(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 931330Notes

Reaction equation

HRID 931330 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 702EthanolSolvent2×

Procedure

To a solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.500 g, 1.56 mmol) in ethanol (25 mL) was added palladium on carbon 10% (500 mg) suspended in ethanol. The reaction mixture was hydrogenated using a balloon filled with hydrogen gas for 3 h at room temperature. The reaction mixture was filtered through Celite and the filtrate was used for the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-817b0b1afc094fb9880d170ade939d05
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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