Hydrochloric Acid → HCID 12991182, compound

HRID 1582978Notes

Reaction equation

HRID 1582978 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[N:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]([CH2:25][CH3:26])[C:16](=[O:27])[C:15]=2[CH2:28][CH2:29][C:30]([OH:32])=O)[CH:11]=[CH:12][CH:13]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl>CN(C=O)C.C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[N:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]([CH2:25][CH3:26])[C:16](=[O:27])[C:15]=2[CH2:28][CH2:29][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:32])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 10156040337357-62-7

Product 1

HCID 12991182HCID 12991182, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.3 ml portion of oxalyl chloride and one drop of DMF were added to a 20 ml THF solution containing 1.00 g of 3-[4-(3-chlorophenyl)-l-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid, followed by stirring at room temperature for further 30 minutes. The reaction mixture was added dropwise to an ice-cooled 10 ml THF solution containing 1.0 ml of morpholine, followed by stirring for 30 minutes. To the reaction mixture was added 1M hydrochloric acid and the whole was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform-methanol) and then recrystallized from diisopropyl ether-ethyl acetate to obtain 780 mg of 4-(3-chlorophenyl)-1-ethyl-7-methyl-3-[3-(morpholin-4-yl)-3-oxopropyl]-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

  1. stirringby stirring for 30 minutes
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by a silica gel column chromatography (chloroform-methanol)
  6. customrecrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-ef7eb9c0d724486ca4e6c4eccbe6510e
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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