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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2300239Generated: October 30, 2026

4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 5-(4-{4-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidine-1-sulfonyl}-benzyl)-thiazolidine-2,4-dione

https://huagongshe.com/reaction/2300239

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 10799105—
Reactant5-[4-(4-Oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dioneHCID 18767792—
Product5-(4-{4-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidine-1-sulfonyl}-benzyl)-thiazolidine-2,4-dioneHCID 10231781—

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dione and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one according to the reductive amination procedure of Intermediate 21 as a pale grey solid; 1H NMR (300 MHz, DMSO-d6): δ 1.20-1.40 (m, 2 H), 1.80-2.00 (m, 2 H), 2.30-4.00 (m, 12 H), 4.65 (dd, J=8.0, 3.5 Hz, 1 H), 6.56 (d, J=3.2 Hz, 1 H), 6.59 (d, J=3.8 Hz, 1 H), 6.85 (t, J=3.5 Hz, 1 H), 7.50 (d, J=8.1 Hz, 2 H), 7.66 (d, J=8.1 Hz, 2 H), 10.70 (s, 1 H), 10.79 (brs, 1 H); MS (ES) m/z : 576.0 (M++H); HRMS Calcd. for C25H30N507S2 (M++H): 576.1587. Found: 576.1596.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06498170B2
Source datasetuspto-grants-2002_12
ORD IDord-c40a6b6d12a04a558d4c63708d9d831f
Source noteuspto-grants-2002_12