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

HRID 560678Notes

Reaction equation

HRID 560678 reaction equation
C1(CBr)CC1.CC1C=CC(S(O[CH2:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)(=O)=O)=CC=1.[CH3:22][C:23]1[N:24]=[C:25]([N:33]2[CH2:37][CH2:36][NH:35][C:34]2=[O:38])[S:26][C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[CH:19]1([CH2:18][CH2:17][N:35]2[CH2:36][CH2:37][N:33]([C:25]3[S:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:23]([CH3:22])[N:24]=3)[C:34]2=[O:38])[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031391Ethyl 2-(3-(2-cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 60%

Procedure

Following the procedure as described in Example 10, making variations as required to replace cyclopropylmethyl bromide with 2-cyclopropylethyl 4-methylbenzenesulfonate to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 60% yield: 1H NMR (300 MHz, CDCl3) δ 4.13 (q, J=7.2 Hz, 2H), 3.65 (t, J=7.4 Hz, 2H), 3.43 (t, J=7.8 Hz, 2H), 3.22 (t, J=7.8 Hz, 2H), 2.34 (s, 3H), 1.44-1.15 (m, 5H), 0.57-0.51 (m, 1H), 0.32-0.22 (m, 2H), −0.07-0.11 (m, 2H): MS (ES+) m/z 324.3 (M+1).

Sources & evidence

ORD record
ord-d78d6a96c65d406ca432e13d83598ea0
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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