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

HRID 49303Notes

Reaction equation

HRID 49303 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([OH:41])[CH:32]=5)=[CH:27][N:26]=4)[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[CH3:42][S:43]([OH:46])(=[O:45])=[O:44]>CO>[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[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([OH:41])[CH:32]=5)=[CH:27][N:26]=4)[CH2:20][CH2:19]3)=[N:16][CH:17]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 20634963HCID 20634963, compound

Product 1

HCID 865872741,4-Bis[5-(3-hydroxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine dimethanesulfonateYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-bis[5-(3-hydroxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine (97.0 mg, 0.170 mmol) in methanol (5.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.35 mL, 0.35 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. The residue was recrystallized from methanol to yield the title compound as a colorless crystalline powder (melting point: 300.0-301.0° C.) (84.0 mg, yield: 63%).

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. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-3e0e47b268694ac4b595df027d6367c1
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Reaction notes

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