tert-Butyl 3-amino-5-nitro-1H-indazole-1-carboxylate → tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

HRID 1823908Notes

Reaction equation

HRID 1823908 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10]([NH2:20])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[C:10]([NH2:20])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 23571039tert-Butyl 3-amino-5-nitro-1H-indazole-1-carboxylate

Product 1

HCID 23571038tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-5-nitroindazole-1-carboxylic acid tert-butyl ester (3 g, 10.8 mmol) was dissolved in MeOH (50 mL) and the solution degassed (3× alternating vacuum/nitrogen purges). Palladium on charcoal 10% w/w (300 mg) was added and the nitrogen atmosphere replace by hydrogen. After 3 hours, the mixture was filtered through a pad of Celite® and the filtrate concentrated to afford the title compound as a highly viscous oil (2.17 g, 81%). 1H NMR (400 MHz, DMSO)1.55 (9H, s), 5.07 (2H, brs), 6.04 (2H, brs), 6.79–6.82 (2H, m), 7.62 (1H, brs). MS (ES+) m/e=249.

Workup

  1. customthe solution degassed (3× alternating vacuum/nitrogen purges)
  2. additionPalladium on charcoal 10% w/w (300 mg) was added
  3. filtrationthe mixture was filtered through a pad of Celite®
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-68f1b8fdf9f94ef882c9ea82613e9fe3
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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