Bromomethylcyclopropane → ethyl 4-methyl-2-(2-oxo-3-((tetrahydro-2H-pyran-2-yl)methyl)imidazolidin-1-yl)thiazole-5-carboxylate

HRID 560682Notes

Reaction equation

HRID 560682 reaction equation
C1(CBr)CC1.Br[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O: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]>>[CH3:14][C:15]1[N:16]=[C:17]([N:25]2[CH2:29][CH2:28][N:27]([CH2:7][CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][O:9]3)[C:26]2=[O:30])[S:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031472ethyl 4-methyl-2-(2-oxo-3-((tetrahydro-2H-pyran-2-yl)methyl)imidazolidin-1-yl)thiazole-5-carboxylateYield 39%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with (bromomethyl) tetrahydro-2H-pyran to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 39% yield: 1H NMR (300 MHZ, CDCl3) δ 4.26 (q, J=7.2 Hz, 2H), 4.11-4.05 (m, 2H), 3.97-3.92 (m, 1H), 3.83-3.62 (m, 2H), 3.55-3.34 (m, 2H), 3.22-3.15 (m, 1H), 2.60 (s, 3H), 1.85-1.82 (m, 1H), 1.57-1.44 (m, 4H), 1.31-1.22 (m, 5H): MS (ES+) m/z 354.3 (M+1).

Sources & evidence

ORD record
ord-85a40bbf96144ab3b156862ed3b37363
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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