HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → HCID 67235313, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methyl Anthranilate | HCID 8635 | — |
| Reactant | 1-Chloro-N,N-2-trimethylpropenylamine | HCID 640792 | — |
| Reactant | 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid | HCID 67235706 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67235313 | HCID 67235313 | 66.6% |
Reaction Steps
To a suspension of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 500 mg, 2.0 mmol) in CH2Cl2 (10 mL) at room temperature is added 1-chloro-N,N,2-trimethylpropenylamine (0.98 mL, 7.2 mmol). After stirring for 3 h, methyl anthranilate (1.3 mL, 10.2 mmol) and pyridine (0.66 mL, 8.2 mmol) are added. The mixture is stirred for another 16 h at room temperature. Water (100 mL) is added and the mixture is extracted with EtOAc (3×100 mL). The organic layers are combined, dried and evaporated. Methanol (50 mL) is added to the oily residue, and a white solid is formed. The solid is filtered to afford the title compound (503 mg, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150577B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-ce82ab99fc0d4d9da3b39e9075fabe82 |
| Source note | uspto-grants-2015_10 |