Pyridine → phenyl N-[4-[[2-(cyclopropanecarbonylamino)-4-pyridyl]oxy]-2-fluoro-phenyl]carbamate

HRID 2200119노트

반응식

HRID 2200119 반응식
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[F:21].N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30].CCOC(C)=O>C(Cl)Cl>[CH:16]1([C:14]([NH:13][C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([NH:1][C:29](=[O:30])[O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:3]([F:21])[CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[O:15])[CH2:18][CH2:17]1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 90020359N-[4-(4-amino-3-fluoro-phenoxy)-2-pyridyl]cyclopropanecarboxamide

생성물 1

HCID 118223426phenyl N-[4-[[2-(cyclopropanecarbonylamino)-4-pyridyl]oxy]-2-fluoro-phenyl]carbamate수율 102.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
2.5 °C

실험 절차

Mix N-[4-(4-amino-3-fluoro-phenoxy)-2-pyridyl]cyclopropanecarboxamide (500 mg, 1.7 mmol), DCM (8 mL) and pyridine (345 mg) and cool to 0-5° C. Add a solution of phenyl chloroformate (350 mg, 2.2 mmol) in DCM (1 mL). Stir the reaction at room temperature for 1.5 hrs. TLC (EtOAc:PE=1;1) shows the reaction is complete. Quench the reaction with water (5 mL). Wash the organic layer with 1N HCl solution, saturated NaHCO3 solution and brine respectively. Dry the organic layer with anhydrous Na2SO4. Filter and concentrate to give the crude product (710 mg) which is used without further purification. MS: (M+1): 408.

후처리

  1. customthe reaction at room temperature for 1.5 hrs
  2. customQuench
  3. customthe reaction with water (5 mL)
  4. washWash the organic layer with 1N HCl solution, saturated NaHCO3 solution and brine respectively
  5. dry with materialDry the organic layer with anhydrous Na2SO4
  6. filtrationFilter
  7. concentrationconcentrate

출처 및 근거

ORD 기록
ord-276437ebb30d45d288d7e17b266aed5d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359338B2

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