ethyl 2-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate → HCID 44192372, Verbindung

HRID 554911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554911
FC1(F)CC1CN1CCN(C2SC(C(OCC)=O)=C(C)N=2)C1=O.[F:24][C:25]1([F:46])[CH2:27][CH:26]1[CH2:28][N:29]1[C:33](=[O:34])[N:32]([C:35]2[S:36][C:37]([C:41]([O:43]CC)=[O:42])=[C:38]([CH3:40])[N:39]=2)[CH:31]=[N:30]1>>[F:46][C:25]1([F:24])[CH2:27][CH:26]1[CH2:28][N:29]1[C:33](=[O:34])[N:32]([C:35]2[S:36][C:37]([C:41]([OH:43])=[O:42])=[C:38]([CH3:40])[N:39]=2)[CH:31]=[N:30]1

Komponenten

3

Edukt 2

HCID 57919808ethyl 2-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateHCID 57919981Ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Produkt 1

HCID 44192372HCID 44192372, VerbindungAusbeute 18 %

Versuchsvorschrift

Following the procedure as describe in Preparation 14, making variations as required to replace ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with ethyl 2-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colourless solid in 18% yield: mp 220-222° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.59 (br, 1H), 7.35 (dd, J=13.9, 7.7 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 7.07 (dd, J=18.9, 9.0 Hz, 2H), 5.14 (s, 2H); 13C NMR (75 MHz, DMSO-d6) δ 162.9 (d), 153.2, 136.3 (d), 130.7 (d), 123.9 (d), 115.8 (d), 115.3 (d), 47.7 (d); MS (ES+) m/z 317.1 (M+1).

Aufarbeitung

  1. customas describe in Preparation 14

Quellen und Nachweise

ORD-Eintrag
ord-683a017b2d8e4073b06b102fc953df3e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049016B2

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