Methanesulfonic Acid → HCID 135800895, compound

HRID 2181313Notes

Reaction equation

HRID 2181313 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:52])[CH2:24][CH2:25][N:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42]CC5C=CC=CC=5)=[C:36]([O:50][CH3:51])[CH:35]=4)=[N:32][CH:33]=3)[CH3:27])=[CH:19][N:18]=2)=[CH:11][C:10]=1[O:53][CH3:54])C1C=CC=CC=1.[CH3:55][S:56]([OH:59])(=[O:58])=[O:57]>C(O)(=O)C.[Pd].CO>[CH3:55][S:56]([OH:59])(=[O:58])=[O:57].[CH3:55][S:56]([OH:59])(=[O:58])=[O:57].[OH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:52])[CH2:24][CH2:25][N:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:35]=[C:36]([O:50][CH3:51])[C:37]([OH:42])=[C:38]([O:40][CH3:41])[CH:39]=4)=[N:32][CH:33]=3)[CH3:27])=[CH:19][N:18]=2)=[CH:11][C:10]=1[O:53][CH3:54]

Participants

6

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485590HCID 22485590, compound

Product 1

HCID 135800895HCID 135800895, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N,N′-bis[2-(4-benzyloxy-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (64.0 mg, 0.090 mmol) in acetic acid (1.0 mL) was added 10% palladium on charcoal (43.0 mg). Under hydrogen, the mixture was stirred at 50° C. for 1 hour and 30 minutes. Insoluble materials were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. A solution of the residue in methanolchloroform (1:10) was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in methanol (2.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.20 mL, 0.20 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 to afford the title compound as a yellow crystalline powder (melting point:≧300.0°) (20.0 mg, yield: 31% based on N,N′-bis[2-(4-benzyloxy-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine).

Workup

  1. customInsoluble materials were removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washA solution of the residue in methanolchloroform (1:10) was washed with saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionEthanol (5.0 mL) was added to the residue
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-bbb01dcf6e774150a490c4913219a294
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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