Piperidine → HCID 178510303, compound

HRID 527278Notes

Reaction equation

HRID 527278 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][CH:18]([F:29])[O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[OH:28].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][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH:18]([F:17])[F:29])=[C:21]([OH:28])[CH:22]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehydeHCID 4311764Sodium borohydrideHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 178510303HCID 178510303, compound

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-(difluoromethoxy)-3-hydroxybenzaldehyde 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 was scraped and collected. (100 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-f2f1f85cf0e84b029d5e37cfb82fc11f
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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