P-Toluic Acid → N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-4-methyl-benzamide

HRID 2386347

Reaktionsgleichung

Reaktionsgleichung von HRID 2386347
[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].[CH3:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1>>[OH:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][NH:23][C:19]2[N:18]=[C:17]([C:13]3[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=3)[CH2:10][N:5]([S:6]([CH3:9])(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2][NH:1][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][C:34]([CH3:33])=[CH:35][CH:36]=3)[CH:22]=[CH:21][N:20]=2)=[CH:31][CH:30]=1

Komponenten

3

Edukt 2

HCID 7470P-Toluic AcidHCID 59341031N-(3-Amino-propyl)-N-(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Produkt 1

HCID 58603399N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-4-methyl-benzamide

Versuchsvorschrift

Compound 2 was coupled with 4-methylbenzoic acid following procedure K. LC-MS showed the product had the expected M+H+ of 574. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.0 (d, 2H) 7.65 (d, 2H) 7.50 (d, 2H) 7.2 (m, 3H) 7.0 (m, 3H), 6.7 (d, 2H), 4.4 (s, 2H), 3.45 (t, 2H), 3.2 (d, 4H), 3.0 (s, 3H) 2.7 (t, 2H), 2.45 (s, 3H), 1.8 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-67b26c0a2c2e4f66baeef14fd5e68146
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268822B2

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