2-[4-(3-Chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine → HCID 178432721, Verbindung

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH2:14])=[CH:8][CH:7]=1.[CH3:22][C:23]1[N:28]=[CH:27][C:26]([CH2:29][C:30]2[C:31](=[O:38])[N:32]=[C:33](SC)[NH:34][CH:35]=2)=[CH:25][N:24]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]([F:19])([F:20])[F:21])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH:14][C:33]2[NH:34][CH:35]=[C:30]([CH2:29][C:26]3[CH:27]=[N:28][C:23]([CH3:22])=[N:24][CH:25]=3)[C:31](=[O:38])[N:32]=2)=[CH:8][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine (0.317 mmol, 1.01 eq) and 5-(2-methyl-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.322 mmol, 1 eq) were dissolved in dry ethanol (300 μL) and stirred at 125° C. for 50 hours. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of MeOH in DCM: 0-10% in 25CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 2-{2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]ethylamino}-5-(2-methyl-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (0.145 mmol, yield: 44%, HPLC-MS/UV:[M+H]+=517.97; rt: 11.53 mins; purity: 90%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.65 (s, 3H), 2.92 (t, J=6.57, 2H), 3.53 (s, 2H), 3.57-3.69 (m, 2H), 5.39 (br.s., 1H), 7.01 (d, J=8.69, 1H), 7.08 (d, J=8.50 2H), 7.27-7.31 (m, 2H), 7.66 (s, 1H), 7.89 (dd, J=9.58, J=2.73, 1H), 8.36-8.42 (m, 1H), 8.51 (s, 2H), 11.21 (br.s., 1H)

Aufarbeitung

customSolvent was evaporated
customcrude product was purified on Biotage SP1 Snap Si 10
customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-28cdd47fdf0c470897e69d6af3d1280a
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08637536B2

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