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N,N-Dimethylglycine → 1-[4-(4-morpholinylcarbonyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

HRID 1988672
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HRID 1988672 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[NH:20][N:19]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu-]=O>[N:10]1([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:20]3[C:21]4[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=4[C:18]([C:17]([F:16])([F:28])[F:27])=[N:19]3)=[CH:3][CH:4]=2)=[O:9])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1
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참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 7726344-[(4-Iodophenyl)carbonyl]morpholineHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

생성물 1

HCID 13166291-[4-(4-morpholinylcarbonyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole수율 82%

시약·촉매·용매 2

HCID 178419072
HCID 178419072, 화합물
촉매
HCID 679Dimethyl Sulfoxide용매

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온도
130 °C

실험 절차

A mixture of 4-[(4-iodophenyl)carbonyl]morpholine (1.90 g, 6.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (1.14 g, 6.0 mmol), copper (I) oxide (10 mol %, 0.6 mmol, 86 mg), N,N-dimethylglycine (20 mol %, 1.2 mmol, 124 mg), and cesium carbonate (12.0 mmol, 3.91 g) in dimethylsulfoxide (16 ml) was stirred in an oil bath heated at 130° C. for 24 h under argon and then allowed to cool to room temperature. The reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml). The organic layer was separated and dried over sodium sulphate. The solvent was removed by rotary evaporation to give a dark brown residue that was added to a 20 g isolute pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a brown gum (1.86 g, 82%).

후처리

  1. temperatureto cool to room temperature
  2. customThe reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed by rotary evaporation
  6. customto give a dark brown residue that
  7. additionwas added to a 20 g isolute pre-packed silica column
  8. washeluted from 0-50% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-c678f62a1f984afa88226c7b7a1b9698
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642256B2

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