1-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-(4-methyl-3-nitrophenyl)urea → 1-(3-amino-4-methylphenyl)-3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]urea

HRID 1921289Notes

Reaction equation

HRID 1921289 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-])=O)[CH:15]=2)=[O:12])[N:7]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:21][C:16]1[CH:15]=[C:14]([NH:13][C:11]([NH:10][C:8]2[N:7]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=2)=[O:12])[CH:19]=[CH:18][C:17]=1[CH3:20]

Participants

5

Reactant 2

HCID 670568701-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-(4-methyl-3-nitrophenyl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 670568481-(3-amino-4-methylphenyl)-3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]ureaYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[3-tert-Butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-(4-methyl-3-nitrophenyl)urea (93 mg) was hydrogenated over 10% Pd/C (50% wet, 10 mg) at atmospheric pressure of hydrogen in MeOH (2 mL) for 4 hr. The catalyst was removed by filtration through Celite® pad and the filtrate was evaporated in vacuo. The residue was triturated with IPE and the precipitates produced were collected by filtration to give 1-(3-amino-4-methylphenyl)-3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]urea (74 mg).

Workup

  1. customThe catalyst was removed by filtration through Celite® pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with IPE
  4. customthe precipitates produced
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-276b6771b8f648a3b5ef5a95942ba16e
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

Loading…