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

HRID 1804242Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-045a7db7c6eb4aedb1222503887af23c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354401B2

Reaction notes

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