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Potassium Carbonate → N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]-N'-methylurea

HRID 1408425
ノート
印刷プレビュー

反応式

HRID 1408425 の反応式
[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]([NH:17][CH3:18])=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].I[C:36]1[CH:37]=[CH:38][C:39]2[O:44][CH2:43][CH2:42][CH2:41][C:40]=2[CH:45]=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:36]3[CH:37]=[CH:38][C:39]4[O:44][CH2:43][CH2:42][CH2:41][C:40]=4[CH:45]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15]([NH:17][CH3:18])=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 109451636-IodochromanHCID 178485847HCID 178485847、化合物2 回

生成物 1

HCID 67151201N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]-N'-methylurea

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a solution of N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]-N′-methylurea (i.e. the product of Step A) (0.30 g, 1.1 mmol) in dioxane (3.0 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.07 mL, 0.45 mmol) followed by copper(I) iodide (0.085 g, 0.45 mmol), potassium carbonate (0.94 g, 6.8 mmol) and 3,4-dihydro-6-iodo-2H-1-benzopyran (0.44 g, 1.7 mmol; prepared as cited in Step E of Synthesis Example 4). The reaction mixture was heated to 110° C. for 20 h and then cooled to ambient temperature. The solvent was evaporated, and the residue was taken up in chloroform, washed with water and brine, and then dried (Na2SO4) and concentrated. The crude residue was purified by preparative TLC (1.5% methanol in dichloromethane as eluant) to provide the title product a compound of the present invention, as a solid (0.036 g).

後処理

  1. temperaturecooled to ambient temperature
  2. customThe solvent was evaporated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by preparative TLC (1.5% methanol in dichloromethane as eluant)

出典と根拠

ORDレコード
ord-fc8bdd57e41d4868b3f83bf9a984f003
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921360B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート