HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl N-(4-aminobutyl)carbamate → Tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl N-(4-aminobutyl)carbamate | HCID 4351 | — |
| 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 | 4-((4-((4-(2-Bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoic acid | HCID 67285180 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate | HCID 68658523 | 87% |
Reaction Steps
4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoic acid (2.63 g, 4.85 mmol), tert-butyl (4-aminobutyl)carbamate (1.37 g, 7.27 mmol), HATU (5.53 g, 14.55 mmol), and Hunig's Base (4.24 mL, 24.25 mmol) were stirred in DCM (20 mL) for 3 h. The solvent was removed and the crude material was purified by silica gel chromatography eluting with 20-40-80% ethyl acetate in hexane to give tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate (3.0 g, 87%) as product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08445490B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-2cfe80b0bede4746ba10cecb2d6a828f |
| Source note | uspto-grants-2013_05 |