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

HRID 2200119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200119
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 118223426phenyl N-[4-[[2-(cyclopropanecarbonylamino)-4-pyridyl]oxy]-2-fluoro-phenyl]carbamateAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-276437ebb30d45d288d7e17b266aed5d
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359338B2

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