Diethyl Oxalate → 8-(4-Amino-3-fluorophenoxy)pyrido[3,2-b]pyrazine-2,3(1H,4H)-dione

HRID 1402992Notes

Reaction equation

HRID 1402992 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16]C(=O)OC(C)(C)C)=[C:12]([F:24])[CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C:25](OCC)(=[O:31])[C:26](OCC)=[O:27]>CCO>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[C:7]3[NH:8][C:25](=[O:31])[C:26](=[O:27])[NH:1][C:2]=3[N:3]=[CH:4][CH:5]=2)=[CH:11][C:12]=1[F:24]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 44185833tert-Butyl (4-((2,3-diaminopyridin-4-yl)oxy)-2-fluorophenyl)carbamate

Product 1

HCID 595888758-(4-Amino-3-fluorophenoxy)pyrido[3,2-b]pyrazine-2,3(1H,4H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(2,3-diaminopyridin-4-yloxy)-2-fluorophenylcarbamate (1.03 g, 3.08 mmol) was dissolved in dry EtOH (10 mL), diethyl oxalate (10 mL) was added and the solution was heated to reflux for 96 h, cooled to RT and filtered. The title compound was isolated as a white solid. Yield: 820 mg (92%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 96 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8f7b07818e674c40ad0ceaae2300a3b3
Source dataset
uspto-grants-2014_12
Patent number
US08912191B2

Reaction notes

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