Triacetoxyperiodinane → 1-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-one

HRID 1399056노트

반응식

HRID 1399056 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([CH:45]([OH:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1>C(#N)C.C(=O)([O-])O.[Na+]>[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([C:45](=[O:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1

참가 물질

5

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 44156374HCID 44156374, 화합물

생성물 1

HCID 577863001-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-one수율 88%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

실험 절차

Dess-Martin reagent (1.27 g, 3.00 mmol) was added to a stirred suspension of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (1.12 g, 2.73 mmol) in acetonitrile (23 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, concentrated in vacuo, and extracted with ethyl acetate/tetrahydrofuran. 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 15-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with diisopropyl ether to give the title compound as a colorless powder (980 mg, 2.40 mmol, 88%).

후처리

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-370834d74e624712b0d3ce01b402244f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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