tert-Butanol → N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79430

Reaktionsgleichung

Reaktionsgleichung von HRID 79430
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.C(O)(C)(C)C.[CH:22]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[NH:34][C:35]([C:37]3[N:41]4[CH:42]=[CH:43][C:44](F)=[CH:45][C:40]4=[N:39][CH:38]=3)=[O:36])[N:27]([CH2:47][C:48]3[C:49](=[O:55])[N:50]([CH3:54])[CH:51]=[CH:52][CH:53]=3)[N:26]=2)[CH2:24][CH2:23]1>O>[CH:22]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[NH:34][C:35]([C:37]3[N:41]4[CH:42]=[CH:43][C:44]([O:16][CH2:15][CH2:14][N:11]5[CH2:12][CH2:13][N:8]([CH3:7])[CH2:9][CH2:10]5)=[CH:45][C:40]4=[N:39][CH:38]=3)=[O:36])[N:27]([CH2:47][C:48]3[C:49](=[O:55])[N:50]([CH3:54])[CH:51]=[CH:52][CH:53]=3)[N:26]=2)[CH2:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxideHCID 67259522N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide

Produkt 1

HCID 68333317N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A one dram vial was charged with solid potassium tert-butoxide (54 mg, 0.48 mmol), 2-(4-methylpiperazin-1-yl)ethanol (0.075 g, 0.52 mmol), and tert-butanol (0.3 mL, 3.4 mmol). The mixture was stirred at ambient temperature for 30 minutes. N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (0.032 g, 0.070 mmol) was added in one portion. The mixture was heated at 88° C. with stirring for 16 hours. The mixture was cooled to ambient temperature and diluted with water until a precipitate formed. The precipitate was isolated by filtration and dried under high vacuum. Purification using silica preparative thin layer chromatography plate (20×20 cm, 0.5 mm) developed in a chamber with 10% methanol/dichloromethane with 0.6% concentrated ammonium hydroxide gave the product. MS (APCI), positive scan, m/z=581.2 (M+).

Aufarbeitung

  1. temperatureThe mixture was heated at 88° C.
  2. stirringwith stirring for 16 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. customformed
  5. customThe precipitate was isolated by filtration
  6. customdried under high vacuum
  7. customPurification
  8. customgave the product

Quellen und Nachweise

ORD-Eintrag
ord-02e9525120c848759abdcc7cc2833b34
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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