Hydrazine hydrate (1:1) → HCID 67200142, compound

HRID 550603Notes

Reaction equation

HRID 550603 reaction equation
C(OC([N:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C:9]=2[C:8]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N:31]2C(=O)C3C(=CC=CC=3)C2=O)=[O:24])=[N:7]1)=O)C.O.NN>CCO>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][C:14]2[NH:6][N:7]=[C:8]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[NH2:31])=[O:24])[C:9]=2[CH2:10]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67200653HCID 67200653, compound

Product 1

HCID 67200142HCID 67200142, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-{[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyridine-4-carbonyl]-amino}-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (1.68 g, 3 mmol) in 35 mL of EtOH was added hydrazine hydrate (0.37 mL) and the solution was heated to reflux for 1 hour. After cooling, the precipitate was filtered off and the filtrate evaporated in vacuum. The product was chromatographed twice, using dichloromethane-MeOH 95:5 as eluant, to afford 3-[(3-amino-pyridine-4-carbonyl)-amino]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (0.8 g, 74% yield).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. customthe filtrate evaporated in vacuum
  6. customThe product was chromatographed twice

Sources & evidence

ORD record
ord-0c2f64db7faa422c8c293c3631c648a8
Source dataset
uspto-grants-2011_05
Patent number
US07947686B2

Reaction notes

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