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
Participants
| Role | Name | HCID | Charge |
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| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(Methylthio)benzoic acid | HCID 19498 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 178438386 | HCID 178438386 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-({5-[2-(Methylthio)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile | HCID 57800200 | 30% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08026262B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-a0a24c1607da414e9f543a47ba68cc72 |
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| Source note | uspto-grants-2011_09 |
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