Oxalyl chloride → 5-[4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrophenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 336277Notes

Reaction equation

HRID 336277 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][C:37]([F:40])([F:39])[F:38])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:13][CH:10]1[CH2:11][CH2:12][CH:8]([CH3:7])[N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]2[O:20][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][C:37]([F:38])([F:39])[F:40])[N:27]=2)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 596065544-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrobenzoic acid

Product 1

HCID 252564785-[4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrophenyl]-3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Procedure

Oxalyl chloride (152 μL; 1.2 mmol; 3 eq.), Intermediate 25 (106 mg; 0.4 mmol; 1 eq.), Intermediate 2 (88 mg; 0.4 mmol, 1 eq.) and DIEA (155 μL; 1.2 mmol; 3 eq.) were reacted according to general procedure 2. Purification by crystallisation from ethyl acetate/n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification
  2. customby crystallisation from ethyl acetate/n-pentane

Sources & evidence

ORD record
ord-dcf820b542964cc7a4e47b1332ec9d59
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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