Methanesulfonic Acid → HCID 22485462, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:43])[CH2:20][CH2:21][CH2:22][N:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]4[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=4)=[N:29][CH:30]=3)[CH3:24])=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:44][S:45]([OH:48])(=[O:47])=[O:46]>CO.C(Cl)(Cl)Cl>[CH3:44][S:45]([OH:48])(=[O:47])=[O:46].[CH3:44][S:45]([OH:48])(=[O:47])=[O:46].[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:43])[CH2:20][CH2:21][CH2:22][N:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]4[CH:32]=[C:33]([O:41][CH3:42])[C:34]([O:39][CH3:40])=[C:35]([O:37][CH3:38])[CH:36]=4)=[N:29][CH:30]=3)[CH3:24])=[CH:15][N:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the crude N,N′-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]-N,N′-dimethyl-1,3-propanediamine (275.0 mg, approx. 0.46 mmol) in methanol-chloroform (1:1, 6.0 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.93 mL, 0.93 mmol), and the reaction mixture was concentrated under reduced pressure. Ethanol (5.0 mL) was added to the residue, and the mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-diethyl ether to yield the title compound as yellow needles (melting point: 216.0-219.0° C.)(255.0 mg, yield: 70% based on N,N′-dimethyl-1,3-propanediamine).
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionEthanol (5.0 mL) was added to the residue
- concentrationthe mixture was concentrated under reduced pressure
- customThe residue was recrystallized from methanol-diethyl ether
Sources & evidence
- ORD record
- ord-38658c34ba734bd19e248f507d57956b
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890940B2
Reaction notes
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