Hydrochloric Acid → 6-[[1-Phenyl-2-propylamino-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

HRID 1070871노트

반응식

HRID 1070871 반응식
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.[CH2:25]([N:28]=[C:29]=S)[CH2:26][CH3:27].[Cl-].[NH4+].IC.Cl>CO.O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]2[N:16]=[C:29]([NH:28][CH2:25][CH2:26][CH3:27])[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]=2[CH:11]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 69403Propyl IsothiocyanateHCID 120430856-(3-Phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester

생성물 1

HCID 102007356-[[1-Phenyl-2-propylamino-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

200 mg of 6-(3-phenylamino-4-aminophenyl)oxyhexanoic acid methyl ester was dissolved in 2 ml of methanol, the solution was mixed with 90 μl of propylisothiocyanate, and the mixture was heated for 3 hours to 50° C. After cooling, it was mixed with saturated ammonium chloride solution, diluted with water, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 140 mg of a thiourea derivative, which was dissolved in 1.5 ml of methanol, was obtained. 0.16 ml of iodomethane was added to this solution, and it was refluxed for 4 hours. After cooling, it was mixed with 1N aqueous hydrochloric acid, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 72 mg was obtained.

후처리

  1. temperaturethe mixture was heated for 3 hours to 50° C
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue was purified by column chromatography on silica gel
  8. dissolution140 mg of a thiourea derivative, which was dissolved in 1.5 ml of methanol
  9. customwas obtained
  10. temperaturewas refluxed for 4 hours
  11. temperatureAfter cooling
  12. extractionextracted three times with ethyl acetate
  13. washthe combined organic phases were washed with saturated sodium chloride solution
  14. customdried on sodium sulfate
  15. concentrationconcentrated by evaporation in a vacuum
  16. customThe residue was purified by column chromatography on silica gel
  17. custom72 mg was obtained

출처 및 근거

ORD 기록
ord-e2834d8f720643849a63065c94dc56af
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903126B2

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