HCID 178418247, Verbindung → HCID 178458599, Verbindung

HRID 968743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968743
[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#N)=[C:16]3[O:25][CH:26]([CH3:28])[CH3:27])[C:9](=[O:11])[N:10]=1.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>[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[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([O:25][CH:26]([CH3:28])[CH3:27])[CH:17]=[CH:18][N:19]=3)[N:14]=2)[C:9](=[O:11])[N:10]=1

Komponenten

5

Edukt 3

HCID 178418247HCID 178418247, VerbindungHCID 178458598HCID 178458598, VerbindungHCID 178458708HCID 178458708, Verbindung

Produkt 1

HCID 178458599HCID 178458599, VerbindungAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (38.5 mg, 0.16 mmol) (see Example 2), AcONa (160 mg, 1.95 mmol), molecular sieves, 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 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. The solid was collected by filtration and washed with water, acetone and ether to give 2-(2-chloro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a brown solid (31.4 mg, 44.7%). HR-ES (+) m/e calcd for C22H19ClN4O2S (M+H)+ 439.0990. found 439.0987.

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
  5. filtrationThe solid was collected by filtration
  6. washwashed with water, acetone and ether

Quellen und Nachweise

ORD-Eintrag
ord-e114255a5b4449fbb2cc310e948eb5bf
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

Notizen zur Reaktion

Wird geladen…