Diisopropylethylamine → HCID 58015499, Verbindung

HRID 219294Notizen

Reaktionsgleichung

[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.O=C1N([C@H](C)C(O)=O)C=CC2N=CC=CC1=2.FC1C(NN)=NC=C(C2ON=C(C)C=2)C=1.CCN(C(C)C)C(C)C>C(#N)C.CO>[NH4+:4].[OH-:12].[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

(2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide HATU (9.0 g, 24 mmol), (R)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrochloride and 1-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazine (3.6 g, 17 mmol) were taken up in acetonitrile (52 ml, 0.3 M) and cooled to 0° C. DIPEA (8.2 ml, 47 mmol) was added dropwise and the reaction was allowed to stir to room temperature for 30 minutes until complete by LCMS. The crude material was concentrated onto silica gel and then purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield (2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide (4.927 g, 77% yield).

Aufarbeitung

concentrationThe crude material was concentrated onto silica gel
custompurified via MPLC
washeluting with 100% DCM to 90% DCM

Quellen und Nachweise

ORD-Eintrag: ord-78f6f24d866d479dba320120ada07ff6
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08198448B2

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