Methylamine → (5R)-N-Methyl-3-(8-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxamide

HRID 896193Notes

Reaction equation

HRID 896193 reaction equation
C[O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([F:21])[CH:20]=2)[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]3)[CH2:6]1)=O.[CH3:24][NH2:25]>CO>[CH3:24][NH:25][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([F:21])[CH:20]=2)[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]3)[CH2:6]1)=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68491736(5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

Product 1

HCID 10286502(5R)-N-Methyl-3-(8-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxamideYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester (EXAMPLE 82, Step 5, 0.300 g, 9.31 mmol) is dissolved in 2M methylamine in methanol solution (8 ml) and stirred overnight at room temperature. The resulting precipitate is filtered, washed with methanol, and dried under vacuum to give the title compound as a white solid (0.145 g, 48%), mp 264-5° C.; 1H NMR (300 MHz, CDCl3) δ 2.47-2.52 (m, 2H), 2.64 (d, 3H), 2.84-2.89 (m, 2H), 3.27 (d, 3H), 4.00 (dd, 1H), 4.24 (t, 1H), 5.06 (dd, 1H), 7.26 (s, 1H), 7.46 (dd, 1H), 8.39 (d, 1H); MS for C15H16FN3O4 m/z 322 (M+H)+.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with methanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3cf13e565c334bbd9ee885bf2d7a74a6
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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