5-Methyl-2-furylmethylamine → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylfuran-2-yl)methyl)thiazole-5-carboxamide

HRID 1887370

Reaktionsgleichung

Reaktionsgleichung von HRID 1887370
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[S:24][C:25]([C:29](O)=[O:30])=[C:26]([CH3:28])[N:27]=2)[C:19](=[O:32])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[S:24][C:25]([C:29]([NH:8][CH2:7][C:5]3[O:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:30])=[C:26]([CH3:28])[N:27]=2)[C:19](=[O:32])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

3

Edukt 2

HCID 27246835-Methyl-2-furylmethylamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Produkt 1

HCID 577445152-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylfuran-2-yl)methyl)thiazole-5-carboxamideAusbeute 48 %

Versuchsvorschrift

Following the procedure as described in Example 22, making variation only as required to use (5-methylfuran-2-yl)methanamine in place of benzo[b]thiophen-2-ylmethanamine to react with 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 48% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.68 (t, J=5.6 Hz, 1H), 8.60 (d, J=8.1 Hz, 1H), 7.45-7.31 (m, 5H), 6.38 (dd, J=8.1, 2.7 Hz, 1H), 6.22 (d, J=2.7 Hz, 1H), 6.09 (d, J=3.0 Hz, 1H), 5.95 (d, J=3.0 Hz, 1H), 5.16 (s, 2H), 4.30 (d, J=5.6 Hz, 2H), 2.52 (s, 3H), 2.19 (s, 3H); MS (ES+) m/z 436.5 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-7b375c6208da490cb11f420fe9d28aae
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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