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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 222891Erstellt: 24. Oktober 2026

Hydrochloric Acid → N-((1S)-2-(D-Alanylamino)-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide

https://huagongshe.com/de/reaction/222891

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktHydrochloric AcidHCID 313—
Edukt1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
EduktBOC-D-alanineHCID 637606—
EduktN-((1S)-2-Amino-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamideHCID 57594540—
LösungsmittelDichloromethaneHCID 6344—
Lösungsmittel1,4-DioxaneHCID 31275—
ProduktN-((1S)-2-(D-Alanylamino)-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamideHCID 5759463925%

Reaktionsschritte

A solution of N-((1S)-2-amino-1-{[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]methyl}ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide (0.28 mmol), N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (0.56 mmol), EDCI (0.56 mmol), and TEA (1.12 mmol) stirred in methylene chloride (2 mL) at RT for 18 h. The reaction was then treated with 4 M HCl in 1,4-dioxane (2 mL) and stirred at RT for 1 h. The mixture was then concentrated in vacuo, redissolved in ethyl acetate (25 mL) and washed with saturated aqueous sodium bicarbonate solution (1×10 mL). The organic layer was concentrated in vacuo, and purification of the residue by Gilson reverse phase HPLC afforded the title product as a white solid (25%). ESMS [M+H]+: 613.2.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08207340B2
Quelldatensatzuspto-grants-2012_06
ORD IDord-4972067d71d24313a6bff0eda1e66ddb
Quellennotizuspto-grants-2012_06