Dimethylformamide → HCID 18179598, compound

HRID 1359132Notes

Reaction equation

HRID 1359132 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:27][CH2:26][C:11]2([O:16][C:15](=[O:17])[NH:14][CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:10][CH2:9]1)=[O:7].CN(C)C=O.[H-].[Na+].Br[CH2:45][CH:46]([F:48])[F:47]>>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[C:6]([N:8]1[CH2:9][CH2:10][C:11]2([O:16][C:15](=[O:17])[N:14]([CH2:45][CH:46]([F:48])[F:47])[CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:26][CH2:27]1)=[O:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1361862-Bromo-1,1-difluoroethaneHCID 9914695HCID 9914695, compound

Product 1

HCID 18179598HCID 18179598, compoundYield 33%

Procedure

To a solution of 261 mg (0.5 mmol) 9-(3,5-bis-trifluoromethyl-benzoyl)-5-(3,4-difluoro-phenyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one in dimethylformamide 24 mg (0.5 mmol) of a 55% sodium hydride suspension in mineral oil was added at room temperature under argon. After 15 min, 80 mg (0.55 mmol) of 2-bromo-1,1-difluoroethane was added. The reaction mixture was stirred at room temperature under argon overnight. After evaporation of the solvent in vacuum water (1 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2, Hexane/ethylacetate=1:1) to yield 96 mg (33%) of the title compound.

Workup

  1. customAfter evaporation of the solvent in vacuum water (1 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2, Hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-9520414768c94c518a35e76b29fe4332
Source dataset
uspto-grants-2003_07
Patent number
US06599900B2

Reaction notes

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