Sodium Azide → 6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl azide

HRID 1817305Notes

Reaction equation

HRID 1817305 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:28]=[CH:27][C:9]([CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:17]([C:21](Cl)=[O:22])=[N:16][CH:15]=[C:14]([O:24][CH3:25])[C:13]=3[C:12]2=[O:26])=[CH:8][CH:7]=1>O.CC(C)=O>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:17]([C:21]([N:1]=[N+:2]=[N-:3])=[O:22])=[N:16][CH:15]=[C:14]([O:24][CH3:25])[C:13]=3[C:12]2=[O:26])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 866139046-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl chloride

Product 1

HCID 866139056-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl azide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of sodium azide (0.24 g, 3.69 mmol) in water (2.5 mL) was added 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl chloride (1.17 g, 3.36 mmol) in acetone (15 mL). After 20 minutes, the product mixture was concentrated under vacuum to provide 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl azide. The crude azide (1.19 g, 3.35 mmol) in DMF (20 mL) was heated to 110° C. After 20 minutes, the product mixture was cooled for 10 minutes, then 1N NaOH (3.3 mL) was added. After 20 minutes, the mixture was concentrated under vacuum, re-dissolved in toluene and CHCl3 and evaporated. The residue was partitioned between CHCl3 and saturated sodium bicarbonate. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound.

Workup

  1. concentrationthe product mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-1cd3d8cc62494db5af45a243f1a200d6
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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