Dimethylamine → HCID 178433659, compound

HRID 553256Notes

Reaction equation

HRID 553256 reaction equation
[OH-].[Na+].C(O[C:6]([C:8]1[NH:9][C:10]([CH3:37])=[C:11]([C:14]2[NH:15][C:16]3[CH:22]=[C:21]([S:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[C:20]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:19][C:17]=3[N:18]=2)[C:12]=1[CH3:13])=[O:7])C.[CH2:38]([N:40]=[C:41]=NCCCN(C)C)C.CNC>CN(C)C=O.C(O)C>[CH3:38][N:40]([CH3:41])[C:6]([C:8]1[NH:9][C:10]([CH3:37])=[C:11]([C:14]2[NH:15][C:16]3[CH:22]=[C:21]([S:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[C:20]([O:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:19][C:17]=3[N:18]=2)[C:12]=1[CH3:13])=[O:7]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178470388HCID 178470388, compound

Product 1

HCID 178433659HCID 178433659, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Five milliliters of ethanol and 3.5 ml (3.5 mmol) of a 1 N sodium hydroxide aqueous solution were added to 0.48 g (1.0 mmol) of the 4-(5-(4-pyridylsulfenyl)-6-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl ester obtained in Comparative Example 1, and the reaction mixture was stirred at 60° C. for 17 hours. The reaction mixture was allowed to cool and concentrated, and the insoluble material was filtered off by adding water. The filtrate was neutralized with a 2 N hydrochloric acid solution, and the precipitate was collected by filtration, washed with water, and dried at reduced pressure to afford crude carboxylic acid (0.22 g). 0.2 g (0.4 mmol) of the crude carboxylic acid was dissolved in 3 ml of N,N-dimethylformamide, and then 92 mg (0.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 0.25 ml (2.2 mmol) of a 40% dimethylamine aqueous solution were added to the solution. The reaction mixture was stirred at 60° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated at reduced pressure. The obtained residue was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:100 to 1:10) to afford (N,N-dimethyl)-4-(5-(4-pyridylsulfenyl)-6-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxamide (83 mg, 43%) as an amorphous.

Workup

  1. customobtained in Comparative Example 1
  2. temperatureto cool
  3. concentrationconcentrated
  4. filtrationthe insoluble material was filtered off
  5. additionby adding water
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. customdried at reduced pressure
  9. customto afford crude carboxylic acid (0.22 g)
  10. stirringThe reaction mixture was stirred at 60° C. for 18 hours
  11. temperatureto cool to room temperature
  12. customthe solvent was evaporated at reduced pressure
  13. customThe obtained residue was purified

Sources & evidence

ORD record
ord-04f194d5df0f4a558cc683b6e39f269b
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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