HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 59314389, compound
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 | 2-Aminoindan-2-acetic acid ethyl ester | HCID 57443998 | — |
| Reactant | 2-Cyclobutyloxy-3-methylbenzoic acid | HCID 59314155 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59314389 | HCID 59314389 | 96% |
Reaction Steps
To a solution of 2-cyclobutyloxy-3-methylbenzoic acid (210 mg-1.02 mmol), 2-aminoindan-2-acetic acid ethyl ester (A6) (260 mg-1.02 mmol) and HATU (470 mg-1.224 mmol-1.2 eq) in dry DMF (10 mL) is added diisopropylethylamine (0.36 mL-2.24 mmol-2.2 eq) and the resulting solution is stirred at RT overnight. After the removal of the DMF in vacuo, the residue is dissolved in EtOAc (60 mL) and washed with water (2×20 mL) and brine (2×20 mL). The organic layer is dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (120 g silica gel, 15% EtOAc in heptane) to give the pure product as colorless oil (400 mg, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08569535B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-9341780258de4a97a3faec159996e1ca |
| Source note | uspto-grants-2013_10 |