Hydrochloric Acid → HCID 135677710, compound

HRID 1793955Notes

Reaction equation

HRID 1793955 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:35]C)=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[NH:24][C:25](=[O:34])[CH2:26][C:27]2[N:31]([CH2:32][CH3:33])[N:30]=[N:29][N:28]=2)(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[Li+].Cl.C(OCC)(=O)C.C[N:47](C)C=O>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:35])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:22])[CH3:23])=[CH:17][C:16]=2[NH:24][C:25](=[O:34])[CH2:26][C:27]2[N:31]([CH2:32][CH3:33])[N:30]=[N:29][N:28]=2)(=[O:10])=[O:11])[CH:8]=1)(=[NH:47])[NH2:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 22219486HCID 22219486, compound

Product 1

HCID 135677710HCID 135677710, compound

Procedure

A solution of 0.112 g of N-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]-2-(1-ethyl-1H-tetrazol-5-yl)acetamide and 28 mg of lithium chloride in 0.65 mL of N,N-dimethylformamide was stirred at 140° C. for 4 hours. To the reaction mixture were added 1 mol/L hydrochloric acid and ethyl acetate, and the mixture was separated. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined. After the organic layer was washed with water, and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in 2.5 mL of 39% hydrogen chloride-ethanol solution, and the solution was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 1.0 mL of ethanol. To the solution was added 66 mg of ammonium acetate, and the mixture was stirred at room temperature for 14 hours. To the reaction mixture were added water, ethyl acetate, and hexane, and the precipitate was collected by filtration to give 42 mg of N-[2-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]-2-(1-ethyl-1H-tetrazol-5-yl)acetamide.

Workup

  1. customthe mixture was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washAfter the organic layer was washed with water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in 2.5 mL of 39% hydrogen chloride-ethanol solution
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in 1.0 mL of ethanol
  9. additionTo the solution was added 66 mg of ammonium acetate
  10. stirringthe mixture was stirred at room temperature for 14 hours
  11. additionTo the reaction mixture were added water, ethyl acetate, and hexane
  12. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9b28c4d2517a4618b674d15e77b2bb9c
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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