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Methanesulfonic Acid → 5-(Benzoxazol-2-yl)-2-(2-(methylthio)ethyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74314
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HRID 74314 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[CH3:24][S:25][CH2:26][CH2:27][C:28](Cl)=O.C(N(CC)CC)C.CS(O)(=O)=O.[OH-].[Na+]>O1CCCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:28]([CH2:27][CH2:26][S:25][CH3:24])=[N:15][C:14]=2[CH:16]=1
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참가 물질

8

반응물 5

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 129214403-(Methylthio)propionyl ChlorideHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

생성물 1

HCID 674985555-(Benzoxazol-2-yl)-2-(2-(methylthio)ethyl)-1-(tetrahydropyran-4-yl)benzimidazole
수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in tetrahydrofuran (5 mL) was added 3-(methylthio)propionyl chloride (98.5 mg, 0.711 mmol) and triethylamine (131 mg, 1.29 mmol), and this was stirred at room temperature for 7 hours. After the reaction was complete, water was added and this was extracted with ethyl acetate. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To a solution of the residue obtained in dioxane (5 mL) was added methanesulfonic acid (0.5 mL), and this was heated to reflux for 3 hours. After the reaction was complete, 1M aqueous sodium hydroxide solution was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were purified by silica gel column chromatography to yield the title compound (170 mg, 67% yield) as colorless crystals.

후처리

  1. extractionthis was extracted with ethyl acetate
  2. customAfter the organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate, it
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customTo a solution of the residue obtained in dioxane (5 mL)
  7. temperaturethis was heated
  8. temperatureto reflux for 3 hours
  9. extractionthis was extracted with ethyl acetate
  10. customThe organic layer obtained
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give crude crystals that
  15. customwere purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e991e3b3e90c4f65bb2af5baec9b596d
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829035B2

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