Oxalyl chloride → 1-[4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(trifluoromethyl)phenyl]piperidine

HRID 336299Notes

Reaction equation

HRID 336299 reaction equation
C(Cl)(=O)C(Cl)=O.[N:7]1([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])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[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>>[F:26][C:27]1[CH:28]=[CH:29][C:30]([O:37][CH3:38])=[C:31]([C:33]2[N:34]=[C:17]([C:16]3[CH:20]=[CH:21][C:13]([N:7]4[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]4)=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:15]=3)[O:19][N:35]=2)[CH:32]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 596065494-Piperidin-1-yl-3-(trifluoromethyl)benzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252227421-[4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(trifluoromethyl)phenyl]piperidine

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 42 (137 mg; 0.5 mmol; 1 eq.), Intermediate 23 (92 mg; 0.5 mmol, 1 eq.) and DIEA (194 mg; 1.5 mmol; 3 eq.) were reacted according to general procedure 2. Purification by crystallisation from n-pentane afforded the title compound as a white solid.

Workup

  1. customPurification
  2. customby crystallisation from n-pentane

Sources & evidence

ORD record
ord-d43bcabc0f564ff6b0116118115286bf
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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