Sodium Bicarbonate → 6-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDE

HRID 1268739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268739
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[S:17][C:16]([NH2:18])=[N:15][C:14]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][N:29]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:18][C:16]2[S:17][C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:12]=3)=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[N:15]=2)=[O:33])=[CH:30][N:29]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 17862984HCID 17862984, VerbindungHCID 185485896-Chloropyridine-3-carbonyl chloride--hydrogen chloride (1/1)

Produkt 1

HCID 102066296-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDEAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of [5-(2-cyclopentylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.4 mmol) and 4-dimethylaminopyridine (0.052 g, 0.43 mmol) in N,N-dimethylacetamide (10 mL) was added 6-chloronicotinoyl chloride hydrochloride (0.46 g, 2.1 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1) and the resulting crystals were recrystallized from ethanol to give the title compound (0.30 g, yield 42%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1)
  6. customthe resulting crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-e9166156b8a941618c1abb54a1f342b6
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199124B2

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