HuagongsheHuagongshe Chemistry Print Report · For research reference only
7-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid → 7-Chloro-3-[p-aminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 7-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid | HCID 70125994 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 7-Chloro-3-[p-aminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid hydrochloride | HCID 70125216 | 123.8% |
Reaction Steps
A solution of 7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid acid (189 mg)in a mixture of 1,4-dioxane (4 mL) and 4N HCl in 1,4-dioxane (4 mL) was Stirred for 20 h at room temperature and concentrated in vacuo. The residual solid was rinsed with THF and dried in vacuo to give 104 mg of the title compound (47%): 1H NMR (DMSO-d6) δ13.05 (br, 2H), 11.45 (s, 1H), 9.24 (s, 1H), 830 (br, 3H), 8.04 (d, 1H, J=8.3 Hz), 7.20 (s, 1H), 7.16 (s, 1H), 7.06 (d, 1H, J=8.3 Hz), 6.84 (s, 1H), 4.74 (s, 2H), 3.90 ~3.95 (m,3H), 3.09 (m, 1H), 2.78 (m1H), 2.69 (m, 2H), 2.08 (m, 1H), 1.85 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05496843 |
| Source dataset | uspto-grants-1996_03 |
| ORD ID | ord-5220a112e5c24f369bf4d8dc6953bce7 |
| Source note | uspto-grants-1996_03 |