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

HRID 16436

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-6ee620eedb5047d4a28ffc9df009b2cb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737153B2

Linked notes

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