Sodium Hydroxide → Sodium (4r)-4-methyl-4-(3-methylbutyl)-2-{7-[(1-naphthylsulfonyl)amino]-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl}-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 494622Notes

Reaction equation

HRID 494622 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:44])(=[O:43])[N:20]=1.[OH-].[Na+:46]>O>[CH3:17][C@@:5]1([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O-:1])=[C:3]([C:19]2[NH:24][C:23]3[CH:25]=[CH:26][C:27]([NH:29][S:30]([C:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[CH:36]=[CH:35][CH:34]=4)(=[O:32])=[O:31])=[CH:28][C:22]=3[S:21](=[O:44])(=[O:43])[N:20]=2)[C:4]1=[O:18].[Na+:46]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136384722n-{3-[(4r)-1-Hydroxy-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-yl}naphthalene-1-sulfonamide

Product 1

HCID 131726901Sodium (4r)-4-methyl-4-(3-methylbutyl)-2-{7-[(1-naphthylsulfonyl)amino]-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl}-3-oxo-3,4-dihydronaphthalen-1-olateYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 105A (30.0 mg, 0.048 mmol) and 0.998 M sodium hydroxide (0.048 mL, 0.048 mmol) in water (3 mL) was stirred at rt for 16 h. The reaction mixture was concentrated in vacuo to give the title compound (21 mg, 68% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.40 (m, 1H) 0.65 (d, J=6.62 Hz, 3H) 0.67 (m, 3H) 0.75 (m, 1H) 1.26 (m, 1H) 1.34 (s, 3H) 1.69 (m, 1H) 2.10 (m, 1H) 7.12 (m, 2H) 7.23 (s, 1H) 7.29 (m, 1H) 7.44 (m, 2H) 7.64 (m, 2H) 7.74 (m, 1H) 8.00 (d, J=7.72 Hz, 1H) 8.07 (d, J=7.72 Hz, 1H) 8.16 (d, J=7.35 Hz, 1H) 8.20 (m, 1H) 8.76 (s, 1H) 10.82 (s, 1H) 15.39 (s, 1H). MS (ESI+) m/z 652.0 (M+H)+, 630.0 (M+H−Na)+, 647 (M−Na+NH4)+, (ESI−) m/z 628.0 (M−H−Na)−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e698f2fdbf284ff7b588e4319fa7b9f4
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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