Diisopropylethylamine → 3-{3-[5-(3-Methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

HRID 1093017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093017
Br.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH3:18])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][N:34]=[C:35]=[O:36])[CH3:29]>C(Cl)Cl>[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][NH:34][C:35]([NH:17][C:15]1[S:16][C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)=[C:13]([CH3:18])[N:14]=1)=[O:36])[CH3:29]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733373Ethyl 3-isocyanatopropanoateHCID 865984455-(3-Methanesulphonyl-phenyl)-4-methyl-thiazol-2-ylamine hydrobromide

Produkt 1

HCID 865984473-{3-[5-(3-Methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A stirred suspension of 5-(3-methanesulphonyl-phenyl)-4-methyl-thiazol-2-ylamine hydrobromide (176d) (0.172 g, 0.64 mmol) in DCM (15 ml) is treated with Hunigs base (0.45 ml, 2.36 mmol) followed by ethyl-3-isocyanatopropionate (0.092 g, 0.64 mmol). The reaction mixture is stirred and heated to 60° C. for 10 hours and then the solvent in removed in vacuo. The product is purified by chromatography on silica to give the titled compound

Aufarbeitung

  1. customthe solvent in removed in vacuo
  2. customThe product is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-1430622135274d8fb67aef7f7a20392c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129541B2

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