Acetic Acid → (+/-)-(5-Amino-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide

HRID 1987760Notes

Reaction equation

HRID 1987760 reaction equation
[N+:1]([C:4]1[CH:33]([CH3:34])[CH:8]2[CH2:9][C:10]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH:32]=[CH:31][N:30]=[CH:29]5)=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])([CH3:12])[O:11][C:7]2=[C:6]([CH3:35])[C:5]=1[CH3:36])([O-])=O.C(O)C.C(O)(=O)C.[OH-].[Na+]>[C].[Pd].O>[NH2:1][C:4]1[CH:33]([CH3:34])[CH:8]2[CH2:9][C:10]([NH:13][C:14]([N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH:32]=[CH:31][N:30]=[CH:29]5)=[CH:24][CH:23]=4)[CH2:20][CH2:21]3)=[O:15])([CH3:12])[O:11][C:7]2=[C:6]([CH3:35])[C:5]=1[CH3:36]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 68849562(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide

Product 1

HCID 68848816(+/-)-(5-Amino-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamideYield 67.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

In an autoclave, 0.88 g of (±)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide and 0.5 g of 10% palladium carbon, 10 ml of ethanol and 5 ml of acetic acid were added, followed by stirring overnight under a hydrogen pressure of 10 kg/cm2. The reaction solution was poured into water, neutralized with a 1N sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:methanol=10:1) to obtain 0.56 g of the objective product (melting point: 189-191° C.).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-1718f495fa0847cea0b200c08883da3b
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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