Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 6-Chloro-5-cyanopyridine-2-carboxylic acid | HCID 53433239 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 44544618 | HCID 44544618 | 75% |
Reaction Steps
A mixture of 6-chloro-5-cyanopicolinic acid (30 mg, 0.16 mmol), isopropylamine (20 ul, 0.23 mmol), and KF (28 mg, 0.48 mmol) in N-methylpyrrolidinone (1 ml) was heated for 18 hrs at 95° C. The mixture was diluted with water (4 ml) and standed overnight. The resulting precipitate was collected by filtration and dried under vacuum to afford 25 mg (75%) of the desired product 70. 1H NMR (600 MHz, DMSO-d6) δ 13.2 (s, 1H), 8.03 (d, 1H, J=7.8 Hz), 7.25-7.21 (m, 1H), 7.17 (d, 1H, J=7.8 Hz), 3.26-3.24 (m, 2H), 1.99-1.95 (m, 1H), 0.89 (d, 6H, 6.6 Hz). MS: m/z Calcd 219.2 Found MH+ 220.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09340505B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-a36c47e17e4c420eabe56afd835b53d7 |
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| Source note | uspto-grants-2016_05 |
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