Hydrochloric Acid → HCID 57793914, compound

HRID 1678386Notes

Reaction equation

HRID 1678386 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[CH:14]=[C:13]([F:15])[C:12]([C:16]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[C:20]([CH3:29])[N:19]=[N:18][C:17]=2[Cl:30])=[C:11]([F:31])[CH:10]=1.[ClH:32]>[Cu](Cl)Cl.C(#N)C>[Cl:30][C:17]1[N:18]=[N:19][C:20]([CH3:29])=[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:16]=1[C:12]1[C:11]([F:31])=[CH:10][C:9]([Cl:32])=[CH:14][C:13]=1[F:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 57793928HCID 57793928, compound

Product 1

HCID 57793914HCID 57793914, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 323 mg of copper (II) chloride (CuCl2), 309 mg of tert-butyl nitrite and 13 ml of acetonitrile was added 732 mg of 4-(4-amino-2,6-difluorophenyl)-3-chloro-5-(4-chlorophenyl)-6-methylpyridazine portion-wise under ice-cooling. Thereafter, the reaction mixture was stirred at room temperature for 2 hours. Then, the reaction mixture was poured into a mixture of ice and dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed sequentially with sodium bicarbonate water and saturated brine, and dried over anhydrous magnesium sulfate then concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=7:1), to obtain 0.62 g of 3-chloro-4-(4-chloro-2,6-difluorophenyl)-5-(4-chlorophenyl)-6-methylpyridazine (hereinafter, referred to as compound (xi) of the present invention).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with sodium bicarbonate water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthen concentrated
  6. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-fda9d200855245ddbf22ed1b7ed18189
Source dataset
uspto-grants-2011_08
Patent number
US08008512B2

Reaction notes

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