Water → 3-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

HRID 1097311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097311
COC(=O)[NH:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:22])[NH:20][CH3:21])[CH:14]=3)[CH:10]=[N:9][N:8]2[C:23]=1Br.[Cl:26][C:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29][N:28]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=3)[C:19]([NH:20][CH3:21])=[O:22])[CH:10]=[N:9][N:8]2[C:23]=1[C:31]1[CH:30]=[CH:29][N:28]=[C:27]([Cl:26])[CH:32]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 59443497N-[3-bromo-7-[3-[(methylamino)carbonyl]phenyl]imidazo[1,2-b]pyridazin-2-yl]carbamic acid methyl ester

Produkt 1

HCID 594435023-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

[3-Bromo-7-(3-Methylcarbamoyl-phenyl)-imidazo-[1,2-b]-pyridazin-2-yl]-carbamic acid methyl ester (1 eq, 0.159 mmol, 65 mg) and 2-chloropyridine-4-boronic acid (1.2 eq, 0.191 mmol, 30.1 mg) are dissolved in DME (3 ml) and water (0.75 ml) and Na2CO3 (3 eq, 0.478 mmol, 50.6 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.008 mmol, 5.59 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 50 min. At the completion of this time the solvent is evaporated and the reaction mixture is dissolved in MeOH, filtered and the solvent is removed in vacuo to yield 3-[2-Amino-3-(2-Chloro-pyridin-4-yl)-imidazo -[1,2-b]-pyridazin-7-yl]-N-methyl benzamide as a yellow solid; [M+H]+=379

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 50 min
  4. customAt the completion of this time the solvent is evaporated
  5. dissolutionthe reaction mixture is dissolved in MeOH
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a76d6e87fc2e4e3ea7671be3a9a2428f
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143253B2

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