Diisopropylethylamine → (S)-ethyl 6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinate

HRID 69582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69582
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][C@H:8]3[C:7](=[O:16])[NH:6][C:5]=2[CH:4]=1.[N:17]1([C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C)(C)C)#N>C(#N)CC.C([O-])([O-])=O.[K+].[K+].O>[O:16]=[C:7]1[NH:6][C:5]2[CH:4]=[C:3]([CH2:2][N:20]3[CH2:21][CH2:22][N:17]([C:23]4[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:24]=4)[CH2:18][CH2:19]3)[CH:12]=[N:11][C:10]=2[N:9]2[CH2:13][CH2:14][CH2:15][C@@H:8]12

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 14987933Ethyl 6-(piperazin-1-yl)nicotinateHCID 58324378(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

Produkt 1

HCID 46864607(S)-ethyl 6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 7854PropionitrileLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (233 mg, 1.06 mmol), ethyl 6-(piperazin-1-yl)nicotinate (270 mg, 0.1.15 mmol), DIPEA (0.80 mL), and (cyanomethyl)trimethylphosphonium iodide (369 mg, 01.82 mmol) were suspended in propionitrile (3 mL) and heated in a closed vial at 90° C. for 5 h. The mixture was cooled, diluted with a solution of K2CO3 (2.50 g) in water (15 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The resulting oil was crystallized with ethyl ether-ethanol (10:1, 22 mL) to afford the title compounds as a tan solid (0.355 mg, 77%). [M+H] calc'd for C23H28N6O3, 437; found, 437.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane (2×10 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was crystallized with ethyl ether-ethanol (10:1, 22 mL)

Quellen und Nachweise

ORD-Eintrag
ord-c9e8f9cfd0ef493faa8f64a57de58b18
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822470B2

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