Diethylamine → 4-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one

HRID 18936

Reaktionsgleichung

Reaktionsgleichung von HRID 18936
[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([OH:15])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:22][C:23]1([CH3:30])[NH:28][CH2:27][CH2:26][NH:25][C:24]1=[O:29].C(NCC)C.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.ClCCl>[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([N:28]2[CH2:27][CH2:26][NH:25][C:24](=[O:29])[C:23]2([CH3:30])[CH3:22])=[O:15])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 8021DiethylamineHCID 24819Phosphorus pentachloride2×HCID 2111572-Piperazinone, 3,3-dimethyl-HCID 516892Sodium BicarbonateHCID 586792985-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid

Produkt 1

HCID 586793674-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 5-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid (100 mg, 0.47 mmol) in benzene (2 mL) was added solid PCl5 (120 mg, 0.57 mmol). The resulting reaction mixture was stirred at RT until all the PCl5 went into the solution. This reaction mixture was then added to 3,3-dimethylpiperazin-2-one (120 mg, 0.94 mmol) and diethylamine (280 ml, 0.94 mmol) in dichloromethane (DCM) (3 mL). After 30 min, the reaction was diluted with DCM (10 mL) and followed by addition of sat. NaHCO3. The organic phase was then washed with 1N HCl and brine, dried, and concentrated in vacuo. This crude product was further purified using flash chromatography (EtOAc/Hexane: 1/4) to provide 4-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one 6 (74 mg, 49%) as yellow foam.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic phase was then washed with 1N HCl and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThis crude product was further purified

Quellen und Nachweise

ORD-Eintrag
ord-f5ad1f4198a44773b190983f0e144bdc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

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