Tetrahydrofuran → HCID 11213473, compound

HRID 964829Notes

Reaction equation

HRID 964829 reaction equation
[H-].[Na+].C1COCC1.[F:8][C:9]([F:41])([F:40])[C:10]1[CH:11]=[C:12]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:13][N:14]([CH2:30][CH2:31][OH:32])[C:15]([C:17]1[C:18](Cl)=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:16]>C(OCC)(=O)C>[F:8][C:9]([F:41])([F:40])[C:10]1[CH:11]=[C:12]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:13][N:14]1[C:15](=[O:16])[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][CH:20]=[N:19][C:18]=2[O:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 18387224HCID 18387224, compound

Product 1

HCID 11213473HCID 11213473, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oily) (60 mg) was added to a THF (15 ml) solution of N-[3,5-bis(trifluoromethyl)benzyl]-2-chloro-N-(2-hydroxyethyl)-4-phenyl-3-pyridinecarboxamide (Reference Example 12) (348 mg) and the mixture was stirred for 2 hours while heating under reflux. Ethyl acetate was added to the reaction mixture, which was then washed with water and dried. After the solvent was removed by distillation, the entitled compound was obtained as colorless crystals (278 mg).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. washwas then washed with water
  4. customdried
  5. customAfter the solvent was removed by distillation

Sources & evidence

ORD record
ord-d25ea34920014bc7844d5754948c5120
Source dataset
uspto-grants-1998_06
Patent number
US05770590

Reaction notes

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