Sodium ethoxide → HCID 69481040, compound

HRID 2364530Notes

Reaction equation

HRID 2364530 reaction equation
[CH:1]1([N:4]([C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2[C:6]([C:19]([O:21]C)=O)=[N:7][CH:8]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[CH2:3][CH2:2]1.[O-]CC.[Na+]>C(O)C>[CH:1]1([N:4]2[C:5]3[C:6](=[N:7][CH:8]=[C:9]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH:10]=3)[C:19]([OH:21])=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]2=[O:30])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69480475Methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

Product 1

HCID 69481040HCID 69481040, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (402 mg, 0.97 mmol) in ethanol (20 mL) at 0° C. was treated with sodium ethoxide (165 mg, 2.4 mmol). The reaction mixture was allowed to warm to room temperature as the bath warmed overnight. Solvents were removed in vacuo and the residue was taken up in water. The pH was adjusted to ˜5 with 1 N HCl (aq) and the aqueous layer extracted with ethyl acetate. The organics were dried over sodium sulfate filtered and concentrated to give ethyl 1-cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (362 mg, 98%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=1.6 Hz, 1 H), 7.78 (s, 1 H), 7.18 (dd, J=8.7, 5.4 Hz, 2 H), 7.04 (t, J=8.7 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.13 (s, 2 H), 2.77 (m, 1 H), 1.46 (t, J=7.3 Hz, 3 H), 1.22 (m, 2 H), 0.76 (m, 2 H); MS m/z 383 (M+1).

Workup

  1. temperaturewarmed overnight
  2. customSolvents were removed in vacuo
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f0de86dc7cd404f817e7b0afb071e09
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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