Sodium borohydride → HCID 178513718, compound

HRID 527295Notes

Reaction equation

HRID 527295 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]([NH2:17])=[O:16].[F:18][C:19]([F:36])([F:35])[C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=2)=[N:24][CH:25]=1.[BH4-].[Na+]>CCO.N1CCCCC1>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]([NH2:17])=[O:16])=[C:2]([NH:1][CH2:31][C:30]3[CH:29]=[CH:28][C:27]([O:26][C:23]4[CH:22]=[CH:21][C:20]([C:19]([F:36])([F:18])[F:35])=[CH:25][N:24]=4)=[CH:34][CH:33]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 269857004-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehydeHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513718HCID 178513718, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide (300 mg) was suspended in EtOH (5 mL) and 4-[{5-(Trifluoromethyl)pyridin-2-yl}oxy]benzaldehyde (318 mg, 1 eq.) and piperidine (3 drops) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain product as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (360 mg, 60% yield). Resulting imine (360 mg) was suspended in 10 mL MeOH and sodium borohydride (10 eq., 272 mg) was added. HPLC confirmed reaction was complete (absence of imine). After completion (1 hr), precipitate was filtered to obtain D33 as a light yellow powder. Product was washed with deionized water to remove excess sodium borohydride. Product was allowed to dry under vacuum for 18 hrs. 255 mg (70% yield) of final product was obtained.

Workup

  1. temperatureat reflux until intermediate
  2. customAfter reaction
  3. custom(18 hrs) it
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto obtain product as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr (360 mg, 60% yield)
  9. customreaction
  10. filtrationAfter completion (1 hr), precipitate was filtered
  11. customto obtain D33 as a light yellow powder
  12. washProduct was washed with deionized water
  13. customto remove excess sodium borohydride
  14. customto dry under vacuum for 18 hrs

Sources & evidence

ORD record
ord-a4776823408141689f472391b93df4f5
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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