HCID 178418247, Verbindung → HCID 178510294, Verbindung

HRID 968731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968731
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][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:23]#[N:24])=[C:16]3OC(C)C)[C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][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:23]#[N:24])=[CH:16]3)[C:9](=[O:11])[N:10]=1

Komponenten

5

Edukt 3

HCID 178418247HCID 178418247, VerbindungHCID 178458708HCID 178458708, VerbindungHCID 178510297HCID 178510297, Verbindung

Produkt 1

HCID 178510294HCID 178510294, VerbindungAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (40.9 mg, 0.17 mmol) (see Example 2), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (53.1 mg, 0.22 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 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 6-[2-(2-chloro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a dark brown solid (20.8 mg, 30.1%). HR-ES (+) m/e calcd for C20H12ClN5OS (M+H)+ 406.0524. found 406.0525.

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 acetone and ether

Quellen und Nachweise

ORD-Eintrag
ord-bfe48c03d0ac436fa2963d9a4a4ffe1a
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

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