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

HRID 460390Notes

Reaction equation

HRID 460390 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-2e7679bc5fff440e87c449e1f29a00fd
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

Loading…