Sodium Hydroxide → sodium 4,4-dibutyl-2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-fluoro-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 2224810Notes

Reaction equation

HRID 2224810 reaction equation
[CH2:1]([C:5]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([OH:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[S:19](=[O:28])(=[O:27])[N:18]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].[OH-].[Na+:35]>C(#N)C>[CH2:1]([C:5]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([O-:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[S:19](=[O:27])(=[O:28])[N:18]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].[Na+:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1363846071,1-Dibutyl-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxynaphthalen-2(1h)-one

Product 1

HCID 68873348sodium 4,4-dibutyl-2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-fluoro-3-oxo-3,4-dihydronaphthalen-1-olateYield 104.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound of Example 18H (33 mg, 0.07 mmol) in acetonitrile (3 mL) and treated with sodium hydroxide solution (1.0 N, 10 μL, 0.07 mmol) followed by stirring at ambient temperature for 20 min. The solution was frozen and lyophilized to afford the title compound (36 mg, 70% overall yield) as a fluffy white solid. 1H NMR (300 MHz, DMSO-d6): 60.52 (d, J=6.25 Hz, 2 H) 0.66 (t, J=7.35 Hz, 6 H) 0.85 (m, 2 H) 1.04 (m, 4 H) 1.68 (m, 2 H) 2.11 (m, 2 H) 7.30 (m, 3 H) 7.53 (m, 2 H) 7.69 (m, 2 H) 15.31 (s, 1 H).

Workup

  1. temperatureThe solution was frozen

Sources & evidence

ORD record
ord-8fb56253aba84ac897311337d696a91d
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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