Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| 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 | HCID 86697523 | HCID 86697523 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71765591 | HCID 71765591 | — |
Reaction Steps
N,N-Diisopropylethylamine (78 μl, 0.45 mmol) was added to a mixture of 3-[9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-6-fluoro-2-methyl-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]cyclobutanecarboxylic acid trifluoroacetate (44 mg, 0.09 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (34 mg, 0.09 mmol) in N,N-dimethylformamide (2 mL) at room temperature. A solution of ammonia in ethanol (2.0 M, 130 μl) was added and the reaction was stirred at room temperature for 1.5 hrs. The reactions were purified by prep HPLC on C-18 column eluting water:acetonitrile gradient buffered pH 10 to give two diastereomers: Peak #1 (Example 43): LCMS calculated for C23H28ClFN7O2 (M+H)+: m/z=488.2; found: 488.2; Peak #2 (Example 44): LCMS calculated for C23H28ClFN7O2 (M+H)+: m/z=488.2; found: 488.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09309251B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-d10c814f94b24a6f99df539622080391 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
