Ethylamine → (5r)-n-Ethyl-3-[4-(4-oxo-3,4-dihydro-1(2h)-pyridinyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide

HRID 723902Notes

Reaction equation

HRID 723902 reaction equation
C(O[C:4]([CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:23]=[CH:22][C:21](=[O:24])[CH2:20][CH2:19]3)=[C:14]([F:25])[CH:13]=2)[CH2:7]1)=[O:5])C.[CH2:26]([NH2:28])[CH3:27]>CO>[CH2:26]([NH:28][C:4]([C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:23]=[CH:22][C:21](=[O:24])[CH2:20][CH2:19]3)=[C:14]([F:25])[CH:13]=2)[CH2:7]1)=[O:5])[CH3:27]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 684890643-[3-fluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester

Product 1

HCID 60018006(5r)-n-Ethyl-3-[4-(4-oxo-3,4-dihydro-1(2h)-pyridinyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester (EXAMPLE 69, within Step 6, 108 mg, 0.31 mmol) in MeOH (1 mL) is added EtNH2 (2 mL, 4.0 mmol, 2.0 M solution in THF). The reaction mixture is stirred for 1 h at room temperature. Solvent is removed and the residue purified by column chromatography (10% MeOH/CH2Cl2) to give the title compound as a pale yellow solid (100 mg, 93%), 1H NMR (300 MHz, DMSO) δ 8.46 (t, 1H), 7.65–7.38 (m, 4H), 5.05 (dd, 1H), 4.99 (d, 1H), 4.27 (t, 1H), 4.01 (dd, 1H), 3.87 (t, 2H), 3.20–3.10 (m, 2H), 1.04 (t, 3H); MS for C17H18FN3O4 m/z 348.5 (M+H)+.

Workup

  1. customSolvent is removed
  2. customthe residue purified by column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6dfa520d1f3241338f371cfeffff23e6
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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