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

HRID 336283Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]1[C:21]([CH3:22])=[CH:20][S:19][CH:18]=1)[C:11]([OH:13])=O.O[N:24]=[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][C:34]([F:37])([F:36])[F:35])[NH2:26].CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:9]=[C:10]([C:11]2[O:13][N:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][C:34]([F:35])([F:36])[F:37])[N:24]=2)[CH:14]=[CH:15][C:16]=1[C:17]1[C:21]([CH3:22])=[CH:20][S:19][CH:18]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamide

HCID 579938003-Methyl-4-(4-methylthiophen-3-yl)benzoic acid

Product 1

HCID 252565645-[3-Methyl-4-(4-methyl-3-thienyl)phenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (131 μL; 1.55 mmol; 3 eq.), Intermediate 20 (120 mg; 0.52 mmol; 1 eq.), Intermediate 2 (114 mg; 0.52 mmol, 1 eq.) and DIEA (267 μL; 1.55 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 95/5) afforded the title compound as a white solid.

Workup

customPurification by column chromatography c-hexane/ethyl acetate, 95/5)

Sources & evidence

ORD record: ord-2025ef6bac874b198a6d2b9a42574ad2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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