Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | HCID 68486037 | HCID 68486037 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 60018010 | HCID 60018010 | 85% |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06919329B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-f37d93e0ec9b446496bd628c40268246 |
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| Source note | uspto-grants-2005_07 |
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