Hydrazine → tert-butyl 3-(pyridin-4-yl)-2H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate

HRID 594932Notes

Reaction equation

HRID 594932 reaction equation
[C:1]([CH:9]1[C:14](=O)[CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[NH2:23][NH2:24]>C(O)C>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[C:9]3[CH2:10][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:13][C:14]=3[NH:24][N:23]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66800689Tert-butyl 3-isonicotinoyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 68065985tert-butyl 3-(pyridin-4-yl)-2H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl 3-isonicotinoyl-4-oxopiperidine-1-carboxylate (7.4 g, 24.3 mmol) and TEA (10.15 ml) in ethanol was added hydrazine (3.65 ml, 73 mmol). The reaction mixture was stirred at room temperature for overnight. The solvent was removed under vacuum and DCM (50 ml) was added, followed by water (50 ml). The organic layer was collected, washed with brine and dried over sodium sulfate. Removal of solvent gave the desired product (7 g). LC-MS found 301.2 (M+H)

Workup

  1. customThe solvent was removed under vacuum and DCM (50 ml)
  2. additionwas added
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-4a84de6f8c264080814eaa64ff3f5553
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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