Oxalyl chloride → 5-[3-Methoxy-4-(4-methyl-3-thienyl)phenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

HRID 336287Notes

Reaction equation

HRID 336287 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.O[N:25]=[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35])[NH2:27].CCN(C(C)C)C(C)C>>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:12]2[O:14][N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[N:25]=2)[CH:15]=[CH:16][C:17]=1[C:18]1[C:22]([CH3:23])=[CH:21][S:20][CH:19]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 594957953-Methoxy-4-(4-methyl-3-thienyl)benzoic acid

Product 1

HCID 596065355-[3-Methoxy-4-(4-methyl-3-thienyl)phenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (120 μL; 1.45 mmol; 3 eq.), Intermediate 29 (120 mg; 0.48 mmol; 1 eq.), Intermediate 1 (80 mg; 0.48 mmol, 1 eq.) and DIEA (250 μL; 1.45 mmol; 3 eq.) were reacted according to general procedure 2. Purification by precipitation from DCM/n-pentane afforded the title compound as a white solid.

Workup

  1. customPurification
  2. customby precipitation from DCM/n-pentane

Sources & evidence

ORD record
ord-1c11f63e78d64beab4d27bc4fd5378eb
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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