Pyridine → 2,2,2-Trichloroethyl (3-tert-butyl-1-methyl-1H-pyrazol-5-yl)carbamate

HRID 499184

반응식

HRID 499184 반응식
[C:1]([C:5]1[CH:6]=[C:7]([NH2:11])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].C(OCC)(=O)C>C1COCC1.O>[Cl:24][C:23]([Cl:26])([Cl:25])[CH2:22][O:21][C:19](=[O:20])[NH:11][C:7]1[N:8]([CH3:10])[N:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 870632,2,2-Trichloroethyl chloroformateHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amine

생성물 1

HCID 594208722,2,2-Trichloroethyl (3-tert-butyl-1-methyl-1H-pyrazol-5-yl)carbamate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To an ice-cooled solution of 5-tert-butyl-2-methyl-2H-pyrazol-3-ylamine (0.50 g, 3.26 mmol) and pyridine (0.27 mL, 3.29 mmol) in THF (THF, 10 mL) is added 2,2,2-trichloroethyl chloroformate (0.44 mL, 3.29 mmol). The reaction mixture is stirred at 0° C. for 30 min and then warmed to room temperature for 2 hours. Then the reaction mixture is distributed between ethyl acetate (100 mL) and water (100 mL). The aqueous phase is extracted with ethyl acetate (50 mL). The combined organic phases are washed with saturated NaCl (2×50 mL) and dried over anhydrous magnesium sulfate. After removal of solvent, the residue is purified on a silica gel chromatography by washing with ethyl acetate to provide a white solid (0.83 g, 78%, ES+(m/z) 329.9 [M+H]).

후처리

  1. temperaturewarmed to room temperature for 2 hours
  2. extractionThe aqueous phase is extracted with ethyl acetate (50 mL)
  3. washThe combined organic phases are washed with saturated NaCl (2×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue is purified on a silica gel chromatography
  7. washby washing with ethyl acetate
  8. customto provide a white solid (0.83 g, 78%, ES+(m/z) 329.9 [M+H])

출처 및 근거

ORD 기록
ord-8ad732784b564b859fc67bd23cbc8055
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767674B2

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