Tetrahydrofuran → HCID 67491572, compound

HRID 1391435Notes

Reaction equation

HRID 1391435 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH:5]=[N:6][NH:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10](F)[C:9]=1[F:17].O[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[H-].[Na+].O1CCC[CH2:33]1>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH:5]=[N:6][NH:7][C:8]1[C:9]([F:17])=[C:10]([O:27][CH2:26][CH2:25][N:24]2[CH2:29][CH2:28][CH2:33][CH2:22][CH2:23]2)[N:11]=[C:12]([F:15])[C:13]=1[F:14]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 67491739HCID 67491739, compound

Product 1

HCID 67491572HCID 67491572, compound

Procedure

N-(3-methyl-benzylidene)-N′-(2,3,5,6-tetrafluoro-pyridin-4-yl)-hydrazine (2.2 g; 7.8 mmol) was dissolved in tetrahydrofuran (1100 mL) and to the solution was added 4-(2-hydroxyethyl)-morpholine (1.3 g; 10 mmol) followed by sodium hydride (480 mg; 20 mmol). The solution was stirred at reflux for 24 hours. The solvent was then evaporated, and the solid was purified by column chromatography to give N-(3-methyl-benzylidene)-N′-[2,3,5-trifluoro-6-(2-piperidin-1-yl-ethoxy)-pyridin-4-yl]-hydrazine (830 mg).

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was then evaporated
  3. customthe solid was purified by column chromatography

Sources & evidence

ORD record
ord-c2f2f29c6cda40148b63c45941273bfc
Source dataset
uspto-grants-2008_03
Patent number
US07338951B2

Reaction notes

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