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

HRID 336293Notes

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][C:35]([F:38])([F:37])[F:36])[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][C:35]([F:36])([F:37])[F:38])[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

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

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

HCID 594957953-Methoxy-4-(4-methyl-3-thienyl)benzoic acid

Product 1

HCID 252566575-[3-Methoxy-4-(4-methyl-3-thienyl)phenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (123 μL; 1.45 mmol; 3 eq.), Intermediate 29 (120 mg; 0.48 mmol; 1 eq.), Intermediate 2 (106 mg; 0.48 mmol, 1 eq.) and DIEA (250 μL; 1.45 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 yellow oil.

Workup

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

Sources & evidence

ORD record: ord-af0b55abe4d2445bb600041016c7fc88
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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