Pyridine → 2,2-Dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester

HRID 1512063Notes

Reaction equation

HRID 1512063 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:19](=[O:20])[NH:18][C:13]2=[N:14][CH:15]=[CH:16][N:17]=[C:12]2[C:11]=1[OH:21].[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:19](=[O:20])[NH:18][C:13]2=[N:14][CH:15]=[CH:16][N:17]=[C:12]2[C:11]=1[O:21][C:24](=[O:25])[C:23]([CH3:28])([CH3:27])[CH3:22]

Participants

7

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 579988247-(2-chloro-3,6-difluoro-phenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one

Product 1

HCID 579988432,2-Dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-(2-chloro-3,6-difluoro-phenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one (0.20 g) (Example 1.2), trimethylacetyl chloride (0.08 ml), and pyridine (0.05 ml) in dichloromethane (5 ml) was stirred at ambient temperature for two hours. The reaction mixture was diluted with ethyl acetate and water. The phases were separated. The organic phase was dried over magnesium sulfate and concentrated to produce a yellow semi-crystalline oil. This was triturated in iso-hexane to produce 2,2-dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester as a pale brown powder (0.113 g). 1H-NMR (400 MHz, CDCl3): 1.21 (s, 9H), 7.08-7.13 (m, 1H), 7.21-7.27 (m, 1H), 8.55-8.57 (m, 2H), 9.51 (s, 1H) ppm.

Workup

  1. customThe phases were separated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto produce a yellow semi-crystalline oil
  5. customThis was triturated in iso-hexane

Sources & evidence

ORD record
ord-ecde343e18e9410f8fbe277d31cd1144
Source dataset
uspto-grants-2012_07
Patent number
US08217055B2

Reaction notes

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