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

HRID 1696938Notes

Reaction equation

HRID 1696938 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[Cl: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[Cl:25])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67275173Ethyl 7-azetidin-1-yl-6-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 100621747-Azetidin-1-yl-6-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of EXAMPLE 81D (0.50 g) in methanol (100 mL) at reflux was treated with a 1M LiOH (50 mL), stirred for 3 hours then cooled, treated with 10% citric acid, and filtered. NMR (300 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.13 (s, 1H), 4.28 (m, 4H), 2.28 (m, 2H).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-efcb6b5d66dd4e0d824fd1ce41fb6ea4
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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