Water → 3-amino-N-methyl-6-{3-[(methylsulfonyl)amino]phenyl}pyrazine-2-carboxamide

HRID 646688Notes

Reaction equation

HRID 646688 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:6][N:7]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:15]([NH:17][CH3:18])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][S:27]([CH3:26])(=[O:29])=[O:28])[CH:9]=2)=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 100374223-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide

Product 1

HCID 103813893-amino-N-methyl-6-{3-[(methylsulfonyl)amino]phenyl}pyrazine-2-carboxamideYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-6-(3-aminophenyl)-N-methylpyrazine-2-carboxamide (26 mg, 0.11 mmol) in dry dichloromethane (2 mL) at 0° C. were added triethylamine (22 mg, 0.22 mmol) and methanesulfonyl chloride (20 mg, 0.17 mmol). The reaction was slowly warmed to room temperature and stirred overnight. Reaction was treated water (10 mL) and diluted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered, and concentrated to afford 3-amino-N-methyl-6-{3-[(methylsulfonyl)amino]phenyl}pyrazine-2-carboxamide (15 mg, 45% yield) as yellow solid. 1H NMR (400 MHz, CDCl3): 8.62 (s, 1H), 7.94 (br s, 1H), 7.75 (br s, 1H), 7.68 (br d, 1H), 7.45 (t, 1H), 7.30 (br d, 1H), 7.25 (br s, 1H), 3.02 (m, 6H); MS (EI) for C13H15N5O3S: 322 (MH+).

Workup

  1. customReaction
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and saturated aqueous sodium chloride (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-adce41ca2c2647b9b5e0f39110247169
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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