Cyclohexene → HCID 90114166, compound

HRID 2275908Notes

Reaction equation

HRID 2275908 reaction equation
[NH2:1][C:2]([CH3:36])([CH2:27][O:28]CC1C=CC=CC=1)[CH2:3][NH:4][C:5]([C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])[C:10]2=[N:9][C:8]=1[CH3:26])=[O:6].C1CCCCC=1>C(O)C.[Pd]>[NH2:1][C:2]([CH3:36])([CH2:27][OH:28])[CH2:3][NH:4][C:5]([C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])[C:10]2=[N:9][C:8]=1[CH3:26])=[O:6]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 90114680HCID 90114680, compound

Product 1

HCID 90114166HCID 90114166, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under argon, 800 mg (1.57 mmol) of rac-N-[2-amino-3-(benzyloxy)-2-methylpropyl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide Example 263 were initially charged in 16.2 ml of ethanol, and 167 mg of palladium on activated carbon (10%) and 4.77 ml (47.1 mmol) of cyclohexene were added. The reaction mixture was stirred under reflux for 18 h and then applied to Celite and purified by silica gel chromatography (mobile phase: dichloromethane/methanol 10/1, dichloromethane/2N ammonia in methanol 10/1). This gave 366 mg of the target compound (56% of theory; purity 97%).

Workup

  1. temperatureunder reflux for 18 h
  2. custompurified by silica gel chromatography (mobile phase: dichloromethane/methanol 10/1, dichloromethane/2N ammonia in methanol 10/1)

Sources & evidence

ORD record
ord-66f70a9673724bdfa81e2813cfffebd3
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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