Methanesulfonyl chloride → HCID 178505093, compound

HRID 2097653Notes

Reaction equation

HRID 2097653 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[C:12]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)C(=O)[O:18][N:17]=2)=[N:13][O:14][N:15]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[Cl:28][C:23]1[CH:22]=[C:21]([NH:20][C:16]([C:12]2[C:11]([CH2:10][CH2:9][NH:8][S:31]([CH3:30])(=[O:33])=[O:32])=[N:15][O:14][N:13]=2)=[N:17][OH:18])[CH:26]=[CH:25][C:24]=1[F:27]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69268230HCID 69268230, compound

Product 1

HCID 178505093HCID 178505093, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-(2-aminoethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate (16.0 mg, 0.037 mmol) in DCM (1.0 mL) was added TEA (15 μL, 0.11 mmol) and methanesulfonyl chloride (4.2 μL, 0.055 mmol). The resulting mixture was stirred at rt for 1 h and then the solvent was removed under reduced pressure. The residue was dissolve in MeOH (1 mL) and 2.0 M sodium hydroxide in water (0.10 mL) was added. After stirring for 4 h, the reaction solution was diluted with MeOH and a few drop of acetic acid and then purified by preparative LCMS to give the desired product as a white solid (14.1 mg, 78.3%). MF═C12H13ClFN5O4S; LCMS calculated C12H14ClFN5O4S(M+H)+: m/z=377.0.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolve in MeOH (1 mL)
  3. addition2.0 M sodium hydroxide in water (0.10 mL) was added
  4. stirringAfter stirring for 4 h
  5. additionthe reaction solution was diluted with MeOH
  6. customa few drop of acetic acid and then purified by preparative LCMS

Sources & evidence

ORD record
ord-7d697205ca9a4587a00d10cb1f23f132
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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