Ammonium Chloride → HCID 178439612, compound

HRID 1007507Notes

Reaction equation

HRID 1007507 reaction equation
[Cl-].[NH4+].[N-:3]=[N+:4]=[N-:5].[Na+].[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:23]([CH2:30][C:31]#[N:32])=[CH:22][C:21]=3[C:33]([F:36])([F:35])[F:34])[CH:17]=2)[NH:12][CH:11]=1)([CH3:9])[CH3:8]>CN(C)C=O>[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]3[C:25]([C:26]([F:27])([F:29])[F:28])=[CH:24][C:23]([CH2:30][C:31]4[NH:32][N:5]=[N:4][N:3]=4)=[CH:22][C:21]=3[C:33]([F:36])([F:34])[F:35])[CH:17]=2)[NH:12][CH:11]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 226696934-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenylacetonitrile

Product 1

HCID 178439612HCID 178439612, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

251 mg (4.69 mmol) of ammonium chloride and 305 mg (4.69 mmol) of sodium azide are added to a solution of 200 mg (0.469 mmol) of nitrile derivative from Example VIII in 8 ml of dimethylformamide and the solution is boiled under reflux for 4 hours. The solution is then highly concentrated, treated with 6N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are dried, filtered and concentrated to an oil in vacuo. The crude product is dissolved in dichloromethane and chromatographed on silica gel 60 using dichloromethane with addition of methanol in the gradient mode (90:5 to 90:40).

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationThe solution is then highly concentrated
  3. additiontreated with 6N hydrochloric acid
  4. extractionextracted three times with ethyl acetate
  5. customThe combined organic phases are dried
  6. filtrationfiltered
  7. concentrationconcentrated to an oil in vacuo
  8. dissolutionThe crude product is dissolved in dichloromethane
  9. customchromatographed on silica gel 60 using dichloromethane with addition of methanol in the gradient mode (90:5 to 90:40)

Sources & evidence

ORD record
ord-8459424eeb5a469ea9c4983d530d1372
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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