Diisopropylethylamine → 3-{3-[5-(3-Methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

HRID 2247400Notes

Reaction equation

Br.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH3:18])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][N:34]=[C:35]=[O:36])[CH3:29]>C(Cl)Cl>[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][NH:34][C:35]([NH:17][C:15]1[S:16][C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)=[C:13]([CH3:18])[N:14]=1)=[O:36])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred suspension of 5-(3-methanesulphonyl-phenyl)-4-methyl-thiazol-2-ylamine hydrobromide (176d) (0.172 g, 0.64 mmol) in DCM (15 ml) is treated with Hunigs base (0.45 ml, 2.36 mmol) followed by ethyl-3-isocyanatopropionate (0.092 g, 0.64 mmol). The reaction mixture is stirred and heated to 60° C. for 10 hours and then the solvent in removed in vacuo. The product is purified by chromatography on silica to give the titled compound

Workup

customthe solvent in removed in vacuo
customThe product is purified by chromatography on silica

Sources & evidence

ORD record: ord-daf156a7324e4f7a8869e26243f184d6
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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