Homoallyl bromide → Ethyl 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 554885Notes

Reaction equation

HRID 554885 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][C@H:15](C)[NH:14][C:13]2=[O:18])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:19][C:20]1N=C(N2CCNC2=O)S[C:24]=1[C:25](OCC)=O.BrCCC=C>>[CH2:25]([N:14]1[CH2:15][CH2:16][N:12]([C:4]2[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=2)[C:13]1=[O:18])[CH2:24][CH:20]=[CH2:19]

Participants

4

Reactant 3

HCID 21241Homoallyl bromideHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylateHCID 57919870(S)-ethyl 4-methyl-2-(4-methyl-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 57919868Ethyl 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Procedure

Following the procedure as described in Preparation 5, making variations as required to replace (S)-ethyl 4-methyl-2-(4-methyl-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate and with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate to react with 4-bromobut-1-ene, the title compound was obtained as an off-white solid (2.05 g, 85%): mp 97-98° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 5.86-5.72 (m, 1H), 5.16-5.02 (m, 2H), 4.22 (q, J=7.1 Hz, 2H), 4.02-3.79 (m, 2H), 3.60-3.55 (m, 2H), 3.34-3.29 (m, 2H), 2.51 (s, 3H), 2.33-2.26 (m, 2H), 1.27 (t, J=7.1 Hz, 3H); MS (ES+) m/z 309.8 (M+1).

Workup

  1. customas described in Preparation 5

Sources & evidence

ORD record
ord-cb4531b7a0e845fc8fa8e47c08c53c20
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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