XL-388

Base Information

• Chemical Name: XL-388
• CAS No.: 1251156-08-7
• Molecular Formula: C23H22FN3O4S
• Molecular Weight: 455.51
• Mol file: 1251156-08-7.mol

Synonyms:XL 388;XL388;XL-388;[7-(6-Amino-3-pyridinyl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)phenyl]-methanone;Methanone, [7-(6-amino-3-pyridinyl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)phenyl]-;[7-(6-Amino-3-pyridinyl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)phenyl]-methanone XL388;XL388, >=98%

Chemical Property of XL-388

Chemical Property:

• Boiling Point: 738.6±60.0 °C(Predicted)
• PKA: 6.22±0.13(Predicted)
• PSA: 111.70000
• Density: 1.354±0.06 g/cm3(Predicted)
• LogP: 4.16540
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% min ^*data from raw suppliers

XL 388 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: XL388 is a highly potent, orally bioavailable, selective, ATP-competitive mammalian target of rapamycin (mTOR) inhibitor. XL388 has shown significant and dose-dependent antitumor activity in athymic nude mice implanted with human tumor xenografts.

Technology Process of XL-388

There total 26 articles about XL-388 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: 84.0%

C15H12FN3O4S + 5-(2,3,4,5-tetrahydrobenzo[f ][1,4]oxazepin-7-yl)pyridin-2-amine bis-(hydrochloride) → [7-(6-aminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)-phenyl]methanone (1251156-08-7)

Guidance literature:

With potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; at 15 ℃; for 18h; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.5b00037

Reference yield: 70.0%

3-fluoro-2-methyl-4-(methylsulfonyl)benzoyl chloride (1251164-88-1) + 5-(2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-7-yl)pyridin-2-amine (1251165-18-0) → [7-(6-aminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)-phenyl]methanone (1251156-08-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

Reference yield:

3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid (118939-18-7) + 5-(2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-7-yl)pyridin-2-amine (1251165-18-0) → [7-(6-aminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl][3-fluoro-2-methyl-4-(methylsulfonyl)-phenyl]methanone (1251156-08-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1021/jm3007933

upstream raw materials:

3-fluoro-2-methyl-4-(methylsulfonyl)benzoyl chloride

5-(2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-7-yl)pyridin-2-amine

tert-butyl 7-(6-aminopyridin-3-yl)-2,3-dihydrobenzo-[f ][1,4]oxazepine-4(5H)-carboxylate

3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid

Refernces

• 1、 Takeuchi, Craig S.,Kim, Byung Gyu,Blazey, Charles M.,Ma, Sunghoon,Johnson, Henry W. B.,Anand, Neel K.,Arcalas, Arlyn,Baik, Tae Gon,Buhr, Chris A.,Cannoy, Jonah,Epshteyn, Sergey,Joshi, Anagha,Lara, Katherine,Lee, Matthew S.,Wang, Longcheng,Leahy, James W.,Nuss, John M.,Aay, Naing,Aoyama, Ron,Foster, Paul,Lee, Jae,Lehoux, Isabelle,Munagala, Narsimha,Plonowski, Arthur,Rajan, Sharmila,Woolfrey, John,Yamaguchi, Kyoko,Lamb, Peter,Miller, Nicole. "Discovery of a novel class of highly potent, selective, ATP-competitive, and orally bioavailable inhibitors of the mammalian target of rapamycin (mTOR)". . p. 2218 - 2234. Retrieved 2013/05/22.