Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | HCID 89402063 | HCID 89402063 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89401848 | HCID 89401848 | 37.5% |
Reaction Steps
(Z)-tert-butyl 6-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylamido)-3-azabicyclo[3.1.0]hexane-3-carboxylate (0.05 g, 1.0 eq.) was dissolved in DCM (3 mL) and cooled to 0° C. where dioxane:HCl (0.2 mL) was added dropwise and stirred for 30 min. The reaction was allowed to warm to room temperature and stirred for 30 min, concentrated under reduced pressure. The crude product was triturated with ether to afford (Z)—N-(3-azabicyclo[3.1.0]hexan-6-yl)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylamide hydrochloride (0.015 g, 37.5% yield). 1H NMR (400 MHz, DMSO) δ, 9.61 (s, 1H), 8.75 (s, 2H), 8.60 (s, 2H), 8.30 (s, 1H), 7.38-7.40 (d, J=10.4 Hz, 1H), 5.87-5.89 (d, J=10.4 Hz, 1H), 2.91 (s, 1H), 2.14 (s, 2H), 1.23 (s, 3H); LCMS for Chemical Formula: C18H16F6N5O [M+H]+ 432.34 found 432.19 at retention time 2.302 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428490B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-6d85114ffc8b41bfbd7149c93afed845 |
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| Source note | uspto-grants-2016_08 |
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