HCID 57682848, compound → HCID 57682931, compound

HRID 494964Notes

Reaction equation

HRID 494964 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH2:32])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:33])[CH:8]=[CH:9][O:10]2)=[CH:5][CH:4]=1>CO.[C].[Pd]>[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH2:32])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:19][CH2:20]2)=[C:11]2[C:6]([C:7](=[O:33])[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 57682848HCID 57682848, compound

Product 1

HCID 57682931HCID 57682931, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

42 mg of 1-(1-(2-(7-methoxy-4-oxo-4H-chromen-8-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide was dissolved in 3 ml of methanol. Thereafter, 15 mg of 10% palladium carbon was added to the reaction solution. The obtained mixture was then stirred at room temperature for 15 hours under hydrogen atmosphere. Thereafter, 15 mg of 10% palladium carbon was further added to the reaction solution. The obtained mixture was then stirred at the same temperature for 4 hours. Thereafter, palladium carbon was removed by filtration, and the filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate), so as to obtain 20 mg of the subject compound.

Workup

  1. stirringThe obtained mixture was then stirred at the same temperature for 4 hours
  2. customThereafter, palladium carbon was removed by filtration
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0985d1ca21d84b16962b897cbee10ad0
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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