Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Chlorophenol | HCID 4684 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 59153115 | HCID 59153115 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59153019 | HCID 59153019 | 75% |
Reaction Steps
The mixture of {(R)-4-[(5-Bromo-6-chloro-pyridine-3-sulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (80 mg, 0.16 mmol), sodium hydride (60% dispersed in mineral oil, 40 mg) and 4-chlorophenol (315 mg, 2.45 mmol) in N,N-dimethylformamide (2 mL) was heated in a microwave oven at 100° C. for 15 minutes, and then acidified with 0.1N hydrochloric acid to pH 5. The precipitate was filtered through a glass funnel and purified by preparative HPLC to afford ((R)-4-{[5-bromo-6-(4-chloro-phenoxy)-pyridine-3-sulfonyl]-methyl-amino}-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (70 mg, 75%) as a white powder. MS cald. for C23H24BrClN4O5S 582, obsd. (ESI+) [(M+H)+]: 583.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08420675B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-6db47fd06dee45db97e451e05bd23746 |
|---|
| Source note | uspto-grants-2013_04 |
|---|