HCID 46882579, compound → HCID 58706344, compound

HRID 1990876Notes

Reaction equation

HRID 1990876 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[N:19]=2)[CH2:12][CH2:13]1)[CH3:2]

Participants

5

Reactant 2

HCID 46882579HCID 46882579, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58706344HCID 58706344, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of [1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-(5-nitro-benzooxazol-2-yl)-amine (1.0 g, 2.35 mmol, 1.0 equiv; example 225) in ethanol (10 mL) was added palladium on activated charcoal 10% (0.1 g, 0.10 mmol, 0.04 equiv), the reaction vessel filled with hydrogen (3.5 bar) and stirred at 60° C. for 18 h. The catalyst was removed by filtration over celite and the solvent removed under reduced pressure yielding 0.79 g (85%) of the title compound which was used directly without further purification. MS (ESI): 397.4 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d2258492a754453796536114178a4d18
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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