8-Isobutyryloxy-5-methyl-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid methyl ester → 8-hydroxy-5-methyl-7-(3-methyl-1,2,4-oxadiazol-5-yl)-5H-pyrido[2,3-b]pyrazin-6-one

HRID 241781Notes

Reaction equation

HRID 241781 reaction equation
CO[C:3]([C:5]1[C:14](=[O:15])[N:13]([CH3:16])[C:8]2=[N:9][CH:10]=[CH:11][N:12]=[C:7]2[C:6]=1[O:17]C(=O)C(C)C)=[O:4].O[NH:24][C:25](=[NH:27])[CH3:26]>C1(C)C=CC=CC=1>[OH:17][C:6]1[C:7]2[C:8](=[N:9][CH:10]=[CH:11][N:12]=2)[N:13]([CH3:16])[C:14](=[O:15])[C:5]=1[C:3]1[O:4][N:27]=[C:25]([CH3:26])[N:24]=1

Participants

4

Reactant 2

HCID 581149418-Isobutyryloxy-5-methyl-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid methyl esterHCID 178465666HCID 178465666, compound

Product 1

HCID 1360134288-hydroxy-5-methyl-7-(3-methyl-1,2,4-oxadiazol-5-yl)-5H-pyrido[2,3-b]pyrazin-6-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8-isobutyryloxy-5-methyl-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazine-7-carboxylic acid methyl ester (Example 7.3) (0.10 g) in toluene (4 ml) was added N-hydroxy-acetamidine (0.025 g). The reaction mixture was heated to reflux for 16 hours. The reaction mixture was cooled to ambient temperature and the solid was isolated by filtration and dried to give Compound No. B5 of Table 5 (0.050 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. customthe solid was isolated by filtration
  4. customdried
  5. customto give Compound No

Sources & evidence

ORD record
ord-2dbacb938d6b4b908427f0f12ab50304
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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