4-Chlorobenzoic Acid → 4-Chloro-N-{3-[(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-benzamide

HRID 14749

Reaktionsgleichung

Reaktionsgleichung von HRID 14749
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[N:18]=2)[CH:12]=1)[S:6]([CH3:9])(=[O:8])=[O:7].[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1>>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][C:26]4[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=4)[N:18]=3)[CH:12]=2)[S:6]([CH3:9])(=[O:8])=[O:7])=[O:39])=[CH:36][CH:35]=1

Komponenten

3

Edukt 2

HCID 63184-Chlorobenzoic AcidHCID 59341031N-(3-Amino-propyl)-N-(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Produkt 1

HCID 586036614-Chloro-N-{3-[(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-benzamide

Versuchsvorschrift

Compound 2 was coupled with 4-chlorobenzoic acid following procedure K. LC-MS showed the product had the expected M+H+ of 594. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.23 (d, 1H) 8.1 (d, 1H) 7.6 (d, 2H) 7.5 (d, 2H) 7.4 (m, 2H), 7.3 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 6.7 (d, 2H), 4.5 (s, 2H) 3.6 (t, 2H), 3.1 (d, 2H), δ 3.0 (s, 3H), 2.8 (t, 2H), δ 1.8 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-5a69559aec8f47adac56556f0a237860
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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