Pyridine → N1-(4-Bromobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)-1,2-benzenediamine

HRID 427558노트

반응식

HRID 427558 반응식
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]([NH:17][C:18]3[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:24][C:19]2[C:18]([NH:17][C:15]([O:14][CH2:13][CH:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:12][CH2:11]3)=[O:16])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:37])=[CH:34][CH:33]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

생성물 1

HCID 21352715N1-(4-Bromobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)-1,2-benzenediamine수율 43%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of N1-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)-1,2-benzenediamine (300 mg, 0.920 mmol) and pyridine (0.74 mL) in chloroform (5 mL) was treated with 4-bromobenzoyl chloride (405 mg, 1.84 mmol). After 20 h, the mixture was concentrated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate and the combined organics were washed with 1 N aqueous sodium hydroxide, water, saturated sodium chloride solution. The solution was dried (potassium carbonate), filtered, and concentrated in vacuo. Recrystallization (methanol/chloroform and hexanes) yielded 200 mg (43%) of the title compound.

후처리

  1. concentrationthe mixture was concentrated
  2. customthe residue partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washthe combined organics were washed with 1 N aqueous sodium hydroxide, water, saturated sodium chloride solution
  5. dry with materialThe solution was dried (potassium carbonate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallization (methanol/chloroform and hexanes)

출처 및 근거

ORD 기록
ord-45cb8d6171984fb4bb3deb0632cf2017
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313122B1

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