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Potassium Carbonate → 5-[9-Chloro-6-(1-ethylpropyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl]-N,N,4-trimethylpyridin-2-amine

HRID 1399225
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HRID 1399225 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:13]=[N:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][C:17]=3[CH3:18])[N:7]([CH2:22][CH2:23][CH2:24]O)[C:6]=2[C:5]([CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:12]4[C:17]([CH3:18])=[CH:16][C:15]([N:19]([CH3:21])[CH3:20])=[N:14][CH:13]=4)[CH2:24][CH2:23][CH2:22][N:7]3[C:6]=2[C:5]([CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:4][CH:3]=1
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7

반응물 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 687713093-[4-chloro-2-{[6-(dimethylamino)-4-methylpyridin-3-yl]amino}-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]propan-1-ol

생성물 1

HCID 577859605-[9-Chloro-6-(1-ethylpropyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl]-N,N,4-trimethylpyridin-2-amine수율 52%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To a solution of 3-[4-chloro-2-{[6-(dimethylamino)-4-methylpyridin-3-yl]amino}-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]propan-1-ol (100 mg, 0.233 mmol) in pyridine (2 mL) was added methanesulfonyl chloride (0.036 mL, 0.465 mmol) dropwise at 0° C. After stirring for 2 hr at room temperature, aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude mesylate was dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) and potassium carbonate (64 mg, 0.465 mmol) was added. The mixture was stirred at 50° C. for 4 hr. Water was added and the mixture was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 50-80% ethyl acetate/n-hexane gradient mixture followed by recrystallization from ethyl acetate/n-hexane to afford the title compound (50 mg, 0-12 mmol, 52%) as a colorless solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude mesylate was dissolved in 1-methyl-2-pyrrolidinone (1.0 mL)
  6. stirringThe mixture was stirred at 50° C. for 4 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washOrganic layer was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on silica gel eluting with a 50-80% ethyl acetate/n-hexane gradient mixture
  12. customfollowed by recrystallization from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-244d49cc0c8d46a1b5958c7867d82c3e
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901141B2

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