Sodium Iodide → 5-(Benzoxazol-2-yl)-2-benzylaminomethyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74202노트

반응식

HRID 74202 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:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:15]([CH2:17]O)=[N:16][C:12]=2[CH:11]=1.S(Cl)(Cl)=O.[I-].[Na+].[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>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:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:15]([CH2:17][NH:40][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:16][C:12]=2[CH:11]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 674979855-(Benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole

생성물 1

HCID 498214585-(Benzoxazol-2-yl)-2-benzylaminomethyl-1-(tetrahydropyran-4-yl)benzimidazole수율 86.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To 5-(benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 13-2) (168 mg, 0.481 mmol) was added thionyl chloride (1.5 mL), and this was heated to reflux with stirring for 2 hours. After the reaction was complete, this was cooled to room temperature and concentrated. The crystals obtained were suspended in tetrahydrofuran, and to this was added sodium iodide (108 mg, 0.722 mmol) and benzylamine (258 mg, 2.41 mmol), and this was heated to reflux with stirring for 1.5 hours. After the reaction was complete, this was cooled to room temperature, water was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give an residue that was purified by silica gel column chromatography to yield the title compound (182 mg, 86% yield) as a colorless amorphous mass.

후처리

  1. temperaturethis was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customThe crystals obtained
  5. temperaturethis was heated
  6. temperatureto reflux
  7. stirringwith stirring for 1.5 hours
  8. temperaturethis was cooled to room temperature
  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 an residue that
  15. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-fbf1b2fbbeb04907aa5c9739d1ef654f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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