Methyl iodide → Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

HRID 2409256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409256
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][C:3]=1[F:22].[H-].[Na+].[CH3:25]I>C1COCC1>[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N:14]([CH3:25])[C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][C:3]=1[F:22]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44184952HCID 44184952, Verbindung

Produkt 1

HCID 44184953Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-carbamate (6a) (480 mg, 1.6 mmol) was dissolved in dry THF (8 mL) and cooled at 0° C. Sodium hydride (60% in mineral oil, 80 mg, 2.0 mmol) was added, and the reaction mixture was stirred for 40 minutes at 0° C. Methyl iodide (130 μL, 1.8 mmol) was added at 0° C. The ice bath was removed, and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated and the residue partitioned between DCM and distilled water. The organic layer was dried and evaporated, and the residue washed with diethyl ether to afford the title compound as a brown solid.

Aufarbeitung

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe solvent was evaporated
  4. customthe residue partitioned between DCM
  5. distillationdistilled water
  6. customThe organic layer was dried
  7. customevaporated
  8. washthe residue washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-79a49a38ea574447a817c0ffcd084b75
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815896B2

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