Methyl iodide → HCID 10227475, compound

HRID 2101736Notes

Reaction equation

HRID 2101736 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[N:11]([CH3:30])[C:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[N:14]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CI.[H-].[Na+].[C:35](=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:35][N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:8]([C:10]1[N:11]([CH3:30])[C:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 9847217HCID 9847217, compound

Product 1

HCID 10227475HCID 10227475, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-cyclohexyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1-methylimidazole-2-carboxamide (15 mg, 0.033 mmol) from Example 36, (Method A) and methyl iodide (0.003 mL, 0.049 mmol) in DMF (2 mL) was added sodium hydride (60% in mineral oil, 2 mg, 0.049 mmol). The mixture was stirred at rt for 2 hr and then poured into aq. sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by Prep TLC (0.5 mm, silica) (25% ethyl acetate in hexanes) to afford the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by Prep TLC (0.5 mm, silica) (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2b8660b8b22b4075bb166f6d79057dc2
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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