HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylamine → 2-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylamine | HCID 6341 | — |
| 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-Amino-5-methoxy-1,3-benzothiazole-7-carboxylic acid | HCID 86663992 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamide | HCID 86663993 | 53% |
Reaction Steps
Ethylamine (2 mL, 4.02 mmol, 2M soln in methanol) was added to a solution of 2-amino-5-methoxy-1,3-benzothiazole-7-carboxylic acid (300 mg, 1.34 mmol), diisopropyl ethylamine (0.93 mL, 5.36 mmol) and HATU (560 mg, 1.47 mmol) in DMF (6 mL). The reaction was stirred at ambient temperature for 2 hours after which time LCMS indicated clean conversion to the product. The reaction was diluted with EtOAc, washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by trituration with DCM to give the product as an off white solid, 178 mg, 53% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181234B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-07cf3e7fd7844c7e8f8bbb7dc390d79a |
| Source note | uspto-grants-2015_11 |