BMS-906024

Base Information

• Chemical Name: BMS-906024
• CAS No.: 1401066-79-2
• Molecular Formula: C26H26F6N4O3
• Molecular Weight: 556.508
• Mol file: 1401066-79-2.mol

Synonyms:UNII-DRL23N424R;(2R,3S)-N-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)succinamide;

Chemical Property of BMS-906024

Chemical Property:

• PSA: 109.34000
• LogP: 5.83600

Purity/Quality:

98% ^*data from raw suppliers

BMS-906024 98.07% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BMS-906024

There total 23 articles about BMS-906024 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(2S,3R)-6,6,6-trifluoro-3-(((35)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)carbamoyl)-2-(3,3,3-trifluoropropyl)hexanoic acid (1401067-34-2) → (2R,3S)-N-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3- trifluoropropyl)succinamide (1401066-79-2)

Guidance literature:

With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; Reagent/catalyst; Temperature; Time; Inert atmosphere;

Reference yield: 79.0%

(3R)-6,6,6-trifluoro-3-(((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)carbamoyl)-2-(3,3,3-trifluoropropyl)hexanoic acid → (2R,3S)-N-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3- trifluoropropyl)succinamide (1401066-79-2)

Guidance literature:

With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; Inert atmosphere;

Reference yield:

(2R)-3-(tert-butoxycarbonyl)-6,6,6-trifluoro-2-(3,3,3-trifluoropropyl)hexanoic acid → (2R,3S)-N-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3- trifluoropropyl)succinamide (1401066-79-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide; diethylaluminium chloride / n-heptane; hexane; tetrahydrofuran; ethylbenzene

1.2: 2.25 h / 30 °C

2.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 - 25 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 0 - 25 °C / Inert atmosphere

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran / 0.25 h / 20 °C

4.2: 4.75 h / 8 - 20 °C

With diethylaluminium chloride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; n-heptane; dichloromethane; ethylbenzene; N,N-dimethyl-formamide;

upstream raw materials:

(S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

(2R,3S)-3-(tert-butoxycarbonyl)-6,6,6-trifluoro-2-(3,3,3-trifluoropropyl)hexanoic acid

tert-butyl (2S,3R)-6,6,6-trifluoro-3-(((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)carbamoyl)-2-(3,3,3-trifluoropropyl)hexanoate

Downstream raw materials:

tert-butyl 2-((2S,3R)-6,6,6-trifluoro-3-((S,Z)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-2-(3,3,3-trifluoropropyl)hexanamidothio) ethylcarbamate

(2S,3R)-N-((isobutylamino)methyl)-N’-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)succinamide

(2S,3R)-N-((2-Aminoethyl)sulfanyl)-N’-((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)succinamide

S-(((2S,3R)-6,6,6-trifluoro-3-(((3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)carbamoyl)-2-(3,3,3-trifluoropropyl)hexanoyl)amino)-L-cysteine

Refernces

• 1、 Gavai, Ashvinikumar V.,Quesnelle, Claude,Norris, Derek,Han, Wen-Ching,Gill, Patrice,Shan, Weifang,Balog, Aaron,Chen, Ke,Tebben, Andrew,Rampulla, Richard,Wu, Dauh-Rurng,Zhang, Yingru,Mathur, Arvind,White, Ronald,Rose, Anne,Wang, Haiqing,Yang, Zheng,Ranasinghe, Asoka,D'Arienzo, Celia,Guarino, Victor,Xiao, Lan,Su, Ching,Everlof, Gerry,Arora, Vinod,Shen, Ding Ren,Cvijic, Mary Ellen,Menard, Krista,Wen, Mei-Li,Meredith, Jere,Trainor, George,Lombardo, Louis J.,Olson, Richard,Baran, Phil S.,Hunt, John T.,Vite, Gregory D.,Fischer, Bruce S.,Westhouse, Richard A.,Lee, Francis Y.. "Discovery of clinical candidate BMS-906024: A potent pan-notch inhibitor for the treatment of leukemia and solid tumors". . p. 523 - 527. Retrieved 2015/05/27.
• 2、 -. "BISFLUOROALKYL-1,4-BENZODIAZEPINONE COMPOUNDS". . . Retrieved 2012/10/08.