Methyl iodide → HCID 86594357, compound

HRID 855551Notes

Reaction equation

HRID 855551 reaction equation
CI.[C:3]([O-])([O-])=O.[K+].[K+].[CH:9]1([CH2:14][CH:15]([C:24]2[CH:25]=[N:26][C:27]([SH:30])=[CH:28][CH:29]=2)[C:16]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1>CN(C=O)C>[CH:9]1([CH2:14][CH:15]([C:24]2[CH:25]=[N:26][C:27]([S:30][CH3:3])=[CH:28][CH:29]=2)[C:16]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522583HCID 178522583, compound

Product 1

HCID 86594357HCID 86594357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

MeI (44 μL of a 2.3M solution in anhydrous DMF, 102 μmol) and K2CO3 (14 mg, 102 μmol) were added to a stirred solution of 3-cyclopentyl-2-(6-mercaptopyridin-3-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 66, 34 mg, 102 μmol) in anhydrous DMF (1 mL). After 16 h, the solvents were evaporated off under reduced pressure, then the residue was partitioned between EtOAc (12 mL) and H2O (5 mL). The organic layer was washed with H2O (5 mL) and brine (5 mL), before being dried (MgSO4). The solution was filtered, passed through a short SiO2 plug, and evaporated to give 3-cyclopentyl-2-(6-methylsulfanylpyridin-3-yl)-N-thiazol-2-ylpropionamide: m/z (ES+)=348.2 [M+H]+. Step 2: Oxidation of this thioether (52 mg, 150 μmol), by the protocol described in EXAMPLE 55, gave the title compound: RTA=3.17 min; m/z (ES+)=364.2 [M+H]+.

Workup

  1. customthe solvents were evaporated off under reduced pressure
  2. customthe residue was partitioned between EtOAc (12 mL) and H2O (5 mL)
  3. washThe organic layer was washed with H2O (5 mL) and brine (5 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationThe solution was filtered
  6. customevaporated

Sources & evidence

ORD record
ord-2f2969737ad24990812b63cf2fd51790
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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