Sodium Iodide → HCID 58012217, compound

HRID 660945Notes

Reaction equation

HRID 660945 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:19]C)=[O:16])[N:9]=2)=[CH:4][CH:3]=1.[C:31](=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Cl[CH2:40][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:40][C:41]3[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=3)[C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][C:18]([CH3:31])([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[CH:22]=3)[CH3:19])=[O:16])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 36664Methyl 4-(chloromethyl)benzoateHCID 136330114HCID 136330114, compound

Product 1

HCID 58012217HCID 58012217, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.23 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 241A are suspended in 2.5 ml of acetone with 111 mg (0.34 mmol) of caesium carbonate and 34 mg (0.23 mmol) of sodium iodide and treated with 55 mg (0.30 mmol) of methyl 4-(chloromethyl)-benzoate. This is stirred for 4 hrs at 50° C. The suspension is then treated with 1.5 ml of water and extracted four times with 2 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate and filtered. After evaporation, the crude product is purified by preparative HPLC [Method 10]. 56.6 mg (42% of theory) of the target compound are thus obtained.

Workup

  1. extractionextracted four times with 2 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. filtrationfiltered
  4. customAfter evaporation
  5. customthe crude product is purified by preparative HPLC [Method 10]
  6. custom56.6 mg (42% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-a612469e04f149a08c4245c40f0549c1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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