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

HRID 336273Notes

Reaction equation

HRID 336273 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24].O[N:28]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][C:38]([F:41])([F:40])[F:39])[NH2:30].CCN(C(C)C)C(C)C>>[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]2[O:20][N:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][C:38]([F:39])([F:40])[F:41])[N:28]=2)=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 252563892-Methyl-1-[4-{3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-YL}-2-(trifluoromethyl)phenyl]piperidine

Procedure

Oxalyl chloride (106 μL; 1.25 mmol; 3 eq.), Intermediate 24 (120 mg; 0.42 mmol; 1 eq.), Intermediate 2 (92 mg; 0.42 mmol, 1 eq.) and DIEA (93 μL; 1.25 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 80/20) followed by precipitation from n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification by column chromatography c-hexane/ethyl acetate, 80/20)
  2. customfollowed by precipitation from n-pentane

Sources & evidence

ORD record
ord-8e41b5de132b4b2fb0661edb6f058639
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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