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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446346Generated: November 1, 2026

Diisopropylethylamine → 3-(1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

https://huagongshe.com/reaction/1446346

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant3-(Pyrrolidin-3-yl)pyridineHCID 3613651—
Reactant3-(4-Methoxyphenyl)isoxazole-4-carboxylic acidHCID 59170121—
SolventDimethylformamideHCID 6228—
Product3-(1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-yl)pyridineHCID 5917003785.9%

Reaction Steps

A solution of 3-(4-methoxyphenyl)isoxazole-4-carboxylic acid (7 mg, 0.03 mmol), N-ethyl-N-isopropylpropan-2-amine (16 μL, 0.09 mmol, 3 equ.) and TBTU (12 mg, 0.036 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-pyrrolidin-3-ylpyridine (4 mg, 0.03 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 (9 mg). MS (ESI, pos. ion) m/z: calcd for C20H19N3O3: 349.1426, found 349.1427.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-9ae7133012e143df8140884af768e37b
Source noteuspto-grants-2010_02