Piperidine → HCID 178491037, compound

HRID 1049183Notes

Reaction equation

HRID 1049183 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]=1[C:14]([NH2:16])=[O:15].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.N1CCCCC1>C(O)C>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[N:1][C:2]2[NH:6][N:5]=[C:4]([NH:7][C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)[C:3]=2[C:14]([NH2:16])=[O:15])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 866989595-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178491037HCID 178491037, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide (1.0 g) was suspended in 10 mL of ethanol and 4-methoxybenzaldehyde (559 mg, 1.0 eq.) and piperidine (0.10 eq, 47 μL) was added. Stirred the reaction at reflux until starting material was absent and confirmed by HPLC. After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 5-((4-methoxybenzylidene)amino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide as a yellow to orange powder. The product was washed with ethanol to remove any excess 4-methoxybenzaldehyde. Product was allowed to dry under vacuum for 1 hr (800 mg, 50% yield).

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. customAfter reaction
  4. custom(18 hrs) it
  5. customwas brought to room temperature
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ed9c90ba29104031903ec602f73f123b
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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