Hydrochloric Acid → HCID 178426676, compound

HRID 1513055Notes

Reaction equation

HRID 1513055 reaction equation
Cl[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].[ClH:35].[NH2:36][OH:37].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C>[Cl:35][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](=[NH:33])[NH:36][OH:37])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 59309716HCID 59309716, compound

Product 1

HCID 178426676HCID 178426676, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl-sulfonyl)phenyl]-5-cyano-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.13 g) in ethanol (4 mL) were added hydroxylamine hydrochloride (91 mg) and potassium carbonate (0.2 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract 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=4/1), and collected by filtration. The collected solids were dried under reduced pressure to give the title compound (0.1 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. filtrationcollected by filtration
  6. customThe collected solids were dried under reduced pressure

Sources & evidence

ORD record
ord-834d396b71a34e9085572b67871016ff
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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