1-Phenylpiperazinium chloride → (S)-3-((4-phenylpiperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

HRID 2077848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2077848
Cl.[C:2]1([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].C(C[P+](C)(C)C)#N.O[CH2:23][C:24]1[CH:33]=[N:32][C:31]2[N:30]3[CH2:34][CH2:35][CH2:36][C@H:29]3[C:28](=[O:37])[NH:27][C:26]=2[CH:25]=1.CCN(C(C)C)C(C)C>C(#N)CC>[C:2]1([N:8]2[CH2:13][CH2:12][N:11]([CH2:23][C:24]3[CH:33]=[N:32][C:31]4[N:30]5[CH2:34][CH2:35][CH2:36][C@H:29]5[C:28](=[O:37])[NH:27][C:26]=4[CH:25]=3)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 751641-Phenylpiperazinium chlorideHCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 58324378(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

Produkt 1

HCID 46864922(S)-3-((4-phenylpiperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-oneAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1-Phenylpiperazine hydrochloride (11.9 mg, 0.060 mmol), (cyanomethyl)trimethylphosphonium iodide (0.025 g, 0.102 mmoles), and (S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (0.014 g, 0.063 mmoles) were diluted with propionitrile (0.5 ml) and treated with DIPEA (0.017 ml, 0.100 mmol). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was washed with water (1 mL) and concentrated. The residue was dissolved in DMSO (1 mL) and purified using HPLC (acetonitrile-water, NH4HCO3 buffered). The fractions were concentrated in vacuo, dissolved in dioxane-water (1:1, 2 mL) and lyophilized to yield the title compound as a white solid (5.1 mg, 23%). [M+H] calc'd for C21H25N5O 364; found, 364.

Aufarbeitung

  1. washThe reaction mixture was washed with water (1 mL)
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DMSO (1 mL)
  4. custompurified
  5. concentrationThe fractions were concentrated in vacuo
  6. dissolutiondissolved in dioxane-water (1:1, 2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-f07ee3ab1fe049f48b163d816a69111f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928105B2

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