Triethylamine → HCID 60018013, compound

HRID 1991315Notes

Reaction equation

HRID 1991315 reaction equation
C(O[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)=[CH:14][CH:13]=2)[CH2:7]1)=[O:5])C.C(N(CC)CC)C.Cl.[F:33][CH2:34][CH2:35][NH2:36]>CO>[F:33][CH2:34][CH2:35][NH:36][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)=[CH:14][CH:13]=2)[CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 68487897HCID 68487897, compound

Product 1

HCID 60018013HCID 60018013, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of (5R)-3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester (EXAMPLE 72, Step 5, 226 mg, 0.68 mmol) in MeOH (2 mL) is added triethylamine (0.48 mL, 5.0 equiv.). Then 2-fluoroethylamine hydrochloride (136 mg, 2.0 equiv.) is added to the solution. The reaction mixture is heated at 50-60° C. for 5 h, followed by stirring overnight at room temperature. Solvent is removed and the residue is dissolved in 20% MeOH/CH2Cl2 and purified by column chromatography (10% MeOH/CH2Cl2). The title compound is obtained as a yellow solid (100 mg, 42%), 1H NMR (300 MHz, DMSO) δ 8.69 (t, 1H), 7.75-7.27 (m, 5H), 5.09 (dd, 1H), 4.98 (d, 1H), 4.55 (t, 1H), 4.39 (t, 1H), 4.29 (t, 1H), 4.02-3.93 (m, 3H), 3.51-3.37 (m, 2H), 2.50-2.45 (m, 2H); MS for C17H18FN3O4 m/z 348.5 (M+H)+.

Workup

  1. customSolvent is removed
  2. dissolutionthe residue is dissolved in 20% MeOH/CH2Cl2
  3. custompurified by column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8c77a377302c4e94a771b8a4f198b0c0
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

Loading…