Pyridine → [5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester

HRID 1993678노트

반응식

HRID 1993678 반응식
[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]([NH2:17])[N:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26].ClC([O-])=O>C1COCC1.O>[Cl:30][C:29]([Cl:32])([Cl:31])[CH2:28][O:27][C:25](=[O:26])[NH:17][C:7]1[N:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:9]=[C:5]([C:2]2([CH3:1])[CH2:3][CH2:4]2)[CH:6]=1

참가 물질

7

반응물 4

HCID 1049Pyridine2회HCID 870632,2,2-Trichloroethyl chloroformateHCID 21226386CarbonochloridateHCID 685368275-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

생성물 1

HCID 57832815[5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester수율 81.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Treat a cooled (0° C.) solution of the 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (5.68 g, 25 mmol) and pyridine (2.2 mL, 27.5 mmol) in THF (3 mL/mmol) with 2,2,2-trichloroethyl chloroformate (3.7 mL, 27.5 mmol). Maintain the reaction temperature at 0° C., and after 2 hours, add small portions of chloroformate (0.3 mL) and pyridine (0.2 mL). One hour later, dilute the reaction with water (150 mL) and extract with EtOAc (3×100 mL). Wash the combined organic phases with water (100 mL), saturated aq. NaHCO3 (50 mL), and saturated aq. sodium chloride (50 mL). Recrystallize the crude syrup from ethyl acetate/hexanes to provide the title compound as a white solid (8.18 g, 20.3 mmol; 81%). LCMS (ES+): m/z=402.2/404.2 [M+H].

후처리

  1. additionTreat
  2. additionOne hour later, dilute
  3. extractionextract with EtOAc (3×100 mL)
  4. washWash the combined organic phases with water (100 mL), saturated aq. NaHCO3 (50 mL), and saturated aq. sodium chloride (50 mL)
  5. customRecrystallize the crude syrup from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-e6bcf66624c14994875b5d5f0d5f30eb
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652015B2

반응 노트

불러오는 중…