Hydrochloric Acid → 3-{4-[4-(2,4-Dimethylphenyl)-[1,4]diazepane-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804242

Reaktionsgleichung

Reaktionsgleichung von HRID 1804242
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=O)=[CH:9][CH:8]=2)[CH2:5][CH2:4][O:3]1.[OH-].[Na+].Cl.Cl.[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[N:30]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>O.C(O)C>[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[N:30]1[CH2:36][CH2:35][CH2:34][N:33]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])=[CH:17][CH:16]=2)=[O:13])[CH2:32][CH2:31]1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 616604Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoateHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673808831-(2,4-Dimethylphenyl)-[1,4]diazepane hydrochloride

Produkt 1

HCID 461902293-{4-[4-(2,4-Dimethylphenyl)-[1,4]diazepane-1-carbonyl]phenyl}oxazolidin-2-oneAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To ethyl 4-(2-oxooxazolidin-3-yl)benzoate (0.235 g) described in Preparation Example 12 were added 1N aqueous sodium hydroxide solution (1.3 mL) and ethanol (5 mL), and the mixture was stirred at 50° C. 1N hydrochloric acid (1.3 mL) was added, 1-(2,4-dimethylphenyl)-[1,4]diazepane hydrochloride (0.241 g) described in Preparation Example 88, 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (0.277 g) and N-methylmorpholine (0.13 mL) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (41.8 mg).

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-045a7db7c6eb4aedb1222503887af23c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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