Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile | HCID 67170882 | — |
| Reactant | HCID 86714640 | HCID 86714640 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66576765 | HCID 66576765 | 5.2% |
Reaction Steps
The title compound was prepared using the procedure described in Example 3(h) starting from 5-(1-hydroxy-2-methyl-propyl)isoxazole-3-carboxylic acid (1.566 mmol, 290 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (1.044 mmol, 272 mg) using a mixture of DCM (5 ml) and DMF (1 ml) as the solvent. DCM and water were added, the phases were separated and the water phase was extracted with DCM. The combined organics were washed twice with water. The DCM phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 23.4 mg of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 0.94 (d, 3H), 0.98 (d, 3H), 1.23 (d, 3H), 2.06-2.21 (m, 1H), 4.21-4.30 (m, 1H), 4.37-4.46 (m, 1H), 4.51-4.67 (m, 2H), 6.57-6.65 (m, 2H), 7.50 (d, 1H), 7.68 (d, 1H), 7.78-7.86 (m, 1H), 7.97 (d, 1H), 8.04 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08921378B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-03165a53171e41089e3747dee6a83aac |
|---|
| Source note | uspto-grants-2014_12 |
|---|