(R)-1-(6-amino-5-nitropyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide → (R)-1-(5,6-Diaminopyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide

HRID 931141Notes

Reaction equation

HRID 931141 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([N:16]([CH2:18][CH3:19])[CH3:17])=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:20]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:20][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([N:16]([CH2:18][CH3:19])[CH3:17])=[O:15])[CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 89853601(R)-1-(6-amino-5-nitropyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 117966322(R)-1-(5,6-Diaminopyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of (R)-1-(6-amino-5-nitropyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide (200 mg, 0.65 mmol) in ethanol (10 mL) was added palladium-on-carbon (0.2 g) in ethanol (10 mL) at room temperature. The mixture was subjected to a hydrogen atmosphere using a balloon filled with hydrogen gas. The mixture was filtered through Celite to afford the title compound. The filtrate was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite

Sources & evidence

ORD record
ord-478cf9e9bc264b29a5894822d46e4826
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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