HCID 18518184, compound → HCID 18518207, compound

HRID 1368930Notes

Reaction equation

HRID 1368930 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=2)=[C:8]([CH:38]=1)[C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:37])[C:16]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:17]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)=[O:10])([O-])=O>C(O)(=O)C.C(OCC)(=O)C.[Pd]>[NH2:22][C:20]1[CH:19]=[CH:18][C:17]([C:25]2[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=2)=[C:16]([CH:21]=1)[C:15]([NH:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[C:8]1[CH:38]=[C:4]([NH2:1])[CH:5]=[CH:6][C:7]=1[C:39]1[CH:40]=[C:41]([O:49][CH3:50])[C:42]([O:47][CH3:48])=[C:43]([O:45][CH3:46])[CH:44]=1)=[O:37]

Participants

4

Reactant 1

HCID 18518184HCID 18518184, compound

Product 1

HCID 18518207HCID 18518207, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

To a solution of 20 mg (0.028 mmol) of N,N′-bis[5-nitro-2-(3,4,5-trimethoxy-phenyl)benzoyl]ethylenediamine synthesized by the process of Example 52 in acetic acid-ethyl acetate (1:3, 2 ml) was added 20 mg of 10% palladium on carbon, and the mixture was stirred for 3 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 solution of the resultant residue in chloroform was washed with a saturated solution of a sodium hydrogencarbonate and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, thereby obtaining 17 mg (quantitative) of crude crystals of the title compound. The crude crystals were recrystallized from methylene chloride-diethyl ether, thereby obtaining a pale yellow crystalline powder.

Workup

  1. customThe catalyst was removed from the reaction mixture by suction filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washA solution of the resultant residue in chloroform was washed with a saturated solution of a sodium hydrogencarbonate
  4. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d7de261fe604b9095c9f7c8e774c15d
Source dataset
uspto-grants-2003_06
Patent number
US06576642B2

Reaction notes

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