(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 931294Notes

Reaction equation

HRID 931294 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.[H][H]>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

5

Reactant 2

HCID 89853768(R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, compound

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

To a solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.2 g, 0.62 mmol) in ethanol (10 mL) was added 10% palladium-on-carbon (200 mg). The mixture was hydrogenated at room temperature for 3 h using a balloon filled with hydrogen gas. The mixture was filtered through Celite and the filtrate was used for the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was used for the next step without further purification

Sources & evidence

ORD record
ord-73ab6afe661f44d9bc5070315f7a454e
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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