1,4,7-Triazacyclononane → Ethyl 6-((4,7-bis((6-(ethoxycarbonyl)-4-(2,4,6-trimethoxyphenyl)-pyridin-2-yl)methyl)-1,4,7-triazonan-1-yl)methyl)-4-(2,4,6-trimethoxyphenyl)-pyridine-2-carboxylate

HRID 655902

Reaktionsgleichung

Reaktionsgleichung von HRID 655902
[NH:1]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19]([C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])[CH:18]=[C:17]([CH2:33]Br)[N:16]=1)=[O:14])[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13]([C:15]1[N:16]=[C:17]([CH2:33][N:1]2[CH2:9][CH2:8][N:7]([CH2:33][C:17]3[CH:18]=[C:19]([C:21]4[C:22]([O:31][CH3:32])=[CH:23][C:24]([O:29][CH3:30])=[CH:25][C:26]=4[O:27][CH3:28])[CH:20]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[N:16]=3)[CH2:6][CH2:5][N:4]([CH2:33][C:17]3[N:16]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH:20]=[C:19]([C:21]4[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=4[O:31][CH3:32])[CH:18]=3)[CH2:3][CH2:2]2)[CH:18]=[C:19]([C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1)=[O:14])[CH3:11]

Komponenten

4

Edukt 2

HCID 1883181,4,7-TriazacyclononaneHCID 590246614-(2,4,6-trimethoxyphenyl)-6-(bromomethyl)pyridine-2-carboxylic Acid Ethyl Ester

Produkt 1

HCID 11194088Ethyl 6-((4,7-bis((6-(ethoxycarbonyl)-4-(2,4,6-trimethoxyphenyl)-pyridin-2-yl)methyl)-1,4,7-triazonan-1-yl)methyl)-4-(2,4,6-trimethoxyphenyl)-pyridine-2-carboxylateAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1,4,7-triazacyclononane (31.5 mg) and compound 14 (0.3 g, 0.76 mmol) were dissolved in dry acetonitrile (20 mL) Potassium carbonate (0.17 g) was added and the mixture was refluxed overnight. The mixture was allowed to cool to room temperature, filtered and concentrated. Purification on silica gel (eluent CH2Cl2:EtOH: HOAc; 80:20:1, v/v/v) yielded the title compound (0.17 g, 62%). ESI-MS: [M+H]+ 1117.5 calc. for C60H73N6O15+1117.5.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed overnight
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel (eluent CH2Cl2:EtOH: HOAc; 80:20:1, v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-77d543bce43c4d27b8ae8d04b40bc3b2
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071626B2

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