Chlorotrimethylsilane → HCID 66657765, compound

HRID 420575Notes

Reaction equation

HRID 420575 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[Li]CCCC.C[Si](Cl)(C)C.Cl[C:20]1[S:21][C:22]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:23]=2[N:24]=1>O1CCCC1.O>[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[N:3]1[C:20]1[S:21][C:22]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 114704192-Chloro-6-trifluoromethylbenzothiazoleHCID 178418339Butyllithium

Product 1

HCID 66657765HCID 66657765, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cis-2,6-dimethyl piperazine (247 mg) in tetrahydrofuran (5 mL) was added n-BuLi (2.67 M hexane solution, 1.62 mL) at −78° C. The mixture was stirred at room temperature for 30 minutes, and trimethyl silyl chloride (0.27 mL) was added thereto. After stirring for 40 minutes, a solution of 2-chloro-6-trifluoromethyl benzothiazole (500 mg) in tetrahydrofuran (2 mL) was added thereto and the mixture was stirred for 2 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium carbonate. The residue was purified by column chromatograph on silica gel to give the title compound (367 mg). Yield: 54%.

Workup

  1. stirringAfter stirring for 40 minutes
  2. stirringthe mixture was stirred for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium carbonate
  6. customThe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-c4348ce5218b4dd5b3ab2997d0580a84
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

Loading…