4-Fluorobenzylamine → 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((5-methylfuran-2-yl)methyl)thiazole-5-carboxamide

HRID 560641

Reaktionsgleichung

Reaktionsgleichung von HRID 560641
FC1C=CC(CN)=CC=1.[CH3:10][C:11]1[O:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36](O)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36]([NH:16][CH2:15][C:14]3[O:17][C:11]([CH3:10])=[CH:12][CH:13]=3)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 3

HCID 673264-FluorobenzylamineHCID 27246835-Methyl-2-furylmethylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Produkt 1

HCID 594812122-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((5-methylfuran-2-yl)methyl)thiazole-5-carboxamideAusbeute 29 %

Versuchsvorschrift

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 5-methylfurfurylamine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 29% yield: mp 138-139° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.36-7.25 (m, 5H), 6.10 (d, J=2.7 Hz, 1H), 5.90-5.86 (m, 2H), 4.50-4.44 (m, 4H), 4.04 (t, J=8.1 Hz, 2H), 3.43 (t, J=8.1 Hz, 2H), 2.58 (s, 3H), 2.24 (s, 3H): 13C NMR (75 MHz, DMSO-d6) δ 162.1, 157.3, 155.4, 153.1, 152.1, 148.9, 135.5, 128.8, 128.3, 128.0, 117.1, 108.5, 106.3, 47.9, 42.0, 41.6, 37.0, 17.1, 13.5: MS (ES+) m/z 411.3 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-13cd94aa04594747a9e00470f904bb48
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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