2,4,6-Trimethylpyridine → N-(4-chlorobenzyl)-4-hydroxy-8-iodo-6-(4-morpholinylmethyl)-3-quinolinecarboxamide

HRID 1841528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1841528
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21]O)=[CH:15][C:14]=3[I:23])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS(Cl)(=O)=O.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[CH:15][C:14]=3[I:23])=[O:9])=[CH:24][CH:25]=1

Komponenten

8

Edukt 4

HCID 79532,4,6-TrimethylpyridineHCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 178522929HCID 178522929, Verbindung

Produkt 1

HCID 178522928N-(4-chlorobenzyl)-4-hydroxy-8-iodo-6-(4-morpholinylmethyl)-3-quinolinecarboxamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-8-iodo-3-quinolinecarboxamide (0.36 g), DMAP (0.016 g) and collidine (0.12 mL) in 13 mL DMF at 0° C. is added methanesulfonyl chloride (0.065 mL). The solution is allowed to warm to room temperature and is stirred overnight. Morpholine (0.67 mL) is then added and the solution is stirred at room temperature overnight. The mixture is poured into water. The resulting solid is collected and dried. The crude product is adsorbed onto silica and chromatographed (Biotage flash 40S, eluant 1% MeOH/CH2Cl2, then 2% MeOH/CH2Cl2). Product containing fractions are combined and concentrated to yield 0.322 g (78%) of N-(4-chlorobenzyl)-4-hydroxy-8-iodo-6-(4-morpholinylmethyl)-3-quinolinecarboxamide, m.p. 230-233° C.

Aufarbeitung

  1. stirringthe solution is stirred at room temperature overnight
  2. customThe resulting solid is collected
  3. customdried
  4. customchromatographed (Biotage flash 40S, eluant 1% MeOH/CH2Cl2
  5. additionProduct containing fractions
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-28f607b3d6974302a82a67f4afce9689
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06683181B2

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