Methyl iodide → HCID 69084057, compound

HRID 594649Notes

Reaction equation

HRID 594649 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)[C:15](=[O:29])[CH2:14][NH:13][CH2:12]1.[CH3:30]I>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:20][CH:19]=2)[C:15](=[O:29])[CH2:14][N:13]([CH3:30])[CH2:12]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 69082599HCID 69082599, compound

Product 1

HCID 69084057HCID 69084057, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A cooled (0° C.) solution of 6-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)-piperazin-2-one (106 mg; 0.25 mmol) in anh. THF (1.5 ml) was treated with a solution of CH3I (33 mg; 0.23 mmol) in anh. THF (0.5 ml). The resulting mixture was allowed to warm-up slowly to rt, and stirring at rt was then continued for 15 h. Brine was added, and the mixture was extracted with AcOEt (3×20 ml). The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions D): tR=0.87 min.; [M+H]+: 425.02 g/mol.

Workup

  1. extractionthe mixture was extracted with AcOEt (3×20 ml)
  2. dry with materialThe mixed organic layers were dried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customSubsequent purification by preparative HPLC
  6. customafforded the target compound

Sources & evidence

ORD record
ord-085b741dc4174c6e824d5626ed4bb687
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…