Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 58368670 | HCID 58368670 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58368453 | HCID 58368453 | 79.2% |
Reaction Steps
A mixture of 4-(3-fluorophenyl)-1-methylisoquinoline-3-carboxylic acid (400 mg, 1 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (700 mg, 1.8 mmol) and triethylamine (0.99 mL, 7.1 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (180 mg, 1.8 mmol) was added and the resulting suspension was stirred at room temperature for 2 hours. The mixture was quenched with water and then extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, concentrated and the residue purified on silica gel (eluting with 0-80% ethyl acetate in hexane) to give the desired product (0.257 g, 60%). LCMS calculated for C19H18FN2O2 (M+H)+: m/z=325.1; Found: 325.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08680108B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-f2de98a517324c9f95f44b22d659ea49 |
|---|
| Source note | uspto-grants-2014_03 |
|---|
