Methanesulfonic Acid → HCID 22485601, compound

HRID 2181320Notes

Reaction equation

HRID 2181320 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:40])[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]([C:36]#[N:37])=[C:30]([O:38][CH3:39])[CH:29]=4)=[N:26][CH:27]=3)[CH3:21])=[CH:13][N:12]=2)=[CH:5][C:4]=1[O:41][CH3:42])#[N:2].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>CO>[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[C:36]([C:31]1[C:32]([O:34][CH3:35])=[CH:33][C:28]([C:25]2[CH:24]=[CH:23][C:22]([N:20]([CH3:21])[CH2:19][CH2:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([C:6]4[CH:5]=[C:4]([O:41][CH3:42])[C:3]([C:1]#[N:2])=[C:8]([O:9][CH3:10])[CH:7]=4)=[N:12][CH:13]=3)[CH3:40])=[CH:27][N:26]=2)=[CH:29][C:30]=1[O:38][CH3:39])#[N:37]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485468HCID 22485468, compound

Product 1

HCID 22485601HCID 22485601, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N,N′-bis[2-(4-cyano-3,5-dimethoxy-phenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (125.0 mg, 0.220 mmol) in methanol (2.0 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.44 mL, 0.44 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. Methanol (2.5 mL) was added to the residue, and the resulting suspension was stirred in a bath maintained at 70° C. After cooling, the resulting precipitate was collected by filtration to afford the title compound as a yellow crystalline powder (melting point:≧300.0° C.)(72.0 mg, yield: 43%).

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. additionMethanol (2.5 mL) was added to the residue
  5. temperatureAfter cooling
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0a6717743457404cbe72aa8ffaa27b7b
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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