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N,N'-Dimethylethylenediamine → 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amide

HRID 912572
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HRID 912572 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][C:16]1[N:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[C:18]([CH3:24])=[CH:19][C:20]=1[C:21]([NH2:23])=[O:22].C([O-])([O-])=O.[K+].[K+].CNCCNC>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:23][C:21]([C:20]2[CH:19]=[C:18]([CH3:24])[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:33])([F:32])[F:34])[C:16]=2[CH3:15])=[O:22])=[CH:3][C:4]=1[CH3:14])(=[O:10])=[O:9]
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참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 595902374-bromo-N,N,2-trimethylbenzenesulfonamideHCID 598082232,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide

생성물 1

HCID 598078142,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amide수율 79,246.703%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

An oven-dried, argon-sparged vial was charged with 4-bromo-2,N,N-trimethyl-benzenesulfonamide (70 mg, 0.25 mmol), 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide (85 mg, 0.30 mmol), anhyd K2CO3 (69 mg, 0.50 mmol), and copper (I) iodide (10 mg, 0.05 mmol), and then briefly sparged with argon. To the vial under argon was added anhyd toluene (0.5 mL) and N,N′-dimethyl-ethylenediamine (11 μL, 0.10 mmol), then capped and heated at 120° C. After 24h the reaction mixture was cooled, diluted with EtOAc, filtered through Celite and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50) to afford the title compound (95 g, 79%) as a white solid. 1H-NMR (DMSO-d6) δ 9.74 (1H, s), 8.01 (1H, d, J=7.8), 7.92 (1H, app t, J=7.8), 7.78-7.86 (3H, m), 7.71 (1H, d, J=8.3), 7.51 (1H, d, J=7.8), 6.65 (1H, s), 2.69 (6H, s), 2.53 (3H, s), 2.14 (3H, s), 1.88 (3H, s); MS (ESI): 480 (MH+).

후처리

  1. customAn oven-dried, argon-sparged vial
  2. custombriefly sparged with argon
  3. customcapped
  4. filtrationfiltered through Celite
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50)

출처 및 근거

ORD 기록
ord-add03c3f02e843098325b81e464b4cf5
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08026237B2

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