HCID 67259374, compound → 3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[C:22]4[C:17](=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][CH:21]=4)[C:16]([CH:26]=[CH2:27])=[N:15]3)=[CH:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1>CCO.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH2:26]([C:16]1[C:17]2[C:18]([NH2:23])=[CH:19][CH:20]=[CH:21][C:22]=2[N:14]([CH2:13][C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:29][CH:28]=3)[N:9]=[CH:10][CH:11]=2)[N:15]=1)[CH3:27]Participants
4
Procedure
To 1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-4-nitro-3-vinyl-1H-indazole (0.86 g, 2.2 mmol) in EtOH/DCM (20 mL/2 mL) was added palladium hydroxide on carbon (400 mg, 20% wt). The reaction mixture was purged with nitrogen and hydrogen three times each. The mixture was then stirred under hydrogen for 3 hours. The reaction mixture was filtered, washed with MeOH/DCM (10:1, 50 mL) and concentrated under reduced pressure to give the crude product 3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-amine. To imidazo[1,2-a]pyridine-3-carboxylic acid (0.43 g, 2.7 mmol) in DCE (5 mL) was added thionyl chloride (1.3 g, 11 mmol). The slurry was stirred for one hour. The reaction mixture was then concentrated under reduced pressure and dried under vacuum for 30 minutes. The resulting acid chloride was then resuspended in THF/DCE (5 mL/5 mL), to which the previously prepared 3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-amine was added. The reaction mixture was heated to 80° C. for three hours. The mixture was cooled to ambient temperature, diluted with DCM (20 mL), washed with saturated NaHCO3 aqueous solution (20 mL) and brine (10 mL), and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:1) provided the product (0.36 g).