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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1061235Generated: November 3, 2026

4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 5-(3-Bromo-4-{4-[(2S)-2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzylidene)-thiazolidine-2,4-dione

https://huagongshe.com/reaction/1061235

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 10799105—
Reactant5-[3-Bromo-4-(4-oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dioneHCID 73876716—
Product5-(3-Bromo-4-{4-[(2S)-2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzylidene)-thiazolidine-2,4-dioneHCID 86588904—

Reaction Steps

The title compound was prepared from 4-((2S)-3-amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one (U.S. Pat. No. 5,786,356/1998) and 5-[3-bromo-4-(4-oxo-piperidine-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 58) according to the procedure of Example 63 as an olive green solid; 1H NMR (300 MHz, DMSO-d6) δ 1.66-1.77 (m, 4H), 2.10-2.19 (m, 4H), 2.68-2.76 (m, 2H), 3.07-3.14 (m, 3H), 3.99-4.09 (m, 2H), 5.62 (brs, 1H), 6.58-6.66 (m, 2H), 6.88 (t, J=8.1 Hz, 1H), 7.20-7.25 (m, 3H), 7.50 (dd, J=8.5, 2.0 Hz, 25 1H), 7.75 (d, J=2.0 Hz, 1H), 10.55 (s, 1H), 10.65 (s, 1H); MS (ES) m/z: 589.9 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06525202B2
Source datasetuspto-grants-2003_02
ORD IDord-3b0b72c870f6434c9bb939020b794820
Source noteuspto-grants-2003_02