1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[3-(2-phenyl-4-pyridin-4-yl-2H-pyrazol-3-yl)-phenyl]-urea

HRID 45820

反応式

HRID 45820 の反応式
C1([N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[C:9]([C:18]3[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=3)=[N:8]2)C=CC=CC=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][C:27]=1[C:35]([F:38])([F:37])[F:36]>ClCCl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:9]3[N:8]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:7]=[CH:11][C:10]=3[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)[CH:19]=2)=[O:34])=[CH:28][C:27]=1[C:35]([F:36])([F:37])[F:38]

参加物

4

反応物 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 671848143-(1-Phenyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine

生成物 1

HCID 671855961-(4-Chloro-3-trifluoromethyl-phenyl)-3-[3-(2-phenyl-4-pyridin-4-yl-2H-pyrazol-3-yl)-phenyl]-urea収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(1-Phenyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (as regioisomeric mixture) was dissolved in dry dichloromethane (1 mL) under nitrogen atmosphere, 4-chloro-3-trifluoromethylphenylisocyanate (61 mg, 0.275 mmol, 1.4 eq) was added and the reaction mixture was stirred at room temperature for 3 hours. The solution was concentrated to dryness and purified by chromatography on silica gel (SP1, gradient n-hexane/ethyl acetate 1:1 to pure ethyl acetate). Two pools of fractions containing the two separated regioisomers were obtained, together with some mixed fractions (total yield 78%). 55 mg of 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[3-(2-phenyl-4-pyridin-4-yl-2H-pyrazol-3-yl)-phenyl]-urea were obtained as colourless oil.

後処理

  1. concentrationThe solution was concentrated to dryness
  2. custompurified by chromatography on silica gel (SP1, gradient n-hexane/ethyl acetate 1:1 to pure ethyl acetate)
  3. additionTwo pools of fractions containing the two separated regioisomers
  4. customwere obtained, together with some mixed fractions (total yield 78%)

出典と根拠

ORDレコード
ord-2c72401469ac462581720f2ec27eb469
出典データセット
uspto-grants-2013_09
特許番号
US08541575B2

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