Potassium Carbonate → HCID 25106721, compound

HRID 1624892Notes

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-7d29d297a547430f8b829819d1ed1e90
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

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