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 494489Notes

Reaction equation

HRID 494489 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): δ 0.52 (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-dee5685ea2104505be4b84cc601c8099
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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