HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-4-ethyl-piperazine-1-sulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Ethyl (2R)-2-[(2-[(2,3-difluorobenzyl)thio]-6-{[(4-ethylpiperazin-1-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate | HCID 53628378 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-4-ethyl-piperazine-1-sulfonamide | HCID 59558846 | — |
Reaction Steps
To a solution of ethyl(2R)-2-[(2-[(2,3-Difluorobenzyl)thio]-6-{[(4-ethylpiperazin-1-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate (the product from step i) (0.72 g) in THF (10 ml) was added 2M LiBH4 in THF (1.3 ml). The reaction was then stirred for 18 h at RT. Saturated NH4Cl (150 ml) was then added to the reaction mixture which was extracted with DCM (3×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting residue was purified by prep HPLC to give the title compound as a white solid. Yield: 45 mg
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722883B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-1df2cbb4dfbe4709b06d0a8cfa8d09b6 |
| Source note | uspto-grants-2014_05 |