Hydrochloric Acid → 3-(2,3-difluorophenyl)-5-(pyridin-3-yl)-1,2,4-oxadiazole Hydrochloric Acid

HRID 713786Notes

Reaction equation

HRID 713786 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[O:11][N:10]=1.[ClH:20]>C(OCC)(=O)C>[ClH:20].[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[O:11][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670260303-(2,3-Difluorophenyl)-5-(pyridin-3-yl)-1,2,4-oxadiazole

Product 1

HCID 670262973-(2,3-difluorophenyl)-5-(pyridin-3-yl)-1,2,4-oxadiazole Hydrochloric Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 32A (320 mg, 1.23 mmol) in ethyl acetate (5 mL) was stirred with hydrochloric acid (Aldrich, 4 M in dioxane, 0.5 mL, 2.0 mmol) at ambient temperature for 4 hours. The titled compound was collected by filtration and dried under vacuum. 1H NMR (300 MHz, MeOH-d4) δ 7.35-7.46 (m, 1H), 7.49-7.63 (m, 1H), 7.93-8.07 (m, 1H), 8.24 (dd, J=8.1, 5.8 Hz, 1H), 9.10 (dd, J=5.8, 1.4 Hz, 1H), 9.23 (dt, J=8.0, 1.8 Hz, 1H), 9.66 (d, J=2.0 Hz, 1H) ppm; MS (DCl/NH3) m/z 260 (M+H)+.

Workup

  1. filtrationThe titled compound was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-8b2a853c273649d59647e92ae348dd83
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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