Water → HCID 16667230, compound

HRID 1927598

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]

Participants

8

Reactant 5

HCID 962WaterHCID 65578Oxalyl chlorideHCID 27733414-Bromo-3-fluorobenzoic acidHCID 11018874(Dimethyl-1,2-oxazol-4-yl)methanamineHCID 69304057HCID 69304057, compound

Product 1

HCID 16667230HCID 16667230, compoundYield 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
Patent number
US08183239B2

Linked notes

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