Hydrochloric Acid → HCID 178480241, compound

HRID 277994Notes

Reaction equation

HRID 277994 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)([O-])=O.Cl.O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178480242HCID 178480242, compound

Product 1

HCID 178480241HCID 178480241, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-3-(1-methylpiperidin-4-yl)-1H-indazole (287 mg, 1.1 mmol), 5N aqueous hydrochloric acid (0.5 mL), water (5ml), and methanol (15 mL) was warmed to give a homogeneous solution. Palladium (86 mg, 5% on carbon) was added to the solution and the resulting mixture was stirred under an atmosphere of hydrogen gas for 24 hours. The palladium catalyst was filtered and the filtrate was concentrated in vacuo. The residue was slurried in methylene chloride and 5N aqueous sodium hydroxide then extracted with chloroform/isopropanol (3:1). The organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give 261 mg of a light brown foam. Purification by radial chromatography (silica gel, 2000 micron rotor, methylene chloride:methanol:ammonium hydroxide, 100:10:1) gave 223 mg (87.8%) of a brown oil. The product was crystallized as the dihydrochloride salt. EA calculated for C13H20Cl2N4: C, 51.49; H, 6.65; N, 18.48. Found: C, 51.44; H, 6.76; N, 18.47.

Workup

  1. temperaturewas warmed
  2. customto give a homogeneous solution
  3. filtrationThe palladium catalyst was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. extraction5N aqueous sodium hydroxide then extracted with chloroform/isopropanol (3:1)
  6. dry with materialThe organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf05bba665e94fce851a6358154ccd46
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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