2-(4-Aminophenyl)ethylamine → N-(3-{2-[2-(4-Amino-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-(3-amino-propyl)-methanesulfonamide

Reaktionsgleichung

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

Komponenten

Edukt 3

HCID 728952-(4-Aminophenyl)ethylamine

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

HCID 88519945methanol-d4 CDCl3

Produkt 1

HCID 58603635N-(3-{2-[2-(4-Amino-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-(3-amino-propyl)-methanesulfonamide

Versuchsvorschrift

Intermediate 4 from above was coupled with 4-(2-Amino-ethyl)-phenylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 455. CDCl3—CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.1 (m, 2H) 7.9 (d, 1H) 7.5 (d, 1H) 7.4 (m, 1H) 7.2 (m, 3H) 7.1 (d, 2H) 4.4 (s, 2H) 3.7 (m, 2H) 3.2 (m, 4H) 2.9 (m, 2H) 2.8 (s, 3H) 2.6 (m, 2H) 1.6 (m, 2H).