4-(6-Nitropyridin-3-yl)-3-oxopiperazine-1-carboxylic acid tert-butyl ester → Tert-butyl 4-(6-aminopyridin-3-yl)-3-oxopiperazine-1-carboxylate

HRID 1919137Notes

Reaction equation

HRID 1919137 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:11]2=[O:23])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:12][C:11]2=[O:23])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 592909524-(6-Nitropyridin-3-yl)-3-oxopiperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59290959Tert-butyl 4-(6-aminopyridin-3-yl)-3-oxopiperazine-1-carboxylateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 332b (1.1 g, 3.4 mmol) in methanol (20 mL) was added Pd/C (10%) (250 mg). After three cycles of vacuum/H2 flash, the mixture was stirred under H2 at room temperature for 10 h. The mixture was filtered and the filtrate was evaporated in vacuo to afford 332c (946 mg, 95%), which was used for the next step without further purification. MS: [M+H]+ 293.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-aa6fbf9fa6e842c49aa56e9a6a53ec46
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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