Acetone → HCID 22969541, compound

HRID 1278890Notes

Reaction equation

HRID 1278890 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C@@H:23]([OH:26])[CH2:24][OH:25])[CH:16]=1.[CH3:28][C:29]([CH3:31])=O>[Cl-].[Zn+2].[Cl-]>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C@@H:23]2[O:26][C:29]([CH3:31])([CH3:28])[O:25][CH2:24]2)[CH:16]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 5327067HCID 5327067, compound

Product 1

HCID 22969541HCID 22969541, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of 5-amino-1-(4-fluorophenyl)-4-[3-{2(S),3-dihydroxypropoxy}benzoyl]pyrazole (0.6 g, 1.6 mmol) in 30 ml acetone was added zinc chloride (0.34 g, 2.6 mmol). The reaction mixture was stirred and heated at reflux. After 13 hours, the reaction mixture was concentrated to dryness and the product was purified by flash column chromatography on silica gel using 40% EtOAc/Hexane as elutent. The product was stirred with 1:1 ether/hexane and 125 mg of 5-amino-1-(4-fluorophenyl)4-{3-[(2,2-dimethyl-1,3-dioxolan-5(S)-yl)methoxy]benzoyl}pyrazole was obtained.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. concentrationthe reaction mixture was concentrated to dryness
  4. customthe product was purified by flash column chromatography on silica gel using 40% EtOAc/Hexane as elutent
  5. stirringThe product was stirred with 1:1 ether/hexane

Sources & evidence

ORD record
ord-cfd68b56170d4db49261c9e47e518f99
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

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