N-bromobutanimide → 9-Bromo-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1629016노트

반응식

HRID 1629016 반응식
[Br:1]N1C(=O)CCC1=O.[F:9][CH:10]([F:40])[O:11][CH:12]([C:17]1[C:22]2[N:23]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]4[C:31]([CH3:39])=[N:32][C:33]([O:37][CH3:38])=[N:34][C:35]=4[CH3:36])[C:24]3=[N:25][C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:13]([F:16])([F:15])[F:14]>C(#N)C.C(=O)([O-])O.[Na+]>[Br:1][C:20]1[C:21]2[N:25]=[C:24]3[N:26]([C:30]4[C:35]([CH3:36])=[N:34][C:33]([O:37][CH3:38])=[N:32][C:31]=4[CH3:39])[CH2:27][CH2:28][CH2:29][N:23]3[C:22]=2[C:17]([CH:12]([O:11][CH:10]([F:9])[F:40])[C:13]([F:16])([F:15])[F:14])=[CH:18][CH:19]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 577860406-[1-(Difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

생성물 1

HCID 577860939-Bromo-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole수율 60.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

실험 절차

N-Bromosuccinimide (190 mg, 1.07 mmol) was added to a stirred solution of 6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (469 mg, 1.02 mmol) in acetonitrile (5.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give a solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as colorless crystals (330 mg, 0.615 mmol, 60%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give a solid, which
  9. customwas recrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-2cd5942eb35d4863b7aaa8652c78dd9c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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