Acryloyl chloride → N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide

HRID 336143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336143
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:25]2[C:26]3[C:38]([NH2:39])=[N:37][CH:36]=[N:35][C:27]=3[N:28]3[C:33]=2[CH2:32][CH2:31][CH:30]([NH2:34])[CH2:29]3)[CH:16]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:39][C:38]1[C:26]2[C:25]([C:17]3[CH:16]=[N:15][C:24]4[C:19]([CH:18]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:33]3[N:28]([C:27]=2[N:35]=[CH:36][N:37]=1)[CH2:29][CH:30]([NH:34][C:10](=[O:13])[CH:11]=[CH2:12])[CH2:31][CH2:32]3

Komponenten

6

Edukt 4

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 867112835-(Quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

Produkt 1

HCID 78149057N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N,N-diisopropylethylamine (0.033 ml) and acryloyl chloride (0.0154 ml) were added to a solution of 5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine (68 mg) obtained in Step 11 in chloroform (2.5 ml) under ice-cooling. After stirring at the same temperature for 15 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a yellow solid (35.4 mg).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-3b2a9dba8a9b44aeb267ed5b1867da5e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889666B2

Notizen zur Reaktion

Wird geladen…