Methanesulfonic Acid → 1,4-Bis[5-(3,5-dimethoxy-4-methylthiophenyl)-2-pyridyl]hexahydro-1,4-diazepine dimethanesulfonate

HRID 49304Notes

Reaction equation

HRID 49304 reaction equation
[CH3:1][O:2][C:3]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[S:5][C:4]=1[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[S:31][C:32]([O:38][CH3:39])=[C:33]([CH3:37])[C:34]=4[O:35][CH3:36])=[CH:26][N:25]=3)[CH2:19][CH2:18]2)=[N:15][CH:16]=1.[CH3:40][S:41]([OH:44])(=[O:43])=[O:42]>CO>[CH3:40][S:41]([OH:44])(=[O:43])=[O:42].[CH3:40][S:41]([OH:44])(=[O:43])=[O:42].[CH3:36][O:35][C:34]1[C:33]([CH3:37])=[C:32]([O:38][CH3:39])[S:31][C:30]=1[C:27]1[CH:28]=[CH:29][C:24]([N:20]2[CH2:21][CH2:22][CH2:23][N:17]([C:14]3[CH:13]=[CH:12][C:11]([C:4]4[S:5][C:6]([O:9][CH3:10])=[C:7]([CH3:8])[C:3]=4[O:2][CH3:1])=[CH:16][N:15]=3)[CH2:18][CH2:19]2)=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 20634954HCID 20634954, compound

Product 1

HCID 865872751,4-Bis[5-(3,5-dimethoxy-4-methylthiophenyl)-2-pyridyl]hexahydro-1,4-diazepine dimethanesulfonateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-bis[5-(3,5-dimethoxy-4-methylthiophenyl)-2-pyridyl]hexahydro-1,4-diazepine (72.0 mg, 0.120 mmol) in methanol (5.0 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 resulting mixture was concentrated under reduced pressure. Methanol-diethyl ether was added to the residue, and the resulting precipitate was collected to yield the title compound as a pale yellow crystalline powder (melting point: 212.0-217.0° C. (58.0 mg, yield: 61%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthanol (5.0 mL) was added to the residue
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. additionMethanol-diethyl ether was added to the residue
  5. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-7221d30bc4c34e7d92a219e7bc9efa64
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Reaction notes

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