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Triethylamine → N-{4-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-2,2-dimethyl-propionamide

HRID 2211859
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HRID 2211859 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[CH3:32][C:33]([CH3:38])([CH3:37])[C:34](Cl)=[O:35]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:34](=[O:35])[C:33]([CH3:38])([CH3:37])[CH3:32])=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[N:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 219631764-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine

생성물 1

HCID 21963341N-{4-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-2,2-dimethyl-propionamide수율 92.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine (135 mg, 0.4 mmol) was dissolved in 5 ml THF and triethylamine was added (112 μL, 0.8 mmol). Trimethyl acetyl chloride (49.3 μL, 0.4 mmol) was added under stirring and the reaction stirred at room temperature overnight. The reaction mixture was concentrated under nitrogen and dissolved in 5 ml methylene chloride and then washed with water. The organic layer was concentrated and evaluated by LCMS. The mixture was purified by MPLC using a Biotage 40s prepacked silica gel cartridge eluting with 3% methanol in methylene chloride. N-{4-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-2,2-dimethyl-propionamide (156 mg) was isolated in 98.2% purity @ 254 nm; LCMS (APCI): 423 [M+H]+

후처리

  1. stirringthe reaction stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under nitrogen
  3. dissolutiondissolved in 5 ml methylene chloride
  4. washwashed with water
  5. concentrationThe organic layer was concentrated
  6. customThe mixture was purified by MPLC
  7. washeluting with 3% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-f54d4568581746cf8f4c693cb3cd3c30
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07101886B2

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