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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 418299Generated: October 29, 2026

Diisopropylethylamine → Ammonia

https://huagongshe.com/reaction/418299

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantPyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 1910189—
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—
ProductHCID 59152092HCID 59152092—

Reaction Steps

To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 9) (75 mg, 0.268 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (48.2 mg, 0.295 mmol) and DIPEA (0.070 ml, 0.403 mmol) in dry DMF (3 ml) at rt under argon was added HATU (122 mg, 0.322 mmol) and the resulting yellow solution stirred at rt for 1 hour. Concentration in vacuo gave a yellow oil, that was purified by MDAP; concentration of the desired fractions gave a clear film (80.2 mg). Flash chromatography (silica; Flash 12S; linear gradient (1-8%) [2M NH3 in MeOH] in DCM) gave the title compound as a clear film (44.9 mg), that became a white solid on standing in vacuo (1 mbar) for 1 h.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08093249B2
Source datasetuspto-grants-2012_01
ORD IDord-3fb47c3eb07a420e9b28416c87579ac5
Source noteuspto-grants-2012_01