Diisopropylethylamine → N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazine-2-carbonyl]-beta-alanine ethyl ester

HRID 1169094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169094
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([O:27][C:28](=[O:44])[CH2:29][CH2:30][NH:31][C:32]([C:34]1[N:35]=[C:36]2[CH:41]=[CH:40][C:39](Cl)=[N:38][N:37]2[CH:43]=1)=[O:33])[CH3:26].C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH2:25]([O:27][C:28](=[O:44])[CH2:29][CH2:30][NH:31][C:32]([C:34]1[N:35]=[C:36]2[CH:41]=[CH:40][C:39]([NH:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:10][CH2:11]3)=[N:38][N:37]2[CH:43]=1)=[O:33])[CH3:26]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 22989218N-(6-Chloroimidazo[1,2-b]pyridazine-2-carbonyl) beta-Alanine Ethyl Ester

Produkt 1

HCID 22989251N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazine-2-carbonyl]-beta-alanine ethyl esterAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

0.649 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 0.594 g of N-(6-chloroimidazo[1,2-b]pyridazine-2-carbonyl)-β-alanine ethyl ester were dissolved in 7 ml of 1-methyl-2-pyrrolidone; 0.345 ml of N-ethyldiisopropylamine was added, followed by stirring in an oil bath (90-100° C.) for 24 hours. After cooling, ice water was added, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (370:30:4). The desired fraction was collected and recrystallized from ethyl ether to yield 0.347 g of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (370:30:4)
  7. customThe desired fraction was collected
  8. customrecrystallized from ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-cb34b1c202f64ddeaa54860284c97c76
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627630B1

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