Oxalyl chloride → 3-(2-Methoxyphenyl)-5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-YL]-1,2,4-oxadiazole

HRID 336301Notes

Reaction equation

HRID 336301 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24].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>>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:29]1[N:28]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH3:7])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)[O:22][N:30]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 594958132'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 252563913-(2-Methoxyphenyl)-5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-YL]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (109 μL; 1.28 mmol; 3 eq.), Intermediate 34 (120 mg; 0.43 mmol; 1 eq.), Intermediate 1 (71 mg; 0.43 mmol, 1 eq.) and DIEA (95 μL; 1.28 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

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

Sources & evidence

ORD record
ord-7a687bfef11942eca58097b6a3bf55ea
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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