Triethylamine → 4-[4-(3-Chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-ylmethyl methanesulfonate

HRID 1845745Notes

Reaction equation

HRID 1845745 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][OH:21])=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.O>[CH3:29][S:30]([O:21][CH2:20][C:19]1[C:15]([C:10]2[N:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=3)[C:13](=[O:14])[O:12][N:11]=2)=[N:16][O:17][N:18]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 589418304-(3-Chloro-4-fluorophenyl)-3-[4-(hydroxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 589418054-[4-(3-Chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-ylmethyl methanesulfonateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Chloro-4-fluorophenyl)-3-[4-(hydroxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (250 mg, 0.7996 mmol) was dissolved in anhydrous DCM (8 mL) followed by addition of triethylamine (TEA) (134 μL, 0.96 mmol). Reaction was cooled to 0° C. and methanesulfonyl chloride (68 μL, 0.88 mmol) was added dropwise. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography eluting with 25%-70% EtOAc to yield the desired product (259 mg, 83%). MF=C12H8ClFN4O6S; LCMS calculated for C12H9ClFN4O6S (M+H)+: m/z=390.992.

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography
  7. washeluting with 25%-70% EtOAc

Sources & evidence

ORD record
ord-b0b86d5556714c3cb33f49819dfa764b
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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