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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1483666Generated: October 31, 2026

Diethylamine → HCID 57969167, compound

https://huagongshe.com/reaction/1483666

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethylamineHCID 8021—
ReactantDiisopropylethylamineHCID 81531—
ReactantChlorotri(1-pyrrolidinyl)phosphonium hexafluorophosphateHCID 16211753—
ReactantHCID 46884278HCID 46884278—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 57969167HCID 5796916794%

Reaction Conditions

Temperature0 °C

Reaction Steps

To the solution of 6-(1-Hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)nicotinic acid (0.813 g, 3 mmol) in anhydrous DMF (70 mL) was added diethylamine (3.2 mL, 30 mmol) and DIPEA (1.6 mL, 9 mmol) under N2. The mixture was cooled with ice bath and a coupling agent PyCloP (Aldrich#26564, 1.4 g, 3.3 mmol) was added. The reaction mixture was stirred at 0° C. for 10 min and at room temperature overnight, and then rotary evaporated. The residue was dissolved in EtOAc and washed with water, evaporated and purified by flash column chromatography over silica gel eluted with EtOAc to provide the title amide compound as a white solid (0.92 g, 2.82 mmol, yield 94%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09416146B2
Source datasetuspto-grants-2016_08
ORD IDord-c9b0080c3073436ca39648530d2223c8
Source noteuspto-grants-2016_08