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

HRID 646688노트

반응식

HRID 646688 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-adce41ca2c2647b9b5e0f39110247169
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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