HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 4-(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(4-methylpentanoyl)-1,4-dihydropyridine-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde | HCID 57438889 | — |
| Reactant | 2-Amino-7-methyloct-2-en-4-one | HCID 71406111 | — |
| Reactant | Sodium 1-cyanoprop-1-en-2-olate | HCID 74083625 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 4-(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(4-methylpentanoyl)-1,4-dihydropyridine-3-carbonitrile | HCID 66992067 | — |
Reaction Steps
A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 69.25 mg (0.45 mmol) of 2-amino-7-methyloct-2-en-4-one (example 14, stage a) and 0.04 ml (0.67 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). 88.1 mg (46.36% of theory) of the title compound are obtained as yellow crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08058447B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-c91b1e7ec6654c1fb1be7605852be108 |
| Source note | uspto-grants-2011_11 |