Pyridine → 2-(3-Chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester

HRID 1094983

반응식

HRID 1094983 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:5]=1[NH2:17].N1C=CC=CC=1.CO[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1OC)[C:30](Cl)=[O:31].[CH2:38]([Cl:40])Cl>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:5]=1[NH:17][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[C:27]([CH2:38][Cl:40])[CH:28]=1

참가 물질

5

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2회HCID 613136502-Amino-5-dipropylamino-benzoic acid methyl ester2회

생성물 1

HCID 666377432-(3-Chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester

반응 조건

온도
0 °C

실험 절차

2-Amino-5-dipropylamino-benzoic acid methyl ester (compound A) (243 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (3.0 ml). Subsequently, pyridine (170 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (166 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester as a useful intermediate (280 mg, yield 64%).

후처리

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c368aed5d7bb4f9cbc810a6899df9373
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134015B2

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