6-(Cyclohexylamino)-5-nitropyridin-2-yl methanesulfonate → 5-Amino-6-(cyclohexylamino)pyridin-2-yl Methanesulfonate

HRID 1890356Notes

Reaction equation

HRID 1890356 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:7]=1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[N:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 866552596-(Cyclohexylamino)-5-nitropyridin-2-yl methanesulfonate

Product 1

HCID 866552605-Amino-6-(cyclohexylamino)pyridin-2-yl Methanesulfonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-(Cyclohexylamino)-5-nitropyridin-2-yl methanesulfonate (1.58 g, 5.01 mmol) was dissolved in methanol (1000 mL). Palladium (5% Pd/C, 1.72 g, 0.075 mmol) was added. The reaction was flushed with nitrogen and stirred under a balloon filled with hydrogen over 3 h at room temperature. The mixture was filtered through Celite® and concentrated to give the title compound as a dark green solid which was used immediately in next step without further purification.

Workup

  1. customThe reaction was flushed with nitrogen
  2. additionfilled with hydrogen over 3 h at room temperature
  3. filtrationThe mixture was filtered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a66edd8cc914e92bdf57fb88b254619
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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