Methyl iodide → HCID 11418800, compound

HRID 2243155Notes

Reaction equation

HRID 2243155 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH:15]([C:21]2[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:24]=[CH:23][CH:22]=2)[CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4].I[CH3:33]>C1COCC1>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH:15]([C:21]2[N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:24]=[CH:23][CH:22]=2)[CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[CH3:33])(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 11177293HCID 11177293, compound

Product 1

HCID 11418800HCID 11418800, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (16.3 nmg, 410 μmol, 60% dispersion in mineral oil) in THF (300 μL) at 0° C. was added a solution of 4-cyano-N-[2-ethyl-1-(1-phenyl-1H-pyrazol-5-yl)butyl]benzenesulfonamide (example 37, 140 mg, 340 μmol) in THF (600 μL). The reaction mixture was warmed to room temperature, and after 20 min iodomethane (45 μL, 714 μmol) was added. The mixture was allowed to stir overnight. TLC indicated that the reaction was not complete. Additional aliquots of NaH and iodomethane were added until the reaction was driven to completion. The mixture was then quenched with H2O and extracted with EtOAc twice. The organic extracts were dried (MgSO4) and concentrated. Column chromatography (EtOAc/hexanes, 1:1) provided 89 mg (57% yield) of the title compound as a glassy yellow solid. mp 37.8-54° C.; Mass Spectrum (ES): 481.1;

Workup

  1. customThe mixture was then quenched with H2O
  2. extractionextracted with EtOAc twice
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-139ea5fdca5342b98ad636af045802d6
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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