Methanesulfonic Acid → HCID 10339590, compound

HRID 1720919Notes

Reaction equation

HRID 1720919 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[N:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[NH:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1.[CH3:22][S:23](O)(=[O:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[C:10]([NH:9][C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH:3]=1)=[N:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])#[N:11]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 9817785HCID 9817785, compound

Product 1

HCID 10339590HCID 10339590, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-N-cyano-N'-[2-(2-chlorophenyl)ethyl]-3-pyridinecarboximidamide (110 mg, 0.39 mmol) in pyridine (2 ml) was added anhydrous methanesulfonic acid (65 mg, 0.37 mmol), and the mixture was stirred at room temperature for 5 hours. After the reaction was completed, ice and a saturated aqueous sodium carbonate solution (20 ml) were added to the reaction mixture, and the mixture was extracted with ethyl acetate (30 ml×3). The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography (Wako Gel C-200, 20 g) and eluted with chloroform:methanol (50:1) to give the title compound (45 mg, yield 32%) as colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 ml×3)
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. washeluted with chloroform:methanol (50:1)

Sources & evidence

ORD record
ord-de7456f6c0954ab2a3687dc0fd821593
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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