Pyridine → (2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-carbamic acid phenethyl ester

HRID 1797314노트

반응식

HRID 1797314 반응식
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(O[C:15](=[O:21])OC(Cl)(Cl)Cl)(Cl)Cl.N1C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH2:42])[CH:32]=[CH:31][C:30]=1[C:43]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH3:51])=[O:44].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CCOCC.O>[CH2:8]([O:9][C:15](=[O:21])[NH:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:35][C:33]1[CH:32]=[CH:31][C:30]([C:43](=[O:44])[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[CH3:51])=[C:29]([Cl:28])[CH:34]=1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

9

반응물 5

HCID 1049PyridineHCID 60542-PhenylethanolHCID 11430Potassium CarbonateHCID 94429TriphosgeneHCID 98191574-(2-Aminophenylamino)-2-chloro-2'-methylbenzophenone

생성물 1

HCID 69662902(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-carbamic acid phenethyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

The reactions were conducted under an argon atmosphere. A solution of 2-phenylethanol (0.108 mL) in DCM (2.5 mL, 0.90 mmol) was cooled to 0° C. A mixture of bis(trichloromethyl)carbonate (0.097 g, 0.33 mmol) and pyridine (0.07 mL, 0.90 mmol) in DCM (2.5 mL) was added slowly under stirring. The reaction mixture was stirred for 2 h at room temperature and then filtered, and concentrated in vacuo. The residue was dissolved in DCM (2.5 mL) and {2-chloro-4-[(2-aminophenyl)amino]phenyl}(2-methylphenyl)methanone (0.150 g, 0.45 mmol)(disclosed in WO 98/32730) and potassium carbonate (0.25 g, 1.78 mmol) were added. The reaction mixture was stirred at room temperature for 48 h after which it was poured into a mixture of water and Et2O. The aqueous phase was extracted with more Et2O. The combined organic phases were washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:3 as the eluent to afford the title compound.

후처리

  1. additionwas added slowly
  2. stirringThe reaction mixture was stirred for 2 h at room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM (2.5 mL)
  6. stirringThe reaction mixture was stirred at room temperature for 48 h after which it
  7. extractionThe aqueous phase was extracted with more Et2O
  8. washThe combined organic phases were washed with water, brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-c363aabfc34f43b4965147df0d55a69c
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034015B2

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