HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [1-(6-Oxo-2-Phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-ylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-((Tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid | HCID 2794744 | — |
| 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 | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | [1-(6-Oxo-2-Phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-ylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester | HCID 136181625 | 53.5% |
Reaction Steps
Preparation of example 119 from the title compound of Example 7 (hydrochloride) (45 mg, 0.142 mmol), 1-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (42 mg, 0.171 mmol), triethylamine (0.059 mL, 0.426 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (65 mg, 0.171 mmol) in CH2Cl2 (0.4 mL) and N,N-dimethylformamide (0.4 mL) was carried out analogously to Example 11. Silica gel chromatography (eluted with 1:1 hexane:acetone), also in an analogous manner, afforded the title compound (38 mg, 0.076 mmol) as a yellow powder in 53% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06967198B2 |
| Source dataset | uspto-grants-2005_11 |
| ORD ID | ord-2375368ec24d45f69feeb45187781278 |
| Source note | uspto-grants-2005_11 |