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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446356Generated: November 1, 2026

Diisopropylethylamine → 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-pyridin-3-ylpyrrolidin-3-ol

https://huagongshe.com/reaction/1446356

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant3-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acidHCID 59170145—
Reactant3-(Pyridin-3-yl)pyrrolidin-3-ol dihydrochlorideHCID 68686267—
SolventDimethylformamideHCID 6228—
Product1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-pyridin-3-ylpyrrolidin-3-olHCID 5917002850%

Reaction Steps

A solution of 3-(3-chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acid (10 mg, 0.04 mmol), N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.08 mmol, 2 equ.) and TBTU (15 mg, 0.046 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-pyridin-3-ylpyrrolidin-3-ol dihydrochloride (9 mg, 0.04 mmol). After 1 h at rt the crude product was purified by RP-HPLC. The pure fractions were basified (NaHCO3) and extracted with ethyl acetate, dried (Na2SO4), evaporated and dried in vacuum to yield the title compound (8 mg). MS (ESI, pos. ion) m/z: calcd for C20H18ClN3O4: 399.0986, found 399.0986.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-43fc551d842042819d2fad8cdf08a228
Source noteuspto-grants-2010_02