Hydrochloric Acid → HCID 178492029, compound

HRID 1822242Notes

Reaction equation

HRID 1822242 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4](=[O:20])[CH:3]=1.[H-].[Na+].[H][H].[C:25]1([CH2:31][C:32](Cl)=O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.O.[NH2:37][NH2:38]>CN(C=O)C.O>[CH2:31]([C:32]1[C:3]2[C:4](=[O:20])[N:5]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:38][N:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 54676182HCID 54676182, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178492029HCID 178492029, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-hydroxy-1-(4-methoxyphenyl)-1,8-naphthyridin-2 (1H)-one (1.07 g, 4.0 mmol; prepared according to JP, A, 61-246183 (1986) and/or J. Med. Chem., 31, 2108 (1988)) in DMF (4 ml) was added sodium hydride (about 60%, 352 mg, 8.8 mmol, 2.2 eq.), and the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (0.63 ml, 4.8 mmol, 1.2 eq.) was added, the mixture was stirred at room temperature, admixed with water, acidified with hydrochloric acid, and then filtered off to give precipitates which were washed with water. The resulting precipitate was suspended in DMF (8 mL) without purification, treated with hydrazine monohydrate (80%, 513 μl, 12.8 mmol, 3.2 eq.), and the mixture was stirred at 100 to 110° C. for 2 hours. The reaction mixture was admixed with water, and filtered off to give precipitates which were dried to afford 3-benzyl-5-(4-methoxyphenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (826 mg, 54%).

Workup

  1. customprepared
  2. filtrationfiltered off
  3. customto give
  4. customprecipitates which
  5. washwere washed with water
  6. customThe resulting precipitate was suspended in DMF (8 mL) without purification
  7. stirringthe mixture was stirred at 100 to 110° C. for 2 hours
  8. filtrationfiltered off
  9. customto give
  10. customprecipitates which
  11. customwere dried

Sources & evidence

ORD record
ord-eafbb271a5a14651933ee788019ec871
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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