Water → HCID 16667230, Verbindung

HRID 1927598

Reaktionsgleichung

Reaktionsgleichung von HRID 1927598
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]

Komponenten

8

Edukt 5

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

Produkt 1

HCID 16667230HCID 16667230, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-10aa7b6ad7d0451c86b4cf2781b44f7c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

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