Triethylamine → [4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 2361149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361149
Cl.IC1C=CNC(=O)C=1[C:10]1[NH:11][C:12]2[C:20]([N:21]=1)=[C:19]([CH3:22])[C:18]1[C:17](=[O:23])[N:16]([CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[C:15](=[O:31])[C:14]=1[CH:13]=2.Cl.Cl[C:34]1[CH:39]=[CH:38][NH:37][C:36](=[O:40])[C:35]=1C1NC2C(N=1)=C(C)C1C(=O)N(C3CCN(C)CC3)C(=O)C=1C=2.[NH2:63][CH2:64][C@@H:65]([OH:76])[CH2:66][O:67][C:68]1[CH:73]=[CH:72][C:71]([CH3:74])=[CH:70][C:69]=1[CH3:75].CCN(CC)CC>CCO>[CH3:75][C:69]1[CH:70]=[C:71]([CH3:74])[CH:72]=[CH:73][C:68]=1[O:67][CH2:66][C@H:65]([OH:76])[CH2:64][NH:63][C:34]1[CH:39]=[CH:38][NH:37][C:36](=[O:40])[C:35]=1[N:11]1[C:12]2[C:20](=[C:19]([CH3:22])[C:18]3[C:17](=[O:23])[N:16]([CH:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[C:15](=[O:31])[C:14]=3[CH:13]=2)[N:21]=[CH:10]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2133977(2R)-1-amino-3-(2,4-dimethylphenoxy)propan-2-olHCID 1363510992-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione HydrochlorideHCID 1363511752-(4-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride

Produkt 1

HCID 86621613[4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dioneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride and 2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione Hydrochloride (0.75 g, 1.45 mmol), (R)-3-amino-1-(2,4-dimethylphenoxy)-2-propanol (0.34 g, 1.73 mmol) in EtOH (20 mL) was added Et3N (0.61 mL, 4.35 mmol) and the resulting mixture was heated at reflux for overnight. The reaction mixture was evaporated in vacuo and the residue was purified by flash chromatography (10% (6% NH3/MeOH)/CHCl3) to afford 2-{[4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-4-methyl-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (0.45 g, 57%) as a yellow solid.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for overnight
  3. customThe reaction mixture was evaporated in vacuo
  4. customthe residue was purified by flash chromatography (10% (6% NH3/MeOH)/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-541e21e78f02494b920b4b1729290e52
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08686005B2

Notizen zur Reaktion

Wird geladen…