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

HRID 14720

Reaktionsgleichung

Reaktionsgleichung von HRID 14720
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.[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH2:39])=[CH:33][CH:32]=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:39][CH2:38][CH2:37][C:34]3[CH:35]=[CH:36][C:31]([CH3:40])=[CH:32][CH:33]=3)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Komponenten

3

Edukt 2

HCID 76751p-MethylphenethylamineHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 58603728N-(3-Amino-propyl)-N-{3-[2-(2-p-tolyl-ethylamino)-pyrimidin-4-yl]-benzyl}-methanesulfonamide

Versuchsvorschrift

Intermediate 4 was coupled to 2-p-tolyl-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 454. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 9.55 (br s, 1H) 8.1 (m, 2H) 7.6 (m, 4H) 7.2 (m, 4H) 4.4 (s, 2H) 3.81 (s, 2H) 3.37 (m, 2H) 2.97 (m, 4H) 2.94 (s, 3H) 2.25 (s, 3H) 1.75 (s, 2H) 1.69 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-97e838f45c2247fbaa9cd15fba817f7d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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