Water → HCID 178423540, compound

HRID 1513054Notes

Reaction equation

HRID 1513054 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([C:32]#[N:33])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:34].[Cl-].[NH4+].[N-:37]=[N+:38]=[N-:39].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([C:32]3[NH:39][N:38]=[N:37][N:33]=3)=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59309716HCID 59309716, compound

Product 1

HCID 178423540HCID 178423540, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)-phenyl]-5-cyano-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (47 mg) in N,N-dimethylformamide (1.5 mL) were added ammonium chloride (0.1 g) and sodium azide (0.12 g), and the mixture was stirred at 60° C. for 1 hour, and then stirred at 120° C. for 3 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. To the mixture was added water, and the organic layer was separated. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/ethyl acetate=3/1), and collected by filtration. The collected solids were dried under reduced pressure to give the title compound (33 mg).

Workup

  1. stirringstirred at 120° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. filtrationcollected by filtration
  8. customThe collected solids were dried under reduced pressure

Sources & evidence

ORD record
ord-f6b5730603bb48a1bfcc21f59661424a
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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