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

HRID 336311Notes

Reaction equation

HRID 336311 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-87a95f1f2cd94da89f80e4d5d8a60609
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

Loading…