2-Thiophenecarboxaldehyde → 5-(Benzoxazol-2-yl)-2-(thiophen-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74212노트

반응식

HRID 74212 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].[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]=O.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.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:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[N:15][C:14]=2[CH:16]=1

참가 물질

7

반응물 4

HCID 73642-ThiophenecarboxaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

생성물 1

HCID 674982805-(Benzoxazol-2-yl)-2-(thiophen-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 36%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.13 g, 0.42 mmol) was dissolved in DMF (3 mL) and water (0.1 mL), 2-thiophenecarbaldehyde (0.05 g, 0.45 mmol) was added followed by oxone (0.17 g, 0.28 mmol), and this was stirred at room temperature for 2.5 hours. Aqueous potassium carbonate solution (0.10 g/15 mL) was added to the reaction solution. This was extracted with ethyl acetate, washed with water, and after drying over magnesium sulfate, this was concentrated and purified by silica gel column chromatography. The crystals obtained were washed with hexane and a small amount of ethyl acetate, and dried to yield the title compound (60 mg, 36% yield) as light brown crystals.

후처리

  1. extractionThis was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialafter drying over magnesium sulfate
  4. concentrationthis was concentrated
  5. custompurified by silica gel column chromatography
  6. customThe crystals obtained
  7. washwere washed with hexane
  8. dry with materiala small amount of ethyl acetate, and dried

출처 및 근거

ORD 기록
ord-a987402ca7234d9289113b220d456175
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

반응 노트

불러오는 중…