Diisopropylethylamine → Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

HRID 871928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871928
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[S:9][CH:10]=1)=[O:5])[CH3:2].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>O1CCOCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

Produkt 1

HCID 53418800Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-thiazole-4-carboxylic acid ethyl ester (1.4 g, 5.93 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.16 g, 1.05 eq.) and DIPEA (1.15 g, 1.5 eq.) in 1,4-dioxane (20 mL) was heated to reflux overnight. After cooling, the solvent was removed in vacuo. The crude product was purified on silica gel (EtOAc:hexanes=1:4) to afford the desired product as a pale yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified on silica gel (EtOAc:hexanes=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-6a56e760261842b5aa74caba15aa1288
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975258B2

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