HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2S,4S)-2-(2-Amino-6-bromo-naphthalen-1-ylcarbamoyl)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | 6-Bromonaphthalene-1,2-diamine | HCID 22097071 | — |
| Reactant | (4S)-1-(tert-Butoxycarbonyl)-4-methyl-L-proline | HCID 26596883 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2S,4S)-2-(2-Amino-6-bromo-naphthalen-1-ylcarbamoyl)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 86700516 | 42% |
Reaction Steps
To a solution of 6-bromo-naphthalene-1,2-diamine (2.0 g, 8.5 mmol) in DMF (150 mL) was added (2S,4S)-4-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.14 g, 10.2 mmol), DIPEA (3.29 g, 25.5 mmol), and HATU (4.84 g, 12.7 mmol). The reaction mixture was stirred at RT overnight and extracted with EtOAc/H2O (150 mL). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (2:1 EtOAc:petroleum ether) to provide the title intermediate (1.6 g)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09066944B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-cd42bf5697d147fbb0c7112af8c7cad8 |
| Source note | uspto-grants-2015_06 |