Diethyl Malonate → HCID 178470070, compound

HRID 478595Notes

Reaction equation

HRID 478595 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC[O-].[Na+].C([O:18][C:19]([C:21]1[C:25]([NH2:26])=[N:24][N:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:22]=1)=O)C>CCO>[CH2:6]([O:5][C:3]([C:2]1[C:1]([OH:9])=[N:26][C:25]2=[N:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH:22]=[C:21]2[C:19]=1[OH:18])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 18002488Ethyl 3-amino-1-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 178470070HCID 178470070, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of diethyl malonate (9.6 g, 60 mmol) in a freshly prepared solution of NaOEt in EtOH (from 2.52 g of 60% oil dispersion NaH and 40 mL of EtOH) was added a solution of 5-amino-2-p-methoxybenzyl4-pyrazolecarboxylic ethyl ester (4.2 g, 15 mmol) in EtOH (60 mL) at rt. The resulting solution was refluxed for 20 h. The mixture was concentrated and the residue was dissolved in H2O (250 mL) and washed with EtOAc (60 mL). The aqueous layer was acidified with AcOH to pH 5. The product (5.1 g) was collected by filtration and dried under high vacuum. LC: 3.47′ (Gradient 1); MH+: 344

Workup

  1. temperatureThe resulting solution was refluxed for 20 h
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in H2O (250 mL)
  4. washwashed with EtOAc (60 mL)
  5. filtrationThe product (5.1 g) was collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-357900f1cd684fbdb64835a67a8e8810
Source dataset
uspto-grants-2003_11
Patent number
US06642244B2

Reaction notes

Loading…