Oxalyl chloride → 4-{5-[3-Methoxy-4-(4-methyl-3-thienyl)phenyl]-1,2,4-oxadiazol-3-yl}benzenesulfonamide

HRID 219920

Reaction equation

HRID 219920 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]1[C:22]([CH3:23])=[CH:21][S:20][CH:19]=1)[C:12]([OH:14])=O.[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][O:8][C:9]1[CH:10]=[C:11]([C:12]2[O:14][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:15]=[CH:16][C:17]=1[C:18]1[C:22]([CH3:23])=[CH:21][S:20][CH:19]=1

Participants

6

Reactant 5

HCID 65578Oxalyl chlorideHCID 76566p-CyanobenzenesulphonamideHCID 81531DiisopropylethylamineHCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 594957953-Methoxy-4-(4-methyl-3-thienyl)benzoic acid

Product 1

HCID 252563854-{5-[3-Methoxy-4-(4-methyl-3-thienyl)phenyl]-1,2,4-oxadiazol-3-yl}benzenesulfonamide

Procedure

Oxalyl chloride (123 mL; 1.45 mmol), Intermediate 8 (120 mg; 0.48 mmol), 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide, prepared as described in WO 2006/013104 A1 from 4-cyanobenzene-1-sulfonamide (ABCR; CD10716), (104 mg; 05 mmol, 1 eq.) and DIEA (250 mL; 1.45 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): 426.3 (M−H)−. HPLC (Method A) Rt 4.93 min (purity 89.2%).

Workup

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

Sources & evidence

ORD record
ord-774060a7a7be4ac19a13f0ed6b2007ab
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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