Ethyl Acetate → HCID 67116145, compound

HRID 389993Notes

Reaction equation

HRID 389993 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:27]([F:28])=[CH:26][C:8]([O:9][C:10]2[CH:24]=[CH:23][C:13]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][C:18](=[O:22])[CH2:17]3)=[O:15])=[CH:12][C:11]=2[F:25])=[C:7]([O:29][CH3:30])[CH:6]=1)[CH3:4].Br[CH2:32][C:33]([NH2:35])=[O:34].C(OCC)(=O)C>O1CCCC1.O>[CH2:3]([C:5]1[C:27]([F:28])=[CH:26][C:8]([O:9][C:10]2[CH:24]=[CH:23][C:13]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:32][C:33]([NH2:35])=[O:34])[C:18](=[O:22])[CH2:17]3)=[O:15])=[CH:12][C:11]=2[F:25])=[C:7]([O:29][CH3:30])[CH:6]=1)[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

Product 1

HCID 67116145HCID 67116145, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 49 mg, 1.2 mmol) was added to a solution of 4-[4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoy]-piperazin-2-one (which may be prepared in accordance with the experimental described in Example 5, step 1; 400 mg, 1 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 15 minutes prior to the addition of 2-bromoacetamide (212 mg, 1.5 mmol). After stirring for 2 days at room temperature, the reaction mixture was diluted by addition of ethyl acetate (20 mL) and water (20 mL). After separation, the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (2×20 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (98:2 to 95:5) as eluent. The title product was obtained as a white solid (300 mg, 65%).

Workup

  1. custommay be prepared in accordance with the
  2. stirringAfter stirring for 2 days at room temperature
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic phases were washed with a saturated solution of sodium chloride (2×20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d0c5402b6aa349f1ac4e215f760afe65
Source dataset
uspto-grants-2013_02
Patent number
US08383621B2

Reaction notes

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