2-(Bromomethyl)-1,1-difluorocyclopropane → (5-Acetyl-4-methylthiazol-2-yl)-3-((2,2-difluorocyclopropyl)methyl)imidazolidin-2-one

반응식

CC1N=C(N2C(=O)NN=C2)SC=1C(OCC)=O.[C:18]([C:21]1[S:25][C:24]([N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19].Br[CH2:34][CH:35]1[CH2:37][C:36]1([F:39])[F:38]>>[C:18]([C:21]1[S:25][C:24]([N:26]2[CH2:30][CH2:29][N:28]([CH2:34][CH:35]3[CH2:37][C:36]3([F:39])[F:38])[C:27]2=[O:31])=[N:23][C:22]=1[CH3:32])(=[O:20])[CH3:19]

참가 물질

반응물 3

HCID 27614022-(Bromomethyl)-1,1-difluorocyclopropane

HCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

HCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

생성물 1

HCID 57919889(5-Acetyl-4-methylthiazol-2-yl)-3-((2,2-difluorocyclopropyl)methyl)imidazolidin-2-one수율 49%

실험 절차

Following the procedure as describe in Preparation 16, making variations as required to replace ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate with 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one to react with bromomethyl-2,2-difluorocyclopropane, the title compound was obtained as a yellow solid in 49% yield: mp 146-148° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.00 (t, J=9.0 Hz, 2H), 3.65-3.48 (m, 2H), 3.20-3.13 (m, 2H), 2.51 (s, 3H), 2.41 (s, 3H), 2.05-2.18 (m, 1H), 1.68-1.56 (m, 1H), 1.38-1.27 (m, 1H); 13C NMR (75 MHz, DMSO-d6) δ 190.8, 160.1, 155.1, 154.9, 125.8, 114.8 (t), 42.4, 42.1, 41.1 (d), 30.4, 20.2 (t), 18.6, 14.9 (t); MS (ES+) m/z 316.9 (M+1).