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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43403Generated: October 29, 2026

Diisopropylethylamine → Ammonia

https://huagongshe.com/reaction/43403

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant6-Methylnicotinic acidHCID 137860—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileHCID 59152067—
SolventMethanolHCID 887—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
ProductAmmoniaHCID 222—
Product3-Methyl-4-({(3S)-3-methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-piperazinyl}sulfonyl)benzonitrileHCID 59161349—

Reaction Steps

To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (Description 11) (75 mg, 0.268 mmol), 6-methyl-3-pyridinecarboxylic acid (40.5 mg, 0.295 mmol) and DIPEA (0.070 ml, 0.403 mmol) in dry DMF (3 ml) at room temperature under Ar was added HATU (122 mg, 0.322 mmol) and the resulting yellow solution stirred at room temperature for 1 h. Concentration in vacuo gave a yellow oil, that was purified by MDAP purification; concentration of the desired fractions gave a clear film (78.8 mg). Flash chromatography (silica; Flash 12S; linear gradient (1-8%) [2M NH3 in MeOH] in DCM) gave the title compound as a clear film (54.5 mg) that became a white solid on standing in vacuo (1 mbar) for 1 hour.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536183B2
Source datasetuspto-grants-2013_09
ORD IDord-136edae82d064d8f87bcad27fb7aff8f
Source noteuspto-grants-2013_09