Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | HCID 54009854 | HCID 54009854 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 54355243 | HCID 54355243 | — |
Reaction Steps
3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid (3.2 g) suspended in dioxane (70 ml) and tetrahydrofurane (30 ml) was reacted with ethyl chlorocarbonate (4.55 g) in the presence of triethylamine (4.05 g) under stirring at 15° C. for 2 hours. Then the reaction mixture was treated with dioxane (200 ml) saturated with gaseous ammonia for 30 minutes under stirring. After dilution with ice water and neutralization with HCl, the precipitate was filtered and purified by washing with dimethylformamide to give 2.52 g of 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxamide, m.p. 350°-357° C., NMR (CF3COOD) δ ppm: 3.40 (bs) (4H, C-1 and C-2 protons), 7.60 (m) (6H, =CH-- and phenyl protons), 8.42 (d) (1H, C-5 proton), 9.03 (d d) (1H, C-6 proton), 10.09 (d) (1H, C-8 proton).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04521419 |
|---|
| Source dataset | uspto-grants-1985_06 |
|---|
| ORD ID | ord-34152f0219304074bf9e4c3463e40e45 |
|---|
| Source note | uspto-grants-1985_06 |
|---|