tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-bromothiazole-4-carbonyl)piperazine-1-carboxylate

HRID 875947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875947
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[O:9])[N:6]=1

Komponenten

5

Edukt 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 58299784Tert-butyl 4-(2-bromothiazole-4-carbonyl)piperazine-1-carboxylateAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

2-bromothiazole-4-carboxylic acid (1.31 g, 6.3 mmol) was combined with tert-butyl piperazine-1-carboxylate (1.2 g, 6.3 mmol) in DCM (15 mL), and then stirred at 20° C. until it formed a clear solution. N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.2 g, 6.3 mmol) was then added, and the reaction was stirred at 20° C. for 2 hours. The reaction was concentrated in vacuum, before transferring it to a separation funnel with ethyl acetate. The organic layer was washed with saturated NaHCO3, water, NH4Cl, and then with brine. After drying the organic layer with MgSO4, it was concentrated in vacuum to yield compound 72 (2.2 g, 91%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.16 (1H, s), 3.61 (4H, m), 3.38 (4H, m), 1.42 (9H, s) ppm; LCMS-ESI (POS), M/Z, M+1−C3H9: Found 320.0.

Aufarbeitung

  1. customformed a clear solution
  2. stirringthe reaction was stirred at 20° C. for 2 hours
  3. concentrationThe reaction was concentrated in vacuum
  4. washThe organic layer was washed with saturated NaHCO3, water, NH4Cl
  5. dry with materialAfter drying the organic layer with MgSO4, it
  6. concentrationwas concentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2154549b26b14482bfd0050cfbf9bf59
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980903B2

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