p-Fluorophenethylamine → N-(3-Amino-propyl)-N-(3-{2-[2-(4-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

HRID 14715

Reaktionsgleichung

Reaktionsgleichung von HRID 14715
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][NH2:40])=[CH:34][CH:33]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:40][CH2:39][CH2:38][C:35]3[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=3)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Komponenten

3

Edukt 2

HCID 4653p-FluorophenethylamineHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 58603411N-(3-Amino-propyl)-N-(3-{2-[2-(4-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Versuchsvorschrift

Intermediate 4 was coupled with 2-(4-fluoro-phenyl)-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 458. 1H NMR (Varian 300 MHz, CDCl3—CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.1 (m, 3H) 7.7 (m, 1H) 7.5 (m, 2H) 7.2 (m, 2H) 6.9 (m, 2H) 4.5 (s, 2H) 3.8 (m, 2H) 3.7 (m, 1H) 3.4 (m, 2H) 2.9 (m, 7H) 1.9 (s, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-9282f1aa0d264342b2c2b408a556e924
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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