HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetohydrazide → N'-Acetyl-3-fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzohydrazide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetohydrazide | HCID 14039 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoic acid | HCID 66682497 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N'-Acetyl-3-fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzohydrazide | HCID 66682489 | 117.1% |
Reaction Steps
3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoic acid (84 mg, 0.179 mmol) synthesized in Example (44a) was dissolved in dichloromethane (5.0 mL), and acetohydrazide (40 mg, 0.540 mmol), HATU (200 mg, 0.526 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.861 mmol) were added, followed by stirring at room temperature overnight under nitrogen atmosphere. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate) to afford the desired compound (110 mg, yield ˜100%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415359B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-8f4ed415bd254c8fa0f1002474eba2a9 |
| Source note | uspto-grants-2013_04 |