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 1351283Notes

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

Participants

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

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried with anhydrous magnesium sulfate
customthe residue resulting from the removal of the solvent by evaporation
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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