Acetonitrile → HCID 12991187, compound

HRID 1582998Notes

Reaction equation

HRID 1582998 reaction equation
C(#N)C.[Br:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[N:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]([CH2:22][CH3:23])[C:13](=[O:24])[C:12]=2[CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:8]=[CH:9][CH:10]=1.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(N(CC)CC)C>C(OCC)(=O)C>[Br:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[N:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]([CH2:22][CH3:23])[C:13](=[O:24])[C:12]=2[CH:25]2[CH2:30][CH2:29][N:28]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:27][CH2:26]2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 12991186HCID 12991186, compound

Product 1

HCID 12991187HCID 12991187, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 5 ml acetonitrile solution containing 400 mg of 4-(3-bromophenyl)-1-ethyl-7-methyl-3-(piperidin-4-yl)-1,8-naphthyridin-2(1H)-one were added 0.11 ml of ethyl bromoacetate and 0.13 ml of triethylamine, followed by stirring at room temperature for 13 hours. Ethyl acetate was added to the reaction solution and the solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine and dried over anhydrous magnesium sulfate. After removal of the solvent from the organic layer, the resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from ethyl acetate-diisopropyl ether to obtain 120 mg of ethyl {4-[4-(3-bromophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-l,8-naphthyridin-3-yl]piperidin-1-yl}acetate as colorless crystals.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removal of the solvent from the organic layer
  4. customthe resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-7b4f4c3f5614443b8b15acbefb575b41
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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