HCID 178418247, Verbindung → HCID 178458601, Verbindung

HRID 968744Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[N:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][C:18](C#N)=[CH:17]3)[C:10](=[O:12])[N:11]=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:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[C:17]([O:38][CH:35]([CH3:37])[CH3:36])[CH:18]=[CH:19][N:20]=3)[N:15]=2)[C:10](=[O:12])[N:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (see Example 19), 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 2 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-(3-chloro-4-fluoro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light brown solid (63.5 mg, 86.9%). 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-21219c33423c4b9a85889191be17a1ed
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07304074B2

Notizen zur Reaktion

Wird geladen…