Ammonium formate → 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13266

Reaction equation

HRID 13266 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13]1[C:14]([CH:36]2[CH2:40][CH2:39][CH2:38][N:37]2[C:41](=[O:43])[CH3:42])=[CH:15][C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[N:18][C:17]=2[CH:35]=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].C(O)C>[OH:12][C:13]1[C:14]([CH:36]2[CH2:40][CH2:39][CH2:38][N:37]2[C:41](=[O:43])[CH3:42])=[CH:15][C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[N:18][C:17]=2[CH:35]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 231455661-(2-(6-benzyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Product 1

HCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

713 mg of ammonium formate and 119 mg of 20% palladium hydroxide-carbon catalyst were added to an ethanol (20 ml) solution of 1.18 g of 1-(2-(6-benzyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone, and the reaction liquid was heated under reflux for 5 hours. 157 mg of ammonium formate and 56 mg of 20% palladium hydroxide-carbon catalyst were added to the reaction liquid, and the reaction liquid was further heated under reflux for 1 hour. After cooled, the catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue was diluted with 1 N hydrochloric acid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/0 to 99/1 to 98/2) to obtain the entitled compound as a brown amorphous substance.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 5 hours
  4. customthe reaction liquid
  5. temperaturewas further heated
  6. temperatureunder reflux for 1 hour
  7. temperatureAfter cooled
  8. customthe catalyst was removed through filtration through Celite
  9. customthe solvent was evaporated away under reduced pressure
  10. additionThe resulting residue was diluted with 1 N hydrochloric acid
  11. extractionextracted with ethyl acetate
  12. dry with materialdried with anhydrous magnesium sulfate
  13. customThe solvent was evaporated away under reduced pressure
  14. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/0 to 99/1 to 98/2)
  15. customto obtain the entitled compound as a brown amorphous substance

Sources & evidence

ORD record
ord-6094219faa2c48f4955233785fa1e572
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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