Methanesulfonyl chloride → HCID 59577193, compound

HRID 2042007Notes

Reaction equation

HRID 2042007 reaction equation
[C:1]([C:5]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]=[CH:19][NH:18][N:17]=2)=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[C:1]([C:5]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[N:20]=[CH:19][N:18]([S:27]([CH3:26])(=[O:29])=[O:28])[N:17]=2)=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178441113HCID 178441113, compound

Product 1

HCID 59577193HCID 59577193, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(2-tert-butyl-4-fluorophenoxy)-1-(1H-1,2,4-triazol-3-ylcarbonyl)piperidine (200 mg, 0.58 mmol) obtained in Example 274 in pyridine (3 mL) was added methanesulfonyl chloride (99 mg, 0.87 mmol), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate-water. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (245 mg, 99%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate-water
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3542bbf82a714801961ddd62cf8b70b8
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

Loading…