HCID 86701074, compound → HCID 86701075, compound

HRID 334503Notes

Reaction equation

HRID 334503 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[N+:13]([O-])=O>CO.[Pd]>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 86701074HCID 86701074, compound

Product 1

HCID 86701075HCID 86701075, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-amino-N-ethyl-5-nitronicotinamide (CXXVII) (180 mg, 0.856 mmol) in MeOH (5 mL) was added 10% Pd/C (27 mg, 15% by wt). The solution was purged with hydrogen and stirred for 16 h at room temperature under hydrogen. The suspension was filtered through Celite and concentrated under vacuum. The residue was purified on a silica gel column (100% CHCl3→10:90 MeOH[7N NH3]:CHCl3) to produce 4,5-diamino-N-ethylnicotinamide (CXXVIII) as a dark yellow solid (80 mg, 0.44 mmol, 51.9% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 1.14 (t, J=7 Hz, 3H), 3.92 (q, J=7 Hz, 2H) 5.56 (brs, 2H), 6.60 (brs, 1H), 7.66 (s, 1H), 8.30 (s, 1H); ESIMS found C8H12N4O m/z 181 (M+H).

Workup

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on a silica gel column (100% CHCl3→10:90 MeOH[7N NH3]:CHCl3)

Sources & evidence

ORD record
ord-3b27498a58994711947326c92fec4ad9
Source dataset
uspto-grants-2014_11
Patent number
US08883822B2

Reaction notes

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