Oxalyl chloride → 5-[4-(4-Methyl-3-thienyl)-3-(trifluoromethyl)phenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 336309Notes

Reaction equation

HRID 336309 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])=[CH:10][S:11][CH:12]=1.O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][C:37]([F:40])([F:39])[F:38])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[C:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17]3[O:19][N:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][C:37]([F:38])([F:39])[F:40])[N:27]=3)=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])=[CH:10][S:11][CH:12]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 594958184-(4-Methyl-3-thienyl)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 252553785-[4-(4-Methyl-3-thienyl)-3-(trifluoromethyl)phenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (106 μL; 1.26 mmol; 3 eq.), Intermediate 32 (120 mg; 0.42 mmol; 1 eq.), Intermediate 2 (92 mg; 0.42 mmol, 1 eq.) and DIEA (217 μL; 1.26 mmol; 3 eq.) were reacted according to general procedure 2. Purification by crystallisation from MeOH afforded the title compound as a white solid.

Workup

  1. customPurification
  2. customby crystallisation from MeOH

Sources & evidence

ORD record
ord-98e9d83e6f694688a7f9f45e0bc3629f
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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