Methylamine → HCID 60018010, compound

HRID 723905Notes

Reaction equation

HRID 723905 reaction equation
C([O:5][C:6]([C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)=O)CCC.[CH3:29][NH2:30]>CO>[CH3:29][NH:30][C:6]([C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[C:16]([F:28])[C:17]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[C:18]([F:20])[CH:19]=2)[CH2:9]1)=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68486037HCID 68486037, compound

Product 1

HCID 60018010HCID 60018010, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (5R)-3-[3,5-Difluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid butyl ester (EXAMPLE 76, Step 5, 132 mg) in MeOH (1 mL) is added MeNH2 (2 mL, 4.0 mmol, 2.0 M solution in MeOH). The reaction mixture is then heated at 40–50° C. until all of the solid disappears. Solvent is removed and the residue is dissolved in 20% MeOH/CH2Cl2 and purified by silica gel chromatography (10% MeOH/CH2Cl2) to give the title compound as a yellow solid (100 mg, 76%), 1H NMR (300 MHz, DMSO) δ 8.40 (m, 1H), 7.52–7.38 (m, 3H), 5.08 (dd, 1H), 5.00 (d, 1H), 4.26 (t, 1H), 4.01 (dd, 1H), 3.78 (t, 2H), 2.65 (d, 3H); MS for C16H15F2N3O4 m/z 352.5 (M+H)+.

Workup

  1. temperatureThe reaction mixture is then heated at 40–50° C. until all of the solid
  2. customSolvent is removed
  3. dissolutionthe residue is dissolved in 20% MeOH/CH2Cl2
  4. custompurified by silica gel chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-59aa519e725b4139852e29b69ca679ba
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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