Ethanol → 3-{3-Amino-4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804234Notes

Reaction equation

[Cl-].[NH4+].C(O)C.[CH3:6][C:7]1[C:8]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:32][CH2:31][O:30][C:29]4=[O:33])=[CH:24][C:23]=3[N+:34]([O-])=O)=[O:21])[CH2:16][CH2:15]2)=[N:9][CH:10]=[C:11]([CH3:13])[CH:12]=1>O>[NH2:34][C:23]1[CH:24]=[C:25]([N:28]2[CH2:32][CH2:31][O:30][C:29]2=[O:33])[CH:26]=[CH:27][C:22]=1[C:20]([N:17]1[CH2:16][CH2:15][N:14]([C:8]2[C:7]([CH3:6])=[CH:12][C:11]([CH3:13])=[CH:10][N:9]=2)[CH2:19][CH2:18]1)=[O:21]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of ammonium chloride (0.779 g), reduced iron (0.56 g), ethanol (16 mL) and water (4.3 mL) was stirred with heating at 60-70° C., and 3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-nitrophenyl}oxazolidin-2-one (1.105 g) described in Example 129 was added. After completion of the reaction, 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 (chloroform:methanol) to give the title compound (0.177 g).

Workup

additionwas added
customAfter completion of the reaction
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 (chloroform:methanol)

Sources & evidence

ORD record: ord-360310f0f93a438cbad49f4a4750116e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354401B2

Reaction notes

Loading…