Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile | HCID 67170587 | — |
| Reactant | HCID 70981141 | HCID 70981141 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70981194 | HCID 70981194 | 79.3% |
Reaction Steps
The title compound was prepared using the procedure described in Example 3(h) using 1-isopropyl-2-methyl-1H-imidazole-4-carboxylic acid (0.303 mmol, 51 mg), (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.253 mmol, 70.4 mg) and only a catalytic amount of HOBt (0.025 mmol, 3.41 mg). DMF (2 ml) was used as the solvent in the reaction. The work up was done by adding water to the reaction mixture and extracting it three times with DCM. The combined organics were washed twice with water. The organic phase was evaporated and the residue was purified by flash chromatography. 86 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.06 (d, 3H), 1.34 (d, 6H), 2.35 (s, 3H), 4.23-4.47 (m, 4H), 7.02 (d, 1H), 7.62 (s, 1H), 7.86 (d, 1H), 7.90-7.96 (m, 1H), 8.00 (s, 1H), 8.04 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921378B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-3b5dddbcefe143e3925644e59b437fc3 |
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| Source note | uspto-grants-2014_12 |
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