Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | 8-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester | HCID 136181612 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 136141735 | HCID 136141735 | 90% |
Reaction Steps
N-Chlorosuccinimide (0.47 g, 3.52 mmol) was added to a solution of Intermediate 147(c) of Example 147 (1.00 g, 3.33 mmol) in anhydrous N,N-dimethylformamide (10 ml) and anhydrous chloroform (6.5 mL). The reaction was heated at 50° C. for 3 hours at which point the volatile components were removed in vacuo. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 23:2:50 dichloromethane:methanol:ethyl acetate to afford the title compound (1 g, 2.99 mmol) as a yellow solid in 90% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07462713B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-d99cb159c05f4e4f91d0e18b161b7586 |
|---|
| Source note | uspto-grants-2008_12 |
|---|
