Hydrochloric Acid → HCID 68282941, Verbindung

HRID 624034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624034
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=O)[CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[N:12]2)=[N:6][CH:7]=1.Cl>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[N:12]2)=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 68283437HCID 68283437, Verbindung

Produkt 1

HCID 68282941HCID 68282941, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To N-(5-fluoropyridin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (493 mg) in THF (2.0 mL), BH3 THF-complex solution (1 M in THF, 7.3 mL, 7.3 mmol) was added dropwise. After stirring at rt for 3 h, the reaction mixture was quenched with 1 N aq. HCl-solution (3 mL, 3 mmol). The mixture was stirred for 15 min at rt, and heated to 60° C. for 1.5 h. The reaction mixture was diluted with EtOAc, washed with sat. aq. Na2CO3-solution. The aq. layer was reextracted with EtOAc and the comb. org. layers were evaporated, dissolved in DCM and washed with brine. The org. layer was dried (MgSO4), filtered and the solvent was removed by reduced pressure to yield 5-fluoro-N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)pyridin-2-amine as a yellow solid. LC-MS conditions A: tR=0.53 min, [M+H]+=252.36.

Aufarbeitung

  1. stirringThe mixture was stirred for 15 min at rt
  2. temperatureheated to 60° C. for 1.5 h
  3. washwashed with sat. aq. Na2CO3-solution
  4. customlayers were evaporated
  5. dissolutiondissolved in DCM
  6. washwashed with brine
  7. dry with materiallayer was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed by reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09856ca05786485782ea34783f9f5fd1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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