Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-(tert-Butoxycarbonyl)-L-cyclohexylglycine | HCID 7004938 | — |
| 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 | 8-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one | HCID 135774079 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 136181608 | HCID 136181608 | 67% |
Reaction Steps
Preparation of example 33 from the title compound of Example 7 (35 mg, 0.13 mmol), (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid (39 mg, 0.15 mmol), triethylamine (0.073 mL, 0.52 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (58 mg, 0.15 mmol) in N,N-dimethylformamide (2.0 mL) was carried out analogously to Example 11 except that after 24 hours additional (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid (17 mg, 0.065 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) were added to drive the reaction to completion. Silica gel chromatography (1:1 ethyl acetate:hexane), also in an analogous manner, followed by diethyl ether trituration afforded the title compound (45 mg, 0.087 mmol) as a yellow powder in 67% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07132533B2 |
|---|
| Source dataset | uspto-grants-2006_11 |
|---|
| ORD ID | ord-b6b650d92f5245c5b624f1daafcc05d7 |
|---|
| Source note | uspto-grants-2006_11 |
|---|
