Methanesulfonamide → HCID 58042509, compound

HRID 2048034Notes

Reaction equation

HRID 2048034 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].N12CCCN=C1CCCCC2.CC1C=CC([C:24]2[C:25]([F:53])=[C:26]([CH:30]=[C:31]([Cl:52])[C:32]=2[O:33][C:34]2[CH:35]=[N:36][C:37]([O:44][CH2:45][C:46]([F:51])([F:50])[CH:47]([F:49])[F:48])=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=2)[C:27]([O-])=[O:28])=CC=1>C(#N)C>[Cl:52][C:31]1[C:32]([O:33][C:34]2[CH:35]=[N:36][C:37]([O:44][CH2:45][C:46]([F:51])([F:50])[CH:47]([F:48])[F:49])=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=2)=[CH:24][C:25]([F:53])=[C:26]([CH:30]=1)[C:27]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:28]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86660844HCID 86660844, compound

Product 1

HCID 58042509HCID 58042509, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulphonamide (89.54 mg, 0.94 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.15 mL, 1.03 mmol) were added to 4-methylphenyl-5-chloro-4-(6-(2,2,3,3-tetrafluoropropoxy)-5-(trifluoromethyl)pyridin-3-yloxy)-2-fluorobenzoate (Preparation 263, 475 mg, 0.86 mmol) in acetonitrile (5 mL) and the reaction mixture was stirred for 18 hours at room temperature. The reaction was concentrated in vacuo and the residue was partitioned between ethyl acetate and water, the organic layer was separated, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was purified by reverse phase chromatography (acetonitrile/water both with 0.1% formic acid) to give the title compound as a white solid (303 mg, 55%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by reverse phase chromatography (acetonitrile/water both with 0.1% formic acid)

Sources & evidence

ORD record
ord-26d05ad8164a4697b883aa39b80b8693
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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