GDC-0152

Base Information

• Chemical Name: GDC-0152
• CAS No.: 873652-48-3
• Molecular Formula: C₂₅H₃₄N₆O₃S
• Molecular Weight: 498.649
• Mol file: 873652-48-3.mol

Synonyms:

Chemical Property of GDC-0152

Chemical Property:

• Melting Point: 175-177oC
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

GDC-0152 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: GDC 0152 is a peptidomimetic small molecule antagonist of inhibitor of apoptosis (IAP) proteins with antitumor activity.

Technology Process of GDC-0152

There total 7 articles about GDC-0152 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: 80.0%

→ 1-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-pyrrolidine-2-carboxylic acid (4-phenyl-[1,2,3]thiadiazol-5-yl)-amide (873652-48-3)

Guidance literature:

In methanol; Isopropyl acetate;

Reference yield:

N-(tert-butoxycarbonyl)-N-methyl-L-alanine (16948-16-6) + 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride (25952-53-8) → (S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-N-(4-phenyl-1,2,3-thiadiazol-5-yl)pyrrolidine-2-carboxamide (873652-48-3)

Guidance literature:

With hydrogenchloride; benzotriazol-1-ol; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(S)-tert-butyl 2-(4-phenyl-1,2,3-thiadiazol-5-ylcarbamoyl)pyrrolidine-1-carboxylate (1071976-38-9) → (S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-N-(4-phenyl-1,2,3-thiadiazol-5-yl)pyrrolidine-2-carboxamide (873652-48-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h

1.2: 0.08 h

1.3: 3 h / 20 °C

2.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h

2.2: 0.08 h

2.3: 3 h / 20 °C

3.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h

With hydrogenchloride; In 1,4-dioxane; water;

DOI:10.1021/jm300060k

upstream raw materials:

(S)-tert-butyl 2-(4-phenyl-1,2,3-thiadiazol-5-ylcarbamoyl)pyrrolidine-1-carboxylate

C₃₀H₄₂N₆O₅S

1-(tert-butoxycarbonyl)-L-proline

5-amino-4-phenyl-1,2,3-thiadiazole

Refernces

• 1、 Flygare, John A.,Beresini, Maureen,Budha, Nageshwar,Chan, Helen,Chan, Iris T.,Cheeti, Sravanthi,Cohen, Frederick,Deshayes, Kurt,Doerner, Karl,Eckhardt, S. Gail,Elliott, Linda O.,Feng, Bainian,Franklin, Matthew C.,Reisner, Stacy Frankovitz,Gazzard, Lewis,Halladay, Jason,Hymowitz, Sarah G.,La, Hank,Lorusso, Patricia,Maurer, Brigitte,Murray, Lesley,Plise, Emile,Quan, Clifford,Stephan, Jean-Philippe,Young, Shin G.,Tom, Jeffrey,Tsui, Vickie,Um, Joanne,Varfolomeev, Eugene,Vucic, Domagoj,Wagner, Andrew J.,Wallweber, Heidi J. A.,Wang, Lan,Ware, Joseph,Wen, Zhaoyang,Wong, Harvey,Wong, Jonathan M.,Wong, Melisa,Wong, Susan,Yu, Ron,Zobel, Kerry,Fairbrother, Wayne J.. "Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152)". . p. 4101 - 4113. Retrieved 2012/06/30.