Diisopropylethylamine → Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate

HRID 2233898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233898
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:10]([O:9][C:8]([NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:16]2[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=2)[CH2:6][CH2:5]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Produkt 1

HCID 59679281Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

tert-Butyl piperidin-4-ylcarbamate (4.5 g, 22 mmol), methyl 2-bromo-1,3-thiazole-5-carboxylate (5.0 g, 22 mmol), and diisopropylethylamine (3.8 ml, 22 mmol) were suspended in anhydrous DMF and heated to an external temperature of 130° C. for 1.5 hours. The DMF was removed and the solid was partitioned with EtOAc and water. The combined organic extracts were washed with brine, dried with MgSO4 and concentrated to a yellow solid (7.05 g, 94%).

Aufarbeitung

  1. customThe DMF was removed
  2. customthe solid was partitioned with EtOAc and water
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated to a yellow solid (7.05 g, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-0e670a2c090c46fc9d6661a58f2d55df
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709503B2

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