Pyridine → tris((3-hydroxy-1-(2-methoxyethyl)-4-oxo-1,4-dihydro-pyridine-2yl) carboxyaminoeth-2-yl)amine lanthanum (III) salt

HRID 1694627

Reaktionsgleichung

Reaktionsgleichung von HRID 1694627
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH2:9][CH2:10][O:11][CH3:12])[C:3]=1[C:13]([N:19]([C:38]([NH:52][C:53]([OH:55])=[O:54])([C:40]1[N:41]([CH2:48][CH2:49][O:50][CH3:51])[CH:42]=[CH:43][C:44](=[O:47])[C:45]=1[OH:46])[CH3:39])[C:20]([NH:34][C:35]([OH:37])=[O:36])([C:22]1[N:23]([CH2:30][CH2:31][O:32][CH3:33])[CH:24]=[CH:25][C:26](=[O:29])[C:27]=1[OH:28])[CH3:21])([NH:15][C:16]([OH:18])=[O:17])[CH3:14].O.O.O.O.O.O.[N+]([O-])([O-])=O.[La+3:66].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.N1C=CC=CC=1>CO.O>[La+3:66].[OH:46][C:45]1[C:44](=[O:47])[CH:43]=[CH:42][N:41]([CH2:48][CH2:49][O:50][CH3:51])[C:40]=1[C:38]([N:19]([C:20]([NH:34][C:35]([OH:37])=[O:36])([C:22]1[N:23]([CH2:30][CH2:31][O:32][CH3:33])[CH:24]=[CH:25][C:26](=[O:29])[C:27]=1[OH:28])[CH3:21])[C:13]([NH:15][C:16]([OH:18])=[O:17])([C:3]1[N:4]([CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:6][C:7](=[O:8])[C:2]=1[OH:1])[CH3:14])([NH:52][C:53]([OH:55])=[O:54])[CH3:39]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 16211478Lanthanum nitrate hexahydrateHCID 86639765tris((3-hydroxy-1-(2-methoxyethyl)-4-oxo-4H-pyridin-2yl-)carboxyaminoeth-2-yl)amine

Produkt 1

HCID 86639764tris((3-hydroxy-1-(2-methoxyethyl)-4-oxo-1,4-dihydro-pyridine-2yl) carboxyaminoeth-2-yl)amine lanthanum (III) saltAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of tris((3-hydroxy-1-(2-methoxyethyl)-4-oxo-4H-pyridin-2yl-)carboxyaminoeth-2-yl)amine (240 mg) in methanol (20 ml) and water (10 ml) was added lanthanum (III) nitrate hexahydrate (160 mg) and pyridine (2 ml). The reaction was heated to reflux for 2 hrs and then the reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase chromatography (Gemini column, 5u, C18, 100×30 mm) eluting with 5-95% (0.1% NH3/MeCN)/(0.10% NH3/H2O) to give the title compound (220 mg, 27%). 1H NMR (300 MHz, DMSO) δ 7.43 (3H, d, J=9 Hz), 6.03 (3H, d, J=9 Hz), 4.80 (6H, m), 3.51 (6H, m), 3.11-3.18 (15H, m), 2.42 (6H, d, J=6 Hz). 13C NMR (300 MHz, DMSO) δ 178.46, 164.99, 164.16, 139.55, 119.21, 106.44, 72.04, 58.10, 56.15, 55.82, 36.68. m/z (ES+) 868 (M+H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hrs
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by reverse phase chromatography (Gemini column, 5u, C18, 100×30 mm)
  5. washeluting with 5-95% (0.1% NH3/MeCN)/(0.10% NH3/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-c273b53ae38b414596af6c1825a04908
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158804B2

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