Dichloromethane → [2-Fluoro-2-(4-{3-[(methylsulfonyl)amino]phenyl}phenyl)propyl][(methylethyl)sulfonyl]amine

HRID 1797181Notes

Reaction equation

HRID 1797181 reaction equation
C1CCN2C(=NCCC2)CC1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:35])([CH3:34])[CH2:26][NH:27][S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1.C(Cl)Cl.Cl[CH2:40][S:41](Cl)(=[O:43])=[O:42]>O>[F:35][C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([NH:12][S:41]([CH3:40])(=[O:43])=[O:42])[CH:14]=2)=[CH:24][CH:23]=1)([CH3:34])[CH2:26][NH:27][S:28]([CH:31]([CH3:32])[CH3:33])(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 77054(Chloromethyl)sulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9863239{2-[4-(3-Aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine

Product 1

HCID 22176578[2-Fluoro-2-(4-{3-[(methylsulfonyl)amino]phenyl}phenyl)propyl][(methylethyl)sulfonyl]amineYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL flask fitted with a stirrer and thermometer was charged with DBU (67 mg, 1.1 eq), {2-[4-(3-aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine (140 mg, 0.44 mmol, prepared in example 5) and methylene chloride (10 mL) under an atmosphere of nitrogen, and cooled to 0° C. To this stirring solution was added dropwise chloro-methane sulfonyl chloride (69 mg, 1.5 eq). The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, the mixture was poured into H2O and the layers were separated. The organic layer was washed once with H2O, dried over anhydrous Na2SO4, filtered, and concentrated under reduced vacuum to yield the crude material (192 mg) as a yellow oil. This crude material was purified via silica gel chromatography employing the Chromatotron using a 4000 micron rotor and eluting with a solvent of Methylene Chloride/ethyl acetate 9:1 to yield the title compound (50 mg, 29%) as a white foam. Ion spray mass spectra 427.1 (M*−1).

Workup

  1. customA 50 mL flask fitted with a stirrer
  2. temperatureto warm to room temperature
  3. customthe layers were separated
  4. washThe organic layer was washed once with H2O
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customto yield the crude material (192 mg) as a yellow oil
  9. customThis crude material was purified via silica gel chromatography
  10. washeluting with a solvent of Methylene Chloride/ethyl acetate 9:1

Sources & evidence

ORD record
ord-85bef331774649d1b9892358b1e3d35a
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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