HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (1r,2r)-2-Phenyl-cyclopropanecarboxylic acid [2-(3-dimethylaminomethyl-phenyl)-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | trans-2-Phenylcyclopropanecarboxylic acid | HCID 237413 | — |
| 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 | N-[2-(3-Dimethylaminomethyl-phenyl)-6-oxo-5,6-dihydro-1H-[1,21diazepino[4.5.6-cd]indol-8-yl]-2-fluoro-3-trifluoromethyl-benzamide | HCID 135405075 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1r,2r)-2-Phenyl-cyclopropanecarboxylic acid [2-(3-dimethylaminomethyl-phenyl)-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl]-amide | HCID 136141630 | 76.1% |
Reaction Steps
Preparation of example 83a from Intermediate 73(d) of Example 73 (0.11 g, 0.33 mmol), (1R,2R)-2-phenyl-cyclopropanecarboxylic acid (0.08 g, 0.5 mmol), triethylamine (0.183 mL, 1.32 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.188 g, 0.5 mmol) and N,N-dimethylformamide (0.2 M, 1.7 mL) was carried out analogously to Example 11. Silica gel chromatography (90:10 to 80:20 CH2Cl2/2M ammonia in isopropyl alcohol) afforded the title compound (0.12 g) as powder in 76% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07132533B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-ce3e7ad7bb5d4bf8b80f530caaaa50d1 |
| Source note | uspto-grants-2006_11 |