Ethanol → Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate

HRID 646691노트

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HRID 646691 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:21][C:22]1[C:23]([C:29]([NH:31][CH3:32])=[O:30])=[N:24][C:25](Br)=[CH:26][N:27]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:21][C:22]1[N:27]=[CH:26][C:25]([C:9]2[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])=[N:24][C:23]=1[C:29]([NH:31][CH3:32])=[O:30]

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideHCID 56972886Benzoic acid, 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

생성물 1

HCID 68651344Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate수율 56%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

To a solution of methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.16 g, 0.55 mmol) in toluene (2 mL)) were added 3-amino-6-bromo-N-methyl-2-pyrazincarboxamide (0.13 g, 0.58 mmol), tetralds(triphenylphosphin)palladium(0) (64 mg, 0.06 mmol), ethanol (2 mL), and 2.0 N sodium carbonate (0.42 g, 4.00 mmol). The solution was degassed with nitrogen gas for 3-5 min and heated at 90-100° C. for 2 h. Reaction cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed water (50 mL) and saturated aqueous sodium chloride (40 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude product. Trituration with methanol (1 mL), filtration and drying gave methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate (96 mg, 56% yield) as yellow solid. 1H NMR (400 MHz, CDCl3): 8.62 (br s, 1H), 8.28 (d, 1H), 7.92 (dd, 2H), 7.52 (d, 1H), 4.02 (s, 3H), 3.02 (s, 3H); MS (EI) for C14H13N4O2Cl: 321 (MH+).

후처리

  1. customThe solution was degassed with nitrogen gas for 3-5 min
  2. customReaction
  3. temperaturecooled to room temperature
  4. washThe organic layer was washed water (50 mL) and saturated aqueous sodium chloride (40 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product
  9. filtrationTrituration with methanol (1 mL), filtration
  10. customdrying

출처 및 근거

ORD 기록
ord-90e8afa896e94634811693ac113e40c4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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