 mmol) and a cat. amount of sodium cyanide were refluxed in methanol (20 ml) for 24 h. An additional amount of propylamine (1.0 g, 17 mmol) was added and the reaction mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dietyl ether as eluent. Crystallization from diethyl ether gave 0.053 g (42%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-a37006e9a6c04d5e9e06e7dcda61209c
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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