1-Butanol → N-((8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methyl)-9H-purin-6-amine

HRID 216827

Reaktionsgleichung

Reaktionsgleichung von HRID 216827
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[C:8]([CH2:21][NH2:22])=[CH:7]2.Br[C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[NH:26][CH:27]=[N:28]2.C(O)CCC>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[C:8]([CH2:21][NH:22][C:24]1[N:32]=[CH:31][N:30]=[C:29]3[C:25]=1[N:26]=[CH:27][NH:28]3)=[CH:7]2

Komponenten

4

Edukt 3

HCID 2631-ButanolHCID 5287830Purine, 6-bromo-HCID 57707949(8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methanamine

Produkt 1

HCID 178491795N-((8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methyl)-9H-purin-6-amine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred mixture of (8-chloro-2-(5-fluoro-2-methoxyphenyl)quinolin-3 yl)-methanamine (190.4 mg, 0.601 mmol) and 6-bromopurine (126 mg, 0.631 mmol) in 1-butanol (3.300 mL, 36.1 mmol) was added N,N-ethyldiisopropylamine (0.209 mL, 1.20 mmol). The mixture was heated to 100° C. overnight. The solvents were removed and the residue subjected to chromatography: gradient/isocratic 1H NMR (500 MHz, DMSO-d6) δ ppm 12.93 (1H, br. s.), 8.28 (1H, br. s.), 8.09 (2H, s), 7.96 (1H, d, J=8.1 Hz), 7.91 (1H, d, J=7.3 Hz), 7.55 (1H, t, J=7.8 Hz), 7.26-7.33 (1H, m), 7.21 (1H, dd, J=8.6, 3.2 Hz), 7.15 (1H, br. s.), 3.77 (3H, s), 3.32 (2H, s) Mass Spectrum (ESI) m/e=335.1 (M+1).

Aufarbeitung

  1. customThe solvents were removed

Quellen und Nachweise

ORD-Eintrag
ord-531e38ec3d8d415c867356ecbb7b2d69
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193199B2

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