HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (R)-6-[[3-[[8-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide | HCID 86659116 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-6-[[3-[[8-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide | HCID 54588137 | 28.5% |
Reaction Steps
A solution of TBAF (1.0 M in THF, 0.244 mL, 0.244 mmol) was added to a stirring solution of Intermediate 148 (76 mg, 0.0813 mmol) in THF (2 mL) at rt. After stirring over night, glacial acetic acid (0.023 mL, 0.407 mmol) was added and stirred for an additional 16 h. The reaction mixture was concentrated and purified by PREP-HPLC to give the title compound (19 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394829B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-7529d12907a94d68b063a7911ae51904 |
| Source note | uspto-grants-2013_03 |