2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide → 5-amino-2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylisonicotinamide

HRID 77396Notes

Reaction equation

HRID 77396 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[C:12]([C:17]([N+:20]([O-])=O)=[CH:18][N:19]=1)[C:13]([NH:15][CH3:16])=[O:14])[CH2:3][CH2:2]2.[H][H]>CO.[Pd]>[NH2:20][C:17]1[C:12]([C:13]([NH:15][CH3:16])=[O:14])=[CH:11][C:10]([N:4]2[CH:5]3[CH2:6][CH2:7][N:1]([CH2:9][CH2:8]3)[CH2:2][CH2:3]2)=[N:19][CH:18]=1

Participants

5

Reactant 2

HCID 671149702-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 671150605-amino-2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylisonicotinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide (Intermediate 28A) (50 mg, 0.16 mmol) in methanol (0.3 mL) under nitrogen was added palladium on carbon (25 mg). Reaction subjected to a hydrogen atmosphere and stirred overnight. The reaction mixture was filtered and concentrated to afford 5-amino-2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylisonicotinamide.

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-346cfba2afa64bdea8d932b0d864ea1d
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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