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

HRID 1950851Notes

Reaction equation

HRID 1950851 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].[F:26][C:27]1[CH:28]=[CH:29][C:30]([O:37][CH3:38])=[C:31]([C:33](=[N:35]O)[NH2:34])[CH:32]=1.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:34]=[C:33]([C:31]3[CH:32]=[C:27]([F:26])[CH:28]=[CH:29][C:30]=3[O:37][CH3:38])[N:35]=2)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 596065544-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrobenzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252564795-[4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrophenyl]-3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (152 μL; 1.2 mmol; 3 eq.), Intermediate 25 (106 mg; 0.4 mmol; 1 eq.), Intermediate 23 (74 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-d0ddec281ef84755a872c4cfa24ea18d
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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