Water → HCID 25106547, compound

HRID 1799473Notes

Reaction equation

HRID 1799473 reaction equation
[C:1]([C:3]1[C:4](=[O:20])[NH:5][C:6](=[O:19])[N:7]([C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=2)[N:8]=1)#[N:2].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CC#N>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:5]2[C:4](=[O:20])[C:3]([C:1]#[N:2])=[N:8][N:7]([C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=3)[C:6]2=[O:19])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 68697573HCID 68697573, compound

Product 1

HCID 25106547HCID 25106547, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 7 Step 3: A suspension of 11(B) (500 mg, 1.8 mmol), 4-chlorobenzyl bromide (455 mg, 2.2 mmol) and potassium carbonate (510 mg, 3.7 mmol) in CH3CN (10 mL) was stirred 12 h under reflux. The mixture was cooled at room temperature and 100 mL of water were added. The aqueous layer was extracted thrice with DCM (100 mL). The organic layers were mixed, dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (AIT Flashmart prepacked column 50 g SiO2) using CH2Cl2/MeOH (98/2) as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-cyano-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 11(C) (460 mg, 63%) as a beige solid.

Workup

  1. temperatureunder reflux
  2. extractionThe aqueous layer was extracted thrice with DCM (100 mL)
  3. additionThe organic layers were mixed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a brown solid
  8. customThe crude solid was purified by flash chromatography with silica gel (AIT Flashmart prepacked column 50 g SiO2)

Sources & evidence

ORD record
ord-4aa563e301c1430cad2d1a03a273fc59
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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