Potassium Carbonate → HCID 69481076, compound

HRID 2364410Notes

Reaction equation

HRID 2364410 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]1=[O:29].[C:30]1(=[O:36])[NH:34][C:33](=[O:35])[CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].[I-]>CN(C)C=O>[O:35]=[C:33]1[CH2:32][CH2:31][C:30](=[O:36])[N:34]1[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]1=[O:29]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 30165Iodide IonHCID 69482803HCID 69482803, compound

Product 1

HCID 69481076HCID 69481076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 1-(3-chloropropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (24 mg, 0.057 mmol) in N,N-dimethylformamide (700 μL) was added succinimide (23 mg, 0.23 mmol), potassium carbonate (32 mg, 0.23 mmol), and possium iodide (38 mg, 0.23 mmol), respectively. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was cooled and quenched with cold 1 N aqueous hydrochloric acid and extracted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 1-[3-(2,5-dioxo-1-pyrrolidinyl)propyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1 H), 7.31 (s, 1 H), 7.19 (dd, J=8.5, 5.3 Hz, 2 H), 7.04 (t, J=8.6 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.17-4.12 (m, 4 H), 3.58 (t, J=7.1 Hz, 2 H), 2.71 (s, 4 H), 1.90 (m, 2 H), 1.47 (t, J=7.1 Hz, 3 H); MS m/z 504 (M+Na)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with cold 1 N aqueous hydrochloric acid
  3. extractionextracted with toluene
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-64ce045777d940fea452844fc366f3ba
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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