Triethylamine → 6-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester

HRID 381345

반응식

HRID 381345 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[N+:28]([C:31]1[C:32]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[N:33][CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:40]2[CH2:41][CH2:42][N:37]([C:32]3[C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:38][CH2:39]2)=[O:13])=[N:9][CH:10]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 62493Pivaloyl chlorideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 37788341-(3-Nitropyridin-2-yl)piperazine

생성물 1

HCID 108616096-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

5-(Methoxycarbonyl)-2-pyridinecarboxylic acid (20 g) was added in methylene chloride (200 ml), and then, dissolved with the addition of triethylamine (17 ml). The mixture was cooled, pivaloyl chloride (14.5 ml) was added at 0° C.˜5° C. and stirred at 5° C. for 2 hours. 1-(3-Nitro-2-pyridyl)piperazine (23 g) and triethylamine (18 ml) were added to the solution in order and the mixture was reacted at 5° C.˜10° C. for 2 hours. The reaction mixture was washed with aqueous sodium bicarbonate and water each twice and then, the separated organic layer was concentrated under reduced pressure. The concentrated residue was treated with ethanol for crystallization and water was added, then the precipitate was filtered. The crude product was recrystallized with ethanol and ether, filtered and dried to give a desired compound of 35.3 g (yield: 86%).

후처리

  1. temperatureThe mixture was cooled
  2. customthe mixture was reacted at 5° C.˜10° C. for 2 hours
  3. washThe reaction mixture was washed with aqueous sodium bicarbonate and water each twice and then, the separated organic layer
  4. concentrationwas concentrated under reduced pressure
  5. additionThe concentrated residue was treated with ethanol for crystallization and water
  6. additionwas added
  7. filtrationthe precipitate was filtered
  8. customThe crude product was recrystallized with ethanol and ether
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-804b4d70de9f4408a13d6d9c560f0edb
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306860B1

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