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

HRID 1797314ノート

反応式

HRID 1797314 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c363aabfc34f43b4965147df0d55a69c
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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