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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60914Generated: October 29, 2026

Diisopropylethylamine → ((2S,3R)-2-(((5-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl) (5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

https://huagongshe.com/reaction/60914

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2-Chloro-5-fluoro-1,3-benzoxazoleHCID 14169817—
Reactant((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanoneHCID 89739171—
SolventAcetonitrileHCID 6342—
Product((2S,3R)-2-(((5-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl) (5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanoneHCID 117728634—

Reaction Steps

A mixture of ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone (40 mg, 115 μmol), 2-chloro-5-fluorobenzoxazole (24 mg, 138 μmol) and DIPEA (60 μl, 345 μmol) in CH3CN (2 mL) was heated at reflux overnight. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with satd. NaHCO3 and brine. The solvent was removed and the crude was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 483 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440982B2
Source datasetuspto-grants-2016_09
ORD IDord-de2be3fe8d474bf381a2eb50d4c5f458
Source noteuspto-grants-2016_09