HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl 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 | Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate | HCID 10921653 | — |
| Reactant | 2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid | HCID 59314301 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester | HCID 59314102 | 10% |
Reaction Steps
To a solution of 2-cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid (410 mg, 1.7 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (425 mg, 1.7 mmol), HATU (760 mg, 2 mmol) in anhydrous DMF (5 mL) is added DIPEA (4354, 2.5 mmol). The resulting solution is stirred at RT overnight. Water (10 mL) is poured into the reaction mixture, and then extracted with EtOAc (3×7 mL). The combined organic layers are concentrated in vacuo. The residue is purified by reverse phase chromatography (gradient elution: 20-100% ACN in water) to give product (285) as colorless oil (70 mg, 10%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08569535B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-4d9b20dc85db436e92f258bb34e08a92 |
| Source note | uspto-grants-2013_10 |