Diisopropylethylamine → (S)-N-ethyl-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

HRID 2077875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2077875
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]3[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=1.[I-].C(C[P+](C)(C)C)#N.CCN(C(C)C)C(C)C.[CH2:35]([NH:37][C:38](=[O:51])[C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1)[CH3:36]>>[CH2:35]([NH:37][C:38](=[O:51])[C:39]1[CH:40]=[CH:41][C:42]([N:45]2[CH2:46][CH2:47][N:48]([CH2:2][C:3]3[CH:12]=[N:11][C:10]4[N:9]5[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]5[C:7](=[O:17])[NH:6][C:5]=4[CH:4]=3)[CH2:49][CH2:50]2)=[CH:43][CH:44]=1)[CH3:36]

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 58324368(S)-3-(hydroxymethyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-6(6aH)-one

Produkt 1

HCID 58324394(S)-N-ethyl-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of (S)-3-(hydroxymethyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-6(6aH)-one (800 mg, 3.43 mmol) was added (cyanomethyl)trimethylphosphonium iodide (1000 mg, 4.12 mmol) and DIEA (1797 μl, 10.29 mmol) and N-ethyl-4-(piperazin-1-yl)benzamide (800 mg, 3.43 mmol)). The vial was heated to 90° C. for 16 hours. The crude reaction was cooled to RT and filtered. The resulting solid were collected and suspended in EtOH (24 mL), heated to reflux, then cooled to RT and filtered. The resulting material was rinsed with EtOH to give a white solid.

Aufarbeitung

  1. customThe crude reaction
  2. temperaturewas cooled to RT
  3. filtrationfiltered
  4. customThe resulting solid were collected
  5. temperatureheated
  6. temperatureto reflux
  7. temperaturecooled to RT
  8. filtrationfiltered
  9. washThe resulting material was rinsed with EtOH
  10. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f9b3d37094cb4096ba2906c74023723d
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928105B2

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