HCID 561427, compound → HCID 57944975, compound

HRID 658659Notes

Reaction equation

HRID 658659 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:8]=1)([O-])=O.[H][H]>[Pd].CO>[S:9]([N:7]1[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]1)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 561427HCID 561427, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57944975HCID 57944975, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-nitro-1-tosyl-1H-pyrazole (example 9-1c) (3 g, 11.2 mmol) and 10% palladium on carbon (800 mg) in MeOH (150 mL) were stirred under 2 atmospheres of hydrogen on the Parr hydrogenator for 3 hours. The mixture was filtered through celite, concentrated and purified by silica gel chromotography (80% ethyl acetate in hexanes) to afford 1-tosyl-1H-pyrazol-4-amine (1.9 g, 71%) as a pink solid. 1H NMR (CDCl3, 400 MHz), 2.40 (s, 3H), 3.01 (bs, 2H), 7.29 (d, 2H, J=8 Hz), 7.41 (d, 1H, J=1.2 Hz), 7.53 (d, 1H, J=1.2 Hz), 7.81 (d, 2H, J=8 Hz).

Workup

  1. filtrationThe mixture was filtered through celite,
  2. concentrationconcentrated
  3. custompurified by silica gel chromotography (80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8e5fbe44ad544135a68173ff7057f959
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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