HCID 66990342, compound → HCID 58508727, compound

HRID 454638Notes

Reaction equation

HRID 454638 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][N:39]2[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[O:12]

Participants

5

Reactant 1

HCID 66990342HCID 66990342, compound

Product 1

HCID 58508727HCID 58508727, compoundYield 65.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(2-(4-methylpiperazin-1-yl)ethyl)benzamido)-4-phenylbenzoate (0.10 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.10 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol] to obtain 0.056 g of tert-butyl 2-(2-hydroxy-5-(2-(4-methylpiperazin-1-yl)ethyl)benzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. additionwas added
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-3311b3d6b4da45ec86513d5ae7c4148f
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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