Pyridine → HCID 25106899, compound

HRID 1624889Notes

Reaction equation

HRID 1624889 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH3:14])=[N:10][NH:9][C:8]2=[O:15])=[CH:4][CH:3]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19].N1C=CC=CC=1>CN(C=O)C.C([O-])(O)=O.[Na+].C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH3:14])=[N:10][N:9]([C:26]3[CH:27]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:23]=[CH:24][CH:25]=3)[C:8]2=[O:15])=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 157274(3-Acetamidophenyl)boronic acidHCID 68701666HCID 68701666, compound

Product 1

HCID 25106899HCID 25106899, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
65 °C

Procedure

According to Scheme 4 Step 2: A mixture of compound 8(A) (100 mg, 0.39 mmol), 3-acetamidophenylboronic acid (107 mg, 0.59 mmol), copper acetate (79 mg, 0.44 mmol) and pyridine (65 μl, 0.79 mmol) in DMF (3 mL) was stirred at 65° C. during 15 hours. The reaction mixture was diluted with 100 mL of a saturated solution of NaHCO3 and the aqueous layer was extracted twice with DCM (100 mL). The organic layers were combined and successively dried over MgSO4, filtered and concentrated under reduce pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 20 g, C18) using Water/CH3CN 6/4 as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-methyl-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 8(B) (97 mg, 63%) as a white solid.

Workup

  1. extractionthe aqueous layer was extracted twice with DCM (100 mL)
  2. dry with materialsuccessively dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a brown solid
  6. customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 20 g, C18)

Sources & evidence

ORD record
ord-ecd250bdf6824fa59faaa4ac032b93e0
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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