cis-3-Chloroacrylic acid → HCID 178520646, Verbindung

HRID 2236777Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9]/[CH:10]=[C:11]2\[C:12](=[O:23])[NH:13][C:14](=[O:22])[C:15]3[C:20]\2=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]=1[NH:24][C:25](=[O:30])/[C:26](/C)=[CH:27]/C.NC1C=CC(CN/C=C2\C(=O)NC(=O)C3C\2=CC(I)=CC=3)=CC=1O[Si](C(C)C)(C(C)C)C(C)C.[Cl:65]/C=C\C(O)=O>>[Cl:65]/[CH:27]=[CH:26]\[C:25]([NH:24][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][NH:9]/[CH:10]=[C:11]2\[C:12](=[O:23])[NH:13][C:14](=[O:22])[C:15]3[C:20]\2=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)=[CH:7][C:2]=1[OH:1])=[O:30]

Komponenten

Edukt 3

HCID 643794cis-3-Chloroacrylic acid

HCID 178447227HCID 178447227, Verbindung

HCID 178460972HCID 178460972, Verbindung

Produkt 1

HCID 178520646HCID 178520646, Verbindung

Versuchsvorschrift

Following the acetylation and desilylation procedure employed for the preparation of (2E)-N-[2-hydroxy-4-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl]-2-methylbut-2-enamide, (4Z)-4-[({4-amino-3-[(triisopropylsilyl)oxy]benzyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione (65 mg, 0.11 mmol) is reacted with acid chloride derived from cis-3-chloroacrylic acid (0.12 g, 1.1 mmol). Following desilylation and precipitation, (2Z)-3-chloro-N-[2-hydroxy-4-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl]acrylamide is obtained as a solid (10 mg, 17

Aufarbeitung

customdesilylation and precipitation

Quellen und Nachweise

ORD-Eintrag: ord-ded8a8a9405a4fad95583118affcb622
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07713994B2

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