Phenylacetyl chloride → HCID 178514870, compound

HRID 1822249Notes

Reaction equation

HRID 1822249 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](O)=[CH:10][C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[H][H].[C:24]1([CH2:30][C:31](Cl)=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.[NH2:35][NH2:36]>CN(C=O)C.O>[CH2:30]([C:31]1[C:10]2[C:9](=[O:19])[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]=2[NH:36][N:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 7679Phenylacetyl chlorideHCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 54676178HCID 54676178, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178514870HCID 178514870, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-(3-fluorophenyl)-4-hydroxy-1,8-naphthyridin-2 (1H)-one (512 mg, 2.0 mmol, obtained in Synthetic Example 31 (3)) in DMF (8 ml) was added sodium hydride (about 60%, 192 mg, 4.8 mmol, 2.4 eq.), the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (371 mg, 2.4 mmol, 1.2 eq.) was added, the mixture was stirred at room temperature, and treated with water. The resultant DMF layer was washed with hexane, acidified with hydrochloric acid, and filtered to give precipitates which were washed with water, and then suspended in DMF (8 mL). To the suspension was added hydrazine monohydrate (80%, 224 μl, 5.6 mmol, 2.8 eq.), and the mixture was stirred overnight at 100 to 110° C. The reaction mixture was admixed with water, and filtered to give precipitates which were washed with water, then dissolved in DMF, and treated with methanol and water. The mixture was filtered to give precipitates which were washed with water and dried to afford 3-benzyl-5-(3-fluorophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (330 mg, 45%).

Workup

  1. washThe resultant DMF layer was washed with hexane
  2. filtrationfiltered
  3. customto give
  4. customprecipitates which
  5. washwere washed with water
  6. stirringthe mixture was stirred overnight at 100 to 110° C
  7. filtrationfiltered
  8. customto give
  9. customprecipitates which
  10. washwere washed with water
  11. dissolutiondissolved in DMF
  12. additiontreated with methanol and water
  13. filtrationThe mixture was filtered
  14. customto give
  15. customprecipitates which
  16. washwere washed with water
  17. customdried

Sources & evidence

ORD record
ord-b4701950977646aeb6d313abdf1c93af
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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