HCID 18677448, compound → HCID 22240469, compound

HRID 1634248Notes

Reaction equation

HRID 1634248 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]([F:18])([F:17])[F:16])[C:10](=O)[C:9]2=[O:21])=[CH:4][CH:3]=1.[Cl-].[C:23]([C:25]1[CH:26]=[C:27]([NH:31][NH2:32])[CH:28]=[CH:29][CH:30]=1)#[N:24]>C(O)(=O)C>[C:23]([C:25]1[CH:26]=[C:27]([N:31]2[C:10]3[C:9](=[O:21])[N:8]([C:5]4[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=4)[CH2:13][CH2:12][C:11]=3[C:14]([C:15]([F:18])([F:17])[F:16])=[N:32]2)[CH:28]=[CH:29][CH:30]=1)#[N:24]

Participants

4

Reactant 2

HCID 18677448HCID 18677448, compoundHCID 222404772,3-Piperidinedione, 1-(4-iodophenyl)-4-(2,2,2-trifluoroacetyl)-

Product 1

HCID 22240469HCID 22240469, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(4-iodophenyl)-4-(2,2,2-trifluoroacetyl)-2,3-piperidinedione prepared by the same methods described in WO 00/39131 (5.02 g, 12.2 mmol) and 3-cyanophenylhydrazine chloride (3.44 g, 20.4 mmol) were added together with 75 mL of Acetic acid. The mixture was refluxed for 4 hours. The mixture was cooled and the solvent was removed. The residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, brine, dried over MgSO4, concentrated, and chromatographed with 1:5 EtOAc:hexane to afford 3.8 g of 1-(3-cyanophenyl)-3-(trifluoromethyl)-6-(4-iodophenyl)-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one as a yellow solid (61.3%). 1H NMR (CDCl3, 300 MHz) δ 7.91-7.90 (m, 1H), 7.87-7.83 (m, 1H), 7.75-7.69 (m, 3H), 7.56 (t, 1H), 7.09-7.04 (m, 2H), 4.15 (t, 2H), 3.19 (t, 2H).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed
  4. customThe residue was partitioned between EtOAc and H2O
  5. washThe EtOAc layer was washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed with 1:5 EtOAc

Sources & evidence

ORD record
ord-66450182167c49b4846e7de82ad69698
Source dataset
uspto-grants-2003_01
Patent number
US06506771B2

Reaction notes

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