Methanesulfonic Acid → HCID 22485496, compound

HRID 2181314Notes

Reaction equation

HRID 2181314 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:38])[CH2:17][CH2:18][N:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:32]=[C:31]([O:33][CH3:34])[C:30]([OH:35])=[C:29]([O:36][CH3:37])[CH:28]=4)=[N:25][CH:26]=3)[CH3:20])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:39][CH3:40].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]>N1C=CC=CC=1.CO>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[C:2]([O:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:38])[CH2:17][CH2:18][N:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:28]=[C:29]([O:36][CH3:37])[C:30]([O:35][C:31](=[O:33])[CH2:30][CH2:29][CH3:28])=[C:31]([O:33][CH3:34])[CH:32]=4)=[N:25][CH:26]=3)[CH3:20])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:39][CH3:40])(=[O:1])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 135800896HCID 135800896, compound

Product 1

HCID 22485496HCID 22485496, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of N,N′-bis[2-(4-hydroxy-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (74.0 mg, 0.135 mmol) synthesized as described in Example 14 in pyridine(1.5 mL)wasaddedbutyricanhydride(101.mg,0.640 mmol). After stirring at room temperature for 12 hours, the reaction mixture was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium carbonate, 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 (0.27 mL, 0.27 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 chloroform-diethyl ether to afford the title compound as a yellow crystalline powder (melting point: 196.0-200.0° C.)(70.0 mg, yield: 59%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium carbonate
  6. concentrationconcentrated under reduced pressure
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. additionEthanol (5.0 mL) was added to the residue
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue was recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-ccd4c7dc37f74a07b0d0e00a6b91382d
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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