Oxalyl chloride → 1-(2-Nitro-4-{3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-YL}phenyl)piperidine

HRID 336270Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:13]([OH:15])=O)([O-:9])=[O:8].O[N:26]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][C:36]([F:39])([F:38])[F:37])[NH2:28].CCN(C(C)C)C(C)C>>[N+:7]([C:10]1[CH:11]=[C:12]([C:13]2[O:15][N:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][C:36]([F:37])([F:38])[F:39])[N:26]=2)[CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([O-:9])=[O:8]

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamide

HCID 28797653-Nitro-4-(piperidin-1-yl)benzoic acid

Product 1

HCID 252563861-(2-Nitro-4-{3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-YL}phenyl)piperidine

Procedure

Oxalyl chloride (71 μL; 0.84 mmol; 3 eq.), Intermediate 4 (70 mg; 0.28 mmol; 1 eq.), Intermediate 2 (62 mg; 0.28 mmol, 1 eq.) and DIEA (145 μL; 0.84 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 80/20) followed by precipitation in n-pentane afforded the title compound as a yellow solid.

Workup

customPurification by column chromatography (c-hexane/ethyl acetate, 80/20)
customfollowed by precipitation in n-pentane

Sources & evidence

ORD record: ord-a854176fbf5d4f0a902c3fd2c87ce9ce
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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