Triethylamine → Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetate

HRID 1269621Notes

Reaction equation

HRID 1269621 reaction equation
[CH2:1]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl[S:24]([C:27]1[CH:39]=[CH:38][C:30]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:29]([CH3:40])[CH:28]=1)(=[O:26])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[CH3:40][C:29]1[CH:28]=[C:27]([S:24]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)(=[O:25])=[O:26])[CH:39]=[CH:38][C:30]=1[O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetateHCID 18448425N-Pentyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amine

Product 1

HCID 58622869Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetateYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-pentyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (70.6 mg, 0.23 mmol) in CH2Cl2 (5 mL) under nitrogen at room temperature was added ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (101 mg, 0.35 mmol) and triethylamine (96 μL, 0.69 mmol). The resultant mixture was stirred for 24 h at room temperature. The reaction mixture was extracted with CH2Cl2 (15 mL) and water (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by SPE (5 g Silica cartridge) eluted with 1:49–1:19 EtOAc:cyclohexane afforded the title compound as a white crystalline solid (76 mg).

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (15 mL) and water (10 mL)
  2. customthe solvent was removed in vacuo
  3. customPurification by SPE (5 g Silica cartridge)
  4. washeluted with 1:49–1:19 EtOAc

Sources & evidence

ORD record
ord-be80d91fa8f54f4bba68b342fb5966ea
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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