Phenylmethanesulfonyl chloride → N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-C-phenyl-methanesulfonamide

HRID 14780

Reaktionsgleichung

Reaktionsgleichung von HRID 14780
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:24]1([CH2:30][S:31](Cl)(=[O:33])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][NH:14][C:10]2[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:31]([CH2:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:33])=[O:32])[CH:7]=[CH:6][CH:5]=3)[CH:13]=[CH:12][N:11]=2)=[CH:22][CH:21]=1

Komponenten

3

Edukt 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 670450394-{2-[4-(3-Amino-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Produkt 1

HCID 58603715N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-C-phenyl-methanesulfonamide

Versuchsvorschrift

Intermediate 24 was coupled with phenyl-methylsulfonyl chloride following procedure D. LC-MS showed the product had the expected M+H+ of 461. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.4 (d, 1H), 8.0 (d, 1H) 7.8 (d, 1H) 7.5 (t, 2H), 7.3 (m, 4H), 7.1 (d, 2H), 7.0 (d, 2H), 6.9 (d, 2H), 4.5 (s, 2H), 3.5 (t, 2H), δ 2.8 (t, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-61324c2fcf2c4fb6a1bfe17b3987314f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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