HuagongsheHuagongshe Chemistry Print Report · For research reference only
methyl N-(prop-2-yn-1-yl)carbamate → Methyl {3-[7-amino-8-ethyl-6-(methylcarbamoyl)-5-oxo-5,8-dihydro-1,8-naphthyridin-2-yl]prop-2-yn-1-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | methyl N-(prop-2-yn-1-yl)carbamate | HCID 6917491 | — |
| Reactant | 2-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide | HCID 86642336 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | triethylamine N,N-dimethylformamide | HCID 22056947 | — |
| Product | Methyl {3-[7-amino-8-ethyl-6-(methylcarbamoyl)-5-oxo-5,8-dihydro-1,8-naphthyridin-2-yl]prop-2-yn-1-yl}carbamate | HCID 25127282 | — |
Reaction Steps
A suspension of 0.8 g (2.85 mmol) of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide in 22 ml of a DMF/Et3N (v/v; 2.2/1) mixture is placed in a 10 ml microwave tube. Argon is sparged into this suspension for 10 minutes and then 0.98 g of methyl (prop-2-yn-1-yl)carbamate (8.66 mmol), 0.076 g of CuI (0.40 mmol) and 0.139 g of bis(triphenylphosphine)palladium(II) dichloride (0.20 mmol) are successively added.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08263614B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-82516f35553e42fa8e630abfacd8aec4 |
| Source note | uspto-grants-2012_09 |