Methanesulfonic Acid → HCID 135800893, compound

HRID 2181339Notes

Reaction equation

HRID 2181339 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:39])[CH2:17][CH2:18][CH2:19][N:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[C:32]([O:34][CH3:35])[C:31]([OH:36])=[C:30]([O:37][CH3:38])[CH:29]=4)=[N:26][CH:27]=3)[CH3:21])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:40][CH3:41].[CH3:42][S:43]([OH:46])(=[O:45])=[O:44]>CO.C(Cl)(Cl)Cl>[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:39])[CH2:17][CH2:18][CH2:19][N:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[C:32]([O:34][CH3:35])[C:31]([OH:36])=[C:30]([O:37][CH3:38])[CH:29]=4)=[N:26][CH:27]=3)[CH3:21])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:40][CH3:41]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 135800894HCID 135800894, compound

Product 1

HCID 135800893HCID 135800893, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of N,N′-bis[2-(4-hydroxy-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethyl-1,3-propanediamine (43.0 mg, 0.076 mmol) in methanol-chloroform (1:2, 3.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.16 mL, 0.16 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 ethanol-diethyl ether to provide the title compound as a yellow crystalline powder (melting point: 198.0-202.0° C.)(17.0 mg, yield: 30%).

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 ethanol-diethyl ether

Sources & evidence

ORD record
ord-e62fa836a4654ab2a182afef5d71b3c1
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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