Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| 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 86708121 | HCID 86708121 | — |
| Reactant | tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate | HCID 137319820 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 73053317 | HCID 73053317 | 100% |
Reaction Steps
2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid (Int. 36, 246 mg, 0.732 mmol) and N-(tert-butyloxycarbonyl)-S-methylisothiourea (139 mg, 0.732 mmol) in THF (5 mL) were treated with triethylamine (306 μL, 2.196 mmol) and HATU (384 mg, 1.098 mmol) and then the reaction mixture was heated at 80° C. for 1.5 hrs. The reaction mixture was treated with saturated aqueous NaHCO3 solution (20 mL) and DCM (20 mL) and the organic phase was separated and concentrated in vacuo. The resulting material was purified by chromatography on silica eluting with a gradient of 0-10% MeOH in DCM to give the title compound as a white solid (348 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09199984B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-36ddc3970d95400fa0606320a0155ea9 |
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| Source note | uspto-grants-2015_12 |
|---|
