N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide → N-(2-amino-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide

HRID 62702Notes

Reaction equation

HRID 62702 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18]

Participants

5

Reactant 1

HCID 70982085N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide

Product 1

HCID 71466382N-(2-amino-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamideYield 70.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.11 g, 0.35 mmol) in methanol (6 mL) and THF (6 mL) was added Pd/C (0.04 g, 0.94 mmol, 0.33 equiv.). The reaction mixture was degassed then stirred at room temperature under H2 atmosphere for 1 h. The reaction was filtered through celite and concentrated. The crude solid was washed with ether, and dried under reduced pressure to obtain of pure N-(2-amino-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.07 g, 70% yield). ESI+ MS: m/z 284([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 9.30 (s, 1H), 8.55 (s, 1H), 8.40-8.39 (m, 1H), 7.88 (s, 1H), 7.71-7.69 (m, 1H), 7.53 (s, 1H), 6.81 (d, J=8.5 Hz, 1H), 5.31 (s, 2H), 3.40-3.37 (m, 4H), 1.86 (m, 4H).

Workup

  1. customThe reaction mixture was degassed
  2. filtrationThe reaction was filtered through celite
  3. concentrationconcentrated
  4. washThe crude solid was washed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3805bcf4ac35487b889e58f78d128e4e
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Reaction notes

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