5-methyl-1H-pyrazole-3-carboxylic acid → 5-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 2400528Notes

Reaction equation

HRID 2400528 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O[N:33]=[C:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][C:43]([F:46])([F:45])[F:44])=[CH:38][CH:37]=1)[NH2:35]>CN(C=O)C.O>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:9][N:35]=[C:34]([C:36]3[CH:37]=[CH:38][C:39]([O:42][C:43]([F:44])([F:45])[F:46])=[CH:40][CH:41]=3)[N:33]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27333094-(Trifluoromethoxy)benzamidoxime

Product 1

HCID 469016545-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mechanically stirred solution of 5-methyl-1H-pyrazole-3-carboxylic acid (15.3 g, 0.121 mol) in dry DMF (600 mL) was added EDCl (23.3 g, 0.121 mol), HOBT (16.4 g, 0.121 mol) and N′-hydroxy-4-(trifluoromethoxy)benzenecarboximidamide (26.7 g, 0.121 mol). The mixture was stirred at rt for 2 h, and then warmed to 140° C. and stirred for further 5 h. After being cooled to rt, the mixture was diluted with water (2 L) and extracted with ethyl acetate.

Workup

  1. temperaturewarmed to 140° C.
  2. stirringstirred for further 5 h
  3. temperatureAfter being cooled to rt
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-6b62cae143dd4f87a1f53fb7529e54c6
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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