Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 58810641 | HCID 58810641 | — |
| Reactant | (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile | HCID 67170587 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86714629 | HCID 86714629 | 19.5% |
Reaction Steps
The title compound was prepared using the procedure described in Example 3(h) using 5-(2-hydroxypropan-2-yl)-1H-pyrazole-3-carboxylic acid (0.646 mmol, 110 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.539 mmol, 150 mg) and only a catalytic amount of HOBt (0.054 mmol, 7.28 mg). DMF was used as the solvent. Water was added to the reaction mixture and the mixture was extracted 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 and preparative HPLC, respectively. 45.4 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.13 (d, 3H), 1.43 (s, 6H), 4.17-4.55 (m, 3H), 5.27 (bs, 1H), 6.37 (bs, 1H), 6.99 (d, 1H), 7.82 (d, 1H), 7.86 (d, 1H), 7.97 (s, 1H), 8.08 (bs, 1H), 12.94 (bs, 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-b2e9b4bb30b7456a9c87fd11faec5206 |
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| Source note | uspto-grants-2014_12 |
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