HCID 178418247, Verbindung → 5-[(8-propan-2-yloxy-1,5-naphthyridin-2-yl)methylidene]-2-(thiophen-2-ylmethylamino)-1,3-thiazol-4-one

HRID 968742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968742
[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:18][C:17]3=[O:28])[N:13]=2)[N:8]=[CH:7][C:6]=1C#N)([CH3:3])[CH3:2].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>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:15]=[C:16]1[S:20][C:19]([NH:21][CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[N:18][C:17]1=[O:28])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 178418247HCID 178418247, VerbindungHCID 178458598HCID 178458598, VerbindungHCID 178458710HCID 178458710, Verbindung

Produkt 1

HCID 1784586025-[(8-propan-2-yloxy-1,5-naphthyridin-2-yl)methylidene]-2-(thiophen-2-ylmethylamino)-1,3-thiazol-4-oneAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one one (34.0 mg, 0.16 mmol) (see Example 4), 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 4.5 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 5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one as a light brown solid (29.8 mg, 45.4%). HR-ES (+) m/e calcd for C20H18N4O2S2 (M+H)+ 411.0944. found 411.0945.

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-74be7b53c5df494cbe8a414eb0377e3d
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

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