Fumaric Acid → (R)-{5-[6-(1-Aza-bicyclo[2.2.2]oct-3-yloxy)-pyridazin-3-yl]-1H-indol-3-ylmethyl}-dimethyl-amine bis(fumarate)

HRID 1441423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441423
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][CH:20]=[C:19]4[CH2:25][N:26]([CH3:28])[CH3:27])=[CH:12][CH:11]=1)[CH2:2]2.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>CCOC(C)=O.CO>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][CH:20]=[C:19]4[CH2:25][N:26]([CH3:28])[CH3:27])=[CH:12][CH:11]=1)[CH2:2]2

Komponenten

4

Edukt 2

HCID 444972Fumaric AcidHCID 11314918(R)-{5-[6-(1-Aza-bicyclo[2.2.2]oct-3-yloxy)-pyridazin-3-yl]-1H-indol-3-ylmethyl}-dimethyl-amine

Produkt 1

HCID 86601386(R)-{5-[6-(1-Aza-bicyclo[2.2.2]oct-3-yloxy)-pyridazin-3-yl]-1H-indol-3-ylmethyl}-dimethyl-amine bis(fumarate)Ausbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

The product of Example 22A (80 mg, 0.21 mmol) was treated with fumaric acid (Aldrich, 49 mg, 0.42 mmol) in EtOAc/MeOH (v. 10:1) to give the title compound as white solid (74.8 mg, 53%). 1H NMR (MeOH-D4, 300 MHz) 1.79-2.17 (m, 3H), 2.25-2.41 (m, 1H), 2.54-2.61 (m, 1H), 2.84 (s, 6H), 3.19-3.42 (m, 5H), 3.78-3.90 (m, 1H), 4.50 (s, 2H), 5.45-5.54 (m, 1H), 6.66 (s, 5H), 7.34 (d, J=9.2 Hz, 1H), 7.54-7.63 (m, 2H), 7.84 (dd, J=8.5, 1.7 Hz, 1H), 8.17 (d, J=9.2 Hz, 1H), 8.35 (s, 1H) ppm. MS (DCI/NH3) m/z 378(M+H)+. Anal. Calculated for C22H27N5O.2.5 C4H4O4.0.5 H2O: C, 56.80; H, 5.66; N, 10.35. Found: C, 56.62; H, 5.78; N, 10.09.

Quellen und Nachweise

ORD-Eintrag
ord-c7719ce0a87a49aa9e2d905e591db1d9
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655657B2

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