Ethyl Acetate → 4-i-Propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amide

HRID 10239

Reaktionsgleichung

Reaktionsgleichung von HRID 10239
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11](=[O:14])(=[O:13])[NH2:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[C:23]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:22](Cl)[N:21]=[C:20]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[N:19]=1.CCOC(C)=O>CN(C=O)C>[Cl:17][C:18]1[N:19]=[C:20]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[N:21]=[C:22]([NH:12][S:11](=[O:13])(=[O:14])[NH:10][C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[C:23]=1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 21041219Sulfamide, [4-(1-methylethyl)phenyl]-(9CI)

Produkt 1

HCID 102798684-i-Propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amideAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 4-i-propyl-phenyl sulfamic acid amide (642 mg; Referential Example 17) in DMF (9 ml) was added sodium hydride (250 mg). The mixture was warmed to 45° C. for 30 min. Then, 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (1.044 g) was added and the reaction mixture was stirred for 60 h at r.t. After acidic work up and chromatography over silicagel with Hex/EtOAc=2/5, 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-amide (0.42 g) can be isolated.

Quellen und Nachweise

ORD-Eintrag
ord-44158203bde3470ebd74d37d12d5fe1d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094781B2

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