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

HRID 2067458Notes

Reaction equation

HRID 2067458 reaction equation
C1(CBr)CC1.CC1C=CC(S(O[CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=O)=O)=CC=1.[CH3:23][C:24]1[N:25]=[C:26]([N:34]2[CH2:38][CH2:37][NH:36][C:35]2=[O:39])[S:27][C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[CH:18]1([CH2:17][N:36]2[CH2:37][CH2:38][N:34]([C:26]3[S:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:24]([CH3:23])[N:25]=3)[C:35]2=[O:39])[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031688Ethyl 2-(3-(cyclopentylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 62%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with cyclopentylmethyl 4-methylbenzenesulfonate to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 62% yield: 1H NMR (300 MHz, CDCl3) δ 4.20 (q, J=7.2 Hz, 2H), 4.04-3.99 (m, 2H), 3.52-3.41 (m, 2H), 3.17 (d, J=7.5 Hz, 2H), 2.46 (s, 3H), 2.16-1.08 (m, 12H); MS (ES+) m/z 338.3 (M+1).

Sources & evidence

ORD record
ord-f2c8e226efdc4575b20ae48b1bac03a4
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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