Methanesulfonic Acid → HCID 22485471, compound

HRID 2181334Notes

Reaction equation

HRID 2181334 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:46])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=4)=[N:32][CH:33]=3)[CH3:27])=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49]>CO.C(Cl)Cl>[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].[CH3:41][O:40][C:38]1[CH:39]=[C:34]([C:31]2[CH:30]=[CH:29][C:28]([N:26]([CH3:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:5]4[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:14][CH:15]=3)[CH3:46])=[CH:33][N:32]=2)[CH:35]=[C:36]([O:44][CH3:45])[C:37]=1[O:42][CH3:43]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485472HCID 22485472, compound

Product 1

HCID 22485471HCID 22485471, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of N,N′-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]-N,N′-dimethyl-1,6-hexanediamine (243.0 mg, 0.370 mmol) in methanol-methylene chloride (6:1, 3.5 mL) was added a 1.0 M aqueous methanesulfonic acid (0.76 mL, 0.76 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: 192.0-195.0° C.) (251.0 mg, yield: 81%).

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-diethyl ether

Sources & evidence

ORD record
ord-f4bf6fa68fc84e988a7a482d01db39c9
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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