5-(2-Amino-ethyl)-2-(5-trifluoromethyl-pyridin-2-yloxy)benzonitrile → HCID 178509837, Verbindung

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Reaktionsgleichung

[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)=[C:8]([CH:11]=1)[C:9]#[N:10].CS[C:25]1[NH:26][CH:27]=[C:28]([CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[N:37][CH:38]=2)[C:29](=[O:31])[N:30]=1>C(O)C>[O:31]=[C:29]1[C:28]([CH2:32][C:33]2[CH:38]=[N:37][CH:36]=[N:35][CH:34]=2)=[CH:27][NH:26][C:25]([NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=3)=[C:8]([CH:11]=2)[C:9]#[N:10])=[N:30]1

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

5-(2-amino-ethyl)-2-(5-trifluoromethyl-pyridin-2-yloxy)benzonitrile (0.163 mmol, 1 eq) and 2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.065 mmol, 0.4 eq) were dissolved in dry ethanol (200 μL) and stirred at 125° C. overnight. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of MeOH in DCM: 0-15% in 20CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 5-[2-(4-oxo-5-pyrimidin-5-ylmethyl-1,4-dihydro-pyrimidin-2-ylamino)-ethyl]-2-(5-trifluoromethyl-pyridin-2-yloxy)benzonitrile (0.028 mmol, yield: 17%, HPLC-MS/UV: [M+H]+=494.17; rt: 9.91 mins; purity: 91%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.98 (t, J=6.57, 2H), 3.52-3.75 (m, 4H), 5.31 (br.s., 1H), 7.12-7.30 (m, 3H), 7.48-7.56 (m, 1H), 7.57-7.62 (m, 1H), 7.71 (s, 1H), 7.98 (dd, J=8.40, J=2.55, 1H), 8.57-5.69 (m, 2H), 9.04 (s, 1H), 11.80 (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-b54ec37da0184fea9384d598d12f932f
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08637536B2

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