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Dimethylformamide → HCID 68489196, compound

HRID 1878022
Notes
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Reaction equation

HRID 1878022 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1.[CH3:37][N:38](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N>[C:37]([C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:23])([F:22])[F:24])[C:6]=2[CH:36]=1)#[N:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 44549804N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

Product 1

HCID 68489196HCID 68489196, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 8857Ethyl Acetate
Solvent

Procedure

A solution of N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (1.0 g, 1.76 mmol), zinc cyanide (414 mg, 3.53 mmol) and tetrakis(triphenyl phosphine)palladium (102 mg, 0.088 mmol) in DMF (4.5 mL) was stirred at 100° C. for 3 hours. The temperature of the solution was brought to room temperature and the solution was diluted with ethyl acetate, which was washed sequentially with an aqueous citric acid solution and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (873 mg, 96%) was obtained as a white solid.

Workup

  1. customwas brought to room temperature
  2. washwas washed sequentially with an aqueous citric acid solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the drying agent was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (873 mg, 96%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-3874db34195e4e7088ab49586c7e315b
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314094B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes