Methyl iodide → HCID 68595843, compound

HRID 341202Notes

Reaction equation

HRID 341202 reaction equation
[SH:1][C:2]1[N:3]([CH3:31])[C:4]([C:7]2[CH:12]=[CH:11][N:10]3[C:13]([C:16]4[CH:17]=[C:18]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[O:24])[CH:19]=[CH:20][CH:21]=4)=[CH:14][N:15]=[C:9]3[CH:8]=2)=[N:5][N:6]=1.[OH-:32].[K+].I[CH3:35]>CCO>[CH:23]([OH:24])=[O:32].[CH3:31][N:3]1[C:2]([S:1][CH3:35])=[N:6][N:5]=[C:4]1[C:7]1[CH:12]=[CH:11][N:10]2[C:13]([C:16]3[CH:17]=[C:18]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:28])[F:29])=[O:24])[CH:19]=[CH:20][CH:21]=3)=[CH:14][N:15]=[C:9]2[CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178481693HCID 178481693, compound

Product 1

HCID 68595843HCID 68595843, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-{3-[7-(5-Mercapto-4-methyl-4H-[1,2,4]triazol-3-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea (72 mg, 0.16 mmol) in EtOH (3 ml) was added KOH (10 mg, 0.18 mmol) and iodomethane (20 μl, 0.16 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was placed in an ice bath and the precipitate formed filtered off. The precipitate was purified by reverse phase HPLC to afford the title compound (18 mg). MS: [M+H]+=462.

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. customthe precipitate formed
  3. filtrationfiltered off
  4. customThe precipitate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8d6bff4ffcfd49a799e445e18f198892
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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