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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1061288Generated: November 4, 2026

5-[3-Fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(3-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-2-fluoro-phenyl]-piperidin-4-ylamino}-(2S)-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1061288

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-[3-Fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 22220552—
Reactant5-((2S)-3-Amino-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl esterHCID 69654969—
Product5-(3-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-2-fluoro-phenyl]-piperidin-4-ylamino}-(2S)-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl esterHCID 86584565—

Reaction Steps

The title compound was prepared from 5-((2S)-3-amino-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester (which was obtained in Example 141) and 5-[3-fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 61) according to the procedure of Example 73 as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, J=7.1 Hz, 3H), 1.56-1.63 (m, 2H), 2.03 (m, 2H), 2.61 (s, 3H), 2.67-2.75 (m, 4H), 2.88-2.96 (m, 4H), 3.04-3.07 (m, 2H), 3.95-3.97 (m, 2H), 4.05 (m, 2H), 4.25 (q, J=7.1 Hz, 2H), 4.61-4.66 (m, 1H), 5.52 (brs, 1H), 6.79 (dd, J=8.7, 2.5 Hz, 1H), 6.94-7.03 (m, 2H), 7.24-7.29 (m, 2H), 7.46 (d, J=2.3 Hz, 1H) 11.65 (s, 1H); MS (ES) m/z: 599.1 (MH+); HRMS for C30H36FN4O6S(MH+): 599.2339. Found: 599.2333.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06525202B2
Source datasetuspto-grants-2003_02
ORD IDord-48a25b214fae43a1912517259f50e524
Source noteuspto-grants-2003_02