HCID 178418247, Verbindung → HCID 178510291, Verbindung

HRID 968727Notizen

Reaktionsgleichung

C(O[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][CH:22]4[CH2:24][CH:23]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][C:17]3=[O:31])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:32]#[N:33])(C)C.C(O[Na])(C)=O.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[O:31]=[C:17]1[C:16](=[CH:15][C:12]2[N:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:32]#[N:33])=[CH:5]3)[S:20][C:19]([NH:21][CH:22]2[CH2:24][CH:23]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 2-(trans)-phenylcyclopylamino-thiazol-4-one (38.0 mg, 0.16 mmol) (see Example 3), AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (see Example 11), 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 acetone and ether to give 6-[4-oxo-2-(2-phenyl-cyclopropylamino)-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (13.7 mg, 18.3%). HR-ES (+) m/e calcd for C22H15N5OS (M+H)+ 398.1070. found 398.1071.

Aufarbeitung

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water acetone and ether

Quellen und Nachweise

ORD-Eintrag: ord-891a2a24a8ba4ebbb77373ae20b30341
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07304074B2

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