Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Chloronicotinic acid | HCID 79222 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 58387909 | HCID 58387909 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 58387963 | HCID 58387963 | 67.2% |
Reaction Steps
6-chloro-nicotinic acid (100 mg, 0.58 mmol), triethylamine (0.194 mL, 1.39 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (308 mg, 0.696 mmol) were dissolved in N,N-dimethylformamide (3 mL), C-(1-(3-fluoro-benzyl)-1H-pyrrol-3-yl)-methylamine (142 mg, 0.695 mmol) described in Preparation Example 59 was added, and the solution was stirred for 15 hours 10 minutes at room temperature. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then the solution was concentrated, the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (0.14 g, 0.39 mmol, 67%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07932272B2 |
|---|
| Source dataset | uspto-grants-2011_04 |
|---|
| ORD ID | ord-3974b6837e344f9c8a272a64dd5c412a |
|---|
| Source note | uspto-grants-2011_04 |
|---|