1-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine → 4-({1-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}amino)-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2422019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422019
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.[Cl:19][C:20]1[C:21]([N:30]2[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]2)=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>CC#N>[Cl:19][C:20]1[C:21]([N:30]2[CH2:31][CH2:32][CH:33]([NH:36][C:2]3[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:34][CH2:35]2)=[N:22][CH:23]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:25]=1

Komponenten

4

Edukt 2

HCID 27961851-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amineHCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Produkt 1

HCID 115773414-({1-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}amino)-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.200 g, 0.700 mmol), TEA (0.106 g, 1.050 mmol) and 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine (0.294 g, 1.050 mmol) in MeCN (mL) was heated in a microwave reactor at 120° C. for 30 mins. The residue was purified by silica gel column chromatography (Horizons Biotage) using a 1:1 mixture of heptane and EtOAc as eluant, to give the title compound (0.344 g, 93%); 1H NMR (500 MHz, CDCl3): δ 8.34-8.33 (m, 1H), 7.74-7.72 (m, 1H), 7.57-7.54 (m, 2H), 7.49-7.46 (m, 3H), 5.27 (d, 1H), 4.47-4.39 (m, 1H), 3.85-3.78 (m, 2H), 3.24-3.14 (m 1H), 2.55-2.48 (m 2H), 1.82-1.76 (m 2H), 1.60 (d 6H), 1.56-1.48 (m 2H); 13C NMR (125 MHz, CDCl3): δ 160.0, 158.7, 143.1, 136.2, 134.5, 131.8, 130.2, 129.0, 125.3, 121.3, 120.6, 120.3, 107.1, 66.1, 50.3, 47.9, 47.4, 32.4, 20.4; Mass Spectrum: M−H+ 529.

Aufarbeitung

  1. customThe residue was purified by silica gel column chromatography (Horizons Biotage)
  2. additiona 1:1 mixture of heptane and EtOAc as eluant

Quellen und Nachweise

ORD-Eintrag
ord-48157fe623254e3f89f7fdbb1b5410b4
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960380B2

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