Hydrochloric Acid → 3-amino-N-methyl-6-(4-hydroxyoxyphenyl)pyrazine-2-carboxamide

HRID 646672Notes

Reaction equation

HRID 646672 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([NH:23][CH3:24])=[O:22])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C3CCCCO3)=[CH:10][CH:9]=2)=[CH:6][N:7]=1.Cl.[OH2:26]>CO>[NH2:1][C:2]1[C:3]([C:21]([NH:23][CH3:24])=[O:22])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][OH:26])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 686501893-amino-N-methyl-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]pyrazine-2-carboxamide

Product 1

HCID 866078323-amino-N-methyl-6-(4-hydroxyoxyphenyl)pyrazine-2-carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-amino-N-methyl-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]pyrazine-2-carboxamide (63 mg) was suspended in methanol followed by addition of aqueous hydrochloric acid (2 mL). The mixture was stirred for 15 min., poured into water (10 mL), and extracted with ethyl acetate (10 mL). The organic layer was washed with saturate aqueous sodium chloride then dried over anhydrous sodium sulfate. Filtration, concentration and column chromatography on silica followed by drying in vacuo afforded 3-amino-N-methyl-6-(4-hydroxyoxyphenyl)pyrazine-2-carboxamide (30 mg, 64% yield): 1H NMR (400 MHz; DMSO-D6): 9.62 (s, 1H); 8.78 (m, 1H); 8.82 (m, 1H); 8.7 (s, 1H); 7.98 (d, 2H); 7.5 (br s, 1H); 6.8 (d, 2H); 2.85 (d, 3H); MS (EI) for C12H12N4O2:245 (MH+).

Workup

  1. extractionextracted with ethyl acetate (10 mL)
  2. washThe organic layer was washed with saturate aqueous sodium chloride
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. filtrationFiltration, concentration and column chromatography on silica
  5. customby drying in vacuo

Sources & evidence

ORD record
ord-c2e418724440495a9ea83d751cab1d7d
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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