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Cyclohexene → 2,3-Dimethyl-8-(2-(2-hydroxyethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427495
Notes
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Reaction equation

HRID 427495 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][CH2:20][O:21]CC3C=CC=CC=3)=[CH:8][C:7]([C:29]([NH2:31])=[O:30])=[CH:6][N:5]2[C:32]=1[CH3:33].C1CCCCC=1>[OH-].[OH-].[Pd+2].C(O)C>[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][CH2:20][OH:21])=[CH:8][C:7]([C:29]([NH2:31])=[O:30])=[CH:6][N:5]2[C:32]=1[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8079Cyclohexene2×HCID 121489202,3-Dimethyl-8-(2-(2-(benzyloxy)ethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 97985982,3-Dimethyl-8-(2-(2-hydroxyethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×
HCID 702
Ethanol
Solvent

Procedure

2,3-dimethyl-8-(2-(2-(benzyloxy)ethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide (0.13 g, 0.29 mmol), cyclohexene (1 ml), Pd(OH)2 cat. (25 mg) were added to ethanol (5 ml) and the mixture was refluxed overnight. An additional amount of cyclohexene (1 ml) and Pd(OH)2 cat. (25 mg) were added and the mixture was refluxed for 4 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Treating the residue with chloroform and filtration gave 0.1 g (99%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. addition(25 mg) were added
  3. temperaturethe mixture was refluxed for 4 h
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. additionTreating the residue
  7. filtrationwith chloroform and filtration

Sources & evidence

ORD record
ord-310a7f2dfdfd4581ac7f7ecce03f9977
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313137B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes