Water → HCID 178485578, compound

HRID 646715Notes

Reaction equation

HRID 646715 reaction equation
[NH2:1][C:2]1[C:3]([C:17]([NH:19][CH3:20])=[O:18])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH2:16])=[NH:15])[CH:9]=2)=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:17]([NH:19][CH3:20])=[O:18])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[NH:16][CH:6]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:15]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 68650453HCID 68650453, compound

Product 1

HCID 178485578HCID 178485578, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-amino-6-{3-[amino(imino)methyl]phenyl}-N-methylpyrazine-2-carboxamide (0.13 6 mg, 0.5 mmol) in DMF (5 mL) was added bronoacetophenone (0.11 g, 0.55 mmol ) followed by K2CO3 (0.276 g). The resulting mixture was heated at 70 ° C. for 0.5 h. The mixture was poured into water (30 mL) and extracted with ethyl acetate (30 mL). The extract was washed with brine, dried (Na2SO4), and concentrated. The product was purified by hplc to provide 3-amino-N-methyl-6-[3-(4-phenyl-1H-imidazol-2-yl)phenyl]pyrazine-2-carboxamide (58 mg): 1H NMR (400 MHz; DMSO-d6): 8.94 (s, 1H); 8.82 (m, 1H); 8.62 (s, 1H); 8.2 (d, 1H); 8.04 (d, 1H); 7.9-7.78 (m, 3H); 7.58 (t, 1H); 7.38 (m, 2H); 7.24 (t, 1H); 2.82 (d, 3H); MS (EI) for C21H18N6O: 371 (MH+).

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product was purified by hplc

Sources & evidence

ORD record
ord-d36bf24c2dc74e84b215ee8004cc0b1f
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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