4-((4-ethylpiperazin-1-yl)Methyl)-3-(trifluoroMethyl)aniline

1-ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in above was dissolved in methanol, followed by stirring. The reaction solution was added with Pd/C (1.8 g, 17.08 mmol), followed by stirring under hydrogen conditions for about 12 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (19.4 g, 99percent). -NMR Spectrum (300 MHz, DMSO-d1-ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in 1-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in Step (2) above was stirred in a solution of methanol. 1-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in Step (2) above was stirred in a solution of methanol. To the solution of the product of Step B (770 mg, 2.43 mmol) in methanol (10 mL) was added Pd/C (70 mg). The solution was stirred at room temperature under hydrogen (4 atm) for 2 hours. TLC (DCM/MeOH = 20/1) showed the reaction was completed. The resulting solutionwas filtered through a silica pad, the filtrate was concentrated and purified by silica gel chromatography (silica weight: 10 g, eluting: DCMIMeOH = 20/1) to afford the title compound (500 mg, yield: 71percent) as yellow oil. MS: M/e 288(M+1).To a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BHTo a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-l-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BHTo a mixture of (4-amino-2-trifluoromethyl-phenyl) - (4-ethyl-piperazin-1-yl) -methanone (20 g 66.4 mmol) in THF (500 mL) was added BHInto a 25-mL round-bottom flask was placed a solution of 7-hydroxy-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylic acid (150 mg, 0.78 mmol) in dimethylsulfoxide (5 mL), then 1-hydroxybenotriazole hydrate (211 mg, 1.56 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (448 mg, 2.34 mmol) were added at room temperature. To the mixture was added In a 25 mL round-bottom flask was dissolved 3-[[1-(benzenesulfonyl)-1H-pyrrolo[2, 3-b]pyridin-4-yl]oxy]-8-methyl-5, 6, 7, 8-tetrahydroquinoline-6-carbonyl chloride (140 mg, 0.29 mmol) in dichloromethane (7 mL), added pyridine (34 mg, 0.44 mmol), Into a 100-mL round-bottom flask was placed 1-methyl-7-((2-methyl-1H-pyrrolo[2, 3-b]pyridin-4-yl)oxy)-1, 2, 3, 4-tetrahydroquinoline-2-carboxylic acid (50 mg, 0.15 mmol), N, N-dimethylformamide (5 mL), Into a 50-mL round-bottom flask was placed 1-(tert-butoxycarbonyl)-7-((2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2m3-b]pyridin-4-yl)oxy)-1, 2, 3, 4-tetrahydroquinoline-2-carboxylic acid (300 mg, 0.53 mmol), dichloromethane (20 mL), Compound 4 (26mg, 0.1mmol) and aromatic amines (0.1 mmol) was dissolved in 1mL sec-butanol, was added a 4N HCl solution (50muL, 0.2mmol), and finally placed in a closed system has been preheated to 110 deg.] C oil bath heated with stirring until the reaction was complete (LC-MS and TLC monitoring). The reaction was stopped, concentrated and purified by reverse phase preparative HPLC (containing 0.35% aqueous trifluoroacetic acid and methanol as mobile phase), dried and concentrated in vacuo to yield compound IA.

Molecular Weight:287.32
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:287.16093214
Monoisotopic Mass:287.16093214
Topological Polar Surface Area:32.5
Heavy Atom Count:20
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes