Sodium Hydroxide → HCID 178439949, compound

HRID 452169Notes

Reaction equation

HRID 452169 reaction equation
CO[C:3]([C:5]1[CH:6]=[C:7]([CH3:17])[C:8]2[NH:12][C:11]([CH2:13][CH2:14][CH3:15])=[N:10][C:9]=2[CH:16]=1)=[O:4].[OH-].[Na+].[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH2:24].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH:24][C:3]([C:5]1[CH:6]=[C:7]([CH3:17])[C:8]2[NH:12][C:11]([CH2:13][CH2:14][CH3:15])=[N:10][C:9]=2[CH:16]=1)=[O:4]

Participants

9

Reactant 6

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 101308354-Methyl-2-propyl-1H-benzimidazole-6-carboxylic acid methyl ester

Product 1

HCID 178439949HCID 178439949, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

[step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 500 mg, 2.29 mmol) was suspended in ethanol (15 mL), 4 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 7 hr. The mixture was concentrated under reduced pressure, and water (20 mL) was added. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, aminoacetaldehyde dimethylacetal (0.50 mL, 4.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol) and 1-hydroxybenzotriazole (421 mg, 2.75 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture were added saturated aqueous sodium hydrogen carbonate solution (100 mL) and chloroform (100 mL), and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole.

Workup

  1. temperatureunder reflux for 7 hr
  2. concentrationThe mixture was concentrated under reduced pressure, and water (20 mL)
  3. additionwas added
  4. temperatureUnder ice-cooling
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in dichloromethane
  10. stirringthe mixture was stirred at room temperature for 6 hr
  11. washthe organic layer was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53cc639b11934d27a4a828fcbfb04ff8
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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