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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1439912Generated: November 1, 2026

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

https://huagongshe.com/reaction/1439912

Reaction equation

Participants

RoleNameHCIDCharge
Reactant7-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acidHCID 70125994—
SolventHydrochloric AcidHCID 313—
Solvent1,4-DioxaneHCID 31275—
Product7-Chloro-3-[p-aminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid hydrochlorideHCID 70125216123.8%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05496843
Source datasetuspto-grants-1996_03
ORD IDord-5220a112e5c24f369bf4d8dc6953bce7
Source noteuspto-grants-1996_03