Hydrochloric Acid → (1R)-3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methyl-1-(3-methylbutyl)naphthalen-2(1 H)-one hydrochloride

HRID 2224879Notes

Reaction equation

HRID 2224879 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:37]=[CH:36][C:11]2[NH:12][C:13]([C:18]3[C:27](=[O:28])[C@:26]([CH3:34])([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]=3[OH:35])=[N:14][S:15](=[O:17])(=[O:16])[C:10]=2[CH:9]=1)(C)(C)C.[ClH:39]>O1CCOCC1>[ClH:39].[NH2:7][C:8]1[CH:37]=[CH:36][C:11]2[NH:12][C:13]([C:18]3[C:27](=[O:28])[C@:26]([CH3:34])([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:25]4[C:20]([C:19]=3[OH:35])=[CH:21][CH:22]=[CH:23][CH:24]=4)=[N:14][S:15](=[O:17])(=[O:16])[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135869452Tert-butyl 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-ylcarbamate

Product 1

HCID 135869462(1R)-3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methyl-1-(3-methylbutyl)naphthalen-2(1 H)-one hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 39G (0.713 g, 1.32 mmol) in 4M hydrochloric acid in 1,4-dioxane (10 mL) was stirred at 25° C. for 1 hour. The solution was concentrated in vacuo and the residue was triturated in diethyl ether to give the title compound (0.537 g, 85%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.42 m, 1 H) 0.74 m, 7 H) 1.32 m, 1 H) 1.58 (m, 3 H) 2.15 m, 2 H) 7.07 m, 2 H) 7.51 m, 2 H) 7.77 m, 2 H) 8.16 m, 1 H) 13.57 (m, 1 H). MS (ESI−) m/z 438 (M−H)−.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-3287589d15d54b898a3fccee222700d7
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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