N'-(3-(Dimethylamino)propyl)-N,N-dimethyl-1,3-propanediamine → 2-[(4-chlorophenoxy)methyl]-1-methyl-3-[[N,N-bis(3-dimethylaminopropyl)amino]carbonyl]-1H-indole
Reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:20])[C:10]3[C:15]([C:16]=2[C:17]([OH:19])=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:20])[C:10]3[C:15]([C:16]=2[C:17]([N:28]([CH2:27][CH2:26][CH2:25][N:24]([CH3:35])[CH3:23])[CH2:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under an argon atmosphere 2-[(4-chlorophenoxy)methyl]-1-methyl-3-carboxy-1H-indole (0.100 g, 0.317 mmol) was dissolved in 3.2 ml of N,N-dimethylformamide. To this solution were added N,N-bis(3-dimethylaminopropyl)amine (0.074 ml, 0.0623 g, 0.332 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.091 g, 0.475 mmol), and hydroxybenztriazole (0.0642 g, 0.475 mmol). The resulting mixture was then heated for 6 hours and then stirred at room temperature overnight. The progress of the reaction was monitored by thin layer chromatography.
Workup
- temperatureThe resulting mixture was then heated for 6 hours
Sources & evidence
- ORD record
- ord-62a8bbca03ad4cf9987c1e7d8265ad15
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245761B1
Reaction notes
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