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

HRID 1950868Notes

Reaction equation

HRID 1950868 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:9]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])=[CH:10][S:11][CH:12]=1.O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:28]1[N:27]=[C:17]([C:16]2[CH:20]=[CH:21][C:13]([C:9]3[C:8]([CH3:7])=[CH:12][S:11][CH:10]=3)=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[O:19][N:29]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 594958184-(4-Methyl-3-thienyl)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 252551723-(2-Methoxyphenyl)-5-[4-(4-methyl-3-thienyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (106 μL; 1.26 mmol; 3 eq.), Intermediate 32 (120 mg; 0.42 mmol; 1 eq.), Intermediate 1 (70 mg; 0.42 mmol, 1 eq.) and DIEA (217 μL; 1.26 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 95/5) followed by crystallization from n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification by column chromatography (c-hexane/ethyl acetate, 95/5)
  2. customfollowed by crystallization from n-pentane

Sources & evidence

ORD record
ord-7151adf54ac04e02b0edea25aea5b873
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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