HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| 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 | 1-(4-Azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanone | HCID 59625678 | — |
| Reactant | 1-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid | HCID 59625947 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline | HCID 59625925 | 69.2% |
Reaction Steps
To a solution of compound 1g (228 mg, 0.74 mmol), compound 25c (22 mg, 0.74 mmol), and Et3N (0.3 mL, 2.22 mmol) in CH2Cl2 (7 mL) was added HATU (338 mg, 0.89 mmol). The reaction mixture was stirred at room temperature for 18 h. The resultant mixture was diluted with CH2Cl2 and washed with aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc+0.5% Et3N) gave compound 25d (265 mg). LC/MS m/z (M+H+), 517.0 (M+2H+), 519.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691805B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-308361a3799f4878a7dbae39dc5f687f |
| Source note | uspto-grants-2014_04 |