Hydrochloric Acid → N-[2-Amino-6-(4-pyridinyl)-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)-phenyl]amine

HRID 16436

Reaktionsgleichung

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[CH:10]3)=[C:4]([F:18])[CH:3]=1.Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:32])[N:21]=1.Cl.C(=O)(O)[O-].[Na+]>O>[NH2:32][C:22]1[N:21]=[C:20]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([O:6][C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[NH:12][N:11]=[CH:10]4)=[C:4]([F:18])[CH:3]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

600 mg (2.47 mmol) of 5-(4-amino-2-fluorophenoxy)-1H-indazole (from example XII) are suspended in 100 ml of water. 510 mg (2.47 mmol) of 4-chloro-6-(4-pyridinyl)-2-pyrimidineamine (from example XXIX) and 0.25 ml of concentrated aqueous hydrogen chloride solution are added, and the mixture is stirred at 100° C. overnight. For work-up, the reaction solution was made alkaline with saturated sodium bicarbonate solution and extracted 3× with ethyl acetate. The precipitate obtained contains crude product and is filtered off with suction. The organic phase is dried with sodium sulfate and concentrated using a rotary evaporator. The residue is combined with the precipitate and purified by preparative HPLC.

Aufarbeitung

extractionextracted 3× with ethyl acetate
customThe precipitate obtained
filtrationis filtered off with suction
dry with materialThe organic phase is dried with sodium sulfate
concentrationconcentrated
customa rotary evaporator
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-6ee620eedb5047d4a28ffc9df009b2cb
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737153B2

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