Oxalyl chloride → 5-(2',4'-Dimethoxy-2-methylbiphenyl-4-YL)-3-(2-methoxyphenyl)-1,2,4-oxadiazole

HRID 336286Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=O)=[CH:19][C:18]=1[CH3:26].O[N:28]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38])[NH2:30].CCN(C(C)C)C(C)C>>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:25][N:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[N:28]=2)=[CH:19][C:18]=1[CH3:26]

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 4652214N-Hydroxy-2-methoxy-benzamidine

HCID 532272044-(2,4-Dimethoxyphenyl)-3-methylbenzoic acid

Product 1

HCID 252565675-(2',4'-Dimethoxy-2-methylbiphenyl-4-YL)-3-(2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (112 μL; 1.32 mmol; 3 eq.), Intermediate 28 (120 mg; 0.44 mmol; 1 eq.), Intermediate 1 (73 mg; 0.44 mmol, 1 eq.) and DIEA (228 μL; 1.32 mmol; 3 eq.) were reacted according to general procedure 2. Purification by precipitation from DCM/n-pentane afforded the title compound as a yellow solid.

Workup

customPurification
customby precipitation from DCM/n-pentane

Sources & evidence

ORD record: ord-83af8c860b1640daa2fbd59c9749c7ec
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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