Sodium ethoxide → HCID 178440265, compound

HRID 1860572Notes

Reaction equation

HRID 1860572 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([NH2:21])=[O:20].[NH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][C:33](OCC)=O)[CH:30]=2)[NH:25][N:24]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:33]([CH2:32][C:29]3[CH:30]=[C:31]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[C:23]4[NH2:22])=[N:21][C:19](=[O:20])[C:3]2=[C:4]([CH:16]([CH3:18])[CH3:17])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 185406305-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideHCID 18540672Ethyl 3-aminoindazol-5-ylacetate

Product 1

HCID 178440265HCID 178440265, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 139 mg (0.40 mmol) of 5-amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 3 mL of absolute ethanol was added 329 mg (1.50 mmol) of ethyl 3-aminoindazol-5-ylacetate followed by 1.13 mL (3.0 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 16 h at reflux, and the heating mantle was then removed. The reaction was treated with 8 mL of 10% aq. HOAc, poured into water, and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4), concentrated under reduced pressure, and chromatographed on silica gel (gradient elution with 5% to 10% MeOH—CH2Cl2) to give, after removal of solvent, 123 mg (61%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-aminoindazol-5-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid. Mass spec.: 502.0712 (M+H)+.

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 8 mL of 10% aq. HOAc
  4. additionpoured into water
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed on silica gel (gradient elution with 5% to 10% MeOH—CH2Cl2)
  11. customto give
  12. customafter removal of solvent, 123 mg (61%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-aminoindazol-5-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid

Sources & evidence

ORD record
ord-b0e726281b794c7d91327139985e7fc5
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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