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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]formamide

HRID 1408423
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HRID 1408423 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][CH:15]=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].I[C:34]1[CH:35]=[CH:36][C:37]2[O:42][CH2:41][CH2:40][CH2:39][C:38]=2[CH:43]=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:34]3[CH:35]=[CH:36][C:37]4[O:42][CH2:41][CH2:40][CH2:39][C:38]=4[CH:43]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][CH:15]=[O:16]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 109451636-IodochromanHCID 178522771HCID 178522771, 화합물2회

생성물 1

HCID 86668919N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]formamide

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]formamide (i.e. the product of Step D) (0.25 g, 1.1 mmol) in dioxane (2.5 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.06 mL, 0.43 mmol) followed copper(I) iodide (0.08 g, 0.43 mmol), potassium carbonate (0.87 g, 6.4 mmol) and 3,4-dihydro-6-iodo-2H-1-benzopyran (0.45 g, 1.7 mmol; prepared according to the procedure of Muraki et al., Tetrahedron Lett. 1996, 37, 2441). The reaction mixture was heated at 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, then dried (Na2SO4) and concentrated. The crude residue was then purified by preparative TLC (2% methanol in chloroform as eluant) to provide the title product, a compound of the present invention, as a solid (0.069 g).

후처리

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

출처 및 근거

ORD 기록
ord-3f511870d6af46aea7cfd48c12963e11
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921360B2

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