Piperidine → 3-((3-chlorophenyl)amino)-5-((4-fluoro-2-methylbenzyl)amino)-1H-pyrazole-4-carbonitrile

HRID 1049182

Reaction equation

HRID 1049182 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]#[N:16].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[C:20]([CH3:26])[CH:19]=1.N1CCCCC1.[BH4-].[Na+]>C(O)C.CO>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]#[N:16])=[C:2]([NH:1][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([F:17])=[CH:19][C:20]=3[CH3:26])[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 27832174-Fluoro-2-methylbenzaldehydeHCID 4311764Sodium borohydrideHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 1784278523-((3-chlorophenyl)amino)-5-((4-fluoro-2-methylbenzyl)amino)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

Dissolved 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile (58 mg) in 4 mL ethanol and added 0.250 mmol of 4-fluoro-2-methylbenzaldehyde followed by a single drop of piperidine. This solution was then heated to 85° C. for 17 hrs, then the ethanol was evaporated and the resulting product was scraped from the reaction vessels. The powder was then resuspended in 4 mL of MeOH and 3 eq. of sodium borohydride was added and left stirring overnight at room temperature. Then MeOH was then evaporated and the product C29 was scraped and collected. (50 mg)

Workup

  1. customthe ethanol was evaporated
  2. customthe resulting product was scraped from the reaction vessels
  3. waitleft
  4. customThen MeOH was then evaporated
  5. customcollected

Sources & evidence

ORD record
ord-eec21f83b19b4e6e8d5c284ec20ce972
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Linked notes

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