Methanesulfonyl chloride → 3-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propyl methanesulfonate

HRID 2097630Notes

Reaction equation

HRID 2097630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][OH:20])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:20][CH2:19][CH2:18][CH2:17][C:16]1[C:12]([C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)=[O:11])=[N:13][O:14][N:15]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58941800N-(3-chloro-4-fluorophenyl)-4-(3-hydroxypropyl)-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 589417693-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propyl methanesulfonateYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-Chloro-4-fluorophenyl)-4-(3-hydroxypropyl)-1,2,5-oxadiazole-3-carboxamide (60 mg, 0.20 mmol) was dissolved in anhydrous DCM (2 mL), followed by addition of TEA (57 μL, 0.41 mmol). The reaction was stirred and cooled to 0° C., and then methanesulfonyl chloride (29 μL, 0.37 mmol) was added dropwise. The reaction was quenched with water and diluted with DCM. The organic solution was separated, dried over Na2SO4, filtered, concentrated and purified by silica gel chromatography (25%-70% EtOAc/hexane) to give the desired product (19 mg). LCMS for C13H14ClFN3O5S(M+H)+: m/z=378.

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with DCM
  3. customThe organic solution was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (25%-70% EtOAc/hexane)

Sources & evidence

ORD record
ord-80c41468acd8457c896c4d71d8112538
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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