Acetone → HCID 22969541, compound

HRID 429384Notes

Reaction equation

HRID 429384 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-60ef80d4360b434485daaa60c07d1d66
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

Loading…