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

HRID 1269622Notes

Reaction equation

HRID 1269622 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.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.O>[CH:1]1([CH2:4][CH2:5][N:6]([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)[S:24]([C:27]2[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]=2)(=[O:26])=[O:25])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetateHCID 18448417N-(2-Cyclopropylethyl)-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amine

Product 1

HCID 58622892Ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetateYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-cyclopropylethyl)-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (155 mg, 0.51 mmol) in anhydrous CH2Cl2 (10 mL) under nitrogen at room temperature was added ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (223 mg, 0.76 mmol) and triethylamine (0.213 mL, 1.53 mmol). The resultant mixture was stirred for 40 h at room temperature. The reaction mixture was diluted with water (15 mL) and extracted with CH2Cl2 (30 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by Biotage™ chromatography (40 g Silica column) eluted with 1:19–1:9 EtOAc:cyclohexane afforded the title compound as a white crystalline solid (156 mg).

Workup

  1. extractionextracted with CH2Cl2 (30 mL)
  2. customthe solvent was removed in vacuo
  3. customPurification by Biotage™ chromatography (40 g Silica column)
  4. washeluted with 1:19–1:9 EtOAc

Sources & evidence

ORD record
ord-c51a01a39e5f40589f1af33024a5cdaf
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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