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 2224942Notes

Reaction equation

HRID 2224942 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, 1 H) 0.65 (d, J=6.62 Hz, 3 H) 0.67 m, 3 H) 0.75 (m, 1 H) 1.26 (m, 1H) 1.34 (s, 3 H) 1.69 m, 1 H) 2.10 m, 1 H) 7.12 m, 2 H) 7.23 (s, 1 H) 7.29 (m, 1 H) 7.44 m, 2 H) 7.64 m, 2 H) 7.74 m, 1 H) 8.00 (d, J=7.72 Hz, 1 H) 8.07 (d, J=7.72 Hz, 1 H) 8.16 (d, J=7.35 Hz, 1 H) 8.20 m, 1 H) 8.76 (s, 1 H) 10.82 (s, 1 H) 15.39 (s, 1 H). 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-16f412d21a9f4a84abdc4f189beec250
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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