5-Chloro-1H-indole-2-carboxylic acid → HCID 11660421, compound

https://huagongshe.com/reaction/901986

Participants

Role	Name	HCID	Charge
Reactant	5-Chloro-1H-indole-2-carboxylic acid	HCID 82693	—
Reactant	HOAt	HCID 181649	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(6R,7R)-6-Amino-5,6,7,8-tetrahydronaphthalene-1,7-diol	HCID 71365891	—
Reactant	(6R,7R)-7-Amino-5,6,7,8-tetrahydronaphthalene-1,6-diol	HCID 71365894	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 11660421	HCID 11660421	—

Reaction Steps

A mixture of trans 3-amino-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene and trans 3-amino-2,8-dihydroxy-1,2,3,4-tetrahydronaphthalene (278 mg, prepared in the manner disclosed in GB 1442851) was dissolved at room temperature with stirring under argon in N,N-dimethylformamide (2 mL) along with 5-chloroindole-2-carboxylic acid (315 mg), 1-hydroxy-7-azabenzotriazole (230 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (330 mg). After 3 days the reaction mixture was purified without work-up by reverse phase preparative HPLC to provide the two isomers as off-white solids, trans 3-(5-chloroindole-2-carbonylamino)-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene, Example 2 (eluted first, 130 mg) and trans 3-(5-chloroindole-2-carbonylamino)-2,8-dihydroxy-1,2,3,4-tetrahydronaphthalene, Example 3 (eluted second, 104 mg). HPLC/MS for both isomers [M+H]+, 357; [M−H]−, 355.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07365061B2
Source dataset	uspto-grants-2008_04
ORD ID	ord-da5a3b036a5c417fa72f6af007806082
Source note	uspto-grants-2008_04