2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → N-benzyl-2-(3-benzyl-2-iminoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 560798

Reaktionsgleichung

Reaktionsgleichung von HRID 560798
[CH2:1]([N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[N:13]C#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCNC1=N)C1C=CC=CC=1.[CH2:29]([NH:36][C:37]([C:39]1[S:43][C:42](Br)=[N:41][C:40]=1[CH3:45])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([NH:36][C:37]([C:39]1[S:43][C:42]([N:10]2[CH2:11][CH2:12][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]2=[NH:13])=[N:41][C:40]=1[CH3:45])=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

4

Edukt 3

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178508456HCID 178508456, VerbindungHCID 178512076HCID 178512076, Verbindung

Produkt 1

HCID 59481177N-benzyl-2-(3-benzyl-2-iminoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideAusbeute 4 %

Versuchsvorschrift

Following the procedure as described in Example 27, making variations as required to replace N-(1-benzylimidazolidin-2-ylidene)cyanamide with 1-benzylimidazolidin-2-imine to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 4% yield: mp 125-126° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.37-7.26 (m, 10H), 5.89 (t, J=5.5 Hz, 1H), 5.56 (br s, 1H), 4.54 (d, J=5.5 Hz, 2H), 4.33 (s, 2H), 4.15-4.01 (m, 2H), 3.44 (t, J=7.7 Hz, 2H), 2.62 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 159.4, 138.0, 128.9, 128.7, 128.0, 127.9, 127.6, 127.5, 105.6, 53.4, 49.3, 44.0, 43.8, 17.3; MS (ES+) m/z 406.4 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-c3443f6b6c4847c1a3350d7a639dd1d6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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