Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(5-methoxy-3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine

HRID 226022

Reaktionsgleichung

Reaktionsgleichung von HRID 226022
C[O-].[K+].[CH3:4][O:5]CCOCCN(CCOCCOC)CCOCCOC.[CH2:26]([CH:28]([C:31]1[C:32]2[N:33]([C:38]([C:42]3[S:46][C:45]4[CH:47]=[CH:48][C:49](F)=[CH:50][C:44]=4[C:43]=3[CH3:52])=[C:39]([CH3:41])[N:40]=2)[N:34]=[C:35]([CH3:37])[CH:36]=1)[CH2:29][CH3:30])[CH3:27]>ClCCl.O>[CH2:26]([CH:28]([C:31]1[C:32]2[N:33]([C:38]([C:42]3[S:46][C:45]4[CH:47]=[CH:48][C:49]([O:5][CH3:4])=[CH:50][C:44]=4[C:43]=3[CH3:52])=[C:39]([CH3:41])[N:40]=2)[N:34]=[C:35]([CH3:37])[CH:36]=1)[CH2:29][CH3:30])[CH3:27]

Komponenten

6

Edukt 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 23664618Potassium methoxideHCID 577525998-(1-Ethyl-propyl)-2,6-dimethyl-3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine

Produkt 1

HCID 577526848-(1-Ethyl-propyl)-2,6-dimethyl-3-(5-methoxy-3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazineAusbeute 293,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In an oven dried, nitrogen purged, 3 neck, 50 mL round bottom flask, 0.014 g (0.197 mmol) of potassium methoxide and 0.005 mL (0.013 mmol) of tris[2-(2-methoxyethoxy)ethyl]amine are heated at 150° C. and stirred vigorously for 5 minutes. 0.050 g (0.131 mmol) of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine is added and the reaction is followed by TLC (2:1 Hexanes/Ethyl Acetate) and MS. After 4 h, the reaction mixture is diluted with 20 mL dichloromethane and 20 mL of water. The layers are separated and the aqueous is extracted 3×50 mL of dichloromethane, dried (MgSO4), and concentrated under vacuum. The crude mixture is purified by chromatography using hexanes:ethyl acetate as a solvent system. Combined fractions to obtain 0.015 g of the title compound, 29% yield. MS, ES+=394.2 (M+1); H1NMR (DMSO-d6) δ 7.863-7.842 (d, J=8.368, 1H); 7.327-7.321 (m, 1H); 7.076-7.049 (m, 1H); 6.991 (s, 1H); 3.857 (s, 3H); 3.094 (m, 1H); 2.477 (s, 3H); 2.350 (s, 3H); 2.180 (s, 3H); 1.853-1.760 (m, 4H); 0.793-0.757 (m, 6H) ppm.

Aufarbeitung

  1. customIn an oven dried
  2. customnitrogen purged
  3. waitAfter 4 h
  4. customThe layers are separated
  5. extractionthe aqueous is extracted 3×50 mL of dichloromethane
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum
  8. customThe crude mixture is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9379509429b54bf1ae38a798032173f3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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