Methyl Ethyl Ketone → 1-(2,4-Dichlorophenyl)-N-(1-methylpropyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

HRID 1399122

반응식

HRID 1399122 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[C:28]2=[N:29][C:30]3[C:31](=[C:32]([NH2:36])[CH:33]=[CH:34][CH:35]=3)[N:27]2[CH2:26][CH2:25][CH2:24]1.[CH3:37][C:38](=O)[CH2:39][CH3:40]>CO.C(=O)([O-])O.[Na+]>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[C:28]2=[N:29][C:30]3[C:31](=[C:32]([NH:36][CH:38]([CH3:37])[CH2:39][CH3:40])[CH:33]=[CH:34][CH:35]=3)[N:27]2[CH2:26][CH2:25][CH2:24]1

참가 물질

6

반응물 3

HCID 6569Methyl Ethyl KetoneHCID 5049666Sodium triacetoxyborohydrideHCID 577861701-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

생성물 1

HCID 577859871-(2,4-Dichlorophenyl)-N-(1-methylpropyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine수율 40%

시약·촉매·용매 2

HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

Sodium triacetoxyborohydride (171 mg, 0.807 mmol) was added to a stirred solution of 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine (183 mg, 0.549 mmol) and butan-2-one (1.0 mL) in methanol (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 8 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 5-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless crystal (86.4 mg, 0.222 mmol, 40%).

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 5-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give the solid, which
  9. customwas recrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-d5f5c40d49f945038d54c469baba06c5
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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