Sodium Bicarbonate → HCID 86662041, compound

HRID 869220Notes

Reaction equation

HRID 869220 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:5]([C:8](OC)=[O:9])=[N:6][CH:7]=1.Cl.[CH3:27][O:28][NH2:29].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C(=O)([O-])O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:5]([C:8]([NH:29][O:28][CH3:27])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2733832Lithium HexamethyldisilazideHCID 86662042HCID 86662042, compound

Product 1

HCID 86662041HCID 86662041, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a mixture of methyl 5-chloro-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxylate (Preparation Example 193) (20 mg) and THF (2 mL), O-methylhydroxylamine hydrochloride (14 mg) was added. To the reaction liquid, lithium hexamethyldisilazide (0.39 mL, 1M THF solution) was added under ice cooling and stirred for 20 minutes. The reaction liquid was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate, and then the organic layer was washed with saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to give 5-chloro-N-methoxy-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (21 mg) as a yellow powder.

Workup

  1. additionwas added
  2. additionwas added under ice cooling
  3. customThe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-efca8a0e41e443268c177cadecbbc56e
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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