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Ammonia → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

HRID 2202899
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HRID 2202899 반응식
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[C:24]([CH2:26][CH3:27])[N:23]([CH3:28])[C:22]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>[Cu](I)I.CS(C)=O>[CH2:26]([C:24]1[N:23]([CH3:28])[C:22]2[CH:29]=[C:18]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:14])[CH:19]=[CH:20][C:21]=2[N:25]=1)[CH3:27]
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참가 물질

8

반응물 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 847010986-bromo-2-ethyl-1-methyl-1H-benzimidazole

생성물 1

HCID 716609141-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one
수율 40%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매

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온도
150 °C

실험 절차

A mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (5 g), 6-bromo-2-ethyl-1-methyl-1H-benzimidazole (6.54 g), potassium carbonate (9.46 g), N,N′-dimethylethylenediamine (2.91 ml), copper iodide (1.3 g) and DMSO (100 ml) was stirred at 150° C. for 4 h. After cooling, the mixture was poured into 28% NH3 solution at 0° C. The precipitate was collected by filtration and dissolved in EtOAc/THF. The resulting solution was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was treated with activated carbon in MeOH, and recrystallized from MeOH/water to give the title compound (3.44 g) as a white solid.

후처리

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration
  3. dissolutiondissolved in EtOAc/THF
  4. washThe resulting solution was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with activated carbon in MeOH
  8. customrecrystallized from MeOH/water

출처 및 근거

ORD 기록
ord-d341405b80b94f5183d5601df1004d0e
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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