2-Bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide → 2-(3-benzyl-2-iminoimidazolidin-1-yl)-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 560800

Reaktionsgleichung

Reaktionsgleichung von HRID 560800
[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.Br[C:30]1[S:31][C:32]([C:36]([NH:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[C:42]([F:47])[CH:41]=2)=[O:37])=[C:33]([CH3:35])[N:34]=1>>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:30]2[S:31][C:32]([C:36]([NH:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([F:46])=[C:42]([F:47])[CH:41]=3)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:9]1=[NH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 666311772-Bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamideHCID 178508456HCID 178508456, VerbindungHCID 178512076HCID 178512076, Verbindung

Produkt 1

HCID 250961902-(3-benzyl-2-iminoimidazolidin-1-yl)-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamideAusbeute 5 %

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 2-bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 5% yield: mp 140-142° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.41 (t, J=5.8 Hz, 1H), 7.39-7.23 (m, 7H), 7.12-7.08 (m, 1H), 6.68 (m, 1H), 4.43 (s, 2H), 4.30 (d, J=5.8 Hz, 2H) 3.94 (m, 2H), 3.35-3.27 (m, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.8, 158.3, 153.5, 151.1, 150.4, 148.0, 147.9, 138.2, 137.2, 129.0, 128.2, 127.8, 124.4, 117.7, 116.5, 48.4, 44.4, 43.9, 42.1, 17.6: MS (ES+) m/z 442.2 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-6035ce5737fd4c8fb78c408383fbb5e4
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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