Hydrochloric Acid → HCID 178435416, compound

HRID 1974814Notes

Reaction equation

HRID 1974814 reaction equation
[CH2:1]([C:3]1[S:35][C:6]2[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][N:33]=[N:32][N:31]=4)=[CH:20][CH:19]=3)[CH:8]=[C:9]([C:12]([O:14]CC)=[O:13])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([C:3]1[S:35][C:6]2[N:7]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:31][N:32]=[N:33][N:34]=4)=[CH:22][CH:23]=3)[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178469727HCID 178469727, compound

Product 1

HCID 178435416HCID 178435416, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-ethyl-7-[[2'-(1H-tetrazol-5-yl) biphenyl-4-yl]methyl]-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (600 mg, 1.235 mmol) was dissolved in 6 ml of 1N sodium hydroxide and the mixture was heated at 100° C. for 20 minutes with stirring. After cooling, 7 ml of 1N hydrochloric acid was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with water, dried (MgSO4), and evaporated to dryness. The resulting crystal was washed with dichloromethane and dried to give 550 mg of the title compound as colorless crystals. This product was identified by comparing with NMR and IR spectra of the compound obtained in Working Example 1B.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. washThe resulting crystal was washed with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-19cca0f37a804fd4b1f2acf84ffd8460
Source dataset
uspto-grants-1994_02
Patent number
US05284661

Reaction notes

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