3-Pyridinemethanamine → 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 554954

Reaktionsgleichung

Reaktionsgleichung von HRID 554954
FC1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C@@H:11](C)[CH2:10][N:9]([C:13]3[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=3)[C:8]2=[O:22])=CC=1.C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)CC=C.[N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][NH2:51])[CH:45]=1>>[CH2:6]([N:7]1[CH2:11][CH2:10][N:9]([C:13]2[S:14][C:15]([C:19]([NH:51][CH2:50][C:46]3[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=3)=[O:21])=[C:16]([CH3:18])[N:17]=2)[C:8]1=[O:22])[CH2:5][CH:23]=[CH2:24]

Komponenten

4

Edukt 3

HCID 310183-PyridinemethanamineHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579200082-(3-(But-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Produkt 1

HCID 579198452-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideAusbeute 62 %

Versuchsvorschrift

Following the procedure as described in Example 2, making variations as required to replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as an off-white solid in 62% yield: mp 144-145° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.57-8.52 (m, 2H), 8.45 (d, J=3.8 Hz, 1H), 7.70 (ddd, J=7.8, 7.8, 1.8 Hz, 1H), 7.35 (dd, J=7.8, 4.8 Hz, 1H), 5.85-5.72 (m, 1H), 5.15-5.01 (m, 2H), 4.39 (d, J=5.8 Hz, 2H), 3.98 (d, J=9.0, 7.1 Hz, 2H), 3.59-3.54 (m, 2H), 3.31 (t, J=7.0 Hz, 2H), 2.47 (s, 3H), 2.32-2.25 (m, 2H); 13C NMR (75 MHz, DMSO-d6) 8161.9, 157.4, 154.9, 151.2, 148.8, 148.0, 135.5, 135.1, 135.1, 123.4, 117.3, 116.8, 42.4, 41.9, 41.6, 40.4, 31.1, 17.1; MS (ES+) m/z 372.1 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-6d0874fd095b43dfa4e1b522f602ede6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049016B2

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