Sodium Hydroxide → HCID 68650317, compound

HRID 646779Notes

Reaction equation

HRID 646779 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[C:14]([C:22]([O:24]C)=[O:23])[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=2)=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].[OH-].[Na+]>O1CCOCC1.Cl>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=2)[C:22]([OH:24])=[O:23])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68650923HCID 68650923, compound

Product 1

HCID 68650317HCID 68650317, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture containing dimethyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzene-1,3-dicarboxylate (1.1 g, 3.2 mmol) and aqueous sodium hydroxide (3 mL of a 1N solution) was heated in dioxane (100 mL) at 95° C. for 3 h. The mixture was diluted with 1 N aqueous hydrochloric acid (300 mL) and extracted with ethyl acetate (3×300 mL) and saturated ammonium chloride solution and dried over sodium sulfate. Filtration, concentration and purification by reverse phase HPLC gave the product as a yellow solid (0.39 g, 37% yield). 1H NMR (400 MHz, d6-DMSO): δ 8.83 (s, 1H), 8.78 (d, 1H), 8.70 (d, 2H), 8.39 (t, 1H), 7.69 (br, 2H), 6.47 (br, 1H), 3.87 (s, 3H), 2.79 (d, 3H). MS (EI) for C15H14N4O5: 331 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×300 mL) and saturated ammonium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration, concentration and purification by reverse phase HPLC

Sources & evidence

ORD record
ord-f66ea012d4df49d2a007fef5bcc264bc
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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