Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Pyrrolidinesulfonyl chloride | HCID 6483902 | — |
| Reactant | HCID 66647207 | HCID 66647207 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 46913145 | HCID 46913145 | 24.7% |
Reaction Steps
To 3-(3-amino-2,6-difluoro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (28, 354 mg, 1.19 mmol) in 9.5 mL of tetrahydrofuran, 0.84 mL of pyridine was added. Pyrrolidine-1-sulfonyl chloride (31, 403 mg, 2.37 mmol) was added and the solution was stirred at 60° C. for 48 hours. The reaction mixture was poured into 1 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and the solvent removed under reduced pressure to provide the desired compound (P-0006, 127 mg). MS(ESI)[M+H+]+=432.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901301B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-27d31fbefa7848ce8b2eac00bf76b8b2 |
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| Source note | uspto-grants-2014_12 |
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