Dimethylformamide → 3-Azidomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

HRID 1887823Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15]Br)=[CH:11][CH:10]=[C:9]([C:18]([F:21])([F:20])[F:19])[N:8]=2)=[O:4].[N-:28]=[N+:29]=[N-:30].[Na+].CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15][N:28]=[N+:29]=[N-:30])=[CH:11][CH:10]=[C:9]([C:18]([F:21])([F:20])[F:19])[N:8]=2)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

In a 25 mL pear-shaped flask, 3-bromomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (150.6 mg, 0.341 mmol) and sodium azide (66.6 mg, 1.02 mmol) were combined with DMF (2 mL) to give a light yellow solution. The reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with H2O (25 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (2×25 mL), dried over MgSO4, and concentrated in vacuo to give 3-azidomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (134.7 mg, 97.8%) as a yellow oil which contained DMF as an impurity. 1H NMR (DMSO-d6) δ ppm 8.89 (d, J=8.2 Hz, 1H) 7.78-8.27 (m, 1H) 7.26-7.76 (m, 5H) 4.30 (s, 2H) 3.52 (s, 2H). MS calcd. for C18H12F3N5O3 [(M+H)+] 404.0, obsd. 404.0, [(M+H-N2)+] 376.0, obsd. 376.0.

Workup

customto give a light yellow solution
extractionextracted with ethyl acetate (3×30 mL)
washwashed with brine (2×25 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f1917e5ac8c24c9289d1d8f4296c3542
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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