HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 9-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| 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 | 9-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylic acid | HCID 58203937 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 9-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide | HCID 58203902 | — |
Reaction Steps
To 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2.13 g, 6.53 mmol) in THF (22 mL) was added ammonium chloride (1.40 g, 26.1 mmol), DIEA (2.27 mL, 13.1 mmol), and then HATU (2.73 g, 7.18 mmol). The reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was diluted with sodium bicarbonate and ethyl acetate. The mixture was filtered and the filtrate was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (2.12, quantitative yield). LC/MS (ESI+): m/z 327 (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08673952B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-1af1d9bdbbbb461d8dc39a2aad6701aa |
| Source note | uspto-grants-2014_03 |