Hydrochloric Acid → 4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde

HRID 1941888Notes

Reaction equation

HRID 1941888 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:21]=3[C:22]([F:25])([F:24])[F:23])[O:14][N:13]=2)=[CH:8][CH:7]=1.Cl>C1COCC1.O.O>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[N:20]1[C:21]([C:22]([F:23])([F:24])[F:25])=[C:17]([C:15]2[O:14][N:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=3)[N:16]=2)[CH:18]=[N:19]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669966503-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 866590394-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehydeYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 3-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole (25 g, 58.2 mmol) and con. HCl (500 mL) in THF/water (500 mL/500 mL) was stirred at RT for 3 hours. Upon completion of the reaction, as monitored by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and then dried and concentrated under reduced pressure to afford 4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (19 g, 49 mmol). The compound had an HPLC retention time=1.90 min.—CHROMOLITH® SpeedROD 4.6×30 mm. flow=5 mL/min (2 min. gradient); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=386.2.

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47af31ed9b014968a462c1f372d422de
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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