Oxalyl chloride → 5-[4-(3,5-Dimethylisoxazol-4-YL)-3-methylphenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

HRID 336289Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=2[CH3:22])=[C:11]([CH3:23])[O:10][N:9]=1.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][C:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]([C:17]3[O:19][N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[N:25]=3)=[CH:15][C:14]=2[CH3:22])=[C:11]([CH3:23])[O:10][N:9]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 4652214N-Hydroxy-2-methoxy-benzamidine

HCID 532250194-(3,5-Dimethylisoxazol-4-YL)-3-methylbenzoic acid

Product 1

HCID 596065305-[4-(3,5-Dimethylisoxazol-4-YL)-3-methylphenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (132 μL; 1.56 mmol; 3 eq.), Intermediate 30 (120 mg; 0.52 mmol; 1 eq.), Intermediate 1 (86 mg; 0.52 mmol, 1 eq.) and DIEA (268 μL; 1.56 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 80/20) afforded the title compound as an orange foam.

Workup

customPurification by column chromatography c-hexane/ethyl acetate, 80/20)

Sources & evidence

ORD record: ord-48d6e92f49644b179b9fafb5ba909d8e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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