Methanesulfonyl chloride → HCID 22176582, compound

HRID 1797206Notes

Reaction equation

HRID 1797206 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:29])([CH3:28])[CH2:20][NH:21][S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:27][N:25]([CH3:26])[S:22]([NH:21][CH2:20][C:19]([F:29])([C:16]1[CH:15]=[CH:14][C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=2)=[CH:18][CH:17]=1)[CH3:28])(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22176548HCID 22176548, compound

Product 1

HCID 22176582HCID 22176582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL 3 neck flask fitted with a stirrer and thermometer, 285 mg of methanesulfonyl chloride is added dropwise to 350 mg of {2-[4-(3-aminophenyl)phenyl]-2-fluoropropyl}[(dimethylamino)sulfonyl]amine (prepared in example 38) and 380 mg of DBU in THF (125 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction is allowed to warm to room temperature and then stirred overnight at this temperature. In the morning, the reaction is concentrated under reduced vacuum. The resulting material is taken into ethyl acetate and the organic layer is washed two times with H2O, dried over Na2SO4, filtered, and concentrated under reduced vacuum. This crude material is purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor with hexane/ethyl acetate eluent to provide the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight at this temperature
  3. concentrationIn the morning, the reaction is concentrated under reduced vacuum
  4. washthe organic layer is washed two times with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customThis crude material is purified via silica gel chromatography

Sources & evidence

ORD record
ord-967dfe1aa32b4af9b75599825c9725f6
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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