Benzenepropanoic acid → N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

HRID 1727940

반응식

HRID 1727940 반응식
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH2:30])=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1.N1C=CC=CC=1>S(Cl)(Cl)=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH:30][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 107Benzenepropanoic acidHCID 1049PyridineHCID 6228DimethylformamideHCID 178545764-(3-Chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine

생성물 1

HCID 58981790N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

51.4 mg (0.342 mmol) of 3-phenylpropionic acid was dissolved in 1 ml of thionyl chloride. A catalytic amount of DMF was added and stirred at room temperature for 3 hours. After the solvent was evaporated under reduced pressure, 45.4 mg (0.171 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine and 1 ml of pyridine were added and stirred at 50° C. overnight. After the solvent was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

후처리

  1. additionwere added
  2. stirringstirred at 50° C. overnight
  3. customAfter the solvent was evaporated under reduced pressure
  4. additionthe reaction mixture was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

출처 및 근거

ORD 기록
ord-355e01a8406546aab0d06881e218ff4f
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07494989B2

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