Oxalyl chloride → 4-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzenesulfonamide

HRID 219921Notes

Reaction equation

HRID 219921 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].[NH2:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34](=[N:36]O)[NH2:35])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C(C1C=CC(S(N)(=O)=O)=CC=1)#N.CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:13]=[C:12]([C:14]2[O:16][N:36]=[C:34]([C:31]3[CH:30]=[CH:29][C:28]([S:25]([NH2:24])(=[O:26])=[O:27])=[CH:33][CH:32]=3)[N:35]=2)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Participants

6

Reactant 5

HCID 65578Oxalyl chlorideHCID 76566p-CyanobenzenesulphonamideHCID 81531DiisopropylethylamineHCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 252564714-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzenesulfonamide

Procedure

Oxalyl chloride (134 mL; 1.59 mmol), Intermediate 3 (120 mg; 0.53 mmol), 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide, prepared as described in WO 2006/013104 A1 from 4-cyanobenzene-1-sulfonamide (ABCR; CD10716), (114 mg; 0.53 mmol, 1 eq.) and DIEA (274 mL; 1.59 mmol) were reacted according to the procedure described for Example 38. Purification by recrystallisation from DCM/n-pentane afforded the title compound as a white solid. LC/MS (Method A): 404.3 (M−H)−. HPLC (Method A) Rt 5.17 min (purity 95.4%).

Workup

  1. customwere reacted
  2. customPurification
  3. customby recrystallisation from DCM/n-pentane

Sources & evidence

ORD record
ord-99b2fbd7fbad4bb0ad85c2da91683ad7
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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