Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 32847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32847
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][CH3:19].O1CCCC1>S(Cl)(Cl)=O.CO>[CH3:17][N:18]([CH3:19])[C:14]([C:12]1[N:13]=[C:9]([NH2:8])[S:10][CH:11]=1)=[O:16].[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:18]([CH3:19])[CH3:17])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

Produkt 2

HCID 545942972-amino-N,N-dimethyl-1,3-thiazole-4-carboxamideHCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl esterAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Amino-thiazole-4-carboxylic acid dimethylamide was prepared as follows. (1) A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (0.5 g, 2 mmol) (prepared as described in Examples 4a and 4b) in thionyl chloride (10 mL) was heated at reflux (80° C.) for 2 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added a 2 M solution of dimethylamine in tetrahydrofuran (10 mL, 20 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 20 hours and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a yellow foam (0.26 g, 48%).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography over silica gel
  4. washeluted with 2:1 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fee1464fa8e24b5288cdc61705cefdd9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427635B2

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