1,3-Dimethyl-2-imidazolidinone → HCID 22120656, compound

HRID 619246Notes

Reaction equation

HRID 619246 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:32])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][C:10]=2[O:24]CC2C=CC=CC=2)=[CH:3][CH:2]=1.CN1CCN(C)C1=O.[H][H]>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:32])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[CH:11][C:10]=2[OH:24])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 22120584HCID 22120584, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22120656HCID 22120656, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 702EthanolSolvent

Procedure

N-(4-Pyridyl)-2-benzyloxy-4-tert-butoxycarbonylaminomethylbenzamide (3.38 g) was subjected to catalytic reduction using 10% palladium hydroxide carbon (1 g) in a solution of ethanol (10 ml) and dimethylimidazolidinone (70 ml) in a stream of hydrogen. After the reaction, the catalyst was removed by filtration, and the mixture was concentrated under reduced pressure to give 1.85 g of N-(4-pyridyl)-4-tert-butoxycarbonylaminomethyl-2-hydroxybenzamide.

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-99656effc1d542f1bc3d6126340acf02
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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