Dimethylformamide → HCID 66618788, compound

HRID 406312Notes

Reaction equation

HRID 406312 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[N:30]=[C:14]3[CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[CH2:16][CH2:17][CH2:18][CH2:19][N:13]3[N:12]=2)[CH:8]=[CH:7][C:6]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1.CN(C=[O:41])C>>[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[N:30]=[C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:27])([F:29])[F:28])([OH:41])[CH2:16][CH2:17][CH2:18][CH2:19][N:13]3[N:12]=2)[CH:8]=[CH:7][C:6]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66778959HCID 66778959, compound

Product 1

HCID 66618788HCID 66618788, compound

Procedure

Sodium hydride (60%) was added to a solution of 2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-9-(2-trifluoromethylphenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepine obtained in Examples 74 and 75 (83 mg) in DMF (5 mL) with stirring under ice-cooling until bubbling was stopped. Thereafter, the mixture was stirred at room temperature in an oxygen atmosphere. After four days, ice water, chloroform and a saturated sodium thiosulfate solution were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was diluted with toluene and concentrated under reduced pressure. The residue was diluted again with toluene and concentrated under reduced pressure. The precipitated solid was collected by filtration, washed with chloroform and then air-dried to obtain 36.8 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customuntil bubbling
  3. stirringThereafter, the mixture was stirred at room temperature in an oxygen atmosphere
  4. additionice water, chloroform and a saturated sodium thiosulfate solution were added to the reaction solution
  5. customthe organic layer was separated
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was diluted with toluene
  9. concentrationconcentrated under reduced pressure
  10. additionThe residue was diluted again with toluene
  11. concentrationconcentrated under reduced pressure
  12. filtrationThe precipitated solid was collected by filtration
  13. washwashed with chloroform
  14. customair-dried

Sources & evidence

ORD record
ord-92956d74332f4f04b2b1fa60362edfc5
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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