4-(2-Amino-3-nitro-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester → 4-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 493110Notes

Reaction equation

HRID 493110 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=2[N+:21]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=2[NH2:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 576808314-(2-Amino-3-nitro-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 576808304-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-Amino-3-nitro-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (5) (260 mg, 0.81 mmol) was dissolved in MeOH (10 ml) with 10% Pd/C (40 mg). It was stirred under a hydrogen atmosphere for 18 hours. It was filtered through CELITE to remove the palladium, and the solvent was removed under vacuum to yield the title product 6 (200 mg (85%), 0.62 mmol). 1H NMR (DMSO-d6): δ 7.29 (d, J=5 Hz, 1H), 6.29 (d, J=5 Hz, 1H), 5.30 (s, 2H), 4.21 (s, 2H), 3.48 (m, 4H), 2.74 (m, 4H), 1.41 (s, 9H). MS (ESI-POS): [M+H]+=294.

Workup

  1. filtrationIt was filtered through CELITE
  2. customto remove the palladium
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d407088a591d4d8bb86a7ea89746a369
Source dataset
uspto-grants-2009_05
Patent number
US07534796B2

Reaction notes

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