p-Toluenesulfonic acid → 4-(3-Chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-5-(3,3-diphenylpropylcarbamoyl)-2-phenyl-1,4-dihydropyrimidine

HRID 24595

반응식

HRID 24595 반응식
[C:1](O[K])([CH3:4])([CH3:3])C.[ClH:7].[C:8]([NH2:16])(=[NH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=[C:25]([C:36](=O)[CH2:37][O:38][CH2:39][CH2:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:26]([O:28]CC1C=CC=CC=1)=O.[C:48]1([CH3:58])[CH:53]=[CH:52][C:51](S(O)(=O)=O)=[CH:50][CH:49]=1>CN(C=O)C>[Cl:7][C:21]1[CH:20]=[C:19]([CH:24]2[C:25]([C:26](=[O:28])[NH:15][CH2:8][CH2:9][CH:58]([C:3]3[CH:1]=[CH:4][CH:12]=[CH:11][CH:10]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[C:36]([CH2:37][O:38][CH2:39][CH2:40][CH:41]3[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]3)[NH:16][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:15]2)[CH:18]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 80289Benzamidine, hydrochlorideHCID 69746534Benzyl 3-(chlorophenyl)-2-[2-(2-cyclohexyl-ethoxy)acetyl]acrylateHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 99393714-(3-Chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-5-(3,3-diphenylpropylcarbamoyl)-2-phenyl-1,4-dihydropyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
100 °C

실험 절차

119 mg (1.06 mmol) of t-butoxypotassium was dissolved in 5 ml of DMF. 166 mg (1.06 mmol) of benzamidine monohydrochloride was added to the obtained solution under cooling with ice, and they were stirred for 30 minutes. A solution of benzyl 3-(chlorophenyl)-2-[2-(2-cyclohexyl-ethoxy)acetyl]acrylate (E/Z mixture) in 5 ml of DMF was added to the reaction mixture under cooling with ice. The obtained mixture was stirred for 3 hours while the temperature was elevated to room temperature. A catalytic amount of p-toluenesulfonic acid was added to the reaction mixture, and they were heated to 100° C. and stirred overnight. DMF was evaporated under reduced pressure, and the residue was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

후처리

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice
  3. stirringThe obtained mixture was stirred for 3 hours while the temperature
  4. customwas elevated to room temperature
  5. stirringstirred overnight
  6. customDMF was evaporated under reduced pressure
  7. additionthe residue was diluted with ethyl acetate
  8. washwashed with saturated aqueous sodium chloride solution
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

출처 및 근거

ORD 기록
ord-3aec86edff8a4e11b228307708364677
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855716B2

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