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

HRID 2270442Notes

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][N:17]3[C:21]4[C:22](=O)[CH2:23][N:24]([CH3:28])[S:25](=[O:27])(=[O:26])[C:20]=4[CH:19]=[CH:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32]>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][N:17]3[C:21]4[C:22](=[N:31][OH:32])[CH2:23][N:24]([CH3:28])[S:25](=[O:27])(=[O:26])[C:20]=4[CH:19]=[CH:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 168 mg (0.4 mmol) of Compound 25 and 111 mg (1.6 mmol) of hydroxylamine hydrochloride in 10 ml of pyridine was stirred for 21 hours over an oil bath of 60° C. Post-treatment was conducted in a similar manner as in Example 18. The residue was purified by chromatography on a silica gel column (eluent:methanol/chloroform=1/99), whereby 144 mg of the title compound were obtained (yield: 83%).

Workup

customThe residue was purified by chromatography on a silica gel column (eluent:methanol/chloroform=1/99)

Sources & evidence

ORD record: ord-cd190ca3a79748178c582e45200bddc5
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331623B1

Reaction notes

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