(R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone → (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931280Notes

Reaction equation

HRID 931280 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]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:21]([O-])=O>C(O)C.[Pd]>[NH2:21][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]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 89853768(R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (1.5 g, 4.7 mmol) in ethanol (20 mL) was added to a suspension of 10% palladium-on-carbon (800 mg) at room temperature. The mixture was hydrogenated for 4 h, filtered through Celite and washed with ethanol. The filtrate was used for the next step without further purification.

Workup

  1. filtrationfiltered through Celite
  2. washwashed with ethanol
  3. customThe filtrate was used for the next step without further purification

Sources & evidence

ORD record
ord-17c8451157c14c9582a579a297d4f994
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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