HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sufugolix → N-(4-(5-chloromethyl-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyurea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sufugolix | HCID 3038517 | — |
| Reactant | Carbonochloridate | HCID 21226386 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | N-(4-(5-chloromethyl-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyurea | HCID 18324813 | — |
Reaction Steps
Into a solution of N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea (7.7 g, 11.53 mmol) in THF (200 ml) which was cooled with a dry ice-acetone bath was added α-choloroethyl chloroformate (1.7 ml, 11.64 mmol). The temperature of the mixture was elevated up to room temperature, and the mixture was stirred for 2.5 hours. The reaction mixture was diluted with saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735401B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-416e6e82b1da40688e12479a0ecd0bb9 |
| Source note | uspto-grants-2014_05 |