HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 8-(1-Allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride | HCID 44181959 | — |
| Reactant | 8-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester | HCID 67193811 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 8-(1-Allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester | HCID 67345482 | 27.7% |
Reaction Steps
1-Allyl-cyclopropanesulfonyl chloride (259 mg, 0.001 mol) was added to a stirred solution of 8-amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (350 mg, 0.001 mol) in pyridine (3 mL). The resulting mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer concentrated to afford the crude product. Purification by column chromatography on silica gel (75% ethylacetate in hexane) afforded 125 mg of the product (27.7% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466289B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-311101becf62489d87638be53675bf5d |
| Source note | uspto-grants-2013_06 |