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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1055746Generated: November 1, 2026

Diisopropylethylamine → 3-Cyano-N-{2-hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

https://huagongshe.com/reaction/1055746

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant3-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 89699812—
Reactant2-Amino-6-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenolHCID 89699920—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-Cyano-N-{2-hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamideHCID 89699588—

Reaction Steps

74 mg (0.178 mmol, 70% pure) of the compound from Example 71A and 44 mg (0.160 mmol) of the compound of Example 23A were dissolved in 1 ml anhydrous DMF, and 81 mg (0.213 mmol) of HATU and 37 μl (0.213 mmol) of N,N-diisopropylethylamine were added in succession. The reaction mixture was stirred at RT for 30 min and then stirred into about 10 ml of water. The resulting precipitate was filtered off with suction, dissolved in about 3 ml of methanol and separated into its components by preparative HPLC (Method 33). The product fractions were combined and freed from the solvent. The residue obtained was triturated with a little dichloromethane at RT. Filtration with suction and drying of the solid under high vacuum gave 36 mg (37% of theory) of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09394309B2
Source datasetuspto-grants-2016_07
ORD IDord-34a03ea2335043e8a2a83cf7b0a0c7a8
Source noteuspto-grants-2016_07