2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178516535, Verbindung

HRID 474746

Reaktionsgleichung

Reaktionsgleichung von HRID 474746
CS[C:3]1[NH:4][CH:5]=[CH:6][C:7](=[O:9])[N:8]=1.[Cl:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=2)=[CH:13][C:12]=1[C:27]([F:30])([F:29])[F:28]>N1C=CC=CC=1>[Cl:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:3]3[NH:4][CH:5]=[CH:6][C:7](=[O:9])[N:8]=3)=[CH:18][CH:17]=2)=[CH:13][C:12]=1[C:27]([F:28])([F:29])[F:30]

Komponenten

4

Edukt 2

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178418670HCID 178418670, Verbindung

Produkt 1

HCID 178516535HCID 178516535, VerbindungAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Methylsulfanyl-1H-pyrimidin-4-one (70 mg, 0.492 mmol, 1.41 eq) and 2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (110 mg, 0.348 mmol, 1 eq) were heated in a sealed vial at 150° C. in 400 μl of dry pyridine for 16 hours. Solvent was then evaporated and the resulting crude was purified by chromatography on BIOTAGE SP1 purification device using 10 g normal phase silica SNAP column and DCM/30% MeOH in DCM solvent system (gradient 2-20% of 30% MeOH in DCM in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and the resulting crude was triturated with diisopropyl ether and cyclohexane to afford 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1H-pyrimidin-4-one (111 mg, yield=73.8%, purity=95%) as a white powder. MS: [M+H]+=410.33 1H NMR (300 MHz; CDCl3) δ/ppm 2.92 (t, J=6.95 Hz, 2H), 3.61-3.72 (m, 2H), 5.59 (d, J=6.38 Hz, 1H), 6.18 (br.s, 1H), 6.95 (d, J=8.51 Hz, 2H), 7.03 (dd, J=9.07 Hz, J=2.69 Hz, 1H), 7.24 (d, J=8.51 Hz, 1H), 7.30 (d, J=2.69 Hz, 1H), 7.41 (d, J=8.80 Hz, 1H), 7.77 (d, J=6.38 Hz, 1H), 11.77 (br.s, 1H)

Aufarbeitung

  1. customSolvent was then evaporated
  2. customthe resulting crude was purified by chromatography on BIOTAGE SP1 purification device
  3. customSolvent from the gathered fractions of appropriate composition was evaporated
  4. customthe resulting crude was triturated with diisopropyl ether and cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-ea525f3c52bd47e6a25880ecd692631f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

Verknüpfte Notizen

Wird geladen…