Dimethylethylamine → (2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]indolizin-4-yl]amine

HRID 1792257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792257
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[C:29]3[N:28]4[C:23]([C:24]([C:30]5[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=5[CH3:38])=[CH:25][CH:26]=[CH:27]4)=[CH:22][C:21]=3[N:20]=[C:19]([CH3:39])[CH:18]=2)=O)=[CH:6][C:5]=1[O:40][CH3:41])[CH3:2].[AlH3].N(CC)(C)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:13][CH2:14][CH2:15][NH:16][C:17]2[C:29]3[N:28]4[C:23]([C:24]([C:30]5[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=5[CH3:36])=[CH:25][CH:26]=[CH:27]4)=[CH:22][C:21]=3[N:20]=[C:19]([CH3:39])[CH:18]=2)=[CH:6][C:5]=1[O:40][CH3:41])[CH3:2]

Komponenten

5

Edukt 3

HCID 11723DimethylethylamineHCID 14488Aluminum hydrideHCID 696624812-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-9-(2,4,6-trimethyl-phenyl)-pyridino[2,3-b]indolizin-4-ylamino]-ethyl}-acetamide

Produkt 1

HCID 69662626(2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]indolizin-4-yl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Treat a solution of 2-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-9-(2,4,6-trimethyl-phenyl)-pyridino[2,3-b]indolizin-4-ylamino]-ethyl}-acetamide (0.08 g, 0.145 mmol) in THF (5 mL) with AlH3.NMe2Et (3 mL, 1.45 mmol) and heat to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O (0.3 g) and stir at ambient temperature for 15 min. Filter the solution through Celite and wash with several portions of CH2Cl2. Concentrate the filtrate in vacuo to dryness and purify by preparative TLC (10% MeOH in CH2Cl2 with 0.5% ammonium hydroxide) to the title compound as a solid.

Aufarbeitung

  1. temperatureto reflux for 14 h
  2. customquench with Na2CO3.10H2O (0.3 g)
  3. filtrationFilter the solution through Celite
  4. washwash with several portions of CH2Cl2
  5. concentrationConcentrate the filtrate in vacuo to dryness
  6. custompurify by preparative TLC (10% MeOH in CH2Cl2 with 0.5% ammonium hydroxide) to the title compound as a solid

Quellen und Nachweise

ORD-Eintrag
ord-1d79be6d72524b4e94ffad33aa9b2707
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074929B2

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