HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 7-[2-(4-Fluoro-benzylamino)-benzoylamino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 21786232 | HCID 21786232 | — |
| Reactant | Tert-butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate | HCID 21959561 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 7-[2-(4-Fluoro-benzylamino)-benzoylamino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 69510865 | — |
Reaction Steps
The mixture of 2-(4-fluorobenzylamino)benzoic acid (Step A, 0.7 g, 1.20 mmol), 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.71 g, 2.57 mmol), TBTU (0.917 g, 2.86 mmol), and DIEA (0.5 mL) in 30 mL of CH2Cl2 was stirred at RT for 2 h, then diluted with more CH2Cl2. The organic layer was washed with water, and brine, dried with MgSO4, filtered, and condensed. The residue was purified by flash column chromatography (0 to 30% of EtOAc in CH2Cl2), and the titled compound was obtained as oil. MS (ES+): 504 (M+H)+. Calc'd for C30H34FN3O3-503.26.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07307088B2 |
| Source dataset | uspto-grants-2007_12 |
| ORD ID | ord-88de52d703214a58a6274f6b7694e780 |
| Source note | uspto-grants-2007_12 |