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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
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HRID 1408425 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]([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]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 109451636-IodochromanHCID 178485847HCID 178485847, 화합물2회

생성물 1

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

시약·촉매·용매 2

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

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온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fc8bdd57e41d4868b3f83bf9a984f003
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921360B2

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