Triethylamine → HCID 22272867, compound

HRID 1064815Notes

Reaction equation

HRID 1064815 reaction equation
C(N(CC)CC)C.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]([NH:29][C:30]2[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][C:33]([OH:39])=[CH:32][C:31]=2[CH:40]([CH3:42])[CH3:41])=[O:28])[CH2:22][CH2:21]1.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C1COCC1.O>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]([NH:29][C:30]2[C:35]([CH:36]([CH3:37])[CH3:38])=[CH:34][C:33]([O:39][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:32][C:31]=2[CH:40]([CH3:42])[CH3:41])=[O:28])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22272702HCID 22272702, compound

Product 1

HCID 22272867HCID 22272867, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (30 mg, 0.3 mmol) was added to a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide (50 mg, 0.1 mmol) in THF (1 ml), then methanesulfonyl chloride (34 mg, 0.3 mmol) was dropped thereinto with ice cooling and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:methanol=19:1) to provide 47 mg (yield 82%) of the desired compound as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-e0e734cee7084fd38e1393cca07f9e44
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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