Triethylamine → {6-Methoxy-7-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-3-yl}-acetic acid ethyl ester

HRID 1727058Notes

Reaction equation

HRID 1727058 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([S:17](Cl)(=[O:19])=[O:18])[C:8]=2[S:9][CH:10]=1)[CH3:2].[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:28][CH:29]=1.C(N(CC)CC)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([S:17]([N:33]3[CH2:34][CH2:35][N:30]([C:27]4[CH:26]=[CH:25][C:24]([C:23]([F:37])([F:22])[F:36])=[CH:29][N:28]=4)[CH2:31][CH2:32]3)(=[O:19])=[O:18])[C:8]=2[S:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineHCID 57565234(7-Chlorosulfonyl-6-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

Product 1

HCID 57565241{6-Methoxy-7-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-3-yl}-acetic acid ethyl esterYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound from step 3 (50 mg, 0.14 mmol) in THF (2 mL) was added 1-[5-(trifluoromethyl)-2-pyridinyl]piperazine (32 mg, 0.14 mmol), followed by triethylamine (39 μL, 0.28 mmol). The reaction solution was stirred for 4 hours at room temperature. The solvent was evaporated and the residues were purified by silica gel chromatography to afford 22 mg of desired compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residues were purified by silica gel chromatography

Sources & evidence

ORD record
ord-989b46d1d79341aca4827a3e52986eda
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

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