Methyl iodide → HCID 59406865, compound

HRID 1948301Notes

Reaction equation

HRID 1948301 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[CH3:9][C:10]([NH:18][C:19]([C:21]1[N:22]=[C:23]([S:29][CH3:30])[S:24][C:25]=1[C:26]([OH:28])=[O:27])=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11]>CN(C=O)C>[CH3:11][C:10]([NH:18][C:19]([C:21]1[N:22]=[C:23]([S:29][CH3:30])[S:24][C:25]=1[C:26]([O:28][CH3:1])=[O:27])=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68513878HCID 68513878, compound2×

Product 1

HCID 59406865HCID 59406865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Potassium carbonate (0.37 g) and iodomethane (0.17 ml) were added to a solution of 4-{[(1-methyl-1-phenylethyl)amino]carbonyl}-2-(methylthio)-1,3-thiazole-5-carboxylic acid (Intermediate 14; 0.9 g) in DMF (20 ml) and heated in a sealed tube at an external temperature of 85° C. for 30 min. The reaction mixture was concentrated to remove DMF and partitioned with EtOAc and water. The combined organic extracts were washed with water, dried with MgSO4, and concentrated to an orange solid (0.63 g). NMR: 1.60-1.65 (m, 6H), 2.76 (s, 3H), 3.78-3.83 (m, 3H), 7.22 (d, J=7.16 Hz, 1H), 7.33 (t, J=7.63 Hz, 2H), 7.46 (d, J=7.35 Hz, 2H), 8.75 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove DMF
  3. custompartitioned with EtOAc and water
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated to an orange solid (0.63 g)

Sources & evidence

ORD record
ord-5da0bf9f35894b5d8e63f66a3d09dfe6
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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