HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl}piperazine-1-carboxylate → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]-1-piperazinesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl}piperazine-1-carboxylate | HCID 53628363 | — |
| Solvent | Trifluoroacetic acid methylene chloride | HCID 21863450 | — |
| Product | N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]-1-piperazinesulfonamide | HCID 59558751 | — |
Reaction Steps
A solution of tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl}piperazine-1-carboxylate (the product of step i) (0.23 g) in 10% trifluoroacetic acid/DCM (5 mL) was stirred at room temperature for 1 h. The mixture was evaporated to dryness in vacuo. The resulting crude oil was purified by reverse phase HPLC (75% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent) to give the title compound as a white solid. Yield: 40 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410123B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-71ba298b07284b4895b0adc5f67ea70e |
| Source note | uspto-grants-2013_04 |