Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446358Generated: October 31, 2026

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

https://huagongshe.com/reaction/1446358

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant3-(Pyrrolidin-3-yl)pyridineHCID 3613651—
Reactant3-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acidHCID 59170145—
SolventDimethylformamideHCID 6228—
Product3-(1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-yl)pyridineHCID 5917009865.1%

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-pyrrolidin-3-ylpyridine (6 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 (10 mg). MS (ESI, pos. ion) m/z 384 (M+1); HRMS, calcd for C20H18ClN3O3: 383.1037, found 383.1033.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-8cdb123c9bca439eb050a3dc8c111105
Source noteuspto-grants-2010_02