Sodium Hydroxide → sodium 2-{7-[(aminosulfonyl)amino]-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl}-7-fluoro-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-1-olate

HRID 2224806Notes

Reaction equation

HRID 2224806 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:34][CH2:35][CH3:36])([CH2:31][CH2:32][CH3:33])[C:7](=[O:30])[C:8]([C:13]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([NH:23][S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][C:16]=4[S:15](=[O:29])(=[O:28])[N:14]=3)=[C:9]2[OH:12])=[CH:4][CH:3]=1.[OH-].[Na+:38]>C(#N)C>[NH2:27][S:24]([NH:23][C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:13]([C:8]3[C:7](=[O:30])[C:6]([CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH3:36])[C:5]4[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)[C:9]=3[O-:12])=[N:14][S:15](=[O:29])(=[O:28])[C:16]=2[CH:22]=1)(=[O:25])=[O:26].[Na+:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136337523N-[3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]sulfamide

Product 1

HCID 68874514sodium 2-{7-[(aminosulfonyl)amino]-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl}-7-fluoro-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-1-olateYield 94.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Example 17E (13 mg) was dissolved in acetonitrile (1 mL) and treated with sodium hydroxide solution (1.0 N, 24.3 μL, 0.0243 mmol). After stirring for 30 min, the solution was frozen and lyophilized to afford the title compound as a fluffy grey solid (12.8 mg, 55% overall). 1H NMR (300 MHz, DMSO-d6): δ 0.65 (m, 8 H) 0.86 (d, J=2.94 Hz, 2 H) 1.65 (d, J=3.68 Hz, 2 H) 2.05 (m, 2 H) 7.43 (m, 6 H) 9.58 (s, 1 H) 15.21 (s, 1 H).

Workup

  1. temperaturethe solution was frozen

Sources & evidence

ORD record
ord-0ab8975cec504bbf8402698749db9a5a
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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