Triethylamine → Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetate

HRID 1192900노트

반응식

HRID 1192900 반응식
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16](NC(=O)OCCCl)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:26]CN(CC)CC.[NH2:33][C:34]1([CH2:41][C:42]([O-:44])=[O:43])[CH2:39][CH2:38][CH2:37][N:36]([CH3:40])[CH2:35]1>CC#N>[CH3:40][N:36]1[CH2:37][CH2:38][CH2:39][C:34]([CH2:41][C:42]([O:44][CH3:26])=[O:43])([NH:33][S:16](=[O:17])(=[O:18])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)[CH2:35]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 581099762-chloroethyl N-(4-octylphenyl)sulfamoylcarbamateHCID 866498462-(3-Amino-1-methylpiperidin-3-yl)acetate

생성물 1

HCID 66864494Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetate수율 27.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2-chloroethyl N-(4-octylphenyl)sulfamoylcarbamate (156 mg, 0.4 mmol) in CH3CN (10 mL) was treated with Et3N (0.14 mL, 1 mmol) and refluxed for 25 min. and cooled. A solution of 2-(3-amino-1-methylpiperidin-3-yl)acetate (62 mg, 0.33 mmol) was added and the resulting mixture was refluxed for 4 h. After removal of the solvent in vacuo, the residue was dissolved in dichloromethane (40 mL) and washed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL) and dried (Na2SO4). After evaporation, the residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc) to give the title compound (41 mg, 27%) as colorless oil. MS ESI 454.3[M+H]+, calcd for [C23H39N3O4S+H]+ 454.27.

후처리

  1. temperaturerefluxed for 25 min.
  2. temperaturecooled
  3. temperaturethe resulting mixture was refluxed for 4 h
  4. customAfter removal of the solvent in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation
  9. customthe residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc)

출처 및 근거

ORD 기록
ord-fd1b85da27084615b130ce0d77af19db
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680282B2

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