HCID 22609520, compound → HCID 22609554, compound

HRID 1250967Notes

Reaction equation

HRID 1250967 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:42]2[CH:47]=[C:46]([O:48][CH3:49])[C:45]([O:50][CH3:51])=[C:44]([O:52][CH3:53])[CH:43]=2)=[C:8]([CH:41]=1)[C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:40])[C:19]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=2[C:28]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=2)[CH2:13][CH2:12]1)=[O:10])([O-])=O>C(O)(=O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:42]2[CH:43]=[C:44]([O:52][CH3:53])[C:45]([O:50][CH3:51])=[C:46]([O:48][CH3:49])[CH:47]=2)=[C:8]([CH:41]=1)[C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:40])[C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:20]=2[C:28]2[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

4

Reactant 1

HCID 22609520HCID 22609520, compound

Product 1

HCID 22609554HCID 22609554, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

Added to a solution of 39 mg (0.050 mmol) of 1,4-bis[5-nitro-2-(3,4,5-trimethoxy-phenyl)benzoyl]hexahydro-1,4-diazepine synthesized by the process described in Example 71 in acetic acid-ethyl acetate (3:2, 2.5 ml) were 39 mg of 10% palladium on carbon, and the mixture was stirred for 2 hours at room temperature under hydrogen. The catalyst was removed from the reaction mixture by suction filtration through Celite, and the filtrate was concentrated under reduced pressure. A chloroform solution of the residue was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 32 mg (yield: 90%) of the title compound as a pale yellow amorphous powder.

Workup

  1. customsynthesized by the process
  2. customThe catalyst was removed from the reaction mixture by suction filtration through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washA chloroform solution of the residue was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-932125c05f8d477d9f1d96892eadedeb
Source dataset
uspto-grants-2002_01
Patent number
US06340682B1

Reaction notes

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