Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol | HCID 86686674 | — |
| Reactant | 6-Fluoro-3-((S)-1,4,4-trimethyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine | HCID 86687128 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86687129 | HCID 86687129 | 74.3% |
Reaction Steps
To a solution of Intermediate A (552 mg, 3.89 mmol) in DMF (25 mL) was added NaH (60% in oil, 338 mg, 8.46 mmol) and the mixture stirred at RT for 20 min, before Intermediate 87c (700 mg, 2.82 mmol) was added. This mixture was stirred at 60° C. for 1 h. The cooled reaction mixture was applied to an SCX-2 cartridge (70 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave a residue. FCC, using 0-10% (2M NH3 in MeOH) in DCM gave the title compound (820 mg, 74%). LCMS (Method 4): Rt 1.53 min, m/z 392 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08907094B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-b409340923b74b8a8078e9a7cb73e842 |
|---|
| Source note | uspto-grants-2014_12 |
|---|
