Ammonia → (5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxamide

HRID 896163Notes

Reaction equation

HRID 896163 reaction equation
[O:1]=[S:2]1(=[O:26])[CH:7]=[CH:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([C:20](OC)=[O:21])[O:17][C:16]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[NH3:27]>CO>[O:26]=[S:2]1(=[O:1])[CH:7]=[CH:6][N:5]([C:8]2[C:9]([F:25])=[CH:10][C:11]([N:15]3[CH2:19][C@H:18]([C:20]([NH2:27])=[O:21])[O:17][C:16]3=[O:24])=[CH:12][C:13]=2[F:14])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68490087methyl (5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 60018009(5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methyl (5R)-3-[4-(1,1-dioxido-2,3-dihydro-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxylate (Step 3, 0.090 g, 0.23 mmol) in methanol (2 mL) is treated with a solution of ammonia in methanol (2 mL of a 2.0M solution). The mixture is stirred for 1.5 h and concentrated. The residual solids are washed with methanol to provide 75 mg (86%) of the title compound as a white solid, MS (m/z) for C14H13F2N3O5S: [M+H]+=374; 1H NMR (300 MHz, d6-DMSO): δ 3.33-3.39 (m, 2H), 3.99-4.06 (m, 3H), 4.26 (t, 1H), 5.04-5.09 (m, 1H), 5.48 (d, 1H), 6.93 (d, 1H), 7.50 (d, 2H), 7.65 (s, 1H), 7.90 (s, 1H).

Workup

  1. concentrationconcentrated
  2. washThe residual solids are washed with methanol

Sources & evidence

ORD record
ord-caab0d3d32d94c10b087dfb437727c7e
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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