HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | N-(3-Aminopropyl)morpholine | HCID 61055 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid | HCID 24966534 | — |
| Product | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide | HCID 24967256 | 58% |
Reaction Steps
To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (57.7 mg, 0.14 mmol) and 3-morpholine-4-yl-propylamine (0.031 ml, 0.29 mmol) in DMF 4.0 mL was added HBTU (109.98 mg, 0.29 mmol) and DIPEA (0.051 ml, 0.29 mmol). After stilling at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrate. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=10:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide as a white solid (38.2 mg, 58% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-898e7d416fc441328c8597a380d352bd |
| Source note | uspto-grants-2013_03 |