Methanesulfonic Acid → HCID 178462509, compound

HRID 985164Notes

Reaction equation

HRID 985164 reaction equation
[CH3:1][CH2:2][N:3]1[C:8](=[O:9])[C:7]([O:10][CH3:11])=[CH:6][C:5]([C:12]#[N:13])=[CH:4]1.C[O-].[Na+].CO.CS(O)(=O)=O.[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@@:31]([C:36]2[CH:37]=[N:38][C:39]([F:42])=[CH:40][CH:41]=2)(N)[C@@H:32]([NH2:34])[CH3:33])=[CH:27][CH:26]=1>CO>[CH2:2]([N:3]1[CH:4]=[C:5]([C:12]2[NH:34][C@@H:32]([CH3:33])[C@:31]([C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)([C:36]3[CH:37]=[N:38][C:39]([F:42])=[CH:40][CH:41]=3)[N:13]=2)[CH:6]=[C:7]([O:10][CH3:11])[C:8]1=[O:9])[CH3:1]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 218858511-Ethyl-3-methoxy-2-pyridone-5-carbonitrileHCID 23694274Sodium methanolate methanolHCID 44139477(1s,2s)-1-(4-Fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine

Product 1

HCID 178462509HCID 178462509, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-ethyl-3-methoxy-2-pyridone-5-carbonitrile (30 mg) was dissolved in methanol (1 mL), and 25% sodium methoxide-methanol solution(6.6 mL) was added thereto. The mixture was stirred at room temperature for 17 hours, and methanesulfonic acid (11 μL) and a solution of (1S,2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine (44.5 mg) in methanol (1 mL) were successively added. The mixture was stirred at room temperature for two days and concentrated in vacuo. The residue was dissolved in ethyl acetate, and the solution was washed with brine, and dried over anhydrous sodium sulfate. After removal of the sodium sulfate by filtration, the organic solvent was evaporated in vacuo to give a residue, which was purified by column chromatography on silica gel (chloroform:methanol=10:1) to give the title compound (1.8 mg) as a brown solid.

Workup

  1. stirringThe mixture was stirred at room temperature for two days
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the sodium sulfate
  7. filtrationby filtration
  8. customthe organic solvent was evaporated in vacuo
  9. customto give a residue, which
  10. customwas purified by column chromatography on silica gel (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-c4b010fa84c74ceea0707d6a57c8fdde
Source dataset
uspto-grants-2005_03
Patent number
US06869966B2

Reaction notes

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