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6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → 6-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile

HRID 968718
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 968718
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH:8][C:9]1[S:10][CH2:11][C:12](=[O:14])[N:13]=1.C(O[Na])(C)=O.[CH:20]([C:22]1[N:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][C:26]([C:32]#[N:33])=[C:25]2[O:34][CH:35]([CH3:37])[CH3:36])=O>CC(O)=O>[CH:35]([O:34][C:25]1[C:24]2[C:29](=[CH:30][CH:31]=[C:22]([CH:20]=[C:11]3[S:10][C:9]([NH:8][CH2:7][C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[N:13][C:12]3=[O:14])[N:23]=2)[N:28]=[CH:27][C:26]=1[C:32]#[N:33])([CH3:37])[CH3:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247, VerbindungHCID 178429647HCID 178429647, Verbindung

Produkt 1

HCID 1784296466-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrileAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2 mg, 0.16 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (50.2 mg, 0.21 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° 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 then suspended in AcOEt (20 mL) and filtered through a glass. The solid was washed with AcOEt and dried to give 4-isopropoxy-6-{2-[(3-methyl-thiophen-2-ylmethyl)-amino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (22.6 mg, 32.4%). HR-ES (+) m/e calcd for C22H19N5O2S2 (M+H)+ 450.1053. found 450.1051.

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. filtrationfiltered through a glass
  6. washThe solid was washed with AcOEt
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7348c88cce3b4c8d9d1a6d5e863996a1
Quelldatensatz
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07304074B2

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