Pyridine → [5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 1993676노트

반응식

HRID 1993676 반응식
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].F[C:11](F)(F)[C:12]1([C:15]2[CH:16]=[C:17]([NH2:27])[N:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=C[CH:21]=3)[N:19]=2)[CH2:14][CH2:13]1.[N:30]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl>[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](=[O:6])[NH:27][C:17]1[N:18]([C:20]2[CH:21]=[N:30][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:19]=[C:15]([C:12]2([CH3:11])[CH2:13][CH2:14]2)[CH:16]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

생성물 1

HCID 68538118[5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester수율 75.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

Add a solution of 2,2,2-trichloroethylchloroformate (1.80 g, 8.5 mmol) in THF (10 mL) dropwise to an ice-salt cooled solution of 5-(1-trifluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (2.29 g, 8.1 mmol) and pyridine (0.9 mL, 11 mmol) in THF (30 mL) at −15° C. Stir at −15° C. for 0.5 hours and then 22° C. for 1 hour, then distribute the reaction mixture between dichloromethane (50 mL) and a saturated aq. sodium bicarbonate solution (50 mL). Isolate the aqueous phase and extract twice with dichloromethane (25 mL each). Dry the combined organic phases over sodium sulfate and concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give a white solid (2.46 g, 66% yield). MS(ES+): m/z=457.2 [M+H].

후처리

  1. wait22° C. for 1 hour
  2. customIsolate the aqueous phase
  3. extractionextract twice with dichloromethane (25 mL each)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. concentrationconcentrate
  6. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

출처 및 근거

ORD 기록
ord-984b9d82af544506a7f3a2f375157f9f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652015B2

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