Dimethylformamide → HCID 10303452, compound

HRID 1359131Notes

Reaction equation

HRID 1359131 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([O:16][C:15](=[O:17])[NH:14][CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7].CN(C)C=O.[H-].[Na+].Cl[CH2:43][C:44]([N:46]([CH3:48])[CH3:47])=[O:45]>>[F:34][C:2]([F:33])([F:1])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([O:16][C:15](=[O:17])[N:14]([CH2:43][C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 10163188HCID 10163188, compound

Product 1

HCID 10303452HCID 10303452, compoundYield 54%

Conditions

Temperature
80 °C

Procedure

To a solution of 243 mg (0.5 mmol) 9-(3,5-bis-trifluoromethyl-benzoyl)-5-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, 126 mg (0.8 mmol) of 2-chloro-N,N-dimethylacetamide was added. The reaction mixture was stirred at 80° C. 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 154 mg (54%) 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-7d83177dcd17415399103f809dad5209
Source dataset
uspto-grants-2003_07
Patent number
US06599900B2

Reaction notes

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