Sodium Iodide → 5-[4-[4-(4-Fluorobenzoyl)piperidino]-butyl]-4-hydroxyimino-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazine 1,1-dioxide

HRID 351979Notes

Reaction equation

HRID 351979 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11](=[N:18][OH:19])[CH2:12][N:13]([CH3:17])[S:14](=[O:16])(=[O:15])[C:9]=2[CH:8]=[CH:7]1.Cl.[F:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>C(#N)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10]4[C:11](=[N:18][OH:19])[CH2:12][N:13]([CH3:17])[S:14](=[O:16])(=[O:15])[C:9]=4[CH:8]=[CH:7]3)[CH2:30][CH2:29]2)=[O:27])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 739931405-(4-Chlorobutyl)-4-hydroxyimino-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazine 1,1-dioxide

Product 1

HCID 749532685-[4-[4-(4-Fluorobenzoyl)piperidino]-butyl]-4-hydroxyimino-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazine 1,1-dioxideYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 61 mg (0.2 mmol) of Compound 20, 54 mg (0.22 mmol) of 4-(4-fluorobenzoyl)piperidine hydrochloride, 74 mg (0.88 mmol) of sodium hydrogencarbonate and 66 mg (0.44 mmol) of sodium iodide in 10 ml of acetonitrile was refluxed for 29 hours. Post-treatment and purification were conducted in a similar manner as in Example 20, whereby 75 mg of the title compound were obtained (yield: 79%).

Workup

  1. temperaturewas refluxed for 29 hours
  2. customPost-treatment and purification

Sources & evidence

ORD record
ord-3bb12653c6b541c6bbc320ed4f7a8c3c
Source dataset
uspto-grants-2004_06
Patent number
US06743913B2

Reaction notes

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