Ethyl Acetate → HCID 12991195, compound

HRID 1582987Notes

Reaction equation

HRID 1582987 reaction equation
C(OCC)(=O)C.C(OC([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:21](=[O:40])[N:22]([CH2:38][CH3:39])[C:23]3[C:28]([C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)=[CH:27][CH:26]=[C:25]([CH3:37])[N:24]=3)[CH2:16][CH2:15]1)=O)(C)(C)C.C(OCC)(=O)C.Cl.[OH-].[Na+]>O>[Cl:36][C:32]1[CH:31]=[C:30]([C:29]2[C:28]3[C:23](=[N:24][C:25]([CH3:37])=[CH:26][CH:27]=3)[N:22]([CH2:38][CH3:39])[C:21](=[O:40])[C:20]=2[N:17]2[CH2:16][CH2:15][NH:14][CH2:19][CH2:18]2)[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12991194HCID 12991194, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 12991195HCID 12991195, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 10 ml ethyl acetate solution containing 570 mg of 3-(1-tert-butoxycarbonylpiperazin-4-yl)-4-(3-chlorophenyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one was added a 10 ml 4M hydrogen chloride-ethyl acetate solution, followed by stirring at room temperature for 1 hour. After adding water, the reaction mixture was neutralized with 1M sodium hydroxide aqueous solution, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia) and then recrystallized from diisopropyl ether to obtain 115 mg of 4-(3-chlorophenyl)-1-ethyl-7-methyl-3-(piperazin-1-yl)-1,8-naphthyridin-2(1H)-one as pale yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia)
  6. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2d193f31159547dfb1cd6a9cc5c63a6e
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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