4,6-Dichloro-2-(methylsulfonyl)pyrimidine → 2,6-Difluoro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamide

HRID 473985

반응식

HRID 473985 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9]([CH3:12])(=O)=O)[N:3]=1.[F:13][C:14]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23]C(S)=[CH:21][CH:20]=1)=[O:17]>C(O)(C)(C)C>[F:13][C:14]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:15]=1[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:12]([S:9][C:4]2[N:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[N:5]=2)=[CH:23][CH:24]=1)=[O:17]

참가 물질

4

반응물 2

HCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidineHCID 668911562,6-difluoro-N-(4-mercapto-phenyl)-benzamide

생성물 1

HCID 594208272,6-Difluoro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamide수율 35%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
90 °C

실험 절차

A 250 ml round bottom flask equipped with a condenser was charged with 4,6-dichloro-2-methanesulfonyl pyrimidine (4.2 g, 18.8 mmol), 2,6-difluoro-N-(4-mercapto-phenyl)-benzamide (4.98 g, 18.8 mmol) and tert-butanol (75 ml) under nitrogen. The reaction mixture was degassed thoroughly and then heated at 90° C. for 2 h. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The solid residue was taken up in ethyl acetate (50 ml) and washed with saturated sodium bicarbonate solution and brine. The organic was dried over magnesium sulfate, filtered and concentrated until the product began to precipitate. The mixture was then cooled and aged for 12 hrs. The product was collected by filtration, washed with cold ethyl acetate and dried. This gave the title compound as an off-white solid (2.7 g, 35%). 1H NMR (DMSO) 7.32 (2H, m), 7.61 (3H, m), 7.79 (1H, s), 7.82 (2H, d), 10.9 (1H, s). MS (ES+): 412.19

후처리

  1. customA 250 ml round bottom flask equipped with a condenser
  2. customThe reaction mixture was degassed thoroughly
  3. temperatureto cool to room temperature
  4. concentrationconcentrated in vacuo
  5. washwashed with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated until the product
  9. customto precipitate
  10. temperatureThe mixture was then cooled
  11. filtrationThe product was collected by filtration
  12. washwashed with cold ethyl acetate
  13. customdried

출처 및 근거

ORD 기록
ord-1c16a2205d114a86b2d46a396d619f44
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637511B2

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