3-Ethylphenyl isocyanate → 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

HRID 530425Notes

Reaction equation

HRID 530425 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[CH2:20]([C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]>C1COCC1.C(OCC)(=O)C>[CH2:20]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([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:4][CH:3]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]

Participants

5

Reactant 2

HCID 27696373-Ethylphenyl isocyanateHCID 1212546212-(4-Amino-phenyl)-indole-1-carboxylic acid amide

Product 1

HCID 1212546082-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The reaction mixture of 2-(4-amino-phenyl)-indole-1-carboxylic acid amide (125.5 mg, 0.5 mmol, 1 eq) and 3-ethylphenyl isocyanate (0.073 mL, 1 eq) in anhydrous THF (4 mL) was stirred at room temperature for 2 hours. It was then diluted with ethyl acetate, washed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine, and dried with anhydrous sodium sulfate. The upper liquor was decanted, concentrated, and the solid residue was triturated with EtOAC-Hex (1:1). 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide was obtained as white solid upon filtration in amount of 156 mg (78%).

Workup

  1. washwashed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper liquor was decanted
  4. concentrationconcentrated
  5. customthe solid residue was triturated with EtOAC-Hex (1:1)

Sources & evidence

ORD record
ord-de42bfbb51354e47b5692def9fbaddc0
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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