HCID 69416179, compound → HCID 69419026, compound

HRID 1296352Notes

Reaction equation

HRID 1296352 reaction equation
[CH3:1][Mg]Br.[CH2:4]([N:11]([CH:35]([CH3:37])[CH3:36])[CH2:12][C:13]([C:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:16]=1)=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1>[CH2:4]([N:11]([CH:35]([CH3:37])[CH3:36])[CH2:12][C:13]([C:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:16]=1)([OH:14])[CH3:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 69416179HCID 69416179, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69419026HCID 69419026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (0.1 ml, 0.144 mmol) was added dropwise into the solution of 2-(benzyl-isopropyl-amino)-1-[5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-1H-pyrazol-3-yl]-ethanone (61 mg, 0.12 mmol) in 0.5 ml THF at room temperature. After 2 h, the reaction mixture was then partitioned with ethyl acetate and saturated NH4Cl. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica gel, 30% ethyl acetate/hexanes) to give the title compound 4A-1 as a white waxy solid (24 mg).

Workup

  1. customthe reaction mixture was then partitioned with ethyl acetate and saturated NH4Cl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7afb3635dd464a108cbd1369b746dfa3
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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