HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → HCID 68323469, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734655 | — |
| 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 | 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid | HCID 67235706 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68323469 | HCID 68323469 | 92.8% |
Reaction Steps
To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 2.3 g, 9.2 mmol) in DMF (30 mL) are added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (3.7 g, 9.7 mmol) and N-methylmorpholine (2.5 mL, 22.5 mmol). The reaction mixture is stirred for 1 h at room temperature and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.4 g, 11.1 mmol) is added. The reaction mixture is stirred for 16 h at room temperature and is poured into water (200 mL). The resulting solid is collected by filtration, rinsed with water and dried to afford the title compound (3.8 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150577B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-3eedbfca3fa4450c8bbdaa1e6924b930 |
| Source note | uspto-grants-2015_10 |