AZD5363

Base Information

• Chemical Name: AZD5363
• CAS No.: 1143532-39-1
• Molecular Formula: C21H25ClN6O2
• Molecular Weight: 428.922
• Mol file: 1143532-39-1.mol

Synonyms:AZD5363;4-Amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinecarboxamide;AZD5356

Chemical Property of AZD5363

Chemical Property:

• PKA: 13.93±0.50(Predicted)
• PSA: 123.65000
• Density: 1.381
• LogP: 3.75450
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

AZD5363 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: AZD5363 is used in inhibiting the proliferation of certain tumor cell lines.

Technology Process of AZD5363

There total 7 articles about AZD5363 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%

(3S)-3-amino-3-(4-chlorophenyl)propan-1-ol (1213362-28-7,886061-26-3) + 8-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-oxa-4,8-diazaspiro[4.5]decane-1,3-dione → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxy-propyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143532-39-1)

Guidance literature:

With potassium hydrogencarbonate; In water; acetonitrile; at 25 ℃; for 10h;

Reference yield: 42.5%

(S)-4-amino-N-(1-(4-chlorophenyl)-3-hydroxypropyl)piperidine-4-carboxamide (1143534-59-1) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxy-propyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143532-39-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 60 ℃; for 18h; Product distribution / selectivity;

Reference yield: 25.0%

(3S)-3-amino-3-(4-chlorophenyl)propan-1-ol (1213362-28-7,886061-26-3) + 4-(tert-butoxycarbonylamino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (956460-96-1) → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxy-propyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143532-39-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,2-dimethoxyethane; for 16h; Inert atmosphere;

DOI:10.1021/jm301762v

upstream raw materials:

(S)-4-amino-N-(1-(4-chlorophenyl)-3-hydroxypropyl)piperidine-4-carboxamide

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

(S)-tert-butyl 4-(1-(4-chlorophenyl)-3-hydroxypropylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

(3S)-3-amino-3-(4-chlorophenyl)propan-1-ol

Refernces

• 1、 Addie, Matt,Ballard, Peter,Buttar, David,Crafter, Claire,Currie, Gordon,Davies, Barry R.,Debreczeni, Judit,Dry, Hannah,Dudley, Philippa,Greenwood, Ryan,Johnson, Paul D.,Kettle, Jason G.,Lane, Clare,Lamont, Gillian,Leach, Andrew,Luke, Richard W. A.,Morris, Jeff,Ogilvie, Donald,Page, Ken,Pass, Martin,Pearson, Stuart,Ruston, Linette. "Discovery of 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7H- pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (AZD5363), an orally bioavailable, potent inhibitor of Akt kinases". . p. 2059 - 2073. Retrieved 2013/05/08.