Triethylamine → 7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide

HRID 1351269Notes

Reaction equation

HRID 1351269 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:19]=[C:20]1[C:25]2[S:26][CH:27]=[C:28]([S:29](Cl)(=[O:31])=[O:30])[C:24]=2[CH2:23][CH2:22][CH2:21]1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH3:11])[S:29]([C:28]2[C:24]3[CH2:23][CH2:22][CH2:21][C:20](=[O:19])[C:25]=3[S:26][CH:27]=2)(=[O:30])=[O:31])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amineHCID 210986857-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride

Product 1

HCID 866009897-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [2-(4-fluorophenyl)-ethyl]-methyl-amine (the compound of Preparation Example 14) (520 mg) and triethylamine (474 μL) in tetrahydrofuran was added a solution of 7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonyl chloride (the compound of Preparation Example 7) (800 mg) in tetrahydrofuran. The solution was stirred on an ice bath for 30 minutes, and at room temperature for 30 minutes. The residue resulting from the removal of the solvent by evaporation was purified by NH silica gel column chromatography (hexane/ethyl acetate), and the title compound (834 mg) was obtained as a colorless candy-like substance.

Workup

  1. waitat room temperature for 30 minutes
  2. customThe residue resulting from the removal of the solvent by evaporation
  3. customwas purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6659fbf53375402481e1cc594238ba74
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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