Methyl iodide → HCID 22285408, compound

HRID 1062448Notes

Reaction equation

HRID 1062448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:10]=[C:11]([C:13]([NH:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:14])[N:12]=1.CI.[CH3:31]CN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[CH:10]=[C:11]([C:13]([NH:15][CH:16]2[CH2:17][CH2:18][N:19]([CH3:31])[CH2:20][CH2:21]2)=[O:14])[N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 22285561HCID 22285561, compound

Product 1

HCID 22285408HCID 22285408, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(4-piperidinyl)-1H-imidazole-4-carboxamide (Example 37) (80 mg, 0.2 mmol) in CH2Cl2 (6 mL) was added CH3I (28.4 mg, 0.2 mmol) and Et3N (0.031 mL, 0.22 mmol). The reaction mixture was heated at reflux for 5 h, cooled to rt, and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (2M NH3 in methanol:EtOAc=1:10) to afford the product 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(1-methyl-4-piperidinyl)-1H-imidazole-4-carboxamide (24 mg, 28% yield): LC-MS m/z 429.1 (MH+), retention time 2.27 min (method 1); Rf=0.31 (EtOAc: 2M NH3 in MeOH=9:1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (2M NH3 in methanol:EtOAc=1:10)

Sources & evidence

ORD record
ord-d88f41a90be24fe398e8ac58db54cf9f
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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