HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1,1-Dimethylethyl 4-{[3-({[(3-bromo-4-fluorophenyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3-Bromo-4-fluorophenyl)methanamine | HCID 2724902 | — |
| 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-((1-(tert-Butoxycarbonyl)piperidin-4-yl)methyl)benzoic acid | HCID 45073959 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1,1-Dimethylethyl 4-{[3-({[(3-bromo-4-fluorophenyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylate | HCID 57736709 | 94.2% |
Reaction Steps
To a solution of [(3-bromo-4-fluorophenyl)methyl]amine (0.802 g, 3.33 mmol) in DMF (12.0 mL) was added 3-[(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)methyl]benzoic acid (1.060 g, 3.32 mmol), HATU (1.389 g, 3.65 mmol), and diisopropylethylamine (2.9 mL, 16.6 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with EtOAc (300 mL), washed with 1N HCl (2×75 mL), then saturated NaHCO3 (3×75 mL), then brine (2×75 mL). The organic layer was dried over MgSO4, filtered, and concentrated under vacuum to give the desired product (1.58 g, 94.2%). EI-MS m/z 506(M−H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932247B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-4d38048d979c438fa15f22845b5c0412 |
| Source note | uspto-grants-2011_04 |