Citric Acid → 7-Azetidin-1-yl-6-bromo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1696940Notes

Reaction equation

HRID 1696940 reaction equation
[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([O:21]CC)=[O:20])=[CH:11][N:12]3CCC#N)=[CH:7][C:6]=2[Br:25])[CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([OH:21])=[O:20])=[CH:11][NH:12]3)=[CH:7][C:6]=2[Br:25])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67275613Ethyl 7-azetidin-1-yl-6-bromo-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 103588577-Azetidin-1-yl-6-bromo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of EXAMPLE 82A (0.50 g) in methanol (100 mL) at reflux was treated with 1M LiOH (50 mL), stirred for 3 hours then cooled, treated with 10% citric acid, and filtered to provide the desired product. NMR (300 MHz, DMSO-d6) δ 17.21 (s, 1H), 8.68 (s, 1H), 8.32 (s, 1H), 4.29 (m, 4H), 2.26 (m, 2H).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-2d6ef4624c914bfc9344e07a87f1b595
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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