Potassium Carbonate → HCID 25106721, compound

HRID 1799470Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[N:4][N:3]1[C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)#[N:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:7]2[C:6](=[O:8])[CH:5]=[N:4][N:3]([C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=3)[C:2]2=[O:1])=[CH:23][CH:22]=1)#[N:20]

Participants

Conditions

Temperature: 60 °C

Procedure

According to Scheme 5 Step 5: A suspension of N-(3-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (50 mg, 0.203 mmol), 4-cyanobenzylbromide (40 mg, 0.203 mmol) and potassium carbonate (31 mg, 0.223 mmol) in acetonitrile (2 mL) was stirred at 60° C. for 15 h The reaction mixture was then partitioned between AcOEt and water The organic layer was washed twice with water and once with brine. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by flash chromatography over silica gel (Merck Flashmart prepacked column 10 g SiO2) using DCM/MeOH 98/2 as eluent to afford N-(3-(4-(4-cyanobenzyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 9(E) (26 mg, 35%) as a white solid.

Workup

customwas then partitioned between AcOEt and water The organic layer
washwas washed twice with water and once with brine
dry with materialThe organic layer was dried over MgSO4
customevaporated under reduced pressure
customThe crude product was purified by flash chromatography over silica gel (Merck Flashmart prepacked column 10 g SiO2)

Sources & evidence

ORD record: ord-8d6608194a654c84a30d3568cc33e051
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344138B2

Reaction notes

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