Hydrochloric Acid → 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine

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Reaction Steps

In a similar manner to Example 1, (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.12 g, 0.25 mmol) was dissolved in methanol (6.0 mL) and crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole was obtained from 5-morpholino-2-nitrobenzaldehyde (65 mg, 0.25 mmol) and potassium carbonate (0.10 g, 0.75 mmol). In a similar manner to Example 2, crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.80 g, 2.3 mmol) was dissolved in ethanol (25 mL) and the solution was added with tin (0.82 g, 6.9 mmol) and concentrated hydrochloric acid (4.0 mL) and heated from room temperature to 40° C. to obtain 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine. Further, in a similar manner to Example 29, 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine (0.45 g, 1.4 mmol) was dissolved in THF (10 mL) and the solution was added with triethylamine (0.61 ml, 4.2 mmol) and 3-methylthiophenecarbonylchloride (0.20 g, 1.4 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to obtain free base of Compound 225. Further, said free base was treated by 4 mol/L hydrogen chloride-methanol solution (1.0 mL) to obtain Compound 225 (0.40 g, 55%).

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