Bromomethylcyclopropane → Ethyl 2-(3-(cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 560681Notes

Reaction equation

C1(CBr)CC1.Br[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:14][C:15]1[N:16]=[C:17]([N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])[S:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[CH:8]1([CH2:7][N:27]2[CH2:28][CH2:29][N:25]([C:17]3[S:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([CH3:14])[N:16]=3)[C:26]2=[O:30])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 3

HCID 81503Bromomethylcyclopropane

HCID 137636Cyclohexane, (bromomethyl)-

HCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031626Ethyl 2-(3-(cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 76%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with (bromomethyl)cyclohexane to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 76% yield: 1H NMR (300 MHZ, CDCl3) δ 4.27 (q, J=7.2 Hz, 2H), 4.09-3.99 (m, 2H), 3.57-3.40 (m, 2H), 3.11 (d, J=6.9 Hz, 2H), 2.59 (s, 3H), 1.86-1.55 (m, 5H), 1.31-1.11 (m, 7H), 0.97-0.82 (m, 2H); MS (ES+) m/z 352.3 (M+1).

Sources & evidence

ORD record: ord-1930347af5424effb6f9ace850376aed
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

Loading…