Potassium Carbonate → 5-(Benzoxazol-2-yl)-2-cyclohexyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74190

반응식

HRID 74190 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].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:2]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:16]3)=[N:15][C:14]=2[CH:16]=1

참가 물질

6

반응물 3

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

생성물 1

HCID 498213845-(Benzoxazol-2-yl)-2-cyclohexyl-1-(tetrahydropyran-4-yl)benzimidazole수율 119.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.15 g, 0.484 mmol) was dissolved in DMF (3 mL) and water (0.1 mL), cyclohexyl aldehyde (0.06 g, 0.561 mmol) was added followed by oxone (0.19 g, 0.310 mmol), and this was stirred at room temperature for 2.5 hours. Aqueous potassium carbonate solution (0.09 g/15 mL) was added to the reaction solution. This was extracted with chloroform, 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 (116 mg, 59.6% yield) as white crystals.

후처리

  1. extractionThis was extracted with chloroform
  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-4e079b0582194ab0a4114a13fd2573db
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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