Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | HCID 90408624 | HCID 90408624 | — |
| Catalyst | HCID 178418390 | HCID 178418390 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 86271579 | HCID 86271579 | 102.6% |
Reaction Steps
A solution of (2-chloro-3-(trifluoromethyl)phenyl)(4-methyl-1-(pyrimidin-5-yl)-1H-[1,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone (237 mg, 0.56 mmol) in MeOH (12 ml) was treated with ammonium formate (147 mg, 2.3 mmol) and Pd/carbon (10 wt %, 20 mg) and the reaction was refluxed for 90 min. The reaction was filtered through celite and the filter cake washed with MeOH and concentrated to a crude solid which was re-suspended with CHCl3 and filtered to remove in-organic salts then purified on 40 g SiO2 with 0-60% EtOAc hexanes to provide 243 mg (22%) of desired product. MS (ESI) mass calcd. C18H14ClF3N6O, 422.09. m/z found, 423.1 [M+H]+. The enantiomers were separated by chiral SFC on (CHIRALPAK AD-H 5 μm 250×20 mm). Mobile phase (70% CO2, 30% EtOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09066946B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-e2d4c9eccda44d05ad18ff61498ab952 |
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| Source note | uspto-grants-2015_06 |
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