1-Hydroxybenzotriazole → HCID 59483777, Verbindung

HRID 1808387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808387
CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]2[CH:45]=[C:46]([C:48]([OH:50])=O)[N:47]=[C:41]2[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[N:51]1[CH:56]=[CH:55][C:54]([N:57]2[CH2:62][CH2:61][C:60]3([CH2:67][CH2:66][NH:65][CH2:64][CH2:63]3)[CH2:59][CH2:58]2)=[CH:53][CH:52]=1>C(Cl)Cl>[N:51]1[CH:52]=[CH:53][C:54]([N:57]2[CH2:62][CH2:61][C:60]3([CH2:63][CH2:64][N:65]([C:48]([C:46]4[N:47]=[C:41]5[CH2:40][N:39]([C:37]([O:36][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:38])[CH2:44][CH2:43][N:42]5[CH:45]=4)=[O:50])[CH2:66][CH2:67]3)[CH2:59][CH2:58]2)=[CH:55][CH:56]=1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 159408113-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecaneHCID 445585487-(tert-Butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid

Produkt 1

HCID 59483777HCID 59483777, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

DIPEA (5.96 mmol, 4.0 equiv.), EDCl (2.24 mmol, 1.5 equiv.) and HOBt (2.24 mmol, 1.5 equiv.) were added at 0° C. to a solution of 7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid (1.49 mmol, 1.0 equiv.) in DCM (20 ml), and the mixture was stirred for 30 min. A solution of 3-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane (F-19) (1.49 mmol, 1.0 equiv.) in DCM (5 ml) was added at 0° C., and then the reaction mixture was stirred for 16 h at 25° C. The mixture was diluted with DCM (100 ml) and washed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml), dried over Na2SO4 and concentrated in vacuo. The resulting crude product was used directly in the following stage. Yield: 63%

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 16 h at 25° C
  2. washwashed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c147575b3e3941c5b61aa1258834be3e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357717B2

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