Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,4-Difluorobenzoyl chloride | HCID 2724519 | — |
| Reactant | HCID 58964268 | HCID 58964268 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58964295 | HCID 58964295 | 19.5% |
Reaction Steps
A mixture of 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenylamine (88 mg, 0.25 mmole), 3,4-difluoro-benzoyl chloride (40 μL, 0.30 mmole), and triethylamine (70 μL, 0.5 mmole) in 1 mL THF was stirred at room temperature for 10 minutes. The mixture was purified by HPLC to give the title compound as a white solid (TFA salt, 24 mg, 19% yield). 1H NMR (CD3OD, 400 MHz) δ 2.17-2.31 (m, 1H), 2.71-2.84 (m, 2H), 2.87-2.97 (m, 2H), 3.14-3.25 (m, 1H), 3.38-3.48 (m, 1H), 3.72-3.79 (m, 1H), 3.75 (s, 3H), 3.89-3.97 (m, 1H), 5.17-5.24 (m, 1H), 7.17-7.30 (m, 1H), 7.41-7.47 (m, 1H), 7.56-7.62 (m, 1H), 7.63-7.69 (m, 1H), 7.78-89 (m, 1H), 7.88-7.93 (m, 2H). Exact mass calculated for C22BrH21F2N4O2 490.1. found 491.5, 493.5 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07884101B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-cb66b9bd36d6455bb2bc4c5010d53783 |
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| Source note | uspto-grants-2011_02 |
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