Hydrochloric Acid → N-((1S)-2-[4-(8-Bromoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl)-3-chloro-4-[(1-methylethyl)oxy]benzamide

A solution of 1,1-dimethylethyl {(1S)-2-[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2 yl)methyl]ethyl}carbamate (3.5 mmol) and hydrogen chloride in 1,4-dioxane (20 mL, 4.0M) stirred for 1 h at RT. The reaction was concentrated to dryness and redissolved in N,N-dimethylformamide (35 mL). Added to the solution was diisopropylethylamine (10.5 mmol) and pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (3.8 mmol), which was stirred at RT for half an hour. The reaction was dissolved in ethyl acetate (80 mL) and washed with water (3×50 mL) and brine (1×50 mL). To the separated organic layer was added hexanes (150 mL) upon which a precipitate was formed, filtered, and dried to afford the title compound as an off white solid (65%).

1. concentrationThe reaction was concentrated to dryness
2. dissolutionredissolved in N,N-dimethylformamide (35 mL)
3. additionAdded to the solution
4. washwashed with water (3×50 mL) and brine (1×50 mL)
5. additionTo the separated organic layer was added hexanes (150 mL) upon which a precipitate
6. customwas formed
7. filtrationfiltered
8. customdried

ORD 기록

ord-87fdb888e75b406f8a59feee647ce196

출처 데이터셋

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07618981B2