HCID 67259374, compound → 3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-amine

HRID 79341Notes

Reaction equation

HRID 79341 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

Reactant 1

HCID 67259374HCID 67259374, compound

Product 1

HCID 672599173-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584144Dichloromethane ethanolSolvent

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).

Workup

  1. customThe reaction mixture was purged with nitrogen and hydrogen three times each
  2. filtrationThe reaction mixture was filtered
  3. washwashed with MeOH/DCM (10:1, 50 mL)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cce56a70cc14811928538e177188094
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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