P,P-Diphenylphosphinic azide → HCID 86721002, Verbindung

HRID 524944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524944
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][CH:13]=[C:12](C(O)=O)[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN1C(=O)CCC1>[NH2:35][C:12]1[CH:13]=[N:14][CH:15]=[C:16]2[C:11]=1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]2

Komponenten

4

Edukt 2

HCID 199401P,P-Diphenylphosphinic azideHCID 847148112,7-Naphthyridine-2,5(1H)-dicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) ester

Produkt 1

HCID 86721002HCID 86721002, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 7-tert-butoxycarbonyl-6,8-dihydro-5H-2,7-naphthyridine-4-carboxylic acid (440 mg, 1.581 mmol) in NMP (6 mL) was added TEA (207.9 mg, 286.4 μL, 2.055 mmol) followed by diphenylphosphoryl azide (478.6 mg, 374.8 μL, 1.739 mmol) at rt under nitrogen. The reaction was heated to 90° C. for 2 hours. At RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc. Combined organic extract was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica, eluting with 1-15% MeOH:DCM to yield tert-butyl 5-amino-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate. (397 mg, 100.7%). MS (2ES+) 501.2.

Aufarbeitung

  1. customAt RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc
  2. extractionCombined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 1-15% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-d0895b005fc84497a3cf56ce1016a9ca
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340546B2

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