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

HRID 18933

Reaktionsgleichung

Reaktionsgleichung von HRID 18933
[C:1]([C:5]1[NH:9][C:8]([C:10]([OH:12])=O)=[C:7]([N+:13]([O-:15])=[O:14])[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].CCN(C(C)C)C(C)C>ClCCl>[C:1]([C:5]1[NH:9][C:8]([C:10]([N:28]2[CH2:27][CH2:26][NH:25][C:24](=[O:29])[C:23]2([CH3:30])[CH3:22])=[O:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 2111572-Piperazinone, 3,3-dimethyl-HCID 183223915-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid

Produkt 1

HCID 586792724-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-oneAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

The previously prepared 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid (0.203 g, 1.11 mmol) and PCl5 (0.232 g, 1.11 mmol) were dissolved in dichloromethane (4 mL) and stirred at room temperature for 5 minutes. The resulting solution was added in one portion to a solution of 3,3-dimethylpiperazin-2-one (0.214 g, 1.67 mmol) and DIEA (0.288 g, 2.23 mmol) in dichloromethane (3 mL) and stirred at room temperature for 5 minutes. The reaction mixture was diluted with dichloromethane and washed sequentially with 1N aqueous HCl, saturated sodium bicarbonate, dried and the solvent removed under vacuum. The crude product was purified by chromatographic column (silica gel, dichloromethane:methanol, 95:5) to afford 0.190 g of expected 4-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one.

Aufarbeitung

  1. stirringstirred at room temperature for 5 minutes
  2. washwashed sequentially with 1N aqueous HCl, saturated sodium bicarbonate
  3. customdried
  4. customthe solvent removed under vacuum
  5. customThe crude product was purified by chromatographic column (silica gel, dichloromethane:methanol, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-322741f3750e433294754e2aba2b83fd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

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