(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 931322Notes

Reaction equation

HRID 931322 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 (0.11 g, 0.34 mmol) in ethanol (15 mL) was added 10% palladium-on-carbon (210 mg). The resulting suspension was hydrogenated using a balloon filled with hydrogen gas for 3 h at room temperature. The mixture was filtered through a pad of Celite and the filtrate was used for the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-d110d2ff6d8d4641985709e82074de01
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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