Triethylamine → HCID 22272796, compound

HRID 1064807Notes

Reaction equation

HRID 1064807 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH:27][C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][CH:31]=[C:30]([OH:37])[C:29]=2[CH:38]([CH3:40])[CH3:39])=[O:26])[CH2:20][CH2:19]1.C(N(CC)CC)C>C1COCC1.O>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH:27][C:28]2[C:33]([CH:34]([CH3:35])[CH3:36])=[CH:32][CH:31]=[C:30]([O:37][S:2]([CH3:1])(=[O:4])=[O:3])[C:29]=2[CH:38]([CH3:40])[CH3:39])=[O:26])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 222726162-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide

Product 1

HCID 22272796HCID 22272796, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (103 mg, 0.9 mmol) was added to a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (149 mg, 0.3 mmol) and triethylamine (91 mg, 0.9 mmol) in THF (2 ml) with ice-cooling and the mixture was stirred for 30 minutes. Then triethylamine (46 mg, 0.45 mmol) and methanesulfonyl chloride (52 mg, 0.45 mmol) were further added thereto and the mixture was stirred for 20 minutes. 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 silica gel column chromatography (20 g of silica gel; developing solvent, chloroform:methanol=20:1) and the resulting crude crystals were recrystallized from acetone and hexane to provide 120 mg (yield 70%) of the desired compound as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 20 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, chloroform:methanol=20:1)
  8. customthe resulting crude crystals were recrystallized from acetone and hexane

Sources & evidence

ORD record
ord-cd1215c8721448ccbb160dc4707abdb8
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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