Benzamidine → HCID 136454423, compound

HRID 1747788Notes

Reaction equation

HRID 1747788 reaction equation
O=[C:2]([C:9]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=O.[C:20]1([C:26](=[NH:28])[NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[C:20]1([C:26]2[NH:28][C:4](=[O:6])[CH:3]=[C:2]([C:9]3[N:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:12]=[CH:11][CH:10]=3)[N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2332BenzamidineHCID 89586101HCID 89586101, compound

Product 1

HCID 136454423HCID 136454423, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-oxo-3-(1-phenyl-1H-pyrazol-5-yl)propanoate (300 mg) in DMF (10.0 mL) was added benzenecarboximidamide (139 mg) at room temperature. The reaction mixture was heated using a microwave reactor at 140° C. for 30 min. The reaction mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (100 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. customat 140° C.
  3. customfor 30 min
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-3c67aabb5f6747748a2e79b054b882cb
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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