1,1-Dimethylethyl [1-(2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate → 1,1-Dimethylethyl [1-(2-{[3-amino-6-(methyloxy)-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate

HRID 656960Notes

Reaction equation

HRID 656960 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:13]2)[C:6]([N+:26]([O-])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:26][C:6]1[C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:16][CH2:17]2)=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 1

HCID 866353271,1-Dimethylethyl [1-(2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate

Product 1

HCID 866353281,1-Dimethylethyl [1-(2-{[3-amino-6-(methyloxy)-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamateYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1-dimethylethyl [1-(2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate (3.0 g, 7.6 mmol) in ethanol (500 ml) was hydrogenated for 2 hours over 10% palladium on charcoal (50% dispersion with water, 1.5 g). The mixture was filtered, evaporated, and azeotroped with chloroform to afford a purple oil (2.8 g, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customazeotroped with chloroform

Sources & evidence

ORD record
ord-8f856df3c1ac46128adea57b29732c04
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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