1-(2,4-Dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → 6-Fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1696911Notes

Reaction equation

HRID 1696911 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)[C:9](=[O:22])[C:8]([C:23]([OH:25])=[O:24])=[CH:7]1>FC(F)(F)C(O)=O>[F:21][C:12]1[CH:11]=[C:10]2[C:15](=[N:14][C:13]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)[NH:6][CH:7]=[C:8]([C:23]([OH:25])=[O:24])[C:9]2=[O:22]

Participants

3

Reactant 1

HCID 672758741-(2,4-Dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 104011066-Fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 30B (130 mg) in trifluoroacetic acid (8 mL) was heated at 50° C. for 2 hours then cooled and concentrated. The concentrate was diluted with diethyl ether, stirred at ambient temperature for 4 hours, and filtered to provide the desired product. NMR (300 MHz, DMSO-d6) δ 14.05 (br s, 1H), 8.78 (s, 1H), 8.53 (m, 1H), 8.14 (m, 1H), 7.48 (m, 1H), 6.87 (m, 1H), 6.55 (s, 1H).

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. additionThe concentrate was diluted with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-16383b4114214b32abda11b60d6ded90
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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