5-(3,4-Difluorophenyl)-3-(pyridazin-4-yl)-1,2,4-oxadiazole → 5-(3,4-Difluorophenyl)-3-(pyridazin-4-yl)-1,2,4-oxadiazole hydrochloride

HRID 578152Notes

Reaction equation

HRID 578152 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][N:17]=[N:16][CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:20].Cl.N1C=CC=C(C2N=C(C3C=CC=C([C@H]4CCCN4)C=3)ON=2)C=1>C(OCC)(=O)C>[ClH:20].[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][N:17]=[N:16][CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 445113055-(3,4-Difluorophenyl)-3-(pyridazin-4-yl)-1,2,4-oxadiazoleHCID 67343123(R)-3-(Pyridin-3-yl)-5-(3-(pyrrolidin-2-yl)phenyl)-1,2,4-oxadiazole bis(hydrochloric acid)

Product 1

HCID 670261705-(3,4-Difluorophenyl)-3-(pyridazin-4-yl)-1,2,4-oxadiazole hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 83E (140 mg, 0.54 mmol) in ethyl acetate (5.0 mL) was stirred with hydrochloric acid (Aldrich, 4 M in dioxane, 0.25 mL, 1.0 mmol) at ambient temperature for 10 hours. The white precipitates were collected by filtration and dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.81 (dt, J=10.5, 8.5 Hz, 1H), 8.08-8.19 (m, 1H), 8.26-8.39 (m, 2H), 9.55 (dd, J=5.4, 1.4 Hz, 1H), 9.83 (dd, J=2.4, 1.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 261 (M+H)+.

Workup

  1. customThe white precipitates
  2. filtrationwere collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-b33812e55d57450ab053f12246ad8da1
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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