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

HRID 1804242

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HRID 1804242 반응식
[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

참가 물질

9

반응물 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

생성물 1

HCID 461902293-{4-[4-(2,4-Dimethylphenyl)-[1,4]diazepane-1-carbonyl]phenyl}oxazolidin-2-one수율 10.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-045a7db7c6eb4aedb1222503887af23c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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