cis-(1-(6-Amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone → cis-(1-(5,6-Diaminopyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931327Notes

Reaction equation

HRID 931327 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:22]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:22][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 89853803cis-(1-(6-Amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 89853812cis-(1-(5,6-Diaminopyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of cis-(1-(6-amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone (500 mg, 1.50 mmol) in ethanol (20 mL) was added to a suspension of 10% palladium-on-carbon (250 mg) in ethanol under a nitrogen atmosphere. The suspension was hydrogenated using a balloon filled with hydrogen gas for 2 h at room temperature. 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-229f87fdb4054d8b9e91cd45e5e36a86
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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