Triethylamine → 3-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile

HRID 2192974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192974
[Cl-].[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][NH2+:19][CH2:18]3)=[N:8][C:9]3[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=3[C:5]=2[CH:4]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:56]([CH2:58][C:59](O)=[O:60])#[N:57]>CN(C=O)C>[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:59](=[O:60])[CH2:58][C:56]#[N:57])[CH2:18]3)=[N:8][C:9]3[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=3[C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67416365(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

Produkt 1

HCID 593753733-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride (40 mg, 0.09 mmol) in DMF (2 mL) were added triethylamine (0.13 mL, 0.94 mmol), HATU (0-(7-Azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate) (36 mg, 0.094 mmol), and cyanoacetic acid (40 mg, 0.47 mmol). The solution was stirred at room temperature overnight. The crude solution was filtered and purified by reverse phase HPLC. LRMS (ESI) calc'd for (C20H19FN5O2) [M+H]+, 380.2; found 380.1.

Aufarbeitung

  1. filtrationThe crude solution was filtered
  2. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aff70e038aba467f9efc2a57f61b5e2b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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