Potassium Carbonate → 2-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic Acid Tert-Butyl Ester

HRID 49976

Reaktionsgleichung

Reaktionsgleichung von HRID 49976
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O:14][C:15]([CH:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][N:22]2[C:10](=[O:11])[N:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[C:15](=[O:14])[CH:17]2[CH2:18]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanateHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

Produkt 1

HCID 224792022-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic Acid Tert-Butyl EsterAusbeute 136,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3,5-Dichlorophenyl isocyanate (2.85 g, 15.2 mmol) was added portionwise to a mixture of piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2.61 g, 10.1 mmol, prepared as described in Bioorg. Med. Chem. Lett. 1999, 9, 1121-6) and potassium carbonate (1.68 g, 12.1 mmol) in DCM (30 mL) at 5° C. After 30 min at 5° C., the reaction mixture was stirred at 20° C. for 48 h. The white precipitate was discarded and the filtrate concentrated in vacuo to give an oil (5.5 g) which was chromatographed over silica gel (CH2Cl2), to yield the above compound (2.77 g) as a white solid. Mp=144° C.

Aufarbeitung

  1. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e46489ca004e4266b9dcc6048fdf3da3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710064B2

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