HCID 178418247, Verbindung → HCID 178510296, Verbindung

HRID 968733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968733
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][CH2:9][C:10](=[O:12])[N:11]=1.C(O[Na])(C)=O.O=C1C(=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)[C:10](=[O:12])[N:11]=1

Komponenten

5

Edukt 3

HCID 178418247HCID 178418247, VerbindungHCID 178510297HCID 178510297, VerbindungHCID 178516941HCID 178516941, Verbindung

Produkt 1

HCID 178510296HCID 178510296, VerbindungAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (prepared as described below) AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (33.6 mg, 0.18 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° 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, AcOEt and ether to give 6-[2-(3-chloro-4-fluoro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a light brown solid (30.6 mg, 45.1%). HR-ES (+) m/e calcd for C20H11FClN5OS (M+H)+ 424.0430. found 424.0431.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, AcOEt and ether

Quellen und Nachweise

ORD-Eintrag
ord-72531deee3564b4c8e28ef1ce1d2bbc0
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

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