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

HRID 1269619Notes

Reaction equation

HRID 1269619 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].N1C=CC=CC=1.[CH2:39]([S:42](Cl)(=[O:44])=[O:43])[CH2:40][CH3:41]>>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([S:42]([CH2:39][CH2:40][CH3:41])(=[O:44])=[O:43])[C:17]2[CH:18]=[C:19]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:27][CH:28]=3)[CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 58622902Ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

Product 1

HCID 58622879Ethyl [2-methyl-4-({(propylsulfonyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetateYield 16.2%

Conditions

Temperature
80 °C

Procedure

To a reactivial containing ethyl [2-methyl-4-({[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)phenoxy]acetate (100 mg, 0.225 mmol) was added pyridine (0.321 mL, 3.97 mmol) and 1-propanesulfonyl chloride (25.3 μL, 0.225 mmol). The resulting mixture was stirred in a sealed reactivial at 80° C. for 16 h. The reaction mixture was allowed to cool to room temperature and was partitioned between CH2Cl2 (2×10 mL) and water (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by Biotage™ chromatography (12 g Silica column) eluted with 1:9 EtOAc:cyclohexane afforded the title compound as a yellow oil (20 mg).

Workup

  1. temperatureto cool to room temperature
  2. customwas partitioned between CH2Cl2 (2×10 mL) and water (10 mL)
  3. customthe solvent was removed in vacuo
  4. customPurification by Biotage™ chromatography (12 g Silica column)
  5. washeluted with 1:9 EtOAc

Sources & evidence

ORD record
ord-5090ad851a6945c1bb8f7073e711bc3a
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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