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

HRID 2201709Notes

Reaction equation

HRID 2201709 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 1h. 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-aab09d77b063443ebc3d0f51a4d8914f
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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