Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | HCID 86670423 | HCID 86670423 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 56932992 | HCID 56932992 | 46.7% |
Reaction Steps
A 20-mL microwave vial was charged with N-(5-((3-(1-propyn-1-yl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinyl)sulfonyl)-1,3,4-thiadiazol-2-yl)acetamide (370 mg, 0.647 mmol), MeOH (2 mL), 1N aq. HCl (3 mL, 3.00 mmol) and 4N HCl in dioxane (3 mL, 12.00 mmol). The reaction vessel was sealed and the mixture heated to 100° C. for 4 h. The reaction was concentrated onto silica and purified via column chromatography on silica gel (0 to 10% MeOH in CH2Cl2) to give 2-(4-(4-((5-amino-1,3,4-thiadiazol-2-yl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (160 mg) as a mixture of two isomers.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431563B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-19537745148f4f0d966635525a104ddb |
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| Source note | uspto-grants-2013_04 |
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