HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-[(Isoquinoline-4-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Isoquinoline-4-carboxylic acid | HCID 459768 | — |
| 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 | Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate | HCID 10921653 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[(Isoquinoline-4-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester | HCID 59314188 | 82% |
Reaction Steps
To a solution of isoquinoline-4-carboxylic acid (211 mg, 1.22 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (250 mg, 1.22 mmol), HATU (696 mg, 1.83 mmol) in anhydrous DMF (8 mL) is added DIPEA (302 μL, 1.83 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (40 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (51) as white solid (359 mg, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08569535B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-a62c408258c0485d86f193d7913cdc9e |
| Source note | uspto-grants-2013_10 |