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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 913685Generated: October 30, 2026

Triethylamine → 1-({5-[2-(Methylthio)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

https://huagongshe.com/reaction/913685

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant2-(Methylthio)benzoic acidHCID 19498—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
ReactantHCID 178438386HCID 178438386—
SolventDimethylformamideHCID 6228—
Product1-({5-[2-(Methylthio)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrileHCID 5780020030%

Reaction Conditions

Temperature150 °C

Reaction Steps

A solution was prepared using 2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol), 2-(methylthio)benzoic acid (0.076 g, 0.463 mmol), HATU (0.176 g, 0.463 mmol), triethylamine (1.0 mL, 13.6 mmol) and anhydrous DMF (10 mL). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.042 g (30% yield) of pure product: MS (ES) m/z 456 (M+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08026262B2
Source datasetuspto-grants-2011_09
ORD IDord-a0a24c1607da414e9f543a47ba68cc72
Source noteuspto-grants-2011_09