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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(6-Methylbenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74210
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HRID 74210 반응식
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:5]=2[N:4]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1O.CCN=C=NCCCN(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.CN(C=O)C>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]2[N:21]=[C:18]([C:16]3[CH:15]=[CH:14][C:6]4[N:7]([CH:8]5[CH2:9][CH2:10][O:11][CH2:12][CH2:13]5)[C:3]([CH3:2])=[N:4][C:5]=4[CH:17]=3)[O:20][C:23]=2[CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 760822-Amino-5-methylphenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

생성물 1

HCID 674988545-(6-Methylbenzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole수율 4.8%

시약·촉매·용매

3
HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.25 g, 0.96 mmol), 2-amino-5-methylphenol (0.13 g, 1.05 mmol), anhydrous DMF (10 mL) and WSC (0.22 g, 1.14 mmol) were stirred overnight at room temperature. After the reaction was complete, water (50 mL) was added, the precipitated crystals were filtered off, and the filter residue was extracted with water/chloroform. After the organic layer was dried over anhydrous sodium sulfate, filtration and concentration gave crystals that were dissolved in toluene (5 mL), to which p-toluenesulfonic acid hydrate (0.45 g, 2.37 mmol) was added and this was stirred at reflux for 2 hours. After the solvent was concentrated at reduced pressure, water (5 mL) was added and the solid obtained was filtered off, and after washing with water, drying at reduced pressure at 50° C. yielded the title compound (16 mg, 4.8% yield) as an orange solid.

후처리

  1. filtrationthe precipitated crystals were filtered off
  2. extractionthe filter residue was extracted with water/chloroform
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, filtration and concentration
  4. customgave crystals that
  5. additionwas added
  6. temperatureat reflux for 2 hours
  7. concentrationAfter the solvent was concentrated at reduced pressure, water (5 mL)
  8. additionwas added
  9. customthe solid obtained
  10. filtrationwas filtered off
  11. washafter washing with water
  12. customdrying at reduced pressure at 50° C.

출처 및 근거

ORD 기록
ord-f65293fb51df415d8995f62816bf2f5c
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829035B2

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