m-Tolyl isocyanate → 2-[3-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

HRID 530430Notes

Reaction equation

HRID 530430 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:17]([NH2:19])=[O:18])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=1.[C:20]1([CH3:29])[CH:25]=[CH:24][CH:23]=[C:22]([N:26]=[C:27]=[O:28])[CH:21]=1>C1COCC1.C(OCC)(=O)C>[CH3:29][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[N:9]([C:17]([NH2:19])=[O:18])[C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:5]=[CH:6][CH:7]=2)=[O:28])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 1212546152-(3-aminophenyl)-1H-indole-1-carboxamide

Product 1

HCID 1212546092-[3-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-(3-aminophenyl)-1H-indole-1-carboxamide (50.2 mg, 0.2 mmol, 1 eq) in anhydrous THF (2 mL) was added m-tolyl isocyanate (25 μL, 1 eq) and the reaction solution was stirred at room temperature for one hour. It was then diluted with ethyl acetate, washed with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated and the oily residue was treated with small amount of dichloromethane. The white solid appeared during this process was filtered to yield 2-[3-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide in amount of 36 mg.

Workup

  1. washwashed with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
  2. dry with materiallastly dried with anhydrous sodium sulfate
  3. customThe upper solution was decanted
  4. concentrationconcentrated
  5. additionthe oily residue was treated with small amount of dichloromethane
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-d42db4aa6cc24268888f1f8b0db00c18
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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