Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)- → HCID 90077584, compound

HRID 2203257Notes

Reaction equation

HRID 2203257 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[C:12](=[O:36])[N:13](CC4C=CC(OC)=CC=4)[C:14](=[O:26])[N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=4)[C:5]=3[C:4]=2[N:3]=1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce]>C(#N)C.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[C:12](=[O:36])[NH:13][C:14](=[O:26])[N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=4)[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 90077618HCID 90077618, compound

Product 1

HCID 90077584HCID 90077584, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

9-chloro-3-(4-methoxybenzyl)-1-(3-(trifluoromethyl)phenyl)pyrimidino[5,4-c][1,5]naphthyridine-2,4(1H,3H)-dione (700 mg, 1.36 mmol) was dissolved in acetonitrile (40 mL) and water (10 mL). Ammonium ceric nitrate (2.9 g, 5.65 mmol) was added in batch at room temperature. The reaction mixture was stirred at room temperature for 18 hrs, and then rotary-evaporated to remove the solvent. The resulting crude product was separated by silicagel column chromatography (EtOAc/PE=0-1/4) to obtain a yellow solid (400 mg).

Workup

  1. customrotary-evaporated
  2. customto remove the solvent
  3. customThe resulting crude product was separated by silicagel column chromatography (EtOAc/PE=0-1/4)

Sources & evidence

ORD record
ord-da6afc03fca9473ea609eccb872d185b
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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