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

HRID 336300Notes

Reaction equation

HRID 336300 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.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>>[F:38][C:37]([F:39])([F:40])[O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:28]1[N:29]=[C:17]([C:16]2[CH:20]=[CH:21][C:13]([N:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]3)=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[O:19][N:27]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 596065494-Piperidin-1-yl-3-(trifluoromethyl)benzoic acid

Product 1

HCID 252551751-[4-{3-[2-(Trifluoromethoxy)phenyl]-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 2 (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 MeOH/water afforded the title compound as a white solid.

Workup

  1. customPurification
  2. customby crystallisation from MeOH/water

Sources & evidence

ORD record
ord-e34e4085b826454ea7be994652e6ce6c
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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