Methyl iodide → HCID 10237359, compound

HRID 2306628Notes

Reaction equation

HRID 2306628 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=1.[C:26](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][CH2:10][C:11](=[O:14])[N:12]([CH3:26])[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10309167HCID 10309167, compound

Product 1

HCID 10237359HCID 10237359, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide (0.100 g, 0.273 mmol), potassium carbonate (0.075 g, 0.546 mmol), and iodomethane (0.0187 ml, 0.300 mmol) in DMF (3 ml) is heated at 80° C. overnight. The reaction mixture is filtered and evaporated to dryness. The residue is purified by PTLC (10% MeOH/DCM) to give product as a white solid (0.104 g, 90%); 1HNMR (300 MHz, DMSO-d6) δ 1.82 (s, 3H), 3.39 (s, 3H), 3.42 (t, J=5.5, 2H), 3.66 (s, 2H), 3.76 (dd, J=6.6, 9.3 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.71-4.80 (m, 1H), 7.43 (dd, J=2.2, 8.8 Hz, 1H), 7.59 (dd, J=1.9, 14 Hz, 1H), 7.72 (t, J=8.8 Hz, 1H), 8.25 (t, J=5.8 Hz, 1H); mp 179-80; MS (m/z): [M+H]+=381.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated to dryness
  3. customThe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-d3b437748cf44e819cf8001bd62a9e6a
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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