Hydrochloric Acid → HCID 22716693, compound

HRID 1582990Notes

Reaction equation

HRID 1582990 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.[I-].[K+].Cl>O.C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][CH2:24][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 31268PyrrolidineHCID 22716661HCID 22716661, compound

Product 1

HCID 22716693HCID 22716693, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a 10 ml THF solution containing 700 mg of 4-(3-chlorophenyl)-1-ethyl-3-(3-methanesulfonyloxypropyl)-7-methyl-1,8-naphthyridin-2(1H)-one were added 0.5 ml of pyrrolidine and 300 mg of potassium iodide, followed by stirring under heating at an oil bath temperature of 60° C. for 1.5 hours. After cooling to room temperature, water and 1M hydrochloric acid were added thereto, and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated and the residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia). The resulting compound was dissolved in ethyl acetate and a 4M hydrogen chloride-ethyl acetate solution was added thereto. Thereafter, the residue obtained by evaporation of the solvent was recrystallized from ethyl acetate-acetonitrile to obtain 133 mg of 4-(3-chlorophenyl)-1-ethyl-7-methyl-3-[3-(pyrrolidin-1-yl)propyl]-1,8-naphthyridin-2(1H)-one monohydrochloride as colorless crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThen, the solvent was evaporated
  6. customthe residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia)
  7. dissolutionThe resulting compound was dissolved in ethyl acetate
  8. additiona 4M hydrogen chloride-ethyl acetate solution was added
  9. customThereafter, the residue obtained by evaporation of the solvent
  10. customwas recrystallized from ethyl acetate-acetonitrile

Sources & evidence

ORD record
ord-63c0c7c54611483c98c7f361b36e1f6d
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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