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

HRID 1696942Notes

Reaction equation

HRID 1696942 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[C:25]#[N:26])[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[C:25]#[N:26])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67274868Ethyl 7-azetidin-1-yl-6-cyano-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 103557547-Azetidin-1-yl-6-cyano-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of EXAMPLE 83A (0.38 g) in methanol (100 mL) was treated with 1M LiOH (50 mL), stirred for 18 hours, treated with 10% citric acid, and filtered. NMR (300 MHz, DMSO-d6) δ 14.83 (s, 1H), 13.27 (br s, 1H), 8.67 (s, 1H), 8.48 (s, 1H), 4.43 (br s, 4H), 2.40 (m, 2H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-c6421dd37b944da38ae9d638265eb79a
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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