HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-ureido}-3-fluoro-phenyl)-propionic acid tert-butyl ester → 3-(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-ureido}-3-fluoro-phenyl)-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-ureido}-3-fluoro-phenyl)-propionic acid tert-butyl ester | HCID 66905341 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-ureido}-3-fluoro-phenyl)-propionic acid | HCID 45111178 | 12% |
Reaction Steps
3-(4-{3-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-3-cyclohexyl-ureido}-3-fluoro-phenyl)-propionic acid tert-butyl ester (20 mg, 34 μmol) was dissolved in a 4 M solution of HCl in dioxane (190 μl) under an argon atmosphere. The solution was stirred for 14 h at ambient temperature, poured onto ice water/1 N aqueous NaOH solution 1/1 and extracted two times with TBME. The aqueous layer was acidified with 1 N HCl and extracted two times with iPrOAc. The extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by preparative thin layer chromatography (silica gel, CH2Cl2/MeOH) to give the title compound (2 mg, 3.7 μmol; 12%) as yellow foam. MS: m/e=535.3 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153663B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-333540bf0b754125b9b1476c5dd743d6 |
| Source note | uspto-grants-2012_04 |