Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 6-Fluoro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine | HCID 58783963 | — |
| Reactant | (1R,4S)-4-Amino-6-fluoro-1,2,3,4-tetrahydro-naphthalen-1-ol | HCID 86686696 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86686698 | HCID 86686698 | 27.3% |
Reaction Steps
Intermediate 19a (837 mg, 4.62 mmol) was dissolved in dry DMF (15 mL) under Ar, then NaH (60% in mineral oil, 556 mg, 13.9 mmol) was added, and the mixture stirred for 15 min. Intermediate 1f (893 mg, 4.99 mmol) was added, and the reaction heated at 60° C. for 2 h. The reaction was cooled, quenched by addition of water and extracted with DCM (4×30 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by FCC, eluting with 0-20% [2M NH3 in MeOH] in DCM, to give the title compound (429 mg, 27%). LCMS (Method 3): Rt 1.96, m/z 363 [MNa+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09029373B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-b774827af4f24bbba87431136ebdeb53 |
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| Source note | uspto-grants-2015_05 |
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