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Water → 4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-N-(3,5-dimethyl-isoxazol-4-ylmethyl)-3-fluoro-benzamide

HRID 1927598
Notes
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Reaction equation

HRID 1927598 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:11]([CH3:16])=[N:12][O:13][C:14]=2[CH3:15])=[O:7])=[CH:4][C:3]=1[F:19].Br[C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=O)=[CH:23][C:22]=1F.[C:31](Cl)([C:33](Cl)=O)=O.CC1[C:42]([CH2:43][NH2:44])=C(C)ON=1.[OH2:46]>ClCCCl.CN(C=O)C>[CH2:6]([N:8]([CH2:31][CH3:33])[C:9]([CH:25]([C:24]1[CH:28]=[CH:29][CH:21]=[CH:22][CH:23]=1)[N:44]1[CH2:43][CH2:42][N:12]([C:2]2[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]3[C:11]([CH3:16])=[N:12][O:13][C:14]=3[CH3:15])=[O:7])=[CH:4][C:3]=2[F:19])[CH2:11][CH2:10]1)=[O:46])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 962WaterHCID 65578Oxalyl chlorideHCID 27733414-Bromo-3-fluorobenzoic acidHCID 11018874(Dimethyl-1,2-oxazol-4-yl)methanamineHCID 693040574-Bromo-N-(3,5-dimethyl-isoxazol-4-ylmethyl)-3-fluoro-benzamide

Product 1

HCID 16667230
4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-N-(3,5-dimethyl-isoxazol-4-ylmethyl)-3-fluoro-benzamide
Yield 69%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

4-Bromo-N-(3,5-dimethyl-isoxazol-4-ylmethyl)-3-fluoro-benzamide. To a mixture of 4-bromo-3-fluoro-benzoic acid (3.0 mmol) and DMF (0.10 mL) in DCE (10 mL) was added (COCl)2 (4.0 mL) dropwise. After 30 min, the mixture was concentrated and dried under vacuum. The residue was dissolved in DCE (20 mL), treated with C-(3,5-dimethyl-isoxazol-4-yl)-methylamine (3.0 mmol) and TEA (8.0 mmol), and stirred at rt for 16 h. The mixture was treated with H2O (10 mL). The resulting precipitate was collected by filtration to give the title compound (650 mg, 69%).

Workup

  1. concentrationthe mixture was concentrated
  2. customdried under vacuum
  3. dissolutionThe residue was dissolved in DCE (20 mL)
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-10aa7b6ad7d0451c86b4cf2781b44f7c
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes