Pyridine → HCID 68701529, compound

HRID 1624884Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

According to Scheme 3 Step 2: A mixture of compound 6(A) (1.10 g, 4.74 mmol), 3-acetamidophenylboronic acid (1.20 g, 6.64 mmol), copper acetate (258 mg, 1.42 mmol) and pyridine (229 μL, 2.84 mmol) in DMF (30 mL) was stirred at 65° C. during 15 h under room atmosphere. The mixture was diluted with 50 mL of a saturated solution of NaHCO3 and the aqueous layer was extracted twice with 60 mL of DCM. The organic layers were combined dried over MgSO4, filtered filtrated 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 10 g SiO2) (Eluant: CH2Cl2/MeOH 98/2) to afford N-(3-(4-allyl-6-bromo-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 6(B) (800 mg, 46%) as a colorless oil.

Workup

extractionthe aqueous layer was extracted twice with 60 mL of DCM
dry with materialThe organic layers were combined dried over MgSO4
filtrationfiltered
filtrationfiltrated
concentrationconcentrated
customto afford a brown solid
customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2) (Eluant: CH2Cl2/MeOH 98/2)

Sources & evidence

ORD record: ord-b76fa3629b7044089b7b8a591b962b4a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

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