Water → 7-(2-(4-isopropylpiperazin-1-yl)ethoxy)-N-(3-methyl-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706585
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]([O-:24])=O)=[CH:20][N:21]=[C:15]3[CH:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Li+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH3:38][C:39]1[C:47]2[C:46]([NH2:48])=[CH:45][CH:44]=[CH:43][C:42]=2[N:41]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([C:56]([F:59])([F:58])[F:57])=[CH:52][N:51]=2)[N:40]=1.O>CN1C(=O)CCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]([NH:48][C:46]4[CH:45]=[CH:44][CH:43]=[C:42]5[C:47]=4[C:39]([CH3:38])=[N:40][N:41]5[CH2:49][C:50]4[CH:55]=[CH:54][C:53]([C:56]([F:59])([F:58])[F:57])=[CH:52][N:51]=4)=[O:24])=[CH:20][N:21]=[C:15]3[CH:14]=2)[CH2:8][CH2:9]1)([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 67260109Lithium 7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylateHCID 679763853-Methyl-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazol-4-amine

Produkt 1

HCID 573861337-(2-(4-isopropylpiperazin-1-yl)ethoxy)-N-(3-methyl-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 11,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Lithium 7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (0.746 g, 2.204 mmol) was dissolved in 16 mL of dry NMP. To this was added 2,4,6-trichlorobenzoyl chloride (0.538 g, 2.20 mmol) and this mixture was stirred at ambient temperature for 30 minutes. 3-Methyl-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazol-4-amine (0.500 g, 1.63 mmol) was added and the mixture was warmed to 90° C. for 16 hours, then allowed to cool to ambient temperature. Water (50 mL) was added and the mixture extracted with EtOAc. The extracts were then washed with 10% aqueous potassium carbonate solution and brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography (7% MeOH/DCM/0.5% NH4OH) afforded 0.112 g (11%) of the final compound. MS (APCI), positive scan, m/z=622.2 (M+H).

Aufarbeitung

  1. temperaturethe mixture was warmed to 90° C. for 16 hours
  2. temperatureto cool to ambient temperature
  3. extractionthe mixture extracted with EtOAc
  4. washThe extracts were then washed with 10% aqueous potassium carbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-24abb0bf9fbd485fa314857c6f1c3548
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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