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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 383741
Notes
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Reaction equation

HRID 383741 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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 24 h 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+).

Workup

  1. customAn oven-dried, argon-sparged vial
  2. custombriefly sparged with argon
  3. customcapped
  4. temperatureAfter 24 h the reaction mixture was cooled
  5. filtrationfiltered through Celite
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50)

Sources & evidence

ORD record
ord-e91362245d3c4d288396aebb904ba55c
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367667B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes