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Ammonia → 2-Amino-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide

HRID 1351283
Notes
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Reaction equation

HRID 1351283 reaction equation
[NH3:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:27])[CH2:10][N:11]([CH3:26])[S:12]([C:15]2[C:16]3[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[C:17]=3[S:18][C:19]=2Br)(=[O:14])=[O:13])=[CH:5][CH:4]=1.Cl>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:27])[CH2:10][N:11]([CH3:26])[S:12]([C:15]2[C:16]3[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[C:17]=3[S:18][C:19]=2[NH2:1])(=[O:14])=[O:13])=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 210985782-Bromo-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide

Product 1

HCID 210985752-Amino-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
110 °C

Procedure

A concentrated aqueous ammonia (24 mL) was added to 2-bromo-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-amide (210 mg). After heating at 110° C. for 4 hours, the reaction solution was poured into water, brought to pH 9 with 5N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, the residue resulting from the removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (145 mg) was obtained as a colorless film.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customthe residue resulting from the removal of the solvent by evaporation
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a6c29fe3b4240619097201759043ec4
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217723B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes