4-(Piperidin-1-yl)aniline → 2-Isopropyl-5-phenyl-4-[(4-piperidin-1-ylphenyl)amino]isothiazol-3(2H)-one 1,1-dioxide

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Reaktionsgleichung

Cl[C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:19]1([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CC#N>[CH:15]([N:4]1[C:3](=[O:18])[C:2]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:30][CH:29]=2)=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:5]1(=[O:14])=[O:13])([CH3:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 4-chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.525 mmol), (4-piperidin-1-ylphenyl)amine (0.093 g, 0.525 mmol) and TEA (0.053 g, 0.525 mmol) in MeCN (2 ml) was heated in a microwave at 160° C. for 30 mins. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography using 30% EtOAc in hexane as eluent, to give the title compound (0.169 g, 76%). 1H NMR (500 MHz CDCl3): δ 7.24-7.16 (m, 1H), 7.16-7.08 (m, 5H), 6.58 (d, 2H), 6.54 (d, 2H), 4.56-4.44 (m, 1H), 3.03 (t, 4H), 1.70-1.61 (m, 10H), 1.61-52(m, 3H); 13C NMR (125 MHz CDCl3): δ 159.2, 150.1, 131.1, 129.6, 128.8, 128.1, 127.6, 125.3, 123.6, 116.3, 109.3, 51.1, 47.9, 25.7, 24.4, 20.5; Mass Spectrum: M+H 426.

Aufarbeitung

customThe reaction mixture was evaporated
customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-5bf8df7c986b4f649e6e94c6b1802f4f
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07582629B2

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