HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2Z)-3-Amino-2-butenenitrile → 4-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2Z)-3-Amino-2-butenenitrile | HCID 5325263 | — |
| Reactant | 4-Formyl-3-methoxybenzonitrile | HCID 16659251 | — |
| Reactant | 1-(4-Methyl-1,3-thiazol-2-yl)butan-2-one | HCID 59492337 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 4-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile | HCID 135844961 | — |
Reaction Steps
100 mg (0.620 mmol) of the compound from example 3A, 100 mg (0.310 mmol, 50% purity) of the compound from example 5A and 51 mg (0.620 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 78 mg (66% of theory) of the title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404723B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-34dfbf5742e74ed1a39e39d638163559 |
| Source note | uspto-grants-2013_03 |