1-Hydroxybenzotriazole → 1-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl)-4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxamide

https://huagongshe.com/de/reaction/348963

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	1-Hydroxybenzotriazole	HCID 75771	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	1-Butyl-4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylic acid	HCID 21085174	—
Edukt	(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol	HCID 57487282	—
Lösungsmittel	Dichloromethane	HCID 6344	—
Lösungsmittel	Triethylamine	HCID 8471	—
Produkt	1-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl)-4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxamide	HCID 57508185	53,2%

Reaktionsbedingungen

Temperatur	40 °C

Reaktionsschritte

To a mixture of 1-Butyl-4-[methyl (methylsulfonyl) amino]-1H-indole-6-carboxylic acid (0.2 g) in methylene chloride (15 mL) was added triethylamine (0.156 g), HOBT (0.105 g), and HATU (0.293 g). The mixture was stirred at 39° C. for 10 minutes at which time (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.293 g) was added. The mixture was stirred at 40° C. for 4 h then poured into methylene chloride (50 mL), washed with water followed by brine then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% methanol in methylene chloride as eluent to give 0.21 g of the title compound: MS (ESI+) for C34H42F2N4O4S1 m/z 640.8 (M+H).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07176242B2
Quelldatensatz	uspto-grants-2007_02
ORD ID	ord-12bd69be504243cebab75aa6c1124857
Quellennotiz	uspto-grants-2007_02