Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile | HCID 67170587 | — |
| Reactant | HCID 86714640 | HCID 86714640 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66576288 | HCID 66576288 | 1.8% |
Reaction Steps
The title compound was prepared using the procedure described in Example 3(h) starting from 5-(1-hydroxy-2-methylpropyl)isoxazole-3-carboxylic acid (2.160 mmol, 0.4 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (1.800 mmol, 0.502 g) using DMF (10 ml) as the solvent. The reaction mixture was diluted with water and EtOAc, the phases were separated and the organic phase was washed with 2 M Na2CO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 0.0146 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 0.89 (d, 3H), 0.92-0.98 (m, 3H), 1.26 (d, 3H), 2.01-2.13 (m, 1H), 4.28-4.45 (m, 2H), 4.51-4.64 (m, 2H), 6.53 (d, 1H), 6.79 (d, 1H), 7.68-7.77 (m, 2H), 7.91 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08921378B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-9d93ba31efe14cbfaedbe03c58648dfe |
|---|
| Source note | uspto-grants-2014_12 |
|---|