HCID 90114164, compound → HCID 90114566, compound

HRID 2275907Notes

Reaction equation

HRID 2275907 reaction equation
[NH2:1][C:2]([CH3:38])([CH2:28][CH2:29][O:30]CC1C=CC=CC=1)[CH2:3][NH:4][C:5]([C:7]1[N:11]2[CH:12]=[C:13]([CH3:26])[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[CH3:27])=[O:6]>C(O)C.[Pd].[C]>[NH2:1][C:2]([CH3:38])([CH2:28][CH2:29][OH:30])[CH2:3][NH:4][C:5]([C:7]1[N:11]2[CH:12]=[C:13]([CH3:26])[CH:14]=[C:15]([O:16][CH2:17][C:18]3[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=3[F:24])[C:10]2=[N:9][C:8]=1[CH3:27])=[O:6]

Participants

4

Reactant 1

HCID 90114164HCID 90114164, compound

Product 1

HCID 90114566HCID 90114566, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Under argon, 295 mg (0.52 mmol) of rac-N-[2-amino-4-(benzyloxy)-2-methylbutyl]-8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxamide Example 262 were initially charged in 5.4 ml of ethanol, 56 mg of Pd/carbon (10%) were added and the mixture was hydrogenated under atmospheric pressure at room temperature for 6.5 h. The reaction mixture was left under hydrogen overnight. The reaction mixture was applied to silica gel, concentrated and purified by silica gel chromatography (mobile phase: dichloromethane/2N ammonia in methanol 10/1 isocratic). This gave 95 mg of the target compound (42% of theory).

Workup

  1. waitThe reaction mixture was left under hydrogen overnight
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (mobile phase: dichloromethane/2N ammonia in methanol 10/1 isocratic)

Sources & evidence

ORD record
ord-5becc49526654c65a234686c20c0cce1
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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