Potassium Carbonate → methyl N-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]-carbamate

HRID 70239

반응식

HRID 70239 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].[Cl:35][C:36]1[CH:41]=[CH:40][C:39](I)=[CH:38][CH:37]=1>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:39]3[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178502067HCID 178502067, 화합물

생성물 1

HCID 66790277methyl N-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]-carbamate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Step B, Example 4) (0.2 g, 0.75 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.043 g, 0.3 mmol), copper(I) iodide (0.03 g, 0.15 mmol) and potassium carbonate (−325 mesh) (0.622 g, 4.5 mmol) in dioxane (4 mL) was added 1-chloro-4-iodobenzene (0.27 g, 1.13 mmol). The reaction mixture heated at reflux overnight and then concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.156 g) melting at 151-153° C.

후처리

  1. temperatureThe reaction mixture heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

출처 및 근거

ORD 기록
ord-c47034b563664e30a415a696704207da
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822521B2

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