1-Methylpiperazine → 3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide

HRID 1005580노트

반응식

HRID 1005580 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)[CH3:9])=[O:7].[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C.C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[C:6]([N:8]([CH3:9])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:36]1[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]1)=[O:25])=[O:7]

참가 물질

9

반응물 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 187914763-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide

생성물 1

HCID 187914403-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide수율 100.1%

시약·촉매·용매 4

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-Methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (5.2 g), 1-methylpiperazine (1.45 g) and 1-hydroxybenzotriazole (1.96 g) were dissolved in N,N-dimethylformamide (50 ml) and the solution was cooled in an ice bath. To the mixture was added N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride (2.78 g) and the solution was stirred at the same temperature for 30 minutes. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for additional 20 hours. The reaction mixture was diluted with ethyl acetate and the solution was washed successively with saturated sodium hydrogen carbonate and brine, and dried over sodium sulfate. The sodium sulfate was removed and the solvent was removed by evaporation to give oil. The crude material was subjected to a silica gel column chromatography (SiO2 ; 120 g, 2% methanol in chloroform) to give 3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide (6.2 g).

후처리

  1. temperaturethe solution was cooled in an ice bath
  2. stirringstirring
  3. waitwas continued for additional 20 hours
  4. washthe solution was washed successively with saturated sodium hydrogen carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customThe sodium sulfate was removed
  7. customthe solvent was removed by evaporation
  8. customto give oil

출처 및 근거

ORD 기록
ord-d2b6340a79fd4946a41edc84ef607bb9
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054457

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