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 351981Notes

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

Participants

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

customPost-treatment and purification

Sources & evidence

ORD record: ord-016961760d41441a8fe63bbae69f9511
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743913B2

Reaction notes

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