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Hydroxyamine hydrochloride → 5-[4-[4-(4-Fluorophenyl)piperazin-1-yl]butyl]4-hydroxyimino-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazine 1,1-dioxide

HRID 2270441
Notes
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Reaction equation

HRID 2270441 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[C:23](=O)[CH2:24][N:25]([CH3:29])[S:26](=[O:28])(=[O:27])[C:21]=4[CH:20]=[CH:19]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:32][OH:33]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[C:23](=[N:32][OH:33])[CH2:24][N:25]([CH3:29])[S:26](=[O:28])(=[O:27])[C:21]=4[CH:20]=[CH:19]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 99107965-[4-[4-(4-Fluorophenyl)piperazin-1-yl]butyl]-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide

Product 1

HCID 726119995-[4-[4-(4-Fluorophenyl)piperazin-1-yl]butyl]4-hydroxyimino-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazine 1,1-dioxideYield 88.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 174 mg (0.4 mmol) of Compound 23 and 111 mg (1.6 mmol) of hydroxylamine hydrochloride in 10 ml of pyridine was stirred for 24 hours over an oil bath of 80° C. Post-treatment and purification were conducted in a similar manner as in Example 21, whereby 159 mg of the title compound were obtained (yield: 88%).

Workup

  1. customPost-treatment and purification

Sources & evidence

ORD record
ord-e419b59dc9f14c3a8cefb7fb03bba9d7
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06331623B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes