Pyridine → HCID 25106638, compound

HRID 1624887Notes

Reaction equation

HRID 1624887 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[N:10][NH:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[C:17]([NH:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:19])[CH3:18].N1C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[N:10][N:9]([C:25]3[CH:26]=[C:21]([NH:20][C:17](=[O:19])[CH3:18])[CH:22]=[CH:23][CH:24]=3)[C:8]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 157274(3-Acetamidophenyl)boronic acidHCID 68699308HCID 68699308, compound

Product 1

HCID 25106638HCID 25106638, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

According to Scheme 4 Step 2: To a stirred solution of 4-(4-chlorobenzyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.250 g, 1.1 mmol) in DMF (5 mL) were added 3-acetamidophenylboronic acid (0.28 g, 1.6 mmol), copper(II) acetate (0.19 g, 1 mmol) and pyridine (0.17 g, 2.1 mmol) and the mixture was stirred overnight at 60° C. The reaction was quenched with a saturated sodium bicarbonate solution and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by C18 reverse phase column, 15 g column: starting from 20% CH3CN and gradually increasing the percentage of CH3CN (10% each 300 ml) the product came out at 60% of CH3CN. 0.160 g (39%) of N-(3-(4-(4-chlorobenzyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 7(B) were obtained.

Workup

  1. customThe reaction was quenched with a saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were successively washed with water
  4. dry with materialwith brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by C18 reverse phase column, 15 g column
  8. temperaturegradually increasing the percentage of CH3CN (10% each 300 ml) the product

Sources & evidence

ORD record
ord-2c3af3b837814a47adbb7bf68e7d1aee
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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