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 2270441Notes

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

Reaction notes

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