Methanesulfonic Acid → HCID 22485585, compound

HRID 2181328Notes

Reaction equation

HRID 2181328 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:44][CH3:45])[CH2:20][CH2:21][CH2:22][N:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=4)=[N:30][CH:31]=3)[CH2:24][CH3:25])=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:46][S:47]([OH:50])(=[O:49])=[O:48]>CO.C(Cl)(Cl)Cl>[CH3:46][S:47]([OH:50])(=[O:49])=[O:48].[CH3:46][S:47]([OH:50])(=[O:49])=[O:48].[CH3:39][O:38][C:36]1[CH:37]=[C:32]([C:29]2[CH:28]=[CH:27][C:26]([N:23]([CH2:24][CH3:25])[CH2:22][CH2:21][CH2:20][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)=[N:14][CH:15]=3)[CH2:44][CH3:45])=[CH:31][N:30]=2)[CH:33]=[C:34]([O:42][CH3:43])[C:35]=1[O:40][CH3:41]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485473HCID 22485473, compound

Product 1

HCID 22485585HCID 22485585, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of the crude N,N′-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]-N,N′-diethyl-1,3-propanediamine (160.0 mg, approx. 0.26 mmol) in methanol-chloroform (1:1, 6.0 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.51 mL, 0.51 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-methylene chloride-diethyl ether to yield the title compound as a yellow crystalline powder (melting point: 239.0-242.0° C.)(92.0 mg, yield: 45% based on N,N′-diethyl-1,3-propanediamine).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthanol (5.0 mL) was added to the residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was recrystallized from methanol-methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-338ad5521de840958c0d66a642b1d24a
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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