Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tert-butyl 3-aminopropanoate hydrochloride | HCID 16218890 | — |
| Reactant | 5-Cyano-2-fluoro-3-picoline | HCID 23288269 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 58554111 | HCID 58554111 | 94% |
Reaction Steps
A mixture of 6-fluoro-5-methylnicotinonitrile (Molekula 11370, 10 g, 73.4 mmol), beta-alanine tert-butyl ester hydrochloride (16 g, 88.1 mmol) and TEA (25.6 mL, 183.6 mmol) was prepared in DMSO (100 mL) under nitrogen, and then heated at 150° C. for 4 hours. The reaction mixture was cooled to 100° C. and water (100 mL) was added drop wise. The resulting mixture was stirred at RT for 2 hours, and then the precipitate was filtered off, washed with water and dried under reduced pressure to afford the title compound as a white solid (18 g, 94%). 1H NMR (DMSO-d6, 400 MHz) δ 8.31 (1H, s), 7.56 (1H, s), 6.97 (1H, m), 3.59 (2H, m), 2.50 (2H, m), 2.02 (3H, s), 1.36 (9H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08791142B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-db5d696003c5405fad302b961f1d6b07 |
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| Source note | uspto-grants-2014_07 |
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