Triethylamine → 2-((1S)-1-{[(5-Methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	5-Methoxy-2-methylindole-3-acetic acid	HCID 76151	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)	HCID 86627948	—
Reactant	1-methyl-3-({[(1S)-7-oxo-1-(5-phenyl-1h-imidazol-1-ium-2-yl)octyl]amino}carbonyl)piperidinium bis(trifluoroacetate)	HCID 87331381	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-((1S)-1-{[(5-Methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate	HCID 86627955	—

Reaction Steps

To a solution of Example 1, A3 and Et3N (1 eq.) in DCM was added a solution of EDC hydrochloride (1.2 eq.), HOBt (1.2 eq.) and (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1.2 eq.) in DCM. The mixture was shaken at RT for 1.5 hr and then the reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18). The desired fractions were lyophilized to afford the titled compound D1 as a white fluffy powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07863294B2
Source dataset	uspto-grants-2011_01
ORD ID	ord-d3eee426e5a44a53908a0e37df5d4eef
Source note	uspto-grants-2011_01