HCID 178418319, compound → HCID 178418422, compound

HRID 3401Notes

Reaction equation

HRID 3401 reaction equation
[CH:1]1([N:7]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH2:27][N:28]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=3)=[O:30])[CH2:23][CH2:22]2)[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[C].[Pd].[Pd].CN(C=O)C>[CH:1]1([N:7]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH2:27][N:28]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[O:30])[CH2:23][CH2:22]2)[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 178418319HCID 178418319, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178418422HCID 178418422, compoundYield 106.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A 0.6 g quantity of 10% palladium carbon was added to 100 ml of a DMF solution containing 5.7 g of trans-1,4-bis[[1-cyclohexyl-3-(4-nitrophenyl)ureido]-metyl]cyclohexane synthesized in accordance with Example 2. Hydrogen was added at ordinal pressure and normal temperature for 15 hours. After completion of the reaction, palladium was separated by filtration and the reaction mixture was concentrated under reduced pressure. The reaction mixture was dissolved in chloroform and a 4N hydrochloric acid-dioxyane solution was added to provide 5.5 g (95%) of white crystals precipitated.

Workup

  1. customsynthesized in accordance with Example 2
  2. customwas separated by filtration
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe reaction mixture was dissolved in chloroform
  5. additiona 4N hydrochloric acid-dioxyane solution was added

Sources & evidence

ORD record
ord-a24726e74e5d4a6ca7abb5ec691259ae
Source dataset
uspto-grants-1998_03
Patent number
US05733931

Reaction notes

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