Phenethylamine → 2-Aminocarbonylamino-6-(2-phenylethylaminocarbonyl)indole-3-carboxamide
Reaction equation
C(N(CC)C(C)C)(C)C.[CH:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=1.[NH2:19][C:20]([NH:22][C:23]1[NH:24][C:25]2[C:30]([C:31]=1[C:32](=[O:34])[NH2:33])=[CH:29][CH:28]=[C:27]([C:35]([OH:37])=O)[CH:26]=2)=[O:21]>CN(C)C=O>[NH2:19][C:20]([NH:22][C:23]1[NH:24][C:25]2[C:30]([C:31]=1[C:32]([NH2:33])=[O:34])=[CH:29][CH:28]=[C:27]([C:35]([NH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)=[O:37])[CH:26]=2)=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N,N-Diisopropylethylamine (0.20 mL, 1.14 mmol) and 2-phenethylamine (48 μL, 0.38 mmol) were added to a solution of 2-aminocarbonylamino-3-carbamoylindole-6-carboxylic acid (Compound 18-1, 0.10 g, 0.38 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate g, 0.38 mmol) in anhydrous N,N-dimethylformamide (4 mL), and the mixture was stirred at room temperature for 2.5 hours. After the reaction mixture was concentrated under reduced pressure, the precipitated solid was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL), water (20 mL), and dried under reduced pressure to give the title compound (0.11 g) as a slightly yellow solid (yield 77%).
Workup
- concentrationAfter the reaction mixture was concentrated under reduced pressure
- washthe precipitated solid was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL), water (20 mL)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-a98e8728cda940329ed17534d7503369
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193237B2
Reaction notes
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