Methanol → HCID 23355442, compound

HRID 234722Notes

Reaction equation

HRID 234722 reaction equation
[CH2:1]([C:3]1[C:10]2[CH2:9][NH:8][C:7](=O)[C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:4]=1)[CH3:2].[H-].[Na+].CI.[CH3:23][OH:24].O1CCC[CH2:26]1>>[CH3:26][CH:9]1[N:8]([CH3:7])[C:23](=[O:24])[C:6]2[N:5]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[N:4]=[C:3]([CH2:1][CH3:2])[C:10]1=2

Participants

6

Reactant 5

HCID 887MethanolHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 23355439HCID 23355439, compound

Product 1

HCID 23355442HCID 23355442, compound

Procedure

A mixture of 3-ethyl-1-(4-fluorophenyl)-6-oxo-4,6-dihydro-1H-pyrazolo[3,4-c]pyrrole (0.20 g, 0.82 mmole) and 60% sodium hydride (0.49 g, 1.2 mmole) in anhydrous tetrahydrofuran (4 ml) was heated to reflux. After 45 minutes the reaction mixture was cooled to room temperature and methyl iodide (0.29 g, 2.0 mmole) added. The mixture was then heated to reflux over 16 hours. The mixture was treated with methanol (1 ml) and the solvent removed under reduced pressure. The crude residue was chromatographed on a silica column using 1:4 ethyl acetate/hexane as eluent to give 0.12 g of the title compound. Recrystallization from ether/petroleum ether gave white crystals. M.P. 65°-65° C., Anal. calcd. for C15H16FN3O: C, 65.92; H, 5.90; N, 15.37. Found: C, 66.15; H, 5.60; N, 15.53; MS m/z 274.

Workup

  1. temperaturewas heated to reflux
  2. temperatureThe mixture was then heated
  3. temperatureto reflux over 16 hours
  4. customthe solvent removed under reduced pressure
  5. customThe crude residue was chromatographed on a silica column

Sources & evidence

ORD record
ord-7eceb69acf764d79b82ea2d170d4672b
Source dataset
uspto-grants-1997_01
Patent number
US05596013

Reaction notes

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