HCID 178418247, Verbindung → HCID 178458603, Verbindung

HRID 968741Notizen

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:17][C:18]3[N:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][C:22](C#N)=[C:21]4[O:30][CH:31]([CH3:33])[CH3:32])[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)(C)C>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[C:21]([O:30][CH:31]([CH3:33])[CH3:32])[CH:22]=[CH:23][N:24]=4)[N:19]=3)[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (38.1 mg, 0.16 mmol) (see Example 7), AcONa (160 mg, 1.95 mmol), and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (38.9 mg, 0.18 mmol) (see Example 20) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 4 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, acetone and ether to give 2-[2-(3-fluoro-phenyl)-ethylamino]-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light green solid (45.9 mg, 65.8%). HR-ES (+) m/e calcd for C23H21FN4O2S (M+H)+ 437.1442. found 437.1443.

Aufarbeitung

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water, acetone and ether

Quellen und Nachweise

ORD-Eintrag: ord-f8fdfb2269dd46038b11e11908c3a6ec
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07304074B2

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