Benzenesulfonyl chloride → HCID 178527565, compound

HRID 1845751Notes

Reaction equation

HRID 1845751 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)C(=O)[O:10][N:9]=2)=[N:5][O:6][N:7]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C.C(Cl)Cl.CN(C1C=CN=CC=1)C.CN(C=O)C.CO>[C:22]1([S:28]([NH:1][CH2:2][C:3]2[C:4]([C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)=[N:9][OH:10])=[N:5][O:6][N:7]=2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 589418433-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178527565HCID 178527565, compoundYield 187.9%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (10 mg, 0.003 mmol) was dissolved in ACN (0.2 mL) and DCM (0.2 mL). Benzenesulfonyl chloride (11 mg, 0.064 mmol) DIPEA (12 mg, 0.096 mmol) and DMAP (0.4 mg, 0.003 mmol) were dissolved in DMF (1 mL). The reaction was stirred at rt for 6 hrs. The reaction was then diluted with MeOH and purified by preparative LCMS. The intermediate was stripped to dryness, redissolved in EtOH (1 mL) and 1 M of sodium hydroxide in water (0.06 mL) was added. The reaction was stirred at rt for 1 hr, quenched with acetic acid, diluted with MeOH and the crude residue was purified by preparative LCMS to afford the desired product (2.4 mg). MF=C16H13ClFN5O4S; LCMS calculated for C16H14ClFN5O4S(M+H)+: m/z=426.0.

Workup

  1. custompurified by preparative LCMS
  2. dissolutionredissolved in EtOH (1 mL)
  3. addition1 M of sodium hydroxide in water (0.06 mL) was added
  4. stirringThe reaction was stirred at rt for 1 hr
  5. customquenched with acetic acid
  6. additiondiluted with MeOH
  7. customthe crude residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-1c64834d148f4857809cd5bd75b1eefe
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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