1H-Indazol-6-amine → 4-(1H-indazol-6-ylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

Participants

Reaction Steps

A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (300 mg, 1 mmol) (prepared as described for the starting material in Example 5), and 6-aminoindazole (130 mg, 0.97 mmol) in 2-pentanol (10 ml) was heated at reflux for 3 hours. The precipitate was collected by filtration, washed with acetone and dried under vacuum. The residue was purified by reverse phase column chromatography eluting with methanol/water containing 1% acetic acid (40/60). Concentrated hydrochloric acid (5 drops) was added to the combined fractions of the product and the volatiles were removed by evaporation to give 4-(1H-indazol-6-ylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (213 mg, 54%).

Provenance & Evidence