Ethyl benzoylacetate → HCID 136338636, compound

HRID 1594027Notes

Reaction equation

HRID 1594027 reaction equation
[C:1]([N:5]1[C:9]([NH2:10])=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:17]([CH2:25][C:26](OCC)=[O:27])(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(O)=O.CCOC(C)=O>[C:1]([N:5]1[C:9]2[NH:10][C:26](=[O:27])[CH:25]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 119912031-tert-Butyl-3-phenyl-1H-pyrazol-5-amine

Product 1

HCID 136338636HCID 136338636, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a stirring solution of crude 2-tert-butyl-5-phenyl-2H-pyrazol-3-ylamine (4.0 g, 18.6 mmol) in AcOH (25 mL) was added ethyl benzoylacetate (6.6 mL, 37.2 mmol). The reaction was then heated to 110° C. for 48 hr, at which time the reaction was cooled to room temperature, diluted with EtOAc, and quenched with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered through a fritted funnel, and concentrated under reduced pressure. Purification of this material was accomplished by flash chromatography, using an ISCO column (ISCO, Inc., Lincoln, Nebr.), eluting with 15% EtOAc/hexanes. The product-containing fractions were collected and concentrated under reduced pressure to give the title compound (1.0 g, 16% yield) as a tan solid. LRMS m/z (APCl) 344 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with a saturated aqueous solution of NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered through a fritted funnel
  5. concentrationconcentrated under reduced pressure
  6. customPurification of this material
  7. washeluting with 15% EtOAc/hexanes
  8. customThe product-containing fractions were collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44014d2224f0441d9fd25af23f5a3c21
Source dataset
uspto-grants-2007_11
Patent number
US07300943B2

Reaction notes

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