Methanesulfonic Acid → HCID 22485505, compound

HRID 2181340Notes

Reaction equation

HRID 2181340 reaction equation
[CH2:1]([N:3]([C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH:45]([CH3:47])[CH3:46])=[C:38]([O:48][CH3:49])[CH:37]=2)=[N:34][CH:35]=1)[CH2:4][CH2:5][CH2:6][N:7]([CH2:28][CH3:29])[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH:23]([CH3:25])[CH3:24])=[C:16]([O:26][CH3:27])[CH:15]=2)=[N:12][CH:13]=1)[CH3:2].[CH3:50][S:51]([OH:54])(=[O:53])=[O:52]>CO.C(Cl)(Cl)Cl>[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH2:28]([N:7]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[C:16]([O:26][CH3:27])[C:17]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([O:20][CH3:21])[CH:19]=2)=[N:12][CH:13]=1)[CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH:45]([CH3:47])[CH3:46])=[C:38]([O:48][CH3:49])[CH:37]=2)=[N:34][CH:35]=1)[CH3:29]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485491HCID 22485491, compound

Product 1

HCID 22485505HCID 22485505, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of N,N′-diethyl-N,N′-bis[2-(4-isopropoxy-3,5-dimethoxyphenyl)-5-pyridyl]-1,3-propanediamine (78.0 mg, 0.110 mmol) in methanol-chloroform (2:1, 3.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.24 mL, 0.24 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-hexane to yield the title compound as yellow flakes (melting point: 173.0-175.0° C.) (66.0 mg, yield: 66%).

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-hexane

Sources & evidence

ORD record
ord-118ac80c81274537911878a89a94f708
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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