HCID 178418247, Verbindung → HCID 178458600, Verbindung

HRID 968745Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[N:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][C:17](C#N)=[CH:16]3)[C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.[CH:35]([O:38]C1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)([CH3:37])[CH3:36]>CC(O)=O>[Cl:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([O:38][CH:35]([CH3:37])[CH3:36])[CH:17]=[CH:18][N:19]=3)[N:14]=2)[C:9](=[O:11])[N:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (see Example 18), 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 3 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-chloro-4-fluoro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light brown solid (43.5 mg, 59.5%). HR-ES (+) m/e calcd for C22H18FClN4O2S (M+H)+ 457.0896. found 457.0897.

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-ba81743b57454a6eac214e6748289ae0
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07304074B2

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