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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1484564Generated: October 30, 2026

Acetic Acid → HCID 67085298, compound

https://huagongshe.com/reaction/1484564

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant1H-Indazole-5-carboxaldehydeHCID 21250644—
Reactant3-Amino-4,4,4-trifluorobut-2-enenitrileHCID 53401096—
ReactantSodium 1-cyanoprop-1-en-2-olateHCID 74083625—
Solvent1-PentanolHCID 6276—
SolventTetrahydrofuranHCID 8028—
ProductHCID 67085298HCID 67085298—

Reaction Steps

A mixture of 250 mg (1.71 mmol) 1H-indazole-5-carbaldehyde, 180 mg (1.71 mmol) sodium 1-cyanoprop-1-en-2-olate and 931 mg (6.84 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation: A. W. Lutz, U.S. Pat. No. 3,635,977; C. G. Krespan, J. Org. Chem. 34, 42 (1969)] in 1-pentanol (2.5 ml) and acetic acid (0.15 ml) was heated to 105° C. overnight. After cooling, the reaction mixture was diluted with THF and directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) yielding 131 mg (23% of th.) of the racemic title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422263B2
Source datasetuspto-grants-2016_08
ORD IDord-a12aa752af594cf4a7d7c35fb3121c5f
Source noteuspto-grants-2016_08