2,7-Diaza-spiro[4.4]nonane → 1-Ethyl-6-fluoro-1,4-dihydro-7-(2,7-diazaspiro[4.4]non-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Hydrochloride

HRID 868046Notes

Reaction equation

HRID 868046 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([Cl:13])[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[CH2:19]1[C:23]2([CH2:27][CH2:26][NH:25][CH2:24]2)[CH2:22][CH2:21][NH:20]1>C(#N)C>[ClH:13].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:20]3[CH2:21][CH2:22][C:23]4([CH2:27][CH2:26][NH:25][CH2:24]4)[CH2:19]3)[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 126918832,7-Diaza-spiro[4.4]nonaneHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 137727291-Ethyl-6-fluoro-1,4-dihydro-7-(2,7-diazaspiro[4.4]non-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid HydrochlorideYield 33.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of of 1.10 g (4.00 mmol) 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid in 40 ml acetonitrile was treated with 1.10 g (8.7 mmol) 2,7-diazaspiro[4.4]nonane and the mixture was stirred at room temperature 4.5 hours. A crude solid was filtered, stirred with 10 ml water, filtered, dissolved in 100 ml 6M ammonium hydroxide and lyophilized to afford 0.53 g of solid. This was dissolved in dilute hydrochloric acid, filtered, lyophilized and crystallized from ethanol-water to give 0.26 g of the title compound, mp >300° C. Analysis calcualted for C18H22N4ClFO3 : C, 54,47; H, 5.59; N, 14.12; Cl, 8.94. Found: C, 54.14; H, 5.60, N, 13.85; Cl, 8.68.

Workup

  1. filtrationA crude solid was filtered
  2. stirringstirred with 10 ml water
  3. filtrationfiltered
  4. dissolutiondissolved in 100 ml 6M ammonium hydroxide

Sources & evidence

ORD record
ord-9671a719289a419bb9520d950ac48977
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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