Methyl iodide → HCID 11993598, compound

HRID 2266321Notes

Reaction equation

HRID 2266321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:10][C:11]2[N:12]([C:14]([C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[O:18])=[N:15][N:16]=2)[N:13]=1.[H-].[Na+].I[CH3:41]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[CH:10][C:11]2[N:12]([C:14]([C:17]([N:19]([CH3:41])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=3)=[O:18])=[N:15][N:16]=2)[N:13]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11992434HCID 11992434, compound

Product 1

HCID 11993598HCID 11993598, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-chlorophenyl)-7-(4-chlorophenyl)-N-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide (Example 34) (22 mg, 0.041 mmol) in anhydrous DMF at room temperature was added sodium hydride (6.5 mg, 0.164 mmol). The resulting suspension was stirred at room temperature for 5 min, then iodomethane (25 μL, 0.4 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with EtOAc (30 mL), washed with water, saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (4 g) eluting with a gradient of EtOAc (0-60%) in hexanes to afford 15 mg (66%) of the title compound as a white powder. HPLC/MS (method A): retention time=3.85 min, (M+H)+=556.3

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. washwashed with water, saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified
  6. washeluting with a gradient of EtOAc (0-60%) in hexanes

Sources & evidence

ORD record
ord-9d5315d12f44419ea21bb0efe3b76409
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

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