Sodium Bicarbonate → HCID 86689173, compound

HRID 1752506Notes

Reaction equation

HRID 1752506 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([C:12]([O:14]CC)=[CH2:13])=[C:7]([Cl:17])[N:6]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([C:12](=[O:14])[CH3:13])=[C:7]([Cl:17])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86689172HCID 86689172, compound

Product 1

HCID 86689173HCID 86689173, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-amino-6-chloro-5-(1-ethoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester (46 mg, 0.190 mmol) and para-toluenesulfonic acid monohydrate (73.8 mg, 0.388 mmol) in THF (2.85 ml) was stirred at rt for 1 h. Saturated aq. NaHCO3 was added and the mixture was extracted twice with DCM. The combined organic layers were washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure to obtain a yellow solid (46 mg). This material was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted twice with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1a41eebdc2d461b936ebf441217d5ed
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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