Methanesulfonyl chloride → N-[5-[3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-(2-methylpiperidin-1-yl)phenyl]methanesulfonamide

HRID 1950883Notes

Reaction equation

HRID 1950883 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[CH:9][C:10]([O:32][CH3:33])=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]4[CH3:31])=[C:22]([CH:24]=3)[NH2:23])[O:15][N:14]=2)[CH:12]=1>N1C=CC=CC=1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([O:32][CH3:33])=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]4[CH3:31])=[C:22]([NH:23][S:2]([CH3:1])(=[O:4])=[O:3])[CH:24]=3)[O:15][N:14]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 252553775-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-(2-methylpiperidin-1-yl)aniline

Product 1

HCID 59606540N-[5-[3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-(2-methylpiperidin-1-yl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (20 μL; 0.26 mmol; 1.2 eq.) was added to a solution of Example 69 (83 mg; 0.22 mmol; 1 eq.) in pyridine (1 mL) and the resulting solution was stirred at room temperature for 16 hours. The solution was then partitioned between water and ethyl acetate. The two phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed (3×) with 0.1M HCl, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (c-hexane/ethyl acetate, 60/40) afforded the title compound as a white solid.

Workup

  1. customThe solution was then partitioned between water and ethyl acetate
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic phase was washed (3×) with 0.1M HCl
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (c-hexane/ethyl acetate, 60/40)

Sources & evidence

ORD record
ord-8dac5eb870114ef6af778717948813a9
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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