HCID 20130164, compound → HCID 20130171, compound

HRID 845749Notes

Reaction equation

HRID 845749 reaction equation
C([O:8][C:9]([CH2:11][O:12][C:13]1[CH:49]=[CH:48][C:16]([C:17]([N:19]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:35][CH2:34][N:33]([C:36](=[O:47])[C:37]5[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=5)[CH2:32][CH2:31]4)=[CH:27][CH:28]=3)[CH2:23][CH2:22][C:20]2=[O:21])=[O:18])=[CH:15][CH:14]=1)=[O:10])C1C=CC=CC=1>CN(C=O)C.C(O)C.[Pd]>[C:9]([CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:19]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:35][CH2:34][N:33]([C:36](=[O:47])[C:37]5[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=5)[CH2:32][CH2:31]4)=[CH:27][CH:28]=3)[CH2:23][CH2:22][C:20]2=[O:21])=[O:18])=[CH:48][CH:49]=1)([OH:10])=[O:8]

Participants

5

Reactant 1

HCID 20130164HCID 20130164, compound

Product 1

HCID 20130171HCID 20130171, compoundYield 89.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-benzyloxycarbonylmethoxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (4 g) in a mixture of DMF (30 ml) and ethanol (30 ml) was added 10% palladium on carbon (500 mg) and the mixture was hydrogenated at room temperature and atmospheric pressure. After completion of reaction, the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in dichloromethane. The solution was washed with water, dried and evaporated under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:2 to 1:1) to give 1-(4-carboxymethoxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (3.1 g).

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter completion of reaction
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washThe solution was washed with water
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:2 to 1:1)

Sources & evidence

ORD record
ord-2dff0494aa0942f7b8d15279ae34033e
Source dataset
uspto-grants-1988_07
Patent number
US04760064

Reaction notes

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